Literature DB >> 19783449

Natural product leads for drug discovery: isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents.

Songpo Guo1, Suresh K Tipparaju, Scott D Pegan, Baojie Wan, Shunyan Mo, Jimmy Orjala, Andrew D Mesecar, Scott G Franzblau, Alan P Kozikowski.   

Abstract

Indolo[2,3-a]carbazole based inhibitors were synthesized from readily available indigo via a seven-step linear synthetic sequence with a moderate overall yield. The inhibitors were selectively and readily functionalized at the nitrogen on the indole portion of the carbazole unit. The synthesized analogs displayed moderate inhibitory activities toward Bacillus anthracis and Mycobacterium tuberculosis, indicating that indolo[2,3-a]carbazoles could serve as promising leads in the development of new drugs to combat anthrax and tuberculosis infections.

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Year:  2009        PMID: 19783449      PMCID: PMC2983099          DOI: 10.1016/j.bmc.2009.08.061

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


  13 in total

Review 1.  Isolation and synthesis of biologically active carbazole alkaloids.

Authors:  Hans-Joachim Knölker; Kethiri R Reddy
Journal:  Chem Rev       Date:  2002-11       Impact factor: 60.622

Review 2.  Indolocarbazole natural products: occurrence, biosynthesis, and biological activity.

Authors:  César Sánchez; Carmen Méndez; José A Salas
Journal:  Nat Prod Rep       Date:  2006-10-19       Impact factor: 13.423

3.  Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.

Authors:  L Collins; S G Franzblau
Journal:  Antimicrob Agents Chemother       Date:  1997-05       Impact factor: 5.191

4.  Production and biological activity of rebeccamycin, a novel antitumor agent.

Authors:  J A Bush; B H Long; J J Catino; W T Bradner; K Tomita
Journal:  J Antibiot (Tokyo)       Date:  1987-05       Impact factor: 2.649

5.  Syntheses and biological activities of rebeccamycin analogues with uncommon sugars.

Authors:  Guisheng Zhang; Jie Shen; Hao Cheng; Lizhi Zhu; Lanyan Fang; Sanzhong Luo; Mark T Muller; Gun Eui Lee; Lijun Wei; Yuguo Du; Duxin Sun; Peng George Wang
Journal:  J Med Chem       Date:  2005-04-07       Impact factor: 7.446

6.  A new alkaloid AM-2282 OF Streptomyces origin. Taxonomy, fermentation, isolation and preliminary characterization.

Authors:  S Omura; Y Iwai; A Hirano; A Nakagawa; J Awaya; H Tsuchya; Y Takahashi; R Masuma
Journal:  J Antibiot (Tokyo)       Date:  1977-04       Impact factor: 2.649

7.  Cytotoxic, antiviral indolocarbazoles from a blue-green alga belonging to the Nostocaceae.

Authors:  G Knübel; L K Larsen; R E Moore; I A Levine; G M Patterson
Journal:  J Antibiot (Tokyo)       Date:  1990-10       Impact factor: 2.649

8.  Synthesis of N-protected staurosporinones.

Authors:  Yasuhiro Wada; Hideo Nagasaki; Masao Tokuda; Kazuhiko Orito
Journal:  J Org Chem       Date:  2007-02-20       Impact factor: 4.354

9.  In pursuit of natural product leads: synthesis and biological evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and its analogues: discovery of N-(2-benzoxazol-2-ylphenyl)benzamides as novel antileishmanial chemotypes.

Authors:  Suresh K Tipparaju; Sipak Joyasawal; Marco Pieroni; Marcel Kaiser; Reto Brun; Alan P Kozikowski
Journal:  J Med Chem       Date:  2008-12-11       Impact factor: 7.446

10.  Combined directed ortho and remote metalation-cross-coupling strategies. General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid.

Authors:  Xiongwei Cai; Victor Snieckus
Journal:  Org Lett       Date:  2004-07-08       Impact factor: 6.005

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  5 in total

Review 1.  Chemodiversity in freshwater and terrestrial cyanobacteria - a source for drug discovery.

Authors:  George E Chlipala; Shunyan Mo; Jimmy Orjala
Journal:  Curr Drug Targets       Date:  2011-10       Impact factor: 3.465

2.  Synthesis and structure-activity relationships of lansine analogues as antileishmanial agents.

Authors:  Marco Pieroni; Sisay Girmay; Dianqing Sun; Rajnish Sahu; Babu L Tekwani; Ghee T Tan
Journal:  ChemMedChem       Date:  2012-09-17       Impact factor: 3.466

3.  Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis.

Authors:  Nicholas A Isley; Sebastian Dobarco; Bruce H Lipshutz
Journal:  Green Chem       Date:  2014-01-02       Impact factor: 10.182

4.  Cytotoxic Effect of a Novel Synthesized Carbazole Compound on A549 Lung Cancer Cell Line.

Authors:  Refilwe P Molatlhegi; Alisa Phulukdaree; Krishnan Anand; Robert M Gengan; Charlette Tiloke; Anil A Chuturgoon
Journal:  PLoS One       Date:  2015-07-02       Impact factor: 3.240

5.  Spectral Analysis and Crystal Structures of 4-(4-Methylphenyl)-6-Phenyl-2,3,3a, 4-Tetrahydro-1H-Pyrido[3,2,1-jk]Carbazole and 4-(4-Methoxyphenyl)-6-Phenyl-2,3,3a, 4-Tetrahydro-1H-Pyrido[3,2,1-jk]Carbazole.

Authors:  J Kalyana Sundar; S Natarajan; S Chitra; Nidhin Paul; P Manisankar; S Muthusubramanian; J Suresh
Journal:  ISRN Org Chem       Date:  2011-04-17
  5 in total

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