Literature DB >> 19307118

Synthesis of boronic acid derivatives of tyropeptin: proteasome inhibitors.

Takumi Watanabe1, Isao Momose, Masatoshi Abe, Hikaru Abe, Ryuichi Sawa, Yoji Umezawa, Daishiro Ikeda, Yoshikazu Takahashi, Yuzuru Akamatsu.   

Abstract

Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro.

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Year:  2009        PMID: 19307118     DOI: 10.1016/j.bmcl.2009.02.117

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


  6 in total

Review 1.  Boron chemicals in diagnosis and therapeutics.

Authors:  Bhaskar C Das; Pritam Thapa; Radha Karki; Caroline Schinke; Sasmita Das; Suman Kambhampati; Sushanta K Banerjee; Peter Van Veldhuizen; Amit Verma; Louis M Weiss; Todd Evans
Journal:  Future Med Chem       Date:  2013-04       Impact factor: 3.808

2.  Design, syntheses, and evaluation of Taspase1 inhibitors.

Authors:  Jeong Tae Lee; David Y Chen; Zhimou Yang; Alexander D Ramos; James J-D Hsieh; Matthew Bogyo
Journal:  Bioorg Med Chem Lett       Date:  2009-07-10       Impact factor: 2.823

3.  Structural optimization, biological evaluation, and application of peptidomimetic prostate specific antigen inhibitors.

Authors:  Maya B Kostova; D Marc Rosen; Ying Chen; Ronnie C Mease; Samuel R Denmeade
Journal:  J Med Chem       Date:  2013-06-04       Impact factor: 7.446

4.  Antitumor effects of tyropeptin-boronic acid derivatives: New proteasome inhibitors.

Authors:  Isao Momose; Hikaru Abe; Takumi Watanabe; Shun-ichi Ohba; Kanami Yamazaki; Shingo Dan; Takao Yamori; Tohru Masuda; Akio Nomoto
Journal:  Cancer Sci       Date:  2014-10-21       Impact factor: 6.716

5.  Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Authors:  Grace E Hubbell; Jetze J Tepe
Journal:  RSC Chem Biol       Date:  2020-09-16

Review 6.  The Boron Advantage: The Evolution and Diversification of Boron's Applications in Medicinal Chemistry.

Authors:  Katia Messner; Billy Vuong; Geoffrey K Tranmer
Journal:  Pharmaceuticals (Basel)       Date:  2022-02-22
  6 in total

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