High-throughput synthesis and optimization of thrombin inhibitors via urazole α-addition and Michael addition

被引：39
|
作者：
Boatman, PD
Urban, J
Nguyen, M
Qabar, M
Kahn, M
机构：
[1] Molecumetics, Bellevue, WA 98005 USA
[2] Pacific NW Res Inst, Seattle, WA 98122 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 08期
关键词：
D O I：
10.1016/S0960-894X(03)00155-0
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A novel alpha-addition of propiolates to urazoles followed by Michael addition of a variety of nucleophiles has been developed for rapid production and optimization of peptidomimetic drug leads. This technology has produced a number of highly potent and selective inhibitors of the serine protease, thrombin. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1445 / 1449
页数：5
相关论文
共 50 条
  • [1] Optimization of an automated IS addition system for use in high-throughput quantitative DBS analysis
    Abu-Rabie, Paul
    Spooner, Neil
    Chowdhry, Babur Z.
    Pullen, Frank S.
    BIOANALYSIS, 2015, 7 (21) : 2763 - 2775
  • [2] Accelerated and Concerted Aza-Michael Addition and SuFEx Reaction in Microdroplets in Unitary and High-Throughput Formats
    Ghosh, Jyotirmoy
    Mendoza, Joshua
    Cooks, R. Graham
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (50)
  • [3] Rotaxanes via Michael addition
    Reuter, C
    Vögtle, F
    ORGANIC LETTERS, 2000, 2 (05) : 593 - 595
  • [4] Identification and Optimization of a Novel Class of HIV Fusion Inhibitors via High-Throughput Synthesis & Screening of Peptide Arrays
    Schepens, W.
    Schaaper, W.
    Timmerman, P.
    Buyck, C.
    Slootstra, J.
    Goethals, O.
    Stoops, B.
    Kriek, N.
    Amssoms, K.
    Benschop, J.
    Wu, J.
    Dams, G.
    Van Emelen, K.
    Thuring, J. W.
    Malcolm, B.
    JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S142 - S142
  • [5] Extremely simple and practical synthesis of (±)-vertinolide via the Michael addition
    Takabe, K
    Mase, N
    Nomoto, M
    Daicho, M
    Tauchi, T
    Yoda, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (04): : 500 - 502
  • [6] CONVENIENT SYNTHESIS OF GAMMA-LACTAMS VIA MICHAEL ADDITION
    CHATTERJEE, BG
    SAHU, DP
    JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (19): : 3162 - 3165
  • [7] Synthesis of γ-lactam lignans via aza-Michael addition
    Dorbec, M
    Florent, JC
    Monneret, C
    Rager, MN
    Bertounesque, E
    SYNLETT, 2006, (04) : 591 - 594
  • [8] A concise synthesis of (-)-dihydrospirotryprostatin B via tandem Michael addition
    Song, Hengqian
    Song, Jiacheng
    Yan, Lihong
    He, Weigang
    Wang, Pengyan
    Xu, Yuanzhen
    Wei, Hongbo
    Xie, Weiqing
    TETRAHEDRON LETTERS, 2021, 85
  • [9] Total Synthesis of (±)-Spiroaxillarone A via a Reversible Sulfa- Michael Addition
    Long, Xianwen
    Zhang, Min
    Yang, Xiaodong
    Deng, Jun
    ORGANIC LETTERS, 2022, 24 (06) : 1303 - 1307
  • [10] Stereocontrolled total synthesis of (±)-culmorin via the intramolecular double Michael addition
    Takasu, K
    Mizutani, S
    Noguchi, M
    Makita, K
    Ihara, M
    ORGANIC LETTERS, 1999, 1 (03) : 391 - 393
12345