Citation: Anna Pratima G. Nikalje, Mangesh S. Ghodke, Firoz A. Kalam Khan, Jaiprakash N. Sangshetti. CAN catalyzed one-pot synthesis and docking study of some novel substituted imidazole coupled 1,2,4-triazole-5-carboxylic acids as antifungal agents[J]. Chinese Chemical Letters, ;2015, 26(1): 108-112. doi: 10.1016/j.cclet.2014.10.020 shu

CAN catalyzed one-pot synthesis and docking study of some novel substituted imidazole coupled 1,2,4-triazole-5-carboxylic acids as antifungal agents

1.
Department of Pharmaceutical Chemistry, Y. B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Aurangabad 431001, MS, India

Corresponding author: Anna Pratima G. Nikalje,
Received Date: 22 May 2014
Available Online: 10 October 2014

The present work describes a facile, one-pot three component synthesis of a series of 3-[(4,5-diphenyl-2-substituted aryl/heteryl)-1H-imidazol-1-yl]-1H-1,2,4-triazole-5-carboxylic acid derivatives M(1-15). Benzil, aromatic aldehydes and 3-amino-1,2,4-triazole-5-carboxylic acid was refluxed in ethanol using cerric ammonium nitrate (CAN) as a catalyst to give the title compounds in good yields. The compounds were evaluated for their in vitro antifungal and antibacterial activity. Compounds M1, M9, and M15 were found to be equipotent against Candida albicans when compared with fluconazole. Compounds M2, M5, and M14 showed higher activity against Streptococcus pneumoniae, Escherichia coli and Streptococcus pyogenes, respectively, compared with ampicillin. Docking study of the newly synthesized compounds was performed, and the results showed good bindingmode in the active sites of C. albicans enzyme cytochrome P450 lanosterol 14α-demethylase. The results of in vitro antifungal activity and docking study showed that synthesized compounds had potential antifungal activity and can be further optimized and developed as a lead compound.
- 1,2,4-Triazole,
- Imidazole,
- Ceric ammonium nitrate,
- Antifungal activity,
- Antibacterial activity,
- Docking study
1. [1]
  [1] A.A. Marzouk, V.M. Abbasov, A.H. Talybov, Synthesis of 2,4,5-triphenyl imidazole derivatives using diethyl ammonium hydrogen phosphate as green, fast and reusable catalyst, World J. Org. Chem. 1 (2013) 6-10.
2. [2]
  [2] P.P. Reddy, K. Mukkanti, K. Purandhar, ALPO₄ mediated one-pot, four-component synthesis of 1, 2, 4, 5-tetrasubstituted imidazoles under conventional heating and microwave irradiation, Rasayan J. Chem. 3 (2010) 335-340.
3. [3]
  [3] P.J. Das, J. Das, M. Ghosh, Solvent free one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles catalyzed by secondary amine based ionic liquid and defective keggin heteropoly acid, Green Sustain. Chem. 3 (2013) 6-13.
4. [4]
  [4] J.H. Block, J.M. Beale (Eds.), Wilson and Griswold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 11th ed., Lippincott's Williams & Wilkins Publication, 2004, p. 240.
5. [5]
  [5] Y. Ozkay, I. Iskdag, Z. Incesu, G. Akalın, Synthesis of 2-substituted-N-[4-(1-methyl- 4,5-diphenyl-1H-imidazole-2-yl)phenyl]acetamide derivatives and evaluation of their anticancer activity, Eur. J. Med. Chem. 45 (2010) 3320-3328.
6. [6]
  [6] M.R. Wiley, L.C. Weir, S.L. Briggs, N.Y. Chirgadze, D. Clawson, The design of potent, selective, non-covalent, peptide thrombin inhibitors utilizing imidazole as a S1 binding element, Bioorg. Med. Chem. Lett. 9 (1999) 2767-2772.
7. [7]
  [7] A. Puratchikodya, M. Doble, Antinociceptive and antiinflammatory activities and QSAR studies on 2-substituted-4,5-diphenyl-1H-imidazoles, Bioorg. Med. Chem. 15 (2007) 1083-1090.
8. [8]
  [8] K.C.S. Achar, K.M. Hosamani, H.R. Seetharamareddy, In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivatives, Eur. J. Med. Chem. 45 (2010) 2048-2054.
9. [9]
  [9] R.V. Shingalapur, K.M. Hosamani, R.S. Keri, Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles, Eur. J. Med. Chem. 44 (2009) 4244-4248.
10. [10]
  [10] D. Sharma, B. Narasimhan, P. Kumar, et al., Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives, Eur. J. Med. Chem. 44 (2009) 2347-2353.
11. [11]
  [11] D. Zampieri, M.G. Mamolo, L. Vio, et al., Synthesis, antifungal and antimycobacterial activities of new bis-imidazole derivatives, and prediction of their binding to P450_14DM by molecular docking and MM/PBSA method, Bioorg. Med. Chem. 15 (2007) 7444-7458.
12. [12]
  [12] D. Olender, J. Zwawiak, V. Lukianchuk, et al., Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents, Eur. J. Med. Chem. 44 (2009) 645-652.
13. [13]
  [13] M. Tonelli, M. Simone, B. Tasso, F. Novelli, V. Boido, Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives, Bioorg. Med. Chem. 18 (2010) 2937-2953.
14. [14]
  [14] P. Gupta, S. Hameed, R. Jain, Ring-substituted imidazoles as a new class of antituberculosis agents, Eur. J. Med. Chem. 39 (2004) 805-814.
15. [15]
  [15] J. Pandey, T.K. Vinod, S.S. Verma, et al., Synthesis and antitubercular screening of imidazole derivatives, Eur. J. Med. Chem. 44 (2009) 3350-3355.
16. [16]
  [16] G. Nurhan, S. Mevlut, C. Elif, S. Ali, D. Neslihan, Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives, Turk. J. Chem. 31 (2007) 335-348.
17. [17]
  [17] S.F. Barbuceanu, L.A. Gabriela, S. Ioana, D. Constanatin, S. Radu, New S-alkylated 1,2,4-triazoles incorporating diphenyl sulfone moieties with potential antibacterial activity, J. Serb. Chem. Soc. 74 (2009) 1041-1049.
18. [18]
  [18] M.R. Banday, A. Rauf, Substituted 1,2,4-triazoles and thiazolidinones from fatty acids spectral characterization and antimicrobial activity, Indian J. Chem. 48 (2009) 97-102.
19. [19]
  [19] J.N. Sangshetti, D.B. Shinde, A.P. Sarkate, Synthesis, antifungal activity and docking study of some new 1,2,4-triazole analogs, Chem. Biol. Drug Des. 78 (2011) 800-809.
20. [20]
  [20] R. Tang, L. Jin, C. Mou, et al., Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety, Chem. Cent. J. (2013) 7-30.
21. [21]
  [21] X. Chai, J. Zhang, Y. Cao, et al., Design, synthesis and molecular docking studies of novel triazole as antifungal agent, Eur. J. Med. Chem. 46 (2011) 3167-3176.
22. [22]
  [22] Y. Jiang, J. Zhang, Y. Cao, et al., Synthesis, in vitro evaluation and molecular docking studies of new triazole derivatives as antifungal agents, Bioorg. Med. Chem. Lett. 21 (2011) 4471-4475.
23. [23]
  [23] K.S. Bhat, Synthesis and antitumor activity studies of some new fused 1,2,4- triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety, Eur. J. Med. Chem. 44 (2009) 5066-5070.
24. [24]
  [24] Y.A. Al-Soud, M.N. Al-Dweri, N.A. Al-Masoudi, Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives, Farmaco 59 (2004) 775-783.
25. [25]
  [25] P. Valentina, K. Ilango, M. Deepthi, et al., Antioxidant activity of some substituted 1, 2, 4-triazo-5-thione Schiff base, J. Pharm. Sci. Res. 2 (2009) 74-77.
26. [26]
  [26] H. Yuksek, S. Kalayli, M.M.O. Mucuk, Synthesis and antioxidant activities of some 4-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Ind. J. Chem. 45 (2006) 715-718.
27. [27]
  [27] (a) A. Ning, Z. Wang, X. Xu, X. Li, One-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles by a tandem three-component reaction of hydroxyl amines, aldehydes and 2-azido acrylates, ARKIVOC VI (2012) 222-228;
28. [28]
  (b) J.N. Sangshetti, N.D. Kokare, S.D. Kotharkar, D.B. Shinde, ZrOCl₂·8H₂O catalyzed one-pot synthesis of 2,4,5-triaryl-1H-imidazoles and substituted 1,4- di(4,5-diphenylimidazol-yl)benzene, Chin. Chem. Lett. 19 (2008) 762-768.
29. [29]
  [28] R.K. Sharma, An efficient and one pot synthesis of poly substituted imidazoles catalyzed by BiCl₃, Indian J. Chem. 51B (2012) 1489-1493.
30. [30]
  [29] A. Saberi, Synthesis of novel highly potent antibacterial and antifungal agents, Asian J. Med. Pharm. Res. 1 (2012) 01-05.
31. [31]
  [30] (a) J.N. Sangshetti, N.D. Kokare, S.A. Kotharkar, D.B. Shinde, Ceric ammonium nitrate catalysed three component one-pot efficient synthesis of 2,4,5-triaryl-1Himidazoles, J. Chem. Sci. 120 (2008) 463-467;
32. [32]
  (b) K.F. Shelke, S.B. Sapkal, M.S. Shingare, Ultrasound-assisted one-pot synthesis of 2,4,5-triarylimidazole derivatives catalyzed by ceric (IV) ammonium nitrate in aqueous media, Chin. Chem. Lett. 20 (2009) 283-287.
33. [33]
  [31] D. Greenwood, R.C.B. Slack, J.F. Peutherer, Medical Microbiology, 14th ed., ELBS, London, 1992.
34. [34]
  [32] J.N. Sangshetti, F.A.K. Khan, R.S. Chouthe, et al., Synthesis, docking and ADMET prediction of novel 5-((5-substituted-1-H-1,2,4-triazol-3-yl)methyl)-4,5,6,7-tetrahydrothieno[ 3,2-c]pyridine as antifungal agents, Chin. Chem. Lett. 25 (2014) 1033-1038.
35. [35]
  [33] N. Strushkevich, S.A. Usanov, H.W. Park, Structural basis of human CYP51 inhibition by antifungal azoles, J. Mol. Biol. 397 (2010) 1067-1078.
36. [36]
  [34] R.W. Hooft, G. Vriend, C. Sander, E.E. Abola, Errors in protein structures, Nature 381 (1996) 272.
37. [37]
  [35] VLife Molecular Design Suite 4.3, VLife Sciences Technologies Pvt. Ltd; www. Vlifesciences.com.
1. [1]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
2. [2]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
3. [3]
  Xingyu Chen , Sihui Zhuang , Weiyao Yan , Zhengli Zeng , Jianguo Feng , Hongen Cao , Lei Yu . Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae. Chinese Chemical Letters, 2024, 35(10): 109635-. doi: 10.1016/j.cclet.2024.109635
4. [4]
  Jiaxi Wang , Zhiwei Gao , Hao Liang , Qianyue Liu , Weiqian Jin , Huyang Gao , Bailei Wang , Ruikai Zhu , Jiahao Huang , Xiaowen Li , Xingmou Wu , Weijiu Mo , Yinhan Liao , Ming Gao , Xiaojie Li , Cuiping Li . NIR stimulated epigallocatechin gallate loaded polydopamine with enhanced antibacterial and ROS scavenging abilities for improved infectious wound healing. Chinese Chemical Letters, 2025, 36(7): 110569-. doi: 10.1016/j.cclet.2024.110569
5. [5]
  Yanye Fan , Jingjing Chen , Bichun Chen , Jinyu Bai , Bowen Yang , Feng Liang , Lijing Fang . Design, synthesis and biological evaluation of Leu₁₀-teixobactin analogues. Chinese Chemical Letters, 2025, 36(4): 110075-. doi: 10.1016/j.cclet.2024.110075
6. [6]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
7. [7]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150
8. [8]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
9. [9]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
10. [10]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
11. [11]
  Yang Li , Jiachen Li , Daidi Fan . 二硫化钼纳米片的制备及其纳米酶性能探究——介绍一个大学化学综合实验. University Chemistry, 2025, 40(8): 233-240. doi: 10.12461/PKU.DXHX202410016
12. [12]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
13. [13]
  Yang Liu , Jing Liang , Mengzhu Zheng , Haoze Song , Lixia Chen , Hua Li . PD-L1/SHP2 dual PROTACs inhibit melanoma by enhancing T-cell killing activity. Chinese Chemical Letters, 2025, 36(6): 110317-. doi: 10.1016/j.cclet.2024.110317
14. [14]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
15. [15]
  Xiang-Da Zhang , Jian-Mei Huang , Xiaorong Zhu , Chang Liu , Yue Yin , Jia-Yi Huang , Yafei Li , Zhi-Yuan Gu . Auto-tandem CO₂ reduction by reconstructed Cu imidazole framework isomers: Unveiling pristine MOF-mediated CO₂ activation. Chinese Chemical Letters, 2025, 36(5): 109937-. doi: 10.1016/j.cclet.2024.109937
16. [16]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
17. [17]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
18. [18]
  Yunli Xu , Xuwen Da , Lei Wang , Yatong Peng , Wanpeng Zhou , Xiulian Liu , Yao Wu , Wentao Wang , Xuesong Wang , Qianxiong Zhou . Ru(Ⅱ)-based aggregation-induced emission (AIE) agents with efficient ¹O₂ generation, photo-catalytic NADH oxidation and anticancer activity. Chinese Chemical Letters, 2025, 36(5): 110168-. doi: 10.1016/j.cclet.2024.110168
19. [19]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
20. [20]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1220)
HTML views(32)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142