Literature DB >> 27301676

Synthesis and investigation of novel benzimidazole derivatives as antifungal agents.

Nishad Thamban Chandrika1, Sanjib K Shrestha1, Huy X Ngo1, Sylvie Garneau-Tsodikova2.   

Abstract

The rise and emergence of resistance to antifungal drugs by diverse pathogenic fungal strains have resulted in an increase in demand for new antifungal agents. Various heterocyclic scaffolds with different mechanisms of action against fungi have been investigated in the past. Herein, we report the synthesis and antifungal activities of 18 alkylated mono-, bis-, and trisbenzimidazole derivatives, their toxicities against mammalian cells, as well as their ability to induce reactive oxygen species (ROS) in yeast cells. Many of our bisbenzimidazole compounds exhibited moderate to excellent antifungal activities against all tested fungal strains, with MIC values ranging from 15.6 to 0.975μg/mL. The fungal activity profiles of our bisbenzimidazoles were found to be dependent on alkyl chain length. Our most potent compounds were found to display equal or superior antifungal activity when compared to the currently used agents amphotericin B, fluconazole, itraconazole, posaconazole, and voriconazole against many of the strains tested.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Aspergillus; Candida; Cytotoxicity; Hoechst 33258; Reactive oxygen species (ROS)

Mesh:

Substances:

Year:  2016        PMID: 27301676      PMCID: PMC4955774          DOI: 10.1016/j.bmc.2016.06.010

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  39 in total

Review 1.  Infections due to emerging and uncommon medically important fungal pathogens.

Authors:  T J Walsh; A Groll; J Hiemenz; R Fleming; E Roilides; E Anaissie
Journal:  Clin Microbiol Infect       Date:  2004-03       Impact factor: 8.067

2.  Synthesis and biological activity of novel inhibitors of topoisomerase I: 2-aryl-substituted 2-bis-1H-benzimidazoles.

Authors:  Manish Singh; Vibha Tandon
Journal:  Eur J Med Chem       Date:  2010-12-08       Impact factor: 6.514

Review 3.  Echinocandins for candidemia in adults without neutropenia.

Authors:  John E Bennett
Journal:  N Engl J Med       Date:  2006-09-14       Impact factor: 91.245

4.  2-Acylhydrazino-5-arylpyrrole derivatives: synthesis and antifungal activity evaluation.

Authors:  Valentina Onnis; Alessandro De Logu; Maria T Cocco; Roberta Fadda; Rita Meleddu; Cenzo Congiu
Journal:  Eur J Med Chem       Date:  2008-08-22       Impact factor: 6.514

5.  Amphiphilic Tobramycin Analogues as Antibacterial and Antifungal Agents.

Authors:  Sanjib K Shrestha; Marina Y Fosso; Keith D Green; Sylvie Garneau-Tsodikova
Journal:  Antimicrob Agents Chemother       Date:  2015-06-01       Impact factor: 5.191

Review 6.  Reactive oxygen species-inducing antifungal agents and their activity against fungal biofilms.

Authors:  Nicolas Delattin; Bruno P A Cammue; Karin Thevissen
Journal:  Future Med Chem       Date:  2014-01       Impact factor: 3.808

7.  Activity of Hoechst 33258 against Pneumocystis carinii f. sp. muris, Candida albicans, and Candida dubliniensis.

Authors:  Matthew D Disney; Ruth Stephenson; Terry W Wright; Constantine G Haidaris; Douglas H Turner; Francis Gigliotti
Journal:  Antimicrob Agents Chemother       Date:  2005-04       Impact factor: 5.191

8.  Design of new bidentate ligands constructed of two Hoechst 33258 units for discrimination of the length of two A3T3 binding motifs.

Authors:  Mikimasa Tanada; Saori Tsujita; Shigeki Sasaki
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

9.  The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii.

Authors:  Robert W Huigens; Samuel Reyes; Catherine S Reed; Cynthia Bunders; Steven A Rogers; Andrew T Steinhauer; Christian Melander
Journal:  Bioorg Med Chem       Date:  2009-12-06       Impact factor: 3.641

10.  Sequence-based design of bioactive small molecules that target precursor microRNAs.

Authors:  Sai Pradeep Velagapudi; Steven M Gallo; Matthew D Disney
Journal:  Nat Chem Biol       Date:  2014-02-09       Impact factor: 15.040

View more
  10 in total

1.  Novel fluconazole derivatives with promising antifungal activity.

Authors:  Nishad Thamban Chandrika; Sanjib K Shrestha; Huy X Ngo; Kaitlind C Howard; Sylvie Garneau-Tsodikova
Journal:  Bioorg Med Chem       Date:  2017-12-17       Impact factor: 3.641

2.  Benzimidazole derivative M084 extends the lifespan of Caenorhabditis elegans in a DAF-16/FOXO-dependent way.

Authors:  Ai-Jun Ding; Gui-Sheng Wu; Bin Tang; Xuechuan Hong; Michael X Zhu; Huai-Rong Luo
Journal:  Mol Cell Biochem       Date:  2016-11-16       Impact factor: 3.396

3.  Alkylated Piperazines and Piperazine-Azole Hybrids as Antifungal Agents.

Authors:  Nishad Thamban Chandrika; Sanjib K Shrestha; Huy X Ngo; Oleg V Tsodikov; Kaitlind C Howard; Sylvie Garneau-Tsodikova
Journal:  J Med Chem       Date:  2017-12-19       Impact factor: 7.446

4.  Construction and Evaluation of Molecular Models: Guide and Design of Novel SE Inhibitors.

Authors:  Yunfei An; Yue Dong; Liu Min; Liyu Zhao; Dongmei Zhao; Jun Han; Bin Sun
Journal:  ACS Med Chem Lett       Date:  2020-05-11       Impact factor: 4.345

5.  New Application of Neomycin B-Bisbenzimidazole Hybrids as Antifungal Agents.

Authors:  Nishad Thamban Chandrika; Sanjib K Shrestha; Nihar Ranjan; Anindra Sharma; Dev P Arya; Sylvie Garneau-Tsodikova
Journal:  ACS Infect Dis       Date:  2017-12-11       Impact factor: 5.084

6.  Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group.

Authors:  Guo-Shao Sun; Xin Xu; Shu-Hui Jin; Le Lin; Jian-Jun Zhang
Journal:  Molecules       Date:  2017-06-08       Impact factor: 4.411

7.  Preparation of 1,2-substituted benzimidazoles via a copper-catalyzed three component coupling reaction.

Authors:  Weiguang Yang; Yu Zhao; Zitong Zhou; Li Li; Liao Cui; Hui Luo
Journal:  RSC Adv       Date:  2021-02-25       Impact factor: 3.361

8.  Bio-priming with a consortium of Streptomyces araujoniae strains modulates defense response in chickpea against Fusarium wilt.

Authors:  Mohammad Tarique Zeyad; Pushpendra Tiwari; Waquar Akhter Ansari; Shiv Charan Kumar; Murugan Kumar; Hillol Chakdar; Alok Kumar Srivastava; Udai B Singh; Anil Kumar Saxena
Journal:  Front Microbiol       Date:  2022-09-08       Impact factor: 6.064

9.  Preparation, Antidermatophyte Activity, and Mechanism of Methylphloroglucinol Derivatives.

Authors:  Lianbao Ye; Pengfei Lin; Wenjun Du; Yuanyuan Wang; Chunping Tang; Zhibin Shen
Journal:  Front Microbiol       Date:  2018-11-02       Impact factor: 5.640

10.  Synthesis, anti-bacterial and anti-protozoal activities of amidinobenzimidazole derivatives and their interactions with DNA and RNA.

Authors:  Andrea Bistrović; Luka Krstulović; Ivana Stolić; Domagoj Drenjančević; Jasminka Talapko; Martin C Taylor; John M Kelly; Miroslav Bajić; Silvana Raić-Malić
Journal:  J Enzyme Inhib Med Chem       Date:  2018-12       Impact factor: 5.051

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.