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Year 2021, Volume: 42 Issue: 4, 795 - 805, 29.12.2021

Asaf Evrim Evren , İsmail Çelik , Ulviye Acar Çevik

Abstract

References

  • [1] Willyard C., The Drug-Resistant Bacteria That Pose The Greatest Health Threats, Nature, 543 (7643) (2017) 15.
  • [2] Bansal Y., Kaur M., Bansal G., Antimicrobial Potential Of Benzimidazole Derived Molecules, Mini Rev. Med. Chem., 19(8) (2019) 624-646.
  • [3] Acar Cevik U., Kaya Cavusoglu B., Saglik B.N., Osmaniye D., Levent S., Ilgin S., Ozkay Y., Kaplancikli Z.A., Synthesis, Docking Studies And Biological Activity Of New Benzimidazole- Triazolothiadiazine Derivatives As Aromatase Inhibitor, Molecules, 25(7) (2020).
  • [4] Evren A.E., Tekinkoca S., Yurttas L., Synthesis And Antimicrobial Activity Of Some New N-(1h-Benzimidazol-2- Yl)-2-Mercaptoacetamide Derivatives, Lett. Drug Des. Discov., 15(2) (2018) 154-159.
  • [5] Evren A.E., Yurttas L., Yılmaz-Cankilic M., Synthesis Of Novel N-(Naphthalen-1-Yl)Propanamide Derivatives And Evaluation Their Antimicrobial Activity, Phosphorus Sulfur, 195(2) (2019) 158-164.
  • [6] Aouad M.R., Soliman M.A., Alharbi M.O., Bardaweel S.K., Sahu P.K., Ali A.A., Messali M., Rezki N., Al-Soud Y.A., Design, Synthesis And Anticancer Screening Of Novel Benzothiazole-Piperazine-1,2,3-Triazole Hybrids, Molecules, 23 (11) (2018).
  • [7] Garuti L., Roberti M., Malagoli M., Rossi T., Castelli M, Synthesis And Antiproliferative Activity Of Some Benzimidazole-4, 7-Dione Derivatives, Bioorg. Med. Chem. Lett., 10(19) (2000) 2193-2195.
  • [8] Ayhan‐Kılcıgil G., Kus C., Özdamar E.D., Can‐Eke B., Iscan M., Synthesis And Antioxidant Capacities Of Some New Benzimidazole Derivatives, Arch. Pharm., 340(11) (2007) 607-611.
  • [9] Can O.D., Osmaniye D., Demir Ozkay U., Saglik B.N., Levent S., Ilgin S., Baysal M., Ozkay Y., Kaplancikli Z.A., Mao Enzymes Inhibitory Activity Of New Benzimidazole Derivatives Including Hydrazone And Propargyl Side Chains, Eur. J. Med. Chem., 131 (2017) 92-106.
  • [10] Vinodkumar R., Vaidya S.D., Kumar B.V.S., Bhise U.N., Bhirud S.B., Mashelkar U.C., Synthesis, Anti-Bacterial, Anti-Asthmatic And Anti-Diabetic Activities Of Novel N-Substituted-2-(4-Phenylethynyl-Phenyl)-1h-Benzimidazoles And N-Substituted 2 [4-(4, 4-Dimethyl-Thiochroman-6-Yl-Ethynyl)-Phenyl)-1h-Benzimidazoles, Eur. J. Med. Chem., 43(5) (2008) 986-995.
  • [11] Torres-Gómez H., Hernández-Núñez E., León-Rivera I., Guerrero-Alvarez J., Cedillo-Rivera R., Moo-Puc R., Argotte-Ramos R., Del Carmen Rodríguez-Gutiérrez M., Chan-Bacab M.J., Navarrete-Vázquez G., Design, Synthesis And In Vitro Antiprotozoal Activity Of Benzimidazole-Pentamidine Hybrids, Bioorg. Med. Chem. Lett., 18(11) (2008) 3147-3151.
  • [12] Shingalapur R.V., Hosamani K.M., Keri R.S., Hugar M.H., Derivatives Of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic And Dna Cleavage Studies, Eur. J. Med. Chem., 45(5) (2010) 1753-1759.
  • [13] Saglik B.N., Sen A.M., Evren A.E., Cevik U.A., Osmaniye D., Kaya Cavusoglu B., Levent S., Karaduman A.B., Ozkay Y., Kaplancikli Z.A., Synthesis, Investigation Of Biological Effects And In Silico Studies Of New Benzimidazole Derivatives As Aromatase Inhibitors, Z Naturforsch C J Biosci., (2020).
  • [14] Evren A.E., Yurttas L., Ekselli B., Akalin-Ciftci G., Synthesis And Biological Evaluation Of 5-Methyl-4-Phenyl Thiazole Derivatives As Anticancer Agents, Phosphorus Sulfur, 194(8) (2019) 820-828.
  • [15] Beyzaei H., Khosravi Z., Aryan R., Ghasemi B., A Green One-Pot Synthesis Of 3 (5)-Substituted 1, 2, 4-Triazol-5 (3)-Amines As Potential Antimicrobial Agents, Journal Of The Iranian Chemical Society, 16(12) (2019) 2565-2573.
  • [16] Pappas P.G., Kauffman C.A., Andes D., Benjamin D.K., Calandra T.F., Edwards J.E., Filler S.G., Fisher J.F., Kullberg B.J., Ostrosky-Zeichner L., Reboli A.C., Rex J.H., Walsh T.J., Sobel J.D., Infectious Diseases Society Of, A. Clinical Practice Guidelines For The Management Of Candidiasis: 2009 Update By The Infectious Diseases Society Of America, Clin. Infect. Dis., 48(5) (2009) 503-535.
  • [17] Hargrove T.Y., Friggeri L., Wawrzak Z., Qi A., Hoekstra W.J., Schotzinger R. J., Lepesheva G.I., Structural analyses of Candida albicans sterol 14α-demethylase complexed with azole drugs address the molecular basis of azole-mediated inhibition of fungal sterol biosynthesis. J. Biolog. Chem., 292(16) (2017) 6728-6743.
  • [18] Friesner R.A., Murphy R.B., Repasky M.P., Frye L.L., Greenwood J.R., Halgren T.A., Mainz D.T., Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes, J. Med. Chem., 49(21) (2006) 6177-6196.
  • [19] Daina, A., Michielin, O., Zoete, V., SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Scientific reports, 7(1) (2017) 1-13.

Synthesis, molecular docking, in silico ADME and antimicrobial activity studies of some new benzimidazole-triazole derivatives

Year 2021, Volume: 42 Issue: 4, 795 - 805, 29.12.2021

Asaf Evrim Evren , İsmail Çelik , Ulviye Acar Çevik

Abstract

In this study, new benzimidazole-triazole derivatives were synthesized in two steps. First, 4-benzaldehyde derivatives are synthesized by reacting 1,2,4-triazole ring and 4-fluorobenzaldehyde. In the last step, the benzimidazole ring was obtained with o-phenylenediamine derivatives under microwave radiation. The structures of synthesized compounds were confirmed by 1H-NMR, 13C-NMR, infrared spectroscopy, mass spectroscopy, and elemental analysis. Antimicrobial activity of synthesized compounds is associated with six different types of bacteria (Escherichia coli ATCC 35218, E.coli ATCC 25922, Klebsiella pneumoniae NCTC 9633, Pseudomonas aeruginosa ATCC 27853, Salmonella typhimurium ATCC 13311, Staphylococcus aureus ATCC 25923), and four different Candida (C. albicans ATCC 24433, C. glabrata ATCC 90030, C. krusei ATCC 6258, C. parapsilosis ATCC 22019). Synthesized compounds showed weak antibacterial activity. However, 3a, 3b, and 3c compounds against C. albicans of the Candida species were found to show promising activity. Given the effect of substituents on antifungal activity, it is seen that the compounds 3a, 3b, and 3c carry chlorine, methyl, and fluoro substituents on the benzimidazole ring attract attention with higher activities. Molecular docking studies of 3a, 3b, and 3c were performed Schrödinger Glide XP against Candidas’ sterol 14-alpha demethylase (CYP51), and estimated ADME calculations were analyzed.

Keywords

Triazole Antimicrobial activity Ketoconazole Chloramphenicol Benzimidazole

References

  • [1] Willyard C., The Drug-Resistant Bacteria That Pose The Greatest Health Threats, Nature, 543 (7643) (2017) 15.
  • [2] Bansal Y., Kaur M., Bansal G., Antimicrobial Potential Of Benzimidazole Derived Molecules, Mini Rev. Med. Chem., 19(8) (2019) 624-646.
  • [3] Acar Cevik U., Kaya Cavusoglu B., Saglik B.N., Osmaniye D., Levent S., Ilgin S., Ozkay Y., Kaplancikli Z.A., Synthesis, Docking Studies And Biological Activity Of New Benzimidazole- Triazolothiadiazine Derivatives As Aromatase Inhibitor, Molecules, 25(7) (2020).
  • [4] Evren A.E., Tekinkoca S., Yurttas L., Synthesis And Antimicrobial Activity Of Some New N-(1h-Benzimidazol-2- Yl)-2-Mercaptoacetamide Derivatives, Lett. Drug Des. Discov., 15(2) (2018) 154-159.
  • [5] Evren A.E., Yurttas L., Yılmaz-Cankilic M., Synthesis Of Novel N-(Naphthalen-1-Yl)Propanamide Derivatives And Evaluation Their Antimicrobial Activity, Phosphorus Sulfur, 195(2) (2019) 158-164.
  • [6] Aouad M.R., Soliman M.A., Alharbi M.O., Bardaweel S.K., Sahu P.K., Ali A.A., Messali M., Rezki N., Al-Soud Y.A., Design, Synthesis And Anticancer Screening Of Novel Benzothiazole-Piperazine-1,2,3-Triazole Hybrids, Molecules, 23 (11) (2018).
  • [7] Garuti L., Roberti M., Malagoli M., Rossi T., Castelli M, Synthesis And Antiproliferative Activity Of Some Benzimidazole-4, 7-Dione Derivatives, Bioorg. Med. Chem. Lett., 10(19) (2000) 2193-2195.
  • [8] Ayhan‐Kılcıgil G., Kus C., Özdamar E.D., Can‐Eke B., Iscan M., Synthesis And Antioxidant Capacities Of Some New Benzimidazole Derivatives, Arch. Pharm., 340(11) (2007) 607-611.
  • [9] Can O.D., Osmaniye D., Demir Ozkay U., Saglik B.N., Levent S., Ilgin S., Baysal M., Ozkay Y., Kaplancikli Z.A., Mao Enzymes Inhibitory Activity Of New Benzimidazole Derivatives Including Hydrazone And Propargyl Side Chains, Eur. J. Med. Chem., 131 (2017) 92-106.
  • [10] Vinodkumar R., Vaidya S.D., Kumar B.V.S., Bhise U.N., Bhirud S.B., Mashelkar U.C., Synthesis, Anti-Bacterial, Anti-Asthmatic And Anti-Diabetic Activities Of Novel N-Substituted-2-(4-Phenylethynyl-Phenyl)-1h-Benzimidazoles And N-Substituted 2 [4-(4, 4-Dimethyl-Thiochroman-6-Yl-Ethynyl)-Phenyl)-1h-Benzimidazoles, Eur. J. Med. Chem., 43(5) (2008) 986-995.
  • [11] Torres-Gómez H., Hernández-Núñez E., León-Rivera I., Guerrero-Alvarez J., Cedillo-Rivera R., Moo-Puc R., Argotte-Ramos R., Del Carmen Rodríguez-Gutiérrez M., Chan-Bacab M.J., Navarrete-Vázquez G., Design, Synthesis And In Vitro Antiprotozoal Activity Of Benzimidazole-Pentamidine Hybrids, Bioorg. Med. Chem. Lett., 18(11) (2008) 3147-3151.
  • [12] Shingalapur R.V., Hosamani K.M., Keri R.S., Hugar M.H., Derivatives Of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic And Dna Cleavage Studies, Eur. J. Med. Chem., 45(5) (2010) 1753-1759.
  • [13] Saglik B.N., Sen A.M., Evren A.E., Cevik U.A., Osmaniye D., Kaya Cavusoglu B., Levent S., Karaduman A.B., Ozkay Y., Kaplancikli Z.A., Synthesis, Investigation Of Biological Effects And In Silico Studies Of New Benzimidazole Derivatives As Aromatase Inhibitors, Z Naturforsch C J Biosci., (2020).
  • [14] Evren A.E., Yurttas L., Ekselli B., Akalin-Ciftci G., Synthesis And Biological Evaluation Of 5-Methyl-4-Phenyl Thiazole Derivatives As Anticancer Agents, Phosphorus Sulfur, 194(8) (2019) 820-828.
  • [15] Beyzaei H., Khosravi Z., Aryan R., Ghasemi B., A Green One-Pot Synthesis Of 3 (5)-Substituted 1, 2, 4-Triazol-5 (3)-Amines As Potential Antimicrobial Agents, Journal Of The Iranian Chemical Society, 16(12) (2019) 2565-2573.
  • [16] Pappas P.G., Kauffman C.A., Andes D., Benjamin D.K., Calandra T.F., Edwards J.E., Filler S.G., Fisher J.F., Kullberg B.J., Ostrosky-Zeichner L., Reboli A.C., Rex J.H., Walsh T.J., Sobel J.D., Infectious Diseases Society Of, A. Clinical Practice Guidelines For The Management Of Candidiasis: 2009 Update By The Infectious Diseases Society Of America, Clin. Infect. Dis., 48(5) (2009) 503-535.
  • [17] Hargrove T.Y., Friggeri L., Wawrzak Z., Qi A., Hoekstra W.J., Schotzinger R. J., Lepesheva G.I., Structural analyses of Candida albicans sterol 14α-demethylase complexed with azole drugs address the molecular basis of azole-mediated inhibition of fungal sterol biosynthesis. J. Biolog. Chem., 292(16) (2017) 6728-6743.
  • [18] Friesner R.A., Murphy R.B., Repasky M.P., Frye L.L., Greenwood J.R., Halgren T.A., Mainz D.T., Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes, J. Med. Chem., 49(21) (2006) 6177-6196.
  • [19] Daina, A., Michielin, O., Zoete, V., SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Scientific reports, 7(1) (2017) 1-13.
There are 19 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Natural Sciences
Authors

Asaf Evrim Evren 0000-0002-8651-826X

İsmail Çelik 0000-0002-8146-1663

Ulviye Acar Çevik 0000-0003-1879-1034

Publication Date December 29, 2021
Submission Date October 26, 2021
Acceptance Date December 15, 2021
Published in Issue Year 2021Volume: 42 Issue: 4

Cite

APA Evren, A. E., Çelik, İ., & Acar Çevik, U. (2021). Synthesis, molecular docking, in silico ADME and antimicrobial activity studies of some new benzimidazole-triazole derivatives. Cumhuriyet Science Journal, 42(4), 795-805.