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| ORIGINAL ARTICLE |
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| Year : 2015 | Volume
: 6
| Issue : 3 | Page : 141-146 |
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Synthesis, antifungal and antibacterial activity of novel 1,2,4-triazole derivatives
Deepa Gupta1, DK Jain2
1 Department of Pharmacy, LBS College of Pharmacy, Jaipur, Rajasthan, India
2 Department of Pharmacy, IPS College of Pharmacy, Indore, Madhya Pradesh, India
| Date of Web Publication | 27-Jul-2015 |
Correspondence Address:
Deepa Gupta
LBS College of Pharmacy, Tilak Nagar, Jaipur, Rajasthan
India
 Source of Support: None, Conflict of Interest: None  | Check |
DOI: 10.4103/2231-4040.161515
A large number of 1,2,4-triazole-containing ring system have been incorporated into a wide variety of therapeutically interesting drug candidates including anti-inflammatory, central nervous system stimulants, antianxiety, and antimicrobial agents. To overcome the rapid development of drug resistance, new agents should preferably have chemical characteristics that clearly differ from those of existing agents. Thus led to the design and synthesize the new antimicrobial agents. A novel series of Schiff bases based on of 4-(benzylideneamino)-5-phenyl-4H-1,2,4-triazole-3-thiol scaffold was prepared by heating thiocarbohydrazide and substituted benzoic acid and subsequently, treating with substituted benzaldehydes. Seventeen derivatives were synthesized and were biologically screened for antifungal and antibacterial activity. The newly synthesized derivatives of triazole showed antifungal activity against fungal species, Microsporum gypseum; and antibacterial activity against bacterial species, Staphylococcus aureus. It was observed that none of the compounds tested showed positive results for fungi Candida albicans fungi Aspergillus niger, nor against bacterial strain Escherichia coli. Strong antifungal effects were obtained for the synthesized compounds against M. gypseum and were superior or comparable to standard drug ketoconazole. Similarly, all of the synthesized compounds exhibit strong antibacterial activity against S. aureus and were superior or comparable to standard drug streptomycin. It was found that among the triazole derivatives so synthesized, six of them, showed antifungal activity superior to ketoconazole while one of them, showed antibacterial activity superior to streptomycin. Thus, these can be the potential new molecule as an antimicrobial agent. Keywords: Antibacterial activity, antifungal activity, Microsporum gypseum, Schiff bases, Staphylococcus aureus
How to cite this article:
Gupta D, Jain D K. Synthesis, antifungal and antibacterial activity of novel 1,2,4-triazole derivatives. J Adv Pharm Technol Res 2015;6:141-6 |
How to cite this URL:
Gupta D, Jain D K. Synthesis, antifungal and antibacterial activity of novel 1,2,4-triazole derivatives. J Adv Pharm Technol Res [serial online] 2015 [cited 2023 Feb 8];6:141-6. Available from: https://www.japtr.org/text.asp?2015/6/3/141/161515 |
| Introduction | |  |
A large number of 1, 2, 4-triazole, a heterocyclic derivative exhibits important therapeutic activities such as antifungal, [1] anticonvulsant, [2] anti-tubercular, [3] antioxidant, [4] anti-inflammatory, [5] COX-2 inhibition, [6] anticancer, [7] and antimicrobial activity. [8] Furthermore, 1, 2, 4-triazole ring system has been incorporated into a wide variety of therapeutically interesting drug candidates like ribavirin (antiviral agent), rizatriptan (antimigraine agent) and fluconazole, itraconazole (an antifungal agent). [9] Thus, there is a need to explore these pharmacophores for the development of novel molecules with different activities.
Fungal and bacterial infections have become an important complication and major cause of mortality in immunocompromised individuals suffering from tuberculosis, cancer, AIDS, etc. [10] Amphotericin B is the most frequently used drug in the treatment of systemic mycoses in spite of its toxic effect on humans. Other antifungals like azole derivatives (fluconazole, an orally active triazole agent, and itraconazole), allylamines, thiocarbamates, fluoropyrimidines are some agents actually working in patients with impaired resistance such as those who have AIDS. While these new compounds are often used in treatment of fungal infections, resistance to these drugs is increasing, moreover many of currently available drugs have undesirable side effects, which clearly indicates an urgent need for development of new antimicrobial agents. [11],[12]
Prompted by these observations, triazole derivatives may be the potential candidate to investigate as a safe antimicrobial agent, as these may not affect the host. All newly synthesized triazole derivatives were screened for their antifungal activity against fungi Candida albicans, Aspergillus niger, and Microsporum gypseum. Also, these newly synthesized triazole derivatives were evaluated for antibacterial activity against bacterial strain Escherichia More Details coli and S. aureus.
| Materials and Methods | | |
Reagents, starting materials and solvents were purchased from common commercial suppliers. The melting points of synthesized compounds were determined by an open capillary method on a Veego digital melting point apparatus. Mass spectral analysis was carried out using Applied Biosystem QTRAP 3200 MS/MS system in ESI mode. The infra-red spectra of the synthesized compounds were recorded on Fourier transformer infra-red spectrophotometer Model Schimadzu 8400S using potassium bromide pellets. 1 H NMR spectra were recorded on the Bruker NMR using DMSO-d6, tetramethylsilane as an internal standard.
Experimental
General Procedure for Synthesis of 4-amino-5-phenyl-4H-1, 2, 4- triazole-3-thiol (3a-3c)
A mixture of substituted benzoic acid (0.01 M) and thiocarbohydrazide (0.01 M) was heated until it melted. The mixture was consistently maintained at 145°C for 40 min. The product obtained on cooling was treated with a sodium bicarbonate solution to neutralize the unreacted acid if any. The product was then washed with water and collected by filtration. The solid product was recrystallized from a mixture of ethanol and dimethylformamide.
General procedure for the synthesis of 4-(benzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol (5a-5q)
To a suspension of substituted benzaldehyde (4) (0.2 M) in ethanol (1 ml), an equimolar amount of corresponding 4-amino-5-phenyl-4H-1, 2, 4-triazole-3-thiol (3a-3c) was added. The suspension was heated until a clear solution was obtained. Then few drops of concentrated sulfuric acid were added, and the solution was refluxed for 6 h on a water-bath. The precipitated solid was filtered off and recrystallized from a mixture of dimethylformamide and ethanol.
4-(4-bromobenzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol (5a)
77% yield - M.P. =142-144°C, IR (KBr) n/cm: 3109.04, 2935.46, 1504.37, 1446.51. 1 H NMR (DMSO-d6 , 400 MHz): d 7.26-7.92 (m, 11H), 10.07 (s, 1H), 13.72 (s, 1H). MS-API: [M + H] + 360.02 (calculated 361) Anal. calculated for C 15 H 13 BrN 4 S: C, 49.87; H, 3.63; Br, 22.12; N, 15.51; S, 8.88 Found: C, 49.53; H, 3.23; Br, 22.42; N, 15.01; S, 8.28.
4-(2,4-dichlorobenzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol (5b)
79% yield - M.P. =125-127°C, IR (KBr) n/cm: 3107.04, 2932.26, 1505.17, 1443.53. 1 H NMR (DMSO-d6 , 400 MHz): d 7.33-7.88 (m, 10H), 10.42 (s, 1H), 13.86 (s, 1H). MS-API: [M + H] + 350.02 (calculated 351) Anal. calculated for C 15 H 12 Cl 2 N 4 S: C, 51.29; H, 3.44; Cl, 20.19; N, 15.95; S, 9.13 Found: C, 51.30; H, 3.20; Cl, 20.50; N, 15.55; S, 9.10.
4-(4-fluorobenzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol (5c)
81% yield - M.P. =167-169°C, IR (KBr) n/cm: 3108.02, 2934.44, 1501.20, 1445.45. 1 H NMR (DMSO-d6 , 400 MHz): d 7.18-7.93 (m, 11H), 10.02 (s, 1H), 13.12 (s, 1H). MS-API: [M + H] + 300.08 (calculated 300) Anal. calculated for C 15 H 13 FN 4 S: C, 59.98; H, 4.36; F, 6.33; N, 18.65; S, 10.68 Found: C, 59.20; H, 4.25; F, 6.10; N, 18.20; S, 10.42.
4-(3-chlorobenzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol (5d)
78% yield - M.P. =155-158°C, IR (KBr) n/cm: 3106.00, 2931.46, 1502.12, 1436.13. 1 H NMR (DMSO-d6 , 400 MHz): d 7.44-7.92 (m, 11H), 10.22 (s, 1H), 13.89 (s, 1H). MS-API: [M + H] + 316.05 (calculated 316) Anal. calculated for C 15 H 13 ClN 4 S: C, 56.87; H, 4.14; Cl, 11.19; N, 17.68; S, 10.12 Found: C, 56.50; H, 4.10; Cl, 11.20; N, 17.80; S, 10.10.
4-(4-chlorobenzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol (5e)
82% yield - M.P. =192-195°C, IR (KBr) n/cm: 3112.08, 2938.26, 1514.17, 1426.25. 1 H NMR (DMSO-d6 , 400 MHz): d 7.42-7.97 (m, 11H), 10.17 (s, 1H), 13.92 (s, 1H). MS-API: [M + H] + 316.05 (calculated 316) Anal. calculated for C 15 H 13 ClN 4 S: C, 56.87; H, 4.14; Cl, 11.19; N, 17.68; S, 10.12 Found: C, 56.75; H, 4.10; Cl, 11.25; N, 17.55; S, 10.30.
4-(4-fluorobenzylideneamino)-5-(2,4-dichlorophenyl)-4H-1, 2, 4-triazole-3-thiol (5f)
75% yield - M.P. =143-145°C, IR (KBr) n/cm: 3223.12, 2921.96, 1508.23, 1226.64. 1 H NMR (DMSO-d6 , 400 MHz): d 7.21-7.93 (m, 9H), 10.05 (s, 1H), 13.52 (s, 1H). MS-API: [M + H] + 368.01 (calculated 369) Anal. calculated for C 15 H 11 Cl 2 FN 4 S: C, 48.79; H, 3.00; Cl, 19.20; F, 5.15; N, 15.17; S, 8.68 Found: C, 48.20; H, 3.10; Cl, 19.25; F, 5.25; N, 15.10; S, 8.40.
4-(4-bromobenzylideneamino)-5-(2,4-dichlorophenyl)-4H-1, 2, 4-triazole-3-thiol (5g)
78% yield - M.P. =187-189°C, IR (KBr) n/cm: 3323.22, 2911.95, 1505.28, 1229.12. 1 H NMR (DMSO-d6 , 400 MHz): d 7.41-7.57 (m, 9H), 10.42 (s, 1H), 13.92 (s, 1H). MS-API: [M + H] + 427.93 (calculated 430) Anal. calculated for C 15 H 11 BrCl 2 N 4 S: C, 41.88; H, 2.58; Br, 18.58; Cl, 16.48; N, 13.02; S, 7.45 Found: C, 41.80; H, 2.50; Br, 18.20; Cl, 16.25; N, 13.10; S, 7.40.
4-(3-chlorobenzylideneamino)-5-(2,4-dichlorophenyl)-4H-1, 2, 4-triazole-3-thiol (5h)
76% yield - M.P. =128-131°C, IR (KBr) n/cm: 3313.12, 2912.96, 1503.13, 1222.61. 1 H NMR (DMSO-d6 , 400 MHz): d 7.26-7.89 (m, 9H), 10.02 (s, 1H), 13.12 (s, 1H). MS-API: [M + H]+383.98 (calculated 385) Anal. calculated for C 15 H 11 Cl 3 N 4 S: C, 46.71; H, 2.87; Cl, 27.58; N, 14.53; S, 8.31 Found: C, 46.60; H, 2.80; Cl, 27.50; N, 14.50; S, 8.30.
4-(2-chlorobenzylideneamino)-5-(2,4-dichlorophenyl)-4H-1, 2, 4-triazole-3-thiol (5i)
80% yield - M.P. =151-153°C, IR (KBr) n/cm: 3228.12, 2941.96, 1501.13, 1221.36. 1 H NMR (DMSO-d6 , 400 MHz): d 7.29-7.85 (m, 9H), 10.95 (s, 1H), 14.05 (s, 1H). MS-API: [M + H] + 383.98 (calculated 385) Anal. calculated for C 15 H 11 Cl 3 N 4 S: C, 46.71; H, 2.87; Cl, 27.58; N, 14.53; S, 8.31 Found: C, 46.65; H, 2.75; Cl, 27.50; N, 14.45; S, 8.25.
4-(2,4-dichlorobenzylideneamino)-5-(2,4-dichlorophenyl)-4H-1, 2, 4-triazole-3-thiol (5j)
79% yield - M.P. =134-137°C, IR (KBr) n/cm: 3313. 12,2915.76,1504.33,1222.60. 1 H NMR (DMSO-d6 , 400 MHz): d 7.39-7.81 (m, 8H), 10.42 (s, 1H), 14.07 (s, 1H). MS-API: [M + H] + 417.94 (calculated 420) Anal. calculated for C 15 H 10 Cl 4 N 4 S: C, 42.88; H, 2.40; Cl, 33.75; N, 13.34; S, 7.63 Found: C, 42.75; H, 2.45; Cl, 33.25; N, 13.30; S, 7.60.
4-(4-chlorobenzylideneamino)-5-(2,4-dichlorophenyl)-4H-1, 2, 4-triazole-3-thiol (5k)
81% yield - M.P. =207-209°C, IR (KBr) n/cm: 3227.72, 2916.34, 1500.23, 1216.34. 1 H NMR (DMSO-d6 , 400 MHz): d 7.27-7.49 (m, 9H), 10.42 (s, 1H), 13.82 (s, 1H). MS-API: [M + H] + 383.98 (calculated 385) Anal. calculated for C 15 H 11 Cl 3 N 4 S: C, 46.71; H, 2.87; Cl, 27.58; N, 14.53; S, 8.31 Found: C, 46.60; H, 2.80; Cl, 27.50; N, 14.40; S, 8.20.
4-(2,4-dichlorobenzylideneamino)-5-(4-fluorophenyl)-4H-1, 2, 4-triazole-3-thiol (5l)
79% yield - M.P. =218-221°C, IR (KBr) n/cm: 3109.04, 2937.38, 1508.23, 1425.30. 1 H NMR (DMSO-d6 , 400 MHz): d 7.17-7.92 (m, 9H), 10.79 (s, 1H), 14.05 (s, 1H). MS-API: [M + H] + 368.01 (calculated 369) Anal. calculated for C 15 H 11 Cl 2 FN 4 S: C, 48.79; H, 3.00; Cl, 19.20; F, 5.15; N, 15.17; S, 8.68 Found: C, 48.70; H, 3.10; Cl, 19.25; F, 5.10; N, 15.10; S, 8.60.
4-(2-chlorobenzylideneamino)-5-(4-fluorophenyl)-4H-1, 2, 4-
triazole-3-thiol (5 m)
83% yield - M.P. =168-171°C, IR (KBr) n/cm: 3107.08,2927.31,1506.23,1415.30. 1 H NMR (DMSO-d6 , 400 MHz): d 7.16-7.95 (m, 10H), 10.78 (s, 1H), 13.92 (s, 1H). MS-API: [M + H] + 334.05 (calculated 334) Anal. calculated for C 15 H 12 ClFN 4 S: C, 53.81; H, 3.61; Cl, 10.59; F, 5.67; N, 16.73; S, 9.58 Found: C, 53.80; H, 3.50; Cl, 10.50; F, 5.65; N, 16.70; S, 9.50.
4-(3-chlorobenzylideneamino)-5-(4-fluorophenyl)-4H-1, 2, 4-
triazole-3-thiol (5n)
77% yield - M.P. =187-190°C, IR (KBr) n/cm: 3119.04, 2931.42, 1502.22, 1428.34. 1 H NMR (DMSO-d6 , 400 MHz): d 7.17-7.94 (m, 10H), 10.23 (s, 1H), 13.85 (s, 1H). MS-API: [M + H] + 334.05 (calculated 334) Anal. calculated for C 15 H 12 ClFN 4 S: C, 53.81; H, 3.61; Cl, 10.59; F, 5.67; N, 16.73; S, 9.58 Found: C, 53.70; H, 3.55; Cl, 10.50; F, 5.60; N, 16.65; S, 9.55.
4-(4-fluorobenzylideneamino)-5-(4-fluorophenyl)-4H-1, 2, 4-triazole-3-thiol (5o)
81% yield - M.P. =196-198°C, IR (KBr) n/cm: 3106.02, 2934.31, 1500.20, 1420.32. 1 H NMR (DMSO-d6 , 400 MHz): d 7.26-7.95 (m, 10H), 10.37 (s, 1H), 14.02 (s, 1H).MS-API: [M + H] + 318.08 (calculated 318) Anal. calculated for C 15 H 12 F 2 N 4 S: C, 56.59; H, 3.80; F, 11.94; N, 17.60; S, 10.07 Found: C, 56.50; H, 3.70; F, 11.90; N, 17.50; S, 10.01.
4-(4-bromobenzylideneamino)-5-(4-fluorophenyl)-4H-1, 2, 4-triazole-3-thiol (5p)
75% yield - M.P. =208-211°C, IR (KBr) n/cm: 3104.05, 2917.28, 1528.23, 1415.30. 1 H NMR (DMSO-d6 , 400 MHz): d 7.16-7.92 (m, 10H), 10.17 (s, 1H), 13.68 (s, 1H). MS-API: [M + H] + 378.01 (calculated 379) Anal. calculated for C 15 H 12 BrFN 4 S: C, 47.50; H, 3.19; Br, 21.07; F, 5.01; N, 14.77; S, 8.45 Found: C, 47.55; H, 3.10; Br, 21.01; F, 5.10; N, 14.70; S, 8.40.
4-(4-chlorobenzylideneamino)-5-(4-fluorophenyl)-4H-1, 2, 4-triazole-3-thiol (5q)
82% yield - M.P. =200-202°C, IR (KBr) n/cm: 3104.85, 2933.98, 1504.55, 1423.38. 1 H NMR (DMSO-d6 , 400 MHz): d 7.32-7.94 (m, 10H), 10.24 (s, 1H), 13.85 (s, 1H). MS-API: [M + H] + 334.05 (calculated 334.80) Anal. calculated for C 15 H 12 ClFN 4 S: C, 53.81; H, 3.61; Cl, 10.59; F, 5.67; N, 16.73; S, 9.58 Found: C, 53.80; H, 3.60; Cl, 10.50; F, 5.60; N, 16.65; S, 9.50.
Antifungal activity
The antifungal activity of triazoles was evaluated by cup-plate method [13] against three fungal species: C. albicans ATCC 10231, A. niger ATCC 1015 and M. gypseum C 115 2000, dermatophyte fungal species. [13] Stock solutions of synthesized compounds were prepared in DMSO. Aliquots of the stock solution were used to prepare series of subsequent concentration. Control experiments were performed under similar conditions without the synthesized compounds. Ketoconazole was used as a standard for antifungal activity.
Antibacterial activity
The antibacterial activity of triazoles was evaluated by the cup-plate method [13] against two bacterial strain E. coli ATCC 25922 and S. aureus ATCC 25923. [13] By this method, minimal inhibitory concentration (MIC) was found out using Streptomycin as a standard drug. All stock solutions were prepared in DMSO. Aliquots of the stock solution were used to prepare series of subsequent concentration. Control experiments were performed under similar conditions without the synthesized compounds.
| Results and discussion | | |
Chemistry
The synthesis of 4-amino-5-phenyl-4H-1, 2, 4- triazole-3-thiol (3a-3c) was carried out from benzoic acid derivatives (1) and thiocarbohydrazide (2) as per the literature. [14] Intermediate compound (3) was treated with substituted aromatic aldehydes (4) in the presence of concentrated H 2 SO 4 , and yielded Schiff bases (5) The structures of the synthesized compounds were confirmed by NMR, IR, Mass and elemental analysis [Scheme 1 [Additional file 1]] and [Scheme 2 [Additional file 2]].
The purity of the compounds was checked by TLC-using Silicagel-G (Merck). Their structures were established with IR, NMR and mass spectrometry analysis.
Biological evaluation
All the synthesized compounds underwent antifungal evaluation against fungal species: C. albicans, A. niger and M. gypseum and antibacterial evaluation against bacterial strain E. coli and S. aureus. The results obtained from the evaluation study are provided in [Table 1] and [Figure 1] and [Figure 2]. The results so obtained indicated that monochloro, 2,4 dichloro and 4 fluoro derivative have antifungal activity superior to ketoconazole against M. gypseum while other synthesized derivatives showed comparable antifungal activity as ketoconazole against M. gypseum. None of the synthesized derivatives was found to be effective against fungal species: C. albicans, and A. niger. | Figure 1: Antifungal activity of triazoles, Ket*: Ketoconazole used as standard, MIC: Minimum inhibitory concentration in (μg/ml)
Click here to view |
 | Figure 2: Antibacterial activity of triazoles. Strept**: Streptomycin used as standard. MIC: Minimum inhibitory concentration in (μg/ml)
Click here to view |
4-chloro derivative showed antibacterial activity superior to streptomycin against bacterial species, S. aureus and other synthesized derivatives showed antibacterial activity comparable to streptomycin against bacterial species, S. aureus. None of the synthesized derivative was found to be effective against bacterial strain E. coli.
Structure-activity relationship
On studying the effect of the substituents on the antifungal activity, an interesting structure activity relationship can be seen. An electron withdrawing group, that is, Cl group when placed in the para position as in the synthesized compound, showed minimum inhibitory concentration better than ketoconazole indicating better potency than ketoconazole. Presence of Cl group at ortho and para position as in the synthesized compound has potency superior to ketoconazole, similar results were found when fluorine group was placed at para position or 3-chloro derivative as their MIC were found to be comparable. The presence of the OCH 3 group as in the synthesized compound showed decrease in potency. On considering the relationship of the antifungal activity of substituted triazole derivatives with the planarity of their molecules, it was observed that as substituent increased, that is, it turned into a bulky group, activity of the compound was observed to be lower as compared to the less bulky triazole derivative.
This shows that the stearic hindrance may reduce the activity.
Similar findings were seen in the case of antbacterial activity. On studying the effect of the substituents on the antibacterial activity, an interesting structure-activity relationship can be seen. Cl group which is electron with drawing group when placed in the para position as in the synthesized compound showed minimum inhibitory concentration better than streptomycin indicating better potency than streptomycin. It was observed that as substituent increased that is the presence of bulky group reduced the antibacterial effect.
| Conclusion | | |
A novel series of Schiff base was successfully synthesized and tested for antifungal activity against three fungal strains and antibacterial activity against two bacterial strains. The results of the biological studies revealed that among the three fungal strains, M. gypseum was found to be more sensitive to the studied 4-(benzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol. In fact, six (5b, 5c, 5d, 5e, 5m, 5n) among the 17 compounds tested were more effective than the clinical candidate ketoconazole. M. gypseum is a type of fungi which causes dermatomycoses, a type of infection difficult to treat, hence, the studied compounds, specifically, (5b, 5c, 5d, 5e, 5 m, 5n) could be promising lead molecules for development of more potent and safer antifungal drugs for the treatment of dermatomycoses.
From the study, it was concluded that the 4-(benzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol derivatives showed antibacterial activity against bacterial species, S. aureus. Amongst 17 compounds synthesized, 5e showed antibacterial effect superior to clinical candidate streptomycin, others also had a significant antibacterial effect. Hence, it may be the better pharmacophore to explore the development of new bioactive moieties.
Acknowledgments
The authors express their thanks to Dr. Rekha Gupta, Head of the Department, Biotechnology, Modern College Pune, for cooperation in biological screening of the synthesized compounds. They are also grateful to Shri Subhash Gupta, Oasis Test House Ltd., Jaipur, for screening of compounds for IR studies, and to the authorities at Punjab University, Chandigarh, for their kind cooperation for NMR studies.
Financial support and sponsorship
Nil.
Conflicts of interest
There are no conflicts of interest.
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[Figure 1], [Figure 2]
[Table 1]
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Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus |
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| Lakshmi Goswami, Lovely Gupta, Sayantan Paul, Maansi Vermani, Pooja Vijayaraghavan, Asish K. Bhattacharya | | RSC Medicinal Chemistry. 2022; | | [Pubmed] | [DOI] | | | 3 |
Metal complexes of new thiocarbohydrazones of Cu(I), Co(II), and Ni(II); identification by NMR, IR, mass, UV spectra, and DFT calculations |
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| Ashraf A. Aly, Elham M. Abdallah, Salwa A. Ahmed, Mohamed K. Awad, Mai M. Rabee, Sara M. Mostafa, Stefan Bräse | | Journal of Sulfur Chemistry. 2022; : 1 | | [Pubmed] | [DOI] | | | 4 |
The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation |
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| Serghei Pogrebnoi, Oleg Radul, Eugenia Stingaci, Lucian Lupascu, Vladimir Valica, Livia Uncu, Anastasia Smetanscaia, Anthi Petrou, Ana Ciric, Jasmina Glamoclija, Marina Sokovic, Athina Geronikaki, Fliur Z. Macaev | | Antibiotics. 2022; 11(5): 588 | | [Pubmed] | [DOI] | | | 5 |
3-Phenyl-4-(prop-2-en-1-yl)-5-[(prop-2-en-1-yl)sulfanyl]-4H-1,2,4-triazole |
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| Yurii I. Slyvka, Evgeny A. Goreshnik, Andrii M. Fedko, Marian G. Mys’kiv | | Molbank. 2022; 2022(3): M1405 | | [Pubmed] | [DOI] | | | 6 |
Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units |
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| Nicolae Baranov,Stefania Racovita,Silvia Vasiliu,Ana Maria Macsim,Catalina Lionte,Valeriu Sunel,Marcel Popa,Jacques Desbrieres,Corina Cheptea | | Molecules. 2021; 26(11): 3330 | | [Pubmed] | [DOI] | | | 7 |
Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation |
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| Marina Zveaghintseva,Eugenia Stingaci,Serghei Pogrebnoi,Anastasia Smetanscaia,Vladimir Valica,Livia Uncu,Victor Ch. Kravtsov,Elena Melnic,Anthi Petrou,Jasmina Glamoclija,Marina Sokovic,Alejandro Carazo,Premysl Mladenka,Vladimir Poroikov,Athina Geronikaki,Fliur Z. Macaev | | Molecules. 2021; 26(14): 4304 | | [Pubmed] | [DOI] | | | 8 |
One-Pot Synthesis of Some New s-Triazole Derivatives and Their Potential Application for Water Decontamination |
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| Zeinab A. Hozien,Ahmed F. M. EL-Mahdy,Laila S. A. Ali,Ahmad Abo Markeb,Hassan A. H. El-Sherief | | ACS Omega. 2021; 6(39): 25574 | | [Pubmed] | [DOI] | | | 9 |
Thermoresponsive polymers as macromolecular coordination ligands: complexation-dependence of thermally induced aggregation in aqueous solution |
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Laser-induced twisting of phosphorus functionalized thiazolotriazole as a way of cholinesterase activity change |
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| Dmitrii Pankin,Anastasia Khokhlova,Ilya Kolesnikov,Anna Vasileva,Anna Pilip,Anastasia Egorova,Elena Erkhitueva,Vladislav Zigel,Maxim Gureev,Alina Manshina | | Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2021; 246: 118979 | | [Pubmed] | [DOI] | | | 11 |
Regioselective Synthesis of Novel [1,2,4]Triazolo[1,5-
a
]pyridine Derivatives |
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| Manel Ben Hassen,Fatma Masmoudi,Lazhar Zribi,Mohamed Trigui,Lhassane Ismaili,José Marco-Contelles,Fakher Chabchoub | | ChemistrySelect. 2021; 6(5): 945 | | [Pubmed] | [DOI] | | | 12 |
New 1,2,4-Triazole Scaffolds as Anticancer Agents: Synthesis, Biological Evaluation and Docking Studies |
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| Narendra Kumar Maddali,V. Kasi Viswanath Ivaturi,L. N. Murthy Yellajyosula,Vasavi Malkhed,Pradeep Kumar Brahman,Sai Kiran S. S. Pindiprolu,Vani Kondaparthi,Sundara Rao Nethinti | | ChemistrySelect. 2021; 6(26): 6788 | | [Pubmed] | [DOI] | | | 13 |
Recent Advances in the Development of 1,2,3-Triazole-containing Derivatives as Potential Antifungal Agents and Inhibitors of Lanoster ol 14a-Demethylase |
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| Michelyne Haroun, Christophe Tratrat, Hafedh Kochkar, Anroop B. Nair | | Current Topics in Medicinal Chemistry. 2021; 21(6): 462 | | [Pubmed] | [DOI] | | | 14 |
Synthesis and anticancer activities of some new coumarin derivatives including the triazole ring and their in silico molecular docking studies |
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| Emre Mentese,Adem Güner,Elifsu Polatli,Mustafa Emirik,Hakan Bektas,Bahittin Kahveci | | Archiv der Pharmazie. 2020; | | [Pubmed] | [DOI] | | | 15 |
Molecular docking studies, biological evaluation and synthesis of novel 3-mercapto-1,2,4-triazole derivatives |
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| Javad Ghanaat,Mohammad A. Khalilzadeh,Daryoush Zareyee | | Molecular Diversity. 2020; | | [Pubmed] | [DOI] | | | 16 |
Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles |
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| Hamid Beyzaei,Farideh Malekraisi,Reza Aryan,Behzad Ghasemi | | Chemistry of Heterocyclic Compounds. 2020; | | [Pubmed] | [DOI] | | | 17 |
Mechanisms involved in the antinociceptive and anti-inflammatory effects of a new triazole derivative: 5-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1H-tetrazole (LQFM-096) |
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| Carina S. Cardoso,Daiany P. B. Silva,Dayane M. Silva,Iziara F. Florentino,James O. Fajemiroye,Lorrane K. S. Moreira,José P. Vasconcelos,Germán Sanz,Boniek G. Vaz,Luciano M. Lião,Danilo da S. Lima,Fernanda Cristina A. dos Santos,Ricardo Menegatti,Elson A. Costa | | Inflammopharmacology. 2020; | | [Pubmed] | [DOI] | | | 18 |
Regioselective synthesis and evaluation of novel sulfonamide 1,2,3-triazole derivatives as antitumor agents |
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| Sameh R. Elgogary,Rizk E. Khidre,Emad M. El-Telbani | | Journal of the Iranian Chemical Society. 2020; | | [Pubmed] | [DOI] | | | 19 |
Design, Synthesis, Molecular Modeling, Anticancer Studies, and Density Functional Theory Calculations of 4-(1,2,4-Triazol-3-ylsulfanylmethyl)-1,2,3-triazole Derivatives |
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| Adeeb Al Sheikh Ali,Daoud Khan,Arshi Naqvi,Fawzia Faleh Al-blewi,Nadjet Rezki,Mohamed Reda Aouad,Mohamed Hagar | | ACS Omega. 2020; | | [Pubmed] | [DOI] | | | 20 |
Synthesis, Characterization and Bioassay of Novel Substituted 1-(3-(1,3-Thiazol-2-yl)phenyl)-5-oxopyrrolidines |
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| Birute Sapijanskaite-Banevic,Božena Šovkovaja,Rita Vaickelioniene,Jurate Šiugždaite,Egle Mickeviciute | | Molecules. 2020; 25(10): 2433 | | [Pubmed] | [DOI] | | | 21 |
Synthesis and Anticancer Activity of a Novel Series of Tetrazolo[1,5-a]quinoline Based 1,2,3-Triazole Derivatives |
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| R. Nagaraju,K. Gopichand,N. N. Rao,A. M. Ganai,E. Kishan,P. Venkateswar Rao | | Russian Journal of General Chemistry. 2020; 90(2): 314 | | [Pubmed] | [DOI] | | | 22 |
Synthesis, crystal structure and biological studies of novel amidrazones, triazoles, Thiatriazole and Triazine compounds |
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| Adel Ben Salem,Bochra Ben Salah,Dhekra Mhalla,Mohamed Trigui,Maxime Mourer,Jean -Bernard Regnouf-de-Vains,Mohamed Kossentini | | Journal of Molecular Structure. 2020; 1214: 128209 | | [Pubmed] | [DOI] | | | 23 |
1,2,4-Triazole: A Privileged Scaffold for the Development of Potent Antifungal Agents - A Brief Review |
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| Christophe Tratrat | | Current Topics in Medicinal Chemistry. 2020; 20(24): 2235 | | [Pubmed] | [DOI] | | | 24 |
Investigation of the reactivity of 4-amino-5-hydrazineyl-4H-1,2, 4-triazole-3-thiol towards some selected carbonyl compounds: synthesis of novel triazolotriazine-, triazolotetrazine-, and triazolopthalazine derivatives |
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| Kamal M. El-Shaieb,Asmaa H. Mohamed,Fathy F. Abdel-latif | | Zeitschrift für Naturforschung B. 2019; 74(11-12): 847 | | [Pubmed] | [DOI] | | | 25 |
Exploring the Chemistry and Therapeutic Potential of Triazoles: A Comprehensive Literature Review |
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| Ankit Jain,Poonam Piplani | | Mini-Reviews in Medicinal Chemistry. 2019; 19(16): 1298 | | [Pubmed] | [DOI] | | | 26 |
Thiophenol-formaldehyde triazole causes apoptosis induction in ovary cancer cells and prevents tumor growth formation in mice model |
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| Yan Jia,Lihui Si,Ruixin Lin,Hongjuan Jin,Wenwen Jian,Qing Yu,Shuli Yang | | European Journal of Medicinal Chemistry. 2019; | | [Pubmed] | [DOI] | | | 27 |
Amphiphilic silicone-bridged bis-triazoles as effective, selective metal ligands and biologically active agents in lipophilic environment |
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| Georgiana-Oana Turcan-Trofin,Mirela-Fernanda Zaltariov,Gheorghe Roman,Sergiu Shova,Nicoleta Vornicu,Mihaela Balan-Porcarasu,Dragos Lucian Isac,Andrei Neamtu,Maria Cazacu | | Journal of Molecular Liquids. 2019; : 111560 | | [Pubmed] | [DOI] | | | 28 |
Synthesis, characterisation of new derivatives with mono ring system of 1,2,4-triazole scaffold and their anticancer activities |
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| Mukhlif Mohsin Slaihim,Fouad Saleih R. Al-Suede,Melati Khairuddean,Mohamed B. Khadeer Ahamed,Amin Malik Shah Abdul Majid | | Journal of Molecular Structure. 2019; 1196: 78 | | [Pubmed] | [DOI] | | | 29 |
Synthesis and Evaluation of Biological Activity of Homodrimane Sesquiterpenoids Bearing Hydrazinecarbothioamide or 1,2,4-Triazole Unit |
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| Lidia Lungu,Alexandru Ciocarlan,Alic Barba,Sergiu Shova,Serghei Pogrebnoi,Ionel Mangalagiu,Costel Moldoveanu,Nicoleta Vornicu,Michele D’Ambrosio,Maria V. Babak,Vladimir B. Arion,Aculina Aricu | | Chemistry of Heterocyclic Compounds. 2019; | | [Pubmed] | [DOI] | | | 30 |
An Easy Access to 4-Trifluoromethylated 7-(4-Substitued-1
H
-1,2,3-Triazol-1-yl)Pyrimido[1,2-
b
]Pyridazin-2-One Systems |
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| Ranin Kawtharani,Khalil Cherry,Mirvat Elmasri,Mohamed Abarbri | | ChemistrySelect. 2019; 4(38): 11222 | | [Pubmed] | [DOI] | | | 31 |
Pyrazole-1-carbothioamide as a Potent Precursor for Synthesis of Some New N
-heterocycles of Potential Biological Activity |
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| Islam H. El Azab,Ola A. Abu Ali,Aishah H. El-Zahrani,Adil A. Gobouri,Tariq A. Altalhi | | Journal of Heterocyclic Chemistry. 2018; | | [Pubmed] | [DOI] | | | 32 |
4-Chlorothiazole-5-carbaldehydes as Potent Precursors for Synthesis of Some New Pendant N
-heterocyces Endowed with Anti-Tumor Activity |
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| Islam H. El Azab,Adil A. Gobouri,Tariq A. Altalhi | | Journal of Heterocyclic Chemistry. 2018; | | [Pubmed] | [DOI] | | | 33 |
Synthesis, molecular docking, and evaluation of novel bivalent pyrazolinyl-1,2,3-triazoles as potential VEGFR TK inhibitors and anti-cancer agents |
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| Ahmed A. Abd-Rabou,Bakr F. Abdel-Wahab,Mohamed S. Bekheit | | Chemical Papers. 2018; | | [Pubmed] | [DOI] | | | 34 |
Design and synthesis of 2,6-di(substituted phenyl)thiazolo[3,2-b]-1,2,4-triazoles as a-glucosidase and a-amylase inhibitors, co-relative Pharmacokinetics and 3D QSAR and risk analysis |
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| Pervaiz Ali Channar,Aamer Saeed,Fayaz Ali Larik,Sajid Rashid,Qaiser Iqbal,Maryam Rozi,Saima Younis,Jamaluddin Mahar | | Biomedicine & Pharmacotherapy. 2017; 94: 499 | | [Pubmed] | [DOI] | | | 35 |
Design, Synthesis, and Biological Evaluation of Coumarin-Triazole Hybrid Molecules as Potential Antitumor and Pancreatic Lipase Agents |
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| Bahittin Kahveci,Fatih Yilmaz,Emre Mentese,Serdar Ülker | | Archiv der Pharmazie. 2017; : 1600369 | | [Pubmed] | [DOI] | | | 36 |
Pharmacological screening of some newly synthesized triazoles for H1 receptor antagonist activity |
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| Jeetendra Kumar Gupta,Pradeep Mishra | | Medicinal Chemistry Research. 2017; | | [Pubmed] | [DOI] | | | 37 |
1-(2-aminophenyl)-1H-1,2,3-triazole-4-carboxylic acid: activity against Gram-positive and Gram-negative pathogens including
Vibrio cholerae |
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| Krishnendu Maji,Debasish Haldar | | Royal Society Open Science. 2017; 4(10): 170684 | | [Pubmed] | [DOI] | | | 38 |
Design, synthesis and pharmaco-toxicological assessment of 5-mercapto-1,2,4-triazole derivatives with antibacterial and antiproliferative activity |
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| Marius Mioc,Codruta Soica,Vasile Bercean,Sorin Avram,Mihaela Balan-Porcarasu,Dorina Coricovac,Roxana Ghiulai,Delia Muntean,Florina Andrica,Cristina Dehelean,Demetrios A. Spandidos,Aristides M. Tsatsakis,Ludovic Kurunczi | | International Journal of Oncology. 2017; 50(4): 1175 | | [Pubmed] | [DOI] | | | 39 |
Antimicrobial activity of the pygidial gland secretion of three ground beetle species (Insecta: Coleoptera: Carabidae) |
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| Marija Nenadic,Marina Sokovic,Jasmina Glamoclija,Ana Ciric,Vesna Peric-Mataruga,Larisa Ilijin,Vele Teševic,Ljubodrag Vujisic,Marina Todosijevic,Nikola Vesovic,Srecko Curcic | | The Science of Nature. 2016; 103(3-4) | | [Pubmed] | [DOI] | | | 40 |
Design, synthesis and biological evaluation of new substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5H)ones. Pharmacophore models for antifungal activity |
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| A. Paparisva,A. Geronikaki,Ch. Kamoutsis,A. Ciric,J. Glamoclija,M. Sokovic,Ch. Fotakis,P. Zoumpoulakis,Shome S. Bhunia,Anil K. Saxena | | Arabian Journal of Chemistry. 2016; | | [Pubmed] | [DOI] | |
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