Literature DB >> 23180892

Rapid, Microwave-Assisted Organic Synthesis of Selective (V600E)BRAF Inhibitors for Preclinical Cancer Research.

Jason R Buck1, Sam Saleh, Md Imam Uddin, H Charles Manning.   

Abstract

We report a dramatically improved total synthesis of two highly selective (V600E)BRAF inhibitors, PLX4720 and PLX4032, that leverages microwave-assisted organic synthesis (MAOS). Compared with previously reported approaches, our novel MAOS method significantly reduces overall reaction time without compromising yield. In addition to providing a gram-scale route to these compounds for preclinical oncology research, we anticipate this approach could accelerate the synthesis of azaindoles in high-throughput, library-based formats.

Entities:  

Year:  2012        PMID： 23180892      PMCID： PMC3501741          DOI： 10.1016/j.tetlet.2012.05.137

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  20 in total

Review 1.  Acquired and intrinsic BRAF inhibitor resistance in BRAF V600E mutant melanoma.

Authors:  Inna V Fedorenko; Kim H T Paraiso; Keiran S M Smalley
Journal:  Biochem Pharmacol       Date:  2011-05-25       Impact factor: 5.858

Review 2.  Guilty as charged: B-RAF is a human oncogene.

Authors:  Mathew J Garnett; Richard Marais
Journal:  Cancer Cell       Date:  2004-10       Impact factor: 31.743

Review 3.  Microwave-assisted synthesis in water as solvent.

Authors:  Doris Dallinger; C Oliver Kappe
Journal:  Chem Rev       Date:  2007-04-24       Impact factor: 60.622

Review 4.  Targeted inhibition of BRAF kinase: opportunities and challenges for therapeutics in melanoma.

Authors:  Rolando Pérez-Lorenzo; Bin Zheng
Journal:  Biosci Rep       Date:  2012-02       Impact factor: 3.840

5.  Constitutive mitogen-activated protein kinase activation in melanoma is mediated by both BRAF mutations and autocrine growth factor stimulation.

Authors:  Kapaettu Satyamoorthy; Gang Li; Michelle R Gerrero; Marcia S Brose; Patricia Volpe; Barbara L Weber; Patricia Van Belle; David E Elder; Meenhard Herlyn
Journal:  Cancer Res       Date:  2003-02-15       Impact factor: 12.701

6.  The RAF inhibitor PLX4032 inhibits ERK signaling and tumor cell proliferation in a V600E BRAF-selective manner.

Authors:  Eric W Joseph; Christine A Pratilas; Poulikos I Poulikakos; Madhavi Tadi; Weiqing Wang; Barry S Taylor; Ensar Halilovic; Yogindra Persaud; Feng Xing; Agnes Viale; James Tsai; Paul B Chapman; Gideon Bollag; David B Solit; Neal Rosen
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-28       Impact factor: 11.205

7.  Discovery of a selective inhibitor of oncogenic B-Raf kinase with potent antimelanoma activity.

Authors:  James Tsai; John T Lee; Weiru Wang; Jiazhong Zhang; Hanna Cho; Shumeye Mamo; Ryan Bremer; Sam Gillette; Jun Kong; Nikolas K Haass; Katrin Sproesser; Ling Li; Keiran S M Smalley; Daniel Fong; Yong-Liang Zhu; Adhirai Marimuthu; Hoa Nguyen; Billy Lam; Jennifer Liu; Ivana Cheung; Julie Rice; Yoshihisa Suzuki; Catherine Luu; Calvin Settachatgul; Rafe Shellooe; John Cantwell; Sung-Hou Kim; Joseph Schlessinger; Kam Y J Zhang; Brian L West; Ben Powell; Gaston Habets; Chao Zhang; Prabha N Ibrahim; Peter Hirth; Dean R Artis; Meenhard Herlyn; Gideon Bollag
Journal:  Proc Natl Acad Sci U S A       Date:  2008-02-19       Impact factor: 11.205

8.  Mutations of the BRAF gene in human cancer.

Authors:  Helen Davies; Graham R Bignell; Charles Cox; Philip Stephens; Sarah Edkins; Sheila Clegg; Jon Teague; Hayley Woffendin; Mathew J Garnett; William Bottomley; Neil Davis; Ed Dicks; Rebecca Ewing; Yvonne Floyd; Kristian Gray; Sarah Hall; Rachel Hawes; Jaime Hughes; Vivian Kosmidou; Andrew Menzies; Catherine Mould; Adrian Parker; Claire Stevens; Stephen Watt; Steven Hooper; Rebecca Wilson; Hiran Jayatilake; Barry A Gusterson; Colin Cooper; Janet Shipley; Darren Hargrave; Katherine Pritchard-Jones; Norman Maitland; Georgia Chenevix-Trench; Gregory J Riggins; Darell D Bigner; Giuseppe Palmieri; Antonio Cossu; Adrienne Flanagan; Andrew Nicholson; Judy W C Ho; Suet Y Leung; Siu T Yuen; Barbara L Weber; Hilliard F Seigler; Timothy L Darrow; Hugh Paterson; Richard Marais; Christopher J Marshall; Richard Wooster; Michael R Stratton; P Andrew Futreal
Journal:  Nature       Date:  2002-06-09       Impact factor: 49.962

9.  Patterns of somatic mutation in human cancer genomes.

Authors:  Christopher Greenman; Philip Stephens; Raffaella Smith; Gillian L Dalgliesh; Christopher Hunter; Graham Bignell; Helen Davies; Jon Teague; Adam Butler; Claire Stevens; Sarah Edkins; Sarah O'Meara; Imre Vastrik; Esther E Schmidt; Tim Avis; Syd Barthorpe; Gurpreet Bhamra; Gemma Buck; Bhudipa Choudhury; Jody Clements; Jennifer Cole; Ed Dicks; Simon Forbes; Kris Gray; Kelly Halliday; Rachel Harrison; Katy Hills; Jon Hinton; Andy Jenkinson; David Jones; Andy Menzies; Tatiana Mironenko; Janet Perry; Keiran Raine; Dave Richardson; Rebecca Shepherd; Alexandra Small; Calli Tofts; Jennifer Varian; Tony Webb; Sofie West; Sara Widaa; Andy Yates; Daniel P Cahill; David N Louis; Peter Goldstraw; Andrew G Nicholson; Francis Brasseur; Leendert Looijenga; Barbara L Weber; Yoke-Eng Chiew; Anna DeFazio; Mel F Greaves; Anthony R Green; Peter Campbell; Ewan Birney; Douglas F Easton; Georgia Chenevix-Trench; Min-Han Tan; Sok Kean Khoo; Bin Tean Teh; Siu Tsan Yuen; Suet Yi Leung; Richard Wooster; P Andrew Futreal; Michael R Stratton
Journal:  Nature       Date:  2007-03-08       Impact factor: 49.962

10.  BRAF mutation is a powerful prognostic factor in advanced and recurrent colorectal cancer.

Authors:  T Yokota; T Ura; N Shibata; D Takahari; K Shitara; M Nomura; C Kondo; A Mizota; S Utsunomiya; K Muro; Y Yatabe
Journal:  Br J Cancer       Date:  2011-02-01       Impact factor: 7.640
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  7 in total

1.  Microwave-assisted, one-pot reaction of 7-azaindoles and aldehydes: a facile route to novel di-7-azaindolylmethanes.

Authors:  Md Imam Uddin; Jason R Buck; Michael L Schulte; Dewei Tang; Samir A Saleh; Yiu-Yin Cheung; Joel Harp; H Charles Manning
Journal:  Tetrahedron Lett       Date:  2014-01-01       Impact factor: 2.415

2.  Preclinical imaging evaluation of novel TSPO-PET ligand 2-(5,7-Diethyl-2-(4-(2-[(18)F]fluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide ([ (18)F]VUIIS1008) in glioma.

Authors:  Dewei Tang; Michael L Nickels; M Noor Tantawy; Jason R Buck; H Charles Manning
Journal:  Mol Imaging Biol       Date:  2014-12       Impact factor: 3.488

3.  Non-Invasive Glutamine PET Reflects Pharmacological Inhibition of BRAFV600E In Vivo.

Authors:  Michael L Schulte; Matthew R Hight; Gregory D Ayers; Qi Liu; Yu Shyr; M Kay Washington; H Charles Manning
Journal:  Mol Imaging Biol       Date:  2017-06       Impact factor: 3.488

4.  A peptide-based positron emission tomography probe for in vivo detection of caspase activity in apoptotic cells.

Authors:  Matthew R Hight; Yiu-Yin Cheung; Michael L Nickels; Eric S Dawson; Ping Zhao; Samir Saleh; Jason R Buck; Dewei Tang; M Kay Washington; Robert J Coffey; H Charles Manning
Journal:  Clin Cancer Res       Date:  2014-02-26       Impact factor: 12.531

5.  3'-Deoxy-3'-18F-fluorothymidine PET predicts response to (V600E)BRAF-targeted therapy in preclinical models of colorectal cancer.

Authors:  Eliot T McKinley; R Adam Smith; Ping Zhao; Allie Fu; Samir A Saleh; Md Imam Uddin; M Kay Washington; Robert J Coffey; H Charles Manning
Journal:  J Nucl Med       Date:  2013-01-22       Impact factor: 10.057

6.  Facile synthesis of SSR180575 and discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[(18)F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide, a potent pyridazinoindole ligand for PET imaging of TSPO in cancer.

Authors:  Yiu-Yin Cheung; Michael L Nickels; Dewei Tang; Jason R Buck; H Charles Manning
Journal:  Bioorg Med Chem Lett       Date:  2014-08-08       Impact factor: 2.823

7.  3'-Deoxy-3'-[18F]-Fluorothymidine PET imaging reflects PI3K-mTOR-mediated pro-survival response to targeted therapy in colorectal cancer.

Authors:  Eliot T McKinley; Ping Zhao; Robert J Coffey; M Kay Washington; H Charles Manning
Journal:  PLoS One       Date:  2014-09-23       Impact factor: 3.240
  7 in total

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