Literature DB >> 19385672

Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-Michael reaction.

Qiyan Lin1, David Meloni, Yongchun Pan, Michael Xia, James Rodgers, Stacey Shepard, Mei Li, Laurine Galya, Brian Metcalf, Tai-Yuen Yue, Pingli Liu, Jiacheng Zhou.   

Abstract

An enantioselective synthesis of INCB018424 via organocatalytic asymmetric aza-Michael addition of pyrazoles (16 or 20) to (E)-3-cyclopentylacrylaldehyde (23) using diarylprolinol silyl ether as the catalyst was developed. Michael adducts (R)-24 and (R)-27 were isolated in good yield and high ee and were readily converted to INCB018424.

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Year:  2009        PMID： 19385672     DOI： 10.1021/ol900350k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  18 in total

Review 1.  Recent advances in C-heteroatom bond forming by asymmetric Michael addition.

Authors:  Majid M Heravi; Parvin Hajiabbasi
Journal:  Mol Divers       Date:  2013-12-31       Impact factor: 2.943

2.  Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Nathan D Collett; Mrinmoy Saha; Rich G Carter
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

3.  Expedient enantioselective synthesis of cermizine D.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Rich G Carter
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

4.  Bifunctional cinchona alkaloid-squaramide-catalyzed highly enantioselective aza-Michael addition of indolines to α,β-unsaturated ketones.

Authors:  Arun K Ghosh; Bing Zhou
Journal:  Tetrahedron Lett       Date:  2013-07-03       Impact factor: 2.415

5.  Ruxolitinib induces autophagy in chronic myeloid leukemia cells.

Authors:  Bakiye Goker Bagca; Ozgun Ozalp; Cansu Caliskan Kurt; Zeynep Mutlu; Guray Saydam; Cumhur Gunduz; Cigir Biray Avci
Journal:  Tumour Biol       Date:  2015-08-23

6.  Organocatalytic enantioselective olefin aminofluorination.

Authors:  Chandrakumar Appayee; Stacey E Brenner-Moyer
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

Review 7.  The current status and the future of JAK2 inhibitors for the treatment of myeloproliferative diseases.

Authors:  Yasumichi Hitoshi; Nan Lin; Donald G Payan; Vadim Markovtsov
Journal:  Int J Hematol       Date:  2010-02-27       Impact factor: 2.490

8.  Preclinical characterization of the selective JAK1/2 inhibitor INCB018424: therapeutic implications for the treatment of myeloproliferative neoplasms.

Authors:  Alfonso Quintás-Cardama; Kris Vaddi; Phillip Liu; Taghi Manshouri; Jun Li; Peggy A Scherle; Eian Caulder; Xiaoming Wen; Yanlong Li; Paul Waeltz; Mark Rupar; Timothy Burn; Yvonne Lo; Jennifer Kelley; Maryanne Covington; Stacey Shepard; James D Rodgers; Patrick Haley; Hagop Kantarjian; Jordan S Fridman; Srdan Verstovsek
Journal:  Blood       Date:  2010-02-03       Impact factor: 22.113

9.  A restricted role for TYK2 catalytic activity in human cytokine responses revealed by novel TYK2-selective inhibitors.

Authors:  Sue J Sohn; Kathy Barrett; Anne Van Abbema; Christine Chang; Pawan Bir Kohli; Hidenobu Kanda; Janice Smith; Yingjie Lai; Aihe Zhou; Birong Zhang; Wenqian Yang; Karen Williams; Calum Macleod; Christopher A Hurley; Janusz J Kulagowski; Nicholas Lewin-Koh; Hart S Dengler; Adam R Johnson; Nico Ghilardi; Mark Zak; Jun Liang; Wade S Blair; Steven Magnuson; Lawren C Wu
Journal:  J Immunol       Date:  2013-07-26       Impact factor: 5.422

10.  Antiviral activity of bone morphogenetic proteins and activins.

Authors:  Lucy A Eddowes; Kinda Al-Hourani; Narayan Ramamurthy; Jamie Frankish; Hannah T Baddock; Cynthia Sandor; John D Ryan; Dahlene N Fusco; João Arezes; Eleni Giannoulatou; Sara Boninsegna; Stephane Chevaliez; Benjamin M J Owens; Chia Chi Sun; Paolo Fabris; Maria Teresa Giordani; Diego Martines; Slobodan Vukicevic; John Crowe; Herbert Y Lin; Jan Rehwinkel; Peter J McHugh; Marco Binder; Jodie L Babitt; Raymond T Chung; Matthew W Lawless; Andrew E Armitage; Caleb Webber; Paul Klenerman; Hal Drakesmith
Journal:  Nat Microbiol       Date:  2018-12-03       Impact factor: 17.745
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