Literature DB >> 11909708

The synthesis and characterization of BMS-204352 (MaxiPost) and related 3-fluorooxindoles as openers of maxi-K potassium channels.

Piyasena Hewawasam1, Valentin K Gribkoff, Yadagiri Pendri, Steven I Dworetzky, Nicholas A Meanwell, Eduardo Martinez, Christopher G Boissard, Debra J Post-Munson, Joanne T Trojnacki, Krishnaswamy Yeleswaram, Lorraine M Pajor, Jay Knipe, Qi Gao, Robert Perrone, John E Starrett.   

Abstract

3-Aryl-3-fluorooxindoles can be efficiently synthesized in two steps by the addition of an aryl Grignard to an isatin, followed by treatment with DAST. Oxindole 1 (BMS-204352; MaxiPost) can be isolated using chiral HPLC or prepared by employing chiral resolution. Cloned maxi-K channels are opened by 1, which demonstrates a brain/plasma ratio >9 in rats.

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Year:  2002        PMID: 11909708     DOI: 10.1016/s0960-894x(02)00101-4

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  14 in total

Review 1.  Potassium channels and neurovascular coupling.

Authors:  Kathryn M Dunn; Mark T Nelson
Journal:  Circ J       Date:  2010-03-16       Impact factor: 2.993

2.  Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.

Authors:  Max Moskowitz; Kaluvu Balaraman; Christian Wolf
Journal:  J Org Chem       Date:  2018-01-22       Impact factor: 4.354

Review 3.  Computational models of neuronal biophysics and the characterization of potential neuropharmacological targets.

Authors:  Michele Ferrante; Kim T Blackwell; Michele Migliore; Giorgio A Ascoli
Journal:  Curr Med Chem       Date:  2008       Impact factor: 4.530

4.  Organocatalytic Asymmetric Synthesis of α-Oxetanyl and α-Azetidinyl Tertiary Alkyl Fluorides and Chlorides.

Authors:  Ransheng Ding; Christian Wolf
Journal:  Org Lett       Date:  2018-01-23       Impact factor: 6.005

5.  Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-27       Impact factor: 15.336

6.  Novel Thioxothiazolo[3,4-a]quinazolin-5(4H)-one Derivatives as BKCa Channel Activators for Urinary Incontinence.

Authors:  Eun Jung Bae; Heeji Jo; Seong Soon Kim; Dae-Seop Shin; Jung Yoon Yang; Myung Ae Bae; Pyeonghwa Jeong; Chul-Seung Park; Jin Hee Ahn
Journal:  ACS Med Chem Lett       Date:  2022-06-21       Impact factor: 4.632

7.  Stereoselective Synthesis of 3,3'-Bisindolines by Organocatalytic Michael Additions of Fluorooxindole Enolates to Isatylidene Malononitriles in Aqueous Solution.

Authors:  Kaluvu Balaraman; Ransheng Ding; Christian Wolf
Journal:  Adv Synth Catal       Date:  2017-09-22       Impact factor: 5.837

8.  Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles.

Authors:  Ryan A Altman; Alan M Hyde; Xiaohua Huang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-06-28       Impact factor: 15.419

9.  Synthetic Studies of 3-(3-Fluorooxindol-3-yl)-l-alanine.

Authors:  Tomoya Fujiwara; Bin Yin; Meixiang Jin; Kenneth L Kirk; Yoshio Takeuchi
Journal:  J Fluor Chem       Date:  2008       Impact factor: 2.050

Review 10.  α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds.

Authors:  Mei Wang; Wei Wang; Dashan Li; Wen-Jing Wang; Rui Zhan; Li-Dong Shao
Journal:  Nat Prod Bioprospect       Date:  2021-06-07
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