Literature DB >> 25221657

2-Phenylindole and Arylsulphonamide: Novel Scaffolds Bactericidal against Mycobacterium tuberculosis.

Maruti Naik1, Sandeep Ghorpade1, Lalit Kumar Jena1, Gopinath Gorai1, Ashwini Narayan1, Supreeth Guptha1, Sreevalli Sharma1, Neela Dinesh1, Parvinder Kaur1, Radha Nandishaiah1, Jyothi Bhat1, Gayathri Balakrishnan1, Vaishali Humnabadkar1, Vasanthi Ramachandran1, Lava Kumar Naviri1, Pallavi Khadtare1, Manoranjan Panda1, Pravin S Iyer1, Monalisa Chatterji1.   

Abstract

A cellular activity-based screen on Mycobacterium tuberculosis (Mtb) H37Rv using a focused library from the AstraZeneca corporate collection led to the identification of 2-phenylindoles and arylsulphonamides, novel antimycobacterial scaffolds. Both the series were bactericidal in vitro and in an intracellular macrophage infection model, active against drug sensitive and drug resistant Mtb clinical isolates, and specific to mycobacteria. The scaffolds showed promising structure-activity relationships; compounds with submicromolar cellular potency were identified during the hit to lead exploration. Furthermore, compounds from both scaffolds were tested for inhibition of known target enzymes or pathways of antimycobacterial drugs including InhA, RNA polymerase, DprE1, topoisomerases, protein synthesis, and oxidative-phosphorylation. Compounds did not inhibit any of the targets suggesting the potential of a possible novel mode of action(s). Hence, both scaffolds provide the opportunity to be developed further as leads and tool compounds to uncover novel mechanisms for tuberculosis drug discovery.

Entities:  

Keywords:  2-phenylindoles; Mycobacterium tuberculosis; Tuberculosis; arylsulphonamides

Year:  2014        PMID: 25221657      PMCID: PMC4160756          DOI: 10.1021/ml5001933

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN: 1948-5875            Impact factor:   4.345


  12 in total

1.  An in vitro model for sequential study of shiftdown of Mycobacterium tuberculosis through two stages of nonreplicating persistence.

Authors:  L G Wayne; L G Hayes
Journal:  Infect Immun       Date:  1996-06       Impact factor: 3.441

2.  Tuberculosis success.

Authors:  Dan Jones
Journal:  Nat Rev Drug Discov       Date:  2013-03       Impact factor: 84.694

Review 3.  Advances in the development of new tuberculosis drugs and treatment regimens.

Authors:  Alimuddin Zumla; Payam Nahid; Stewart T Cole
Journal:  Nat Rev Drug Discov       Date:  2013-05       Impact factor: 84.694

4.  SQ109 targets MmpL3, a membrane transporter of trehalose monomycolate involved in mycolic acid donation to the cell wall core of Mycobacterium tuberculosis.

Authors:  Kapil Tahlan; Regina Wilson; David B Kastrinsky; Kriti Arora; Vinod Nair; Elizabeth Fischer; S Whitney Barnes; John R Walker; David Alland; Clifton E Barry; Helena I Boshoff
Journal:  Antimicrob Agents Chemother       Date:  2012-01-17       Impact factor: 5.191

5.  Azaindoles: noncovalent DprE1 inhibitors from scaffold morphing efforts, kill Mycobacterium tuberculosis and are efficacious in vivo.

Authors:  Pravin S Shirude; Radha Shandil; Claire Sadler; Maruti Naik; Vinayak Hosagrahara; Shahul Hameed; Vikas Shinde; Chandramohan Bathula; Vaishali Humnabadkar; Naveen Kumar; Jitendar Reddy; Vijender Panduga; Sreevalli Sharma; Anisha Ambady; Naina Hegde; James Whiteaker; Robert E McLaughlin; Humphrey Gardner; Prashanti Madhavapeddi; Vasanthi Ramachandran; Parvinder Kaur; Ashwini Narayan; Supreeth Guptha; Disha Awasthy; Chandan Narayan; Jyothi Mahadevaswamy; K G Vishwas; Vijaykamal Ahuja; Abhishek Srivastava; K R Prabhakar; Sowmya Bharath; Ramesh Kale; Manjunatha Ramaiah; Nilanjana Roy Choudhury; Vasan K Sambandamurthy; Suresh Solapure; Pravin S Iyer; Shridhar Narayanan; Monalisa Chatterji
Journal:  J Med Chem       Date:  2013-11-21       Impact factor: 7.446

6.  Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis.

Authors:  Vadim Makarov; Giulia Manina; Katarina Mikusova; Ute Möllmann; Olga Ryabova; Brigitte Saint-Joanis; Neeraj Dhar; Maria Rosalia Pasca; Silvia Buroni; Anna Paola Lucarelli; Anna Milano; Edda De Rossi; Martina Belanova; Adela Bobovska; Petronela Dianiskova; Jana Kordulakova; Claudia Sala; Elizabeth Fullam; Patricia Schneider; John D McKinney; Priscille Brodin; Thierry Christophe; Simon Waddell; Philip Butcher; Jakob Albrethsen; Ida Rosenkrands; Roland Brosch; Vrinda Nandi; Sowmya Bharath; Sheshagiri Gaonkar; Radha K Shandil; Venkataraman Balasubramanian; Tanjore Balganesh; Sandeep Tyagi; Jacques Grosset; Giovanna Riccardi; Stewart T Cole
Journal:  Science       Date:  2009-03-19       Impact factor: 47.728

7.  Regiochemistry of the microwave-assisted reaction between aromatic amines and alpha-bromoketones to yield substituted 1H-indoles.

Authors:  Yosu Vara; Eneko Aldaba; Ana Arrieta; José L Pizarro; María I Arriortua; Fernando P Cossío
Journal:  Org Biomol Chem       Date:  2008-03-25       Impact factor: 3.876

Review 8.  Mycobacterium tuberculosis pathogenesis and molecular determinants of virulence.

Authors:  Issar Smith
Journal:  Clin Microbiol Rev       Date:  2003-07       Impact factor: 26.132

9.  Antibacterial activity of a novel series of 3-bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives--an extended structure-activity relationship study.

Authors:  Siavosh Mahboobi; Emerich Eichhorn; Matthias Winkler; Andreas Sellmer; Ute Möllmann
Journal:  Eur J Med Chem       Date:  2007-06-03       Impact factor: 6.514

10.  Synthesis and evaluation of non-dimeric HCV NS5A inhibitors.

Authors:  Franck Amblard; Hongwang Zhang; Longhu Zhou; Junxing Shi; Drew R Bobeck; James H Nettles; Satish Chavre; Tamara R McBrayer; Philip Tharnish; Tony Whitaker; Steven J Coats; Raymond F Schinazi
Journal:  Bioorg Med Chem Lett       Date:  2013-02-13       Impact factor: 2.823

View more
  1 in total

1.  Access to Bicyclo[4.2.0]octene Monomers To Explore the Scope of Alternating Ring-Opening Metathesis Polymerization.

Authors:  Lei Chen; Liqiang Li; Nicole S Sampson
Journal:  J Org Chem       Date:  2018-02-14       Impact factor: 4.354

  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.