Literature DB >> 19586033

Synthesis and evaluation of 3-aroylindoles as anticancer agents: metabolite approach.

Yu-Shan Wu1, Mohane Selvaraj Coumar, Jang-Yang Chang, Hsu-Yi Sun, Fu-Ming Kuo, Ching-Chuan Kuo, Ying-Jun Chen, Chi-Yen Chang, Chia-Ling Hsiao, Jing-Ping Liou, Ching-Ping Chen, Hsien-Tsung Yao, Yi-Kun Chiang, Uan-Kang Tan, Chiung-Tong Chen, Chang-Ying Chu, Su-Ying Wu, Teng-Kuang Yeh, Chin-Yu Lin, Hsing-Pang Hsieh.   

Abstract

BPR0L075 (2) is a potential anticancer drug candidate designed from Combretastatin A-4 (1) based on the bioisosterism principle. Metabolites of 2, proposed from in vitro human microsome studies, were synthesized, leading to the identification of metabolite-derived analogue 10 with 40-350 pM potency against various cancer cell lines. Insights gained from the major inactive metabolite of 2 led to the development of 29, with better pharmacokinetics and improved potency in the tumor xenograft model than 2.

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Year:  2009        PMID： 19586033     DOI： 10.1021/jm900060s

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


  11 in total

1.  Synthesis of a 2-aryl-3-aroyl indole salt (OXi8007) resembling combretastatin A-4 with application as a vascular disrupting agent.

Authors:  Mallinath B Hadimani; Matthew T Macdonough; Anjan Ghatak; Tracy E Strecker; Ramona Lopez; Madhavi Sriram; Benson L Nguyen; John J Hall; Raymond J Kessler; Anupama R Shirali; Li Liu; Charles M Garner; George R Pettit; Ernest Hamel; David J Chaplin; Ralph P Mason; Mary Lynn Trawick; Kevin G Pinney
Journal:  J Nat Prod       Date:  2013-09-09       Impact factor: 4.050

2.  Esterase-activated release of naproxen from supramolecular nanofibres.

Authors:  Martin Conda-Sheridan; Sungsoo S Lee; Adam T Preslar; Samuel I Stupp
Journal:  Chem Commun (Camb)       Date:  2014-11-18       Impact factor: 6.222

3.  Investigations on the 4-quinolone-3-carboxylic acid motif part 5: modulation of the physicochemical profile of a set of potent and selective cannabinoid-2 receptor ligands through a bioisosteric approach.

Authors:  Claudia Mugnaini; Stefania Nocerino; Valentina Pedani; Serena Pasquini; Andrea Tafi; Maria De Chiaro; Luca Bellucci; Massimo Valoti; Francesca Guida; Livio Luongo; Stefania Dragoni; Alessia Ligresti; Avraham Rosenberg; Daniele Bolognini; Maria Grazia Cascio; Roger G Pertwee; Ruin Moaddel; Sabatino Maione; Vincenzo Di Marzo; Federico Corelli
Journal:  ChemMedChem       Date:  2012-03-02       Impact factor: 3.466

4.  Identification, synthesis, and biological evaluation of the metabolites of 3-amino-6-(3'-aminopropyl)-5H-indeno[1,2-c]isoquinoline-5,11-(6H)dione (AM6-36), a promising rexinoid lead compound for the development of cancer chemotherapeutic and chemopreventive agents.

Authors:  Lian Chen; Martin Conda-Sheridan; P V Narasimha Reddy; Andrew Morrell; Eun-Jung Park; Tamara P Kondratyuk; John M Pezzuto; Richard B van Breemen; Mark Cushman
Journal:  J Med Chem       Date:  2012-06-19       Impact factor: 7.446

5.  Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties.

Authors:  Bernard L Flynn; Gurmit S Gill; Damian W Grobelny; Jason H Chaplin; Dharam Paul; Annabell F Leske; Tina C Lavranos; David K Chalmers; Susan A Charman; Edmund Kostewicz; David M Shackleford; Julia Morizzi; Ernest Hamel; M Katherine Jung; Gabriel Kremmidiotis
Journal:  J Med Chem       Date:  2011-08-05       Impact factor: 7.446

Review 6.  The Molecular Diversity of 1H-Indole-3-Carbaldehyde Derivatives and Their Role in Multicomponent Reactions.

Authors:  Ghodsi Mohammadi Ziarani; Samira Hasani; Fatemeh Mohajer; Rajender S Varma; Fatemeh Rafiee
Journal:  Top Curr Chem (Cham)       Date:  2022-04-25

7.  Phase I Dose-Escalation Study of SCB01A, a Microtubule Inhibitor with Vascular Disrupting Activity, in Patients with Advanced Solid Tumors.

Authors:  Her-Shyong Shiah; Nai-Jung Chiang; Chia-Chi Lin; Chia-Jui Yen; Hui-Jen Tsai; Shang-Yin Wu; Wu-Chou Su; Kwang-Yu Chang; Ching-Chiung Wang; Jang-Yang Chang; Li-Tzong Chen
Journal:  Oncologist       Date:  2020-12-18

8.  Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2.

Authors:  Noah F Fine Nathel; Tejas K Shah; Sarah M Bronner; Neil K Garg
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

9.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

10.  A General and Scalable Synthesis of Polysubstituted Indoles.

Authors:  David Tejedor; Raquel Diana-Rivero; Fernando García-Tellado
Journal:  Molecules       Date:  2020-11-28       Impact factor: 4.411
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