Literature DB >> 30316633

Discovery of heterocyclic replacements for the coumarin core of anti-tubercular FadD32 inhibitors.

Chao Fang1, Katie K Lee2, Raymond Nietupski1, Robert H Bates3, Raquel Fernandez-Menendez3, Eva Maria Lopez-Roman3, Laura Guijarro-Lopez3, Yunxing Yin4, Zuozhong Peng5, James E Gomez2, Stewart Fisher1, David Barros-Aguirre3, Brian K Hubbard1, Michael H Serrano-Wu1, Deborah T Hung6.   

Abstract

Previous work established a coumarin scaffold as a starting point for inhibition of Mycobacterium tuberculosis (Mtb) FadD32 enzymatic activity. After further profiling of the coumarin inhibitor 4 revealed chemical instability, we discovered that a quinoline ring circumvented this instability and had the advantage of offering additional substitution vectors to further optimize. Ensuing SAR studies gave rise to quinoline-2-carboxamides with potent anti-tubercular activity. Further optimization of ADME/PK properties culminated in 21b that exhibited compelling in vivo efficacy in a mouse model of Mtb infection.
Copyright © 2018 The Authors. Published by Elsevier Ltd.. All rights reserved.

Entities:  

Keywords:  FadD32 inhibitor; In vivo efficacy; Mycobacterium tuberculosis; Quinoline-2-carboxamide; Structure-activity relationship

Mesh：

Substances：

Year:  2018        PMID： 30316633      PMCID： PMC6233306          DOI： 10.1016/j.bmcl.2018.09.037

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  10 in total

1.  Structure-activity relationship of quinoline derivatives as potent and selective alpha(2C)-adrenoceptor antagonists.

Authors:  Iisa P J Höglund; Satu Silver; Mia T Engström; Harri Salo; Andrei Tauber; Hanna-Kaisa Kyyrönen; Pauli Saarenketo; Anna-Marja Hoffrén; Kurt Kokko; Katariina Pohjanoksa; Jukka Sallinen; Juha-Matti Savola; Siegfried Wurster; Oili A Kallatsa
Journal:  J Med Chem       Date:  2006-10-19       Impact factor: 7.446

2.  Insight into Structure-Function Relationships and Inhibition of the Fatty Acyl-AMP Ligase (FadD32) Orthologs from Mycobacteria.

Authors:  Valérie Guillet; Ségolène Galandrin; Laurent Maveyraud; Simon Ladevèze; Vincent Mariaule; Cécile Bon; Nathalie Eynard; Mamadou Daffé; Hedia Marrakchi; Lionel Mourey
Journal:  J Biol Chem       Date:  2016-02-21       Impact factor: 5.157

3.  Chemiluminescent nitrogen detection (CLND) to measure kinetic aqueous solubility.

Authors:  Aimee Kestranek; Andrew Chervenak; Justin Longenberger; Steven Placko
Journal:  Curr Protoc Chem Biol       Date:  2013

4.  Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against Mycobacterium tuberculosis.

Authors:  Wei Zhang; Shichun Lun; Shu-Huan Wang; Xing-Wu Jiang; Fan Yang; Jie Tang; Abigail L Manson; Ashlee M Earl; Hendra Gunosewoyo; William R Bishai; Li-Fang Yu
Journal:  J Med Chem       Date:  2018-01-29       Impact factor: 7.446

5.  Diarylcoumarins inhibit mycolic acid biosynthesis and kill Mycobacterium tuberculosis by targeting FadD32.

Authors:  Sarah A Stanley; Tomohiko Kawate; Noriaki Iwase; Motohisa Shimizu; Anne E Clatworthy; Edward Kazyanskaya; James C Sacchettini; Thomas R Ioerger; Noman A Siddiqi; Shoko Minami; John A Aquadro; Sarah Schmidt Grant; Eric J Rubin; Deborah T Hung
Journal:  Proc Natl Acad Sci U S A       Date:  2013-06-24       Impact factor: 11.205

6.  Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors.

Authors:  Alfonso Maresca; Claudia Temperini; Hoan Vu; Ngoc B Pham; Sally-Ann Poulsen; Andrea Scozzafava; Ronald J Quinn; Claudiu T Supuran
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

7.  Synthesis and structure-activity relationships of phenyl-substituted coumarins with anti-tubercular activity that target FadD32.

Authors:  Tomohiko Kawate; Noriaki Iwase; Motohisa Shimizu; Sarah A Stanley; Samantha Wellington; Edward Kazyanskaya; Deborah T Hung
Journal:  Bioorg Med Chem Lett       Date:  2013-09-19       Impact factor: 2.823

8.  Structure of the Essential Mtb FadD32 Enzyme: A Promising Drug Target for Treating Tuberculosis.

Authors:  Misty L Kuhn; Evan Alexander; George Minasov; Holland J Page; Zdzislaw Warwrzak; Ludmilla Shuvalova; Kristin J Flores; Daniel J Wilson; Ce Shi; Courtney C Aldrich; Wayne F Anderson
Journal:  ACS Infect Dis       Date:  2016-07-01       Impact factor: 5.084

9.  A Survey of Solvents for the Conrad-Limpach Synthesis of 4-Hydroxyquinolones.

Authors:  Jean-Cristophe Brouet; Shen Gu; Norton P Peet; John D Williams
Journal:  Synth Commun       Date:  2009-01-01       Impact factor: 2.007

10.  Crystal structure of FadD32, an enzyme essential for mycolic acid biosynthesis in mycobacteria.

Authors:  Wenjuan Li; Shoujin Gu; Joy Fleming; Lijun Bi
Journal:  Sci Rep       Date:  2015-12-02       Impact factor: 4.379
  10 in total
  7 in total

1.  Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis.

Authors:  Marzena Baran; Kimberly D Grimes; Paul A Sibbald; Peng Fu; Helena I M Boshoff; Daniel J Wilson; Courtney C Aldrich
Journal:  Eur J Med Chem       Date:  2020-06-13       Impact factor: 6.514

Review 2.  Recent Progress in the Development of Novel Mycobacterium Cell Wall Inhibitor to Combat Drug-Resistant Tuberculosis.

Authors:  Tafere Mulaw Belete
Journal:  Microbiol Insights       Date:  2022-05-23

3.  In Silico Drug Repurposing Approach: Investigation of Mycobacterium tuberculosis FadD32 Targeted by FDA-Approved Drugs.

Authors:  Nolwazi Thobeka Portia Ngidi; Kgothatso Eugene Machaba; Ndumiso Nhlakanipho Mhlongo
Journal:  Molecules       Date:  2022-01-20       Impact factor: 4.411

4.  Synthesis of 1-(β-coumarinyl)-1-(β-indolyl)trifluoroethanols through regioselective Friedel-Crafts alkylation of indoles with β-(trifluoroacetyl)coumarins catalyzed by Sc(OTf)3.

Authors:  Lijun Shi; Ying Liu; Caixia Wang; Xinxin Yuan; Xiaobiao Liu; Lulu Wu; Zhenliang Pan; Qicheng Yu; Cuilian Xu; Guoyu Yang
Journal:  RSC Adv       Date:  2020-04-15       Impact factor: 4.036

Review 5.  Overcoming Mycobacterium tuberculosis through small molecule inhibitors to break down cell wall synthesis.

Authors:  Wenbin Kuang; Haolin Zhang; Xiao Wang; Peng Yang
Journal:  Acta Pharm Sin B       Date:  2022-04-27       Impact factor: 14.903

Review 6.  MmpL3 Inhibition: A New Approach to Treat Nontuberculous Mycobacterial Infections.

Authors:  Jigar P Sethiya; Melanie A Sowards; Mary Jackson; Elton Jeffrey North
Journal:  Int J Mol Sci       Date:  2020-08-27       Impact factor: 5.923

Review 7.  Antibiotics and resistance: the two-sided coin of the mycobacterial cell wall.

Authors:  Sarah M Batt; Christopher E Burke; Alice R Moorey; Gurdyal S Besra
Journal:  Cell Surf       Date:  2020-09-02
  7 in total

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