Literature DB >> 14667220

Structure-based design, synthesis, and antimicrobial activity of indazole-derived SAH/MTA nucleosidase inhibitors.

Xiaoming Li1, Sam Chu, Victoria A Feher, Mitra Khalili, Zhe Nie, Stephen Margosiak, Victor Nikulin, James Levin, Kelly G Sprankle, Martina E Tedder, Robert Almassy, Krzysztof Appelt, Kraig M Yager.   

Abstract

The structure-based design, synthesis, and biological activity of a novel indazole-containing inhibitor series for S-adenosyl homocysteine/methylthioadenosine (SAH/MTA) nucleosidase are described. Use of 5-aminoindazole as the core scaffold provided a structure-guided series of low nanomolar inhibitors with broad-spectrum antimicrobial activity. The implementation of structure-based methodologies provided a 6000-fold increase in potency over a short timeline (several months) and an economy of synthesized compounds.

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Year:  2003        PMID： 14667220     DOI： 10.1021/jm0302039

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  12 in total

Review 1.  Methylthioadenosine/S-adenosylhomocysteine nucleosidase, a critical enzyme for bacterial metabolism.

Authors:  Nikhat Parveen; Kenneth A Cornell
Journal:  Mol Microbiol       Date:  2010-11-18       Impact factor: 3.501

2.  Assessment of methylthioadenosine/S-adenosylhomocysteine nucleosidases of Borrelia burgdorferi as targets for novel antimicrobials using a novel high-throughput method.

Authors:  Kenneth A Cornell; Shekerah Primus; Jorge A Martinez; Nikhat Parveen
Journal:  J Antimicrob Chemother       Date:  2009-04-17       Impact factor: 5.790

3.  Characterization of 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidases from Borrelia burgdorferi: Antibiotic targets for Lyme disease.

Authors:  Kenneth A Cornell; Reece J Knippel; Gerald R Cortright; Meghan Fonken; Christian Guerrero; Amy R Hall; Kristen A Mitchell; John H Thurston; Patrick Erstad; Aoxiang Tao; Dong Xu; Nikhat Parveen
Journal:  Biochim Biophys Acta Gen Subj       Date:  2019-10-31       Impact factor: 3.770

4.  2-Allyl-7-nitro-2H-indazole.

Authors:  Assoman Kouakou; El Mostapha Rakib; Domenico Spinelli; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-10-02

5.  Novel Azoles as Antiparasitic Remedies against Brain-Eating Amoebae.

Authors:  Ayaz Anwar; Mohammad Ridwane Mungroo; Simal Khan; Itrat Fatima; Rafaila Rafique; Khalid Mohammed Khan; Ruqaiyyah Siddiqui; Naveed Ahmed Khan
Journal:  Antibiotics (Basel)       Date:  2020-04-17

6.  A regioselective C7 bromination and C7 palladium-catalyzed Suzuki-Miyaura cross-coupling arylation of 4-substituted NH-free indazoles.

Authors:  Khalid Boujdi; Nabil El Brahmi; Jérôme Graton; Didier Dubreuil; Sylvain Collet; Monique Mathé-Allainmat; Mohamed Akssira; Jacques Lebreton; Saïd El Kazzouli
Journal:  RSC Adv       Date:  2021-02-10       Impact factor: 3.361

7.  1-Allyl-3-chloro-5-nitro-1H-indazole.

Authors:  Hakima Chicha; El Mostapha Rakib; Domenico Spinelli; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-08-10

8.  3-Substituted-N-(4-hydroxynaphthalen-1-yl)arylsulfonamides as a novel class of selective Mcl-1 inhibitors: structure-based design, synthesis, SAR, and biological evaluation.

Authors:  Fardokht A Abulwerdi; Chenzhong Liao; Ahmed S Mady; Jordan Gavin; Chenxi Shen; Tomasz Cierpicki; Jeanne A Stuckey; H D Hollis Showalter; Zaneta Nikolovska-Coleska
Journal:  J Med Chem       Date:  2014-05-07       Impact factor: 7.446

9.  Crystal structure of triethyl 2-(5-nitro-2H-indazol-2-yl)propane-1,2,3-tri-carboxyl-ate.

Authors:  Mohammed Boulhaoua; Mohammed Benchidmi; El Mokhtar Essassi; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-09-26

10.  Methylthioadenosine Suppresses Salmonella Virulence.

Authors:  James J Gilchrist; Dennis C Ko; Jeffrey S Bourgeois; Daoguo Zhou; Teresa L M Thurston
Journal:  Infect Immun       Date:  2018-08-22       Impact factor: 3.441
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