Literature DB >> 24432136

Design, synthesis, and evaluations of antifungal activity of novel phenyl(2H-tetrazol-5-yl)methanamine derivatives.

Amol B Salake1, Aparna S Chothe1, Shrikant S Nilewar2, Madhavi Khilare2, Rutuja S Meshram2, Abhishek A Pandey2, M K Kathiravan2.   

Abstract

Fungal infections pose a continuous and serious threat to human health and life. The intrinsic resistance has been observed in many genera of fungi. Many fungal infections are caused by opportunistic pathogens that may be endogenous (Candida infections) or acquired from the environment (Cryptococcus and Aspergillus infections). So, new therapeutic strategies are needed to combat various fungal infections. Fluconazole shows good antifungal activity with relatively low toxicity and is preferred as first line antifungal therapy, but it has suffered from severe drug resistance. So, there is a need to design novel analogues by modification of fluconazole-like structure. A novel series of phenyl(2H-tetrazol-5-yl)methanamine derivatives were synthesized by reaction of α-amino nitrile with sodium azide and ZnCl2 in presence of isopropyl alcohol. They were evaluated for antifungal activity against Candida albicans and Aspergillus niger and subjected to docking study against 1EA1.

Entities:  

Keywords:  Antifungal agent; Aspergillus niger; Candida albicans; Fluconazole; Phenyl(2H-tetrazol-5-yl)methanamine

Year:  2013        PMID: 24432136      PMCID: PMC3877410          DOI: 10.1007/s12154-013-0103-8

Source DB:  PubMed          Journal:  J Chem Biol        ISSN: 1864-6158


  15 in total

1.  Synthesis of novel substituted tetrazoles having antifungal activity.

Authors:  Ram Shankar Upadhayaya; Sanjay Jain; Neelima Sinha; Nawal Kishore; Ramesh Chandra; Sudershan K Arora
Journal:  Eur J Med Chem       Date:  2004-07       Impact factor: 6.514

Review 2.  Antifungal drug resistance: limited data, dramatic impact?

Authors:  Thomas R Rogers
Journal:  Int J Antimicrob Agents       Date:  2006-05-15       Impact factor: 5.283

Review 3.  Antimicrobial resistance: resistance to antifungal agents: mechanisms and clinical impact.

Authors:  Zeina A Kanafani; John R Perfect
Journal:  Clin Infect Dis       Date:  2008-01-01       Impact factor: 9.079

4.  Preparation of 5-substituted 1H-tetrazoles from nitriles in water.

Authors:  Z P Demko; K B Sharpless
Journal:  J Org Chem       Date:  2001-11-30       Impact factor: 4.354

5.  Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles.

Authors:  Pallav D Patel; Maulik R Patel; Bela Kocsis; Erika Kocsis; Steven M Graham; Andrew R Warren; Stacia M Nicholson; Blase Billack; Frank R Fronczek; Tanaji T Talele
Journal:  Eur J Med Chem       Date:  2010-02-06       Impact factor: 6.514

6.  Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation.

Authors:  Ornella Mesenzani; Alberto Massarotti; Mariateresa Giustiniano; Tracey Pirali; Valentina Bevilacqua; Antonio Caldarelli; Pierluigi Canonico; Giovanni Sorba; Ettore Novellino; Armando A Genazzani; Gian Cesare Tron
Journal:  Bioorg Med Chem Lett       Date:  2010-11-28       Impact factor: 2.823

7.  Benzothieno[3,2-b]quinolinium and 3-(phenylthio)quinolinium compounds: Synthesis and evaluation against opportunistic fungal pathogens.

Authors:  Comfort A Boateng; Suresh V K Eyunni; Xue Y Zhu; Jagan R Etukala; Barbara A Bricker; M K Ashfaq; Melissa R Jacob; Shabana I Khan; Larry A Walker; Seth Y Ablordeppey
Journal:  Bioorg Med Chem       Date:  2010-11-10       Impact factor: 3.641

8.  Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives.

Authors:  Petr Senel; Lucie Tichotová; Ivan Votruba; Vladimír Buchta; Marcel Spulák; Jirí Kunes; Milan Nobilis; Ondrej Krenk; Milan Pour
Journal:  Bioorg Med Chem       Date:  2010-01-25       Impact factor: 3.641

9.  1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, new imidazoles with potent activity against Candida albicans and dermatophytes. Synthesis, structure-activity relationship, and molecular modeling studies.

Authors:  Giuseppe La Regina; Felicia Diodata D'Auria; Andrea Tafi; Francesco Piscitelli; Stefania Olla; Fabiana Caporuscio; Lucia Nencioni; Roberto Cirilli; Francesco La Torre; Nadja Rodrigues De Melo; Steven L Kelly; David C Lamb; Marino Artico; Maurizio Botta; Anna Teresa Palamara; Romano Silvestri
Journal:  J Med Chem       Date:  2008-06-05       Impact factor: 7.446

10.  In vitro fluconazole susceptibility of 1565 clinical isolates of Candida species evaluated by the disk diffusion method performed using NCCLS M44-A guidelines.

Authors:  Gian Piero Testore; Luca Dori; Anna Rita Buonomini; Gian Carlo Schito; Ornella Soro; Giacomo Fortina; Stefano Andreoni; Nicola Carlone; Vivian Tullio; Massimo Andreoni
Journal:  Diagn Microbiol Infect Dis       Date:  2004-11       Impact factor: 2.803

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