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Antifungal Activity of Some Benzimidazole-Hydrazones

Year 2019, , 695 - 699, 30.09.2019

Derya Osmaniye , Ulviye Acar Çevik

https://doi.org/10.17776/csj.579734
Cited By: 1

Abstract

In the present work, 15 4-(1-(prop-2-in-1-yl)-1H-benzoimidazole-2-yl)-N'-(substitutedmethylene)benzohydrazide
derivatives (4a-4o) were re-synthesized to evaluate their antifungal activity. Structure
identification of synthesized compounds was elucidated by 1H-NMR, 13C-NMR,
and HRMS spectroscopic methods.
Inhibitory potential of the re-synthesized compounds was investigated against Candida supp. The compounds 4e
and 4l showed significant anti fungal activity. Consistent with the
activity studies, 4e was found to be potent derivative with its MIC50
value of (1.95 µg/mL) against Candida
glabrata. And 4l was found to
be potent derivative with its MIC50 value of (1.95 µg/mL) against Candida krusei.

Keywords

Benzimidazole hydrazone

References

  • [1] Wang, S.Q., Wang, Y.F., Xu, Z., Tetrazole hybrids and their antifungal activities, Eur. J. Med. Chem., 170 (2019) 225-234.
  • [2] Zhao, L., Tian, L., Sun, N., Chen, Y., Wang, X., Zhao, S., Su, X., Zhao, D., Cheng, M., Design, synthesis, and structure-activity relationship studies of l-amino alcohol derivatives as broad-spectrum antifungal agents, Eur. J. Med. Chem., https://doi.org/10.1016/j.ejmech.2019.05.047
  • [3] Zhao, S., Zhang, X., Wei, P., Su, X., Zhao, L., Wu, M., Hao, C., Liu, C., Zhao, D., Cheng, M., Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents. Eur. J. Med. Chem., 137 (2017) 96-107.
  • [4] Lino, C.I., de Souza, I.G., Borelli, B.M., Silverio Matos, T.T., Santos Teixeira, I.N., Ramos, J.P., de Souza Fagundes, E.M., de Oliveira Fernandes, P., Maltarollo, V.G., Johann, S., de Oliveira, R.B., Synthesis, molecular modeling studies and evaluation of antifungal activity of a novel series of thiazole derivatives, Eur. J. Med. Chem., 151 (2018) 248-260.
  • [5] Shi, Y., Jiang, K., Zheng, R., Fu, J., Yan, L., Gu, Q., Zhang, Y., Lin, F., Design, Microwave-Assisted Synthesis and in Vitro Antibacterial and Antifungal Activity of 2,5-Disubstituted Benzimidazole, Chem. Biodiversity, 16 (2016) e1800510.
  • [6] Villa, P., Arumugam, N., Almansour, A.I., Kumar, R.S., Mahalingam, S.M., Maruoka, K., Thangamani, S., Benzimidazole tethered pyrrolo[3,4-b]quinoline with broad-spectrum activity against fungal pathogens, Bioorg. Med. Chem. Lett., 29 (2019) 729-733.
  • [7] Karaburun, A.C.,Kaya Çavuşoğlu, B., Acar Çevik, U., Osmaniye, D., Sağlık, B.N., Levent, S., Özkay, Y., Atlı, Ö., Koparal, A.S., Kaplancıklı, Z.A., Synthesis and Antifungal Potential of Some Novel Benzimidazole-1,3,4-Oxadiazole Compounds, Molecules, 24 (2019), 191.
  • [8] Wu, J., Ni, T., Chai, X., Wang, T., Wang, H., Chen, J., Jin, Y., Zhang, D., Yu, S., Jiang, Y., Molecular docking, design, synthesis and antifungal activity study of novel triazole derivatives, Eur. J. Med. Chem., 143 (2018), 1840-1846.
  • [9] Si, W.J., Wang, X.B., Chen, M., Wang, M.Q., Lu, A.M., Yang, C.L., Design, synthesis, antifungal activity and 3D-QSAR study of novel pyrazole carboxamide and niacinamide derivatives containing benzimidazole moiety, New. J. Chem., 43 (2019), 3000.
  • [10] Kashid, B.B., Ghanwat, A.A., Khedkar, V.M., Dongare, B.B., Shaikh, M.H., Deshpande, P.P., Wakchaure, Y.B., Design, Synthesis, In Vitro Antimicrobial, Antioxidant Evaluation, and Molecular Docking Study of Novel Benzimidazole and Benzoxazole Derivatives, J. Heterocycle. Chem., 56(2019), 895.
  • [11] Yadav, S., Lim, S.M., Ramasamy, K., Vasudevan, M., Ali Shah, S.A., Mathur, A., Narasimhan, B., Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of 2‑(1‑benzoyl‑1H‑benzo[d] imidazol‑2‑ylthio)‑N‑substituted acetamides, Chemistry Central Journal, 12:66 (2018), 1-14.
  • [12] Abdel-Wahab, S.M., Abdelsamii, Z.K., Abdel-Fattah, H.A., El-Etrawy, A.S., Dawe, L.N., Swaroop, T.R., Georghiou, P.E., Synthesis of 2-Aryl- and 2-Haloarylbenzimidazole-N1-acetamido Conjugates and a Preliminary Evaluation of Their Antifungal Properties, ChemistrySelect, 3(2018), 8106-8110.
  • [13] Chandrika, N.T., Shrestha, S.K., Ngo, H.X., Tsodikov, O.V., Howard, K.C., Garneau-Tsodikova, S., Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents, J. Med. Chem., 61(2018), 158-173.
  • [14] Vıjey Aanandhı, M., Anbhule Sachın, J., Synthesıs, Characterızatıon, And Evaluatıon Of Antıfungal Propertıes Of Substıtuted Benzımıdazole Analog, Asian J. Pharm. Clin. Res., 11 (2018), 66-69.
  • [15] Li, L.X., Jiao, J., Wang, X.B., Chen, M., Fu, X.C., Si, W.J., Yang, C.L., Synthesis, Characterization, and Antifungal Activity of Novel Benzo[4,5]imidazo[1,2-d][1,2,4]triazine Derivatives, Molecules, 23 (2018), 746.
  • [16] Eren, B., Yılmaz, Ö., Çetin, G., Darcan, C., Microwave Assisted Synthesis and Potent Antimicrobial Activity of Some Novel 1,3-Dialkyl-2-arylbenzimidazolium Salts, Lett. Drug. Des. Discov., 15 (2018), 621-633.
  • [17]Liu, H.B., Gao, W.W., Tangadanchu, V.K.R., Zhou, C.H., Geng, R.X., Novel aminopyrimidinyl benzimidazoles as potentially antimicrobial agents: Design, synthesis and biological evaluation, Eur. J. Med. Chem., 143 (2018), 66-84.
  • [18] Özkay, Y., Tunalı, Y., Karaca, H., Işıkdağ, İ., Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety, Eur. J. Med. Chem., 45 (2010), 3293-3298.
  • [19] Küçükgüzel, S.G., Mazi, A., Sahin, F., Öztürk, S., Stables, J., Synthesis and biological activities of diflunisal hydrazide_/hydrazones, Eur. J. Med. Chem., 38 (2003), 1005-1013.
  • [20] Can, Ö.D., Osmaniye, D., Demir Özkay, U., Sağlık, B.N., Levent, S., Ilgın, S., Baysal, M., Özkay, Y., Kaplacıklı, Z.A., MAO enzymes inhibitory activity of new benzimidazole derivativesincluding hydrazone and propargyl side chains, Eur. J. Med. Chem., 131 (2017), 92-106.
  • [21] Rodriguez-Tudela, J.L., Barchiesi, F. Subcommittee on Antifungal Susceptibility Testing (AFST). EUCAST Definitive Document EDef 7.1: Method for the determination of broth dilution MICs of antifungal agents for fermentative yeast. Clin. Microbiol. Infect., 14 (2008), 398-405.
  • [22] Can, N.Ö., Çevik, U.A., Saglık, B.N., Özkay, Y., Atlı, Ö., Baysal, M., Özkay, Ü.D., Can, Ö.D., Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors, Molecules, 22 (2017), 1374.

Bazı Benzimidazol-Hidrazonların Antifungal Etkinliği

Year 2019, , 695 - 699, 30.09.2019

Derya Osmaniye , Ulviye Acar Çevik

https://doi.org/10.17776/csj.579734
Cited By: 1

Abstract

Mevcut
çalışmada, 15 4-(1-(prop-2-in-1-il)-1H-benzimidazol-2-il)-N’-(sübstitüemetilen) benzohidrazit
türevleri (4a-4o), antifungal
aktivitelerini değerlendirmek üzere yeniden sentezlendi. Sentezlenen bileşiklerin
yapı tanımlamaları 1H-NMR, 13C-NMR ve HRMS spektroskopik
yöntemlerle açıklandı. Yeniden sentezlenen bileşiklerin antifungal etkinlikleri
Candida türlerine karşı değerlendirildi. Bileşik 4e ve 4l önemli aktivite
gösterdi. Aktivite çalışmaları ile uyumlu olarak, 4e bileşiği Candida glabrata'ya
karşı 1.95 µg / mL MIC50 değeri ile güçlü bir türev olarak bulundu.
Aynı zamanda 4l bileşiği Candida krusei’ye karşı 1.95 µg / mL MIC50
değeri ile güçlü bir türev olarak bulundu.

References

  • [1] Wang, S.Q., Wang, Y.F., Xu, Z., Tetrazole hybrids and their antifungal activities, Eur. J. Med. Chem., 170 (2019) 225-234.
  • [2] Zhao, L., Tian, L., Sun, N., Chen, Y., Wang, X., Zhao, S., Su, X., Zhao, D., Cheng, M., Design, synthesis, and structure-activity relationship studies of l-amino alcohol derivatives as broad-spectrum antifungal agents, Eur. J. Med. Chem., https://doi.org/10.1016/j.ejmech.2019.05.047
  • [3] Zhao, S., Zhang, X., Wei, P., Su, X., Zhao, L., Wu, M., Hao, C., Liu, C., Zhao, D., Cheng, M., Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents. Eur. J. Med. Chem., 137 (2017) 96-107.
  • [4] Lino, C.I., de Souza, I.G., Borelli, B.M., Silverio Matos, T.T., Santos Teixeira, I.N., Ramos, J.P., de Souza Fagundes, E.M., de Oliveira Fernandes, P., Maltarollo, V.G., Johann, S., de Oliveira, R.B., Synthesis, molecular modeling studies and evaluation of antifungal activity of a novel series of thiazole derivatives, Eur. J. Med. Chem., 151 (2018) 248-260.
  • [5] Shi, Y., Jiang, K., Zheng, R., Fu, J., Yan, L., Gu, Q., Zhang, Y., Lin, F., Design, Microwave-Assisted Synthesis and in Vitro Antibacterial and Antifungal Activity of 2,5-Disubstituted Benzimidazole, Chem. Biodiversity, 16 (2016) e1800510.
  • [6] Villa, P., Arumugam, N., Almansour, A.I., Kumar, R.S., Mahalingam, S.M., Maruoka, K., Thangamani, S., Benzimidazole tethered pyrrolo[3,4-b]quinoline with broad-spectrum activity against fungal pathogens, Bioorg. Med. Chem. Lett., 29 (2019) 729-733.
  • [7] Karaburun, A.C.,Kaya Çavuşoğlu, B., Acar Çevik, U., Osmaniye, D., Sağlık, B.N., Levent, S., Özkay, Y., Atlı, Ö., Koparal, A.S., Kaplancıklı, Z.A., Synthesis and Antifungal Potential of Some Novel Benzimidazole-1,3,4-Oxadiazole Compounds, Molecules, 24 (2019), 191.
  • [8] Wu, J., Ni, T., Chai, X., Wang, T., Wang, H., Chen, J., Jin, Y., Zhang, D., Yu, S., Jiang, Y., Molecular docking, design, synthesis and antifungal activity study of novel triazole derivatives, Eur. J. Med. Chem., 143 (2018), 1840-1846.
  • [9] Si, W.J., Wang, X.B., Chen, M., Wang, M.Q., Lu, A.M., Yang, C.L., Design, synthesis, antifungal activity and 3D-QSAR study of novel pyrazole carboxamide and niacinamide derivatives containing benzimidazole moiety, New. J. Chem., 43 (2019), 3000.
  • [10] Kashid, B.B., Ghanwat, A.A., Khedkar, V.M., Dongare, B.B., Shaikh, M.H., Deshpande, P.P., Wakchaure, Y.B., Design, Synthesis, In Vitro Antimicrobial, Antioxidant Evaluation, and Molecular Docking Study of Novel Benzimidazole and Benzoxazole Derivatives, J. Heterocycle. Chem., 56(2019), 895.
  • [11] Yadav, S., Lim, S.M., Ramasamy, K., Vasudevan, M., Ali Shah, S.A., Mathur, A., Narasimhan, B., Synthesis and evaluation of antimicrobial, antitubercular and anticancer activities of 2‑(1‑benzoyl‑1H‑benzo[d] imidazol‑2‑ylthio)‑N‑substituted acetamides, Chemistry Central Journal, 12:66 (2018), 1-14.
  • [12] Abdel-Wahab, S.M., Abdelsamii, Z.K., Abdel-Fattah, H.A., El-Etrawy, A.S., Dawe, L.N., Swaroop, T.R., Georghiou, P.E., Synthesis of 2-Aryl- and 2-Haloarylbenzimidazole-N1-acetamido Conjugates and a Preliminary Evaluation of Their Antifungal Properties, ChemistrySelect, 3(2018), 8106-8110.
  • [13] Chandrika, N.T., Shrestha, S.K., Ngo, H.X., Tsodikov, O.V., Howard, K.C., Garneau-Tsodikova, S., Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents, J. Med. Chem., 61(2018), 158-173.
  • [14] Vıjey Aanandhı, M., Anbhule Sachın, J., Synthesıs, Characterızatıon, And Evaluatıon Of Antıfungal Propertıes Of Substıtuted Benzımıdazole Analog, Asian J. Pharm. Clin. Res., 11 (2018), 66-69.
  • [15] Li, L.X., Jiao, J., Wang, X.B., Chen, M., Fu, X.C., Si, W.J., Yang, C.L., Synthesis, Characterization, and Antifungal Activity of Novel Benzo[4,5]imidazo[1,2-d][1,2,4]triazine Derivatives, Molecules, 23 (2018), 746.
  • [16] Eren, B., Yılmaz, Ö., Çetin, G., Darcan, C., Microwave Assisted Synthesis and Potent Antimicrobial Activity of Some Novel 1,3-Dialkyl-2-arylbenzimidazolium Salts, Lett. Drug. Des. Discov., 15 (2018), 621-633.
  • [17]Liu, H.B., Gao, W.W., Tangadanchu, V.K.R., Zhou, C.H., Geng, R.X., Novel aminopyrimidinyl benzimidazoles as potentially antimicrobial agents: Design, synthesis and biological evaluation, Eur. J. Med. Chem., 143 (2018), 66-84.
  • [18] Özkay, Y., Tunalı, Y., Karaca, H., Işıkdağ, İ., Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety, Eur. J. Med. Chem., 45 (2010), 3293-3298.
  • [19] Küçükgüzel, S.G., Mazi, A., Sahin, F., Öztürk, S., Stables, J., Synthesis and biological activities of diflunisal hydrazide_/hydrazones, Eur. J. Med. Chem., 38 (2003), 1005-1013.
  • [20] Can, Ö.D., Osmaniye, D., Demir Özkay, U., Sağlık, B.N., Levent, S., Ilgın, S., Baysal, M., Özkay, Y., Kaplacıklı, Z.A., MAO enzymes inhibitory activity of new benzimidazole derivativesincluding hydrazone and propargyl side chains, Eur. J. Med. Chem., 131 (2017), 92-106.
  • [21] Rodriguez-Tudela, J.L., Barchiesi, F. Subcommittee on Antifungal Susceptibility Testing (AFST). EUCAST Definitive Document EDef 7.1: Method for the determination of broth dilution MICs of antifungal agents for fermentative yeast. Clin. Microbiol. Infect., 14 (2008), 398-405.
  • [22] Can, N.Ö., Çevik, U.A., Saglık, B.N., Özkay, Y., Atlı, Ö., Baysal, M., Özkay, Ü.D., Can, Ö.D., Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors, Molecules, 22 (2017), 1374.
There are 22 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Derya Osmaniye 0000-0002-0499-436X

Ulviye Acar Çevik 0000-0003-1879-1034

Publication Date September 30, 2019
Submission Date June 19, 2019
Acceptance Date September 19, 2019
Published in Issue Year 2019

Cite

APA Osmaniye, D., & Acar Çevik, U. (2019). Antifungal Activity of Some Benzimidazole-Hydrazones. Cumhuriyet Science Journal, 40(3), 695-699. https://doi.org/10.17776/csj.579734

Cited By

“Design, Synthesis, Mechanistic Studies and In Silico ADME predictions of Benzimidazole derivatives as Novel Antifungal Agents”
Bioorganic Chemistry
Martha M. Morcoss
https://doi.org/10.1016/j.bioorg.2020.103956