3-acryloylamino-benzoic acid tert-butyl ester | 1268152-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-acryloylamino-benzoic acid tert-butyl ester
• 英文别名: Tert-butyl 3-(prop-2-enoylamino)benzoate
• CAS: 1268152-51-7
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: DPTFXKVMDLFCOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acryloylamino-benzoic acid tert-butyl ester 在 氨 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 24.5h， 生成 3-(3-amino-2-hydroxy-propionylamino)-benzoic acid tert-butyl ester
  参考文献：
  名称：

  Investigation of α-phenylnorstatine and α-benzylnorstatine as transition state isostere motifs in the search for new BACE-1 inhibitors

  摘要：

  Inhibition of the BACE-1 protease enzyme has over the recent decade developed into a promising drug strategy for Alzheimer therapy. In this report, more than 20 new BACE-1 protease inhibitors based on alpha-phenylnorstatine, alpha-benzylnorstatine, iso-serine, and beta-alanine moieties have been prepared. The inhibitors were synthesized by applying Fmoc solid phase methodology and evaluated for their inhibitory properties. The most potent inhibitor, tert-alcohol containing (R)-12 (IC50 = 0.19 mu M) was co-crystallized in the active site of the BACE-1 protease, furnishing a novel binding mode in which the N-terminal amine makes a hydrogen bond to one of the catalytic aspartic acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.042
• 作为产物：
  描述：

  3-氨基苯甲酸叔丁酯 、 丙烯酰氯 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到3-acryloylamino-benzoic acid tert-butyl ester
  参考文献：
  名称：

  Investigation of α-phenylnorstatine and α-benzylnorstatine as transition state isostere motifs in the search for new BACE-1 inhibitors

  摘要：

  Inhibition of the BACE-1 protease enzyme has over the recent decade developed into a promising drug strategy for Alzheimer therapy. In this report, more than 20 new BACE-1 protease inhibitors based on alpha-phenylnorstatine, alpha-benzylnorstatine, iso-serine, and beta-alanine moieties have been prepared. The inhibitors were synthesized by applying Fmoc solid phase methodology and evaluated for their inhibitory properties. The most potent inhibitor, tert-alcohol containing (R)-12 (IC50 = 0.19 mu M) was co-crystallized in the active site of the BACE-1 protease, furnishing a novel binding mode in which the N-terminal amine makes a hydrogen bond to one of the catalytic aspartic acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.042

文献信息

• Thiazolidinones and the use therof as polo-like kinase inhibitors
  申请人：Schwede Wolfgang

  公开号：US20060079503A1

  公开（公告）日：2006-04-13

  Thiazolidones of general formula I in which R 1 , R 2 , R 3 , X and Y have the meanings that are indicated in the description, their production and use as inhibitors of polo-like kinases (PLK) for treating various diseases as well as intermediate products for the production of thiazolidones are described.

  本文描述了通式I的噻唑烷酮，其中R1、R2、R3、X和Y的含义如描述中所示，它们的生产和用途作为极化样激酶（PLK）的抑制剂，用于治疗各种疾病，以及用于生产噻唑烷酮的中间体。
• Investigation of α-phenylnorstatine and α-benzylnorstatine as transition state isostere motifs in the search for new BACE-1 inhibitors
  作者：Fredrik Wångsell、Patrik Nordeman、Jonas Sävmarker、Rikard Emanuelsson、Katarina Jansson、Jimmy Lindberg、Åsa Rosenquist、Bertil Samuelsson、Mats Larhed

  DOI：10.1016/j.bmc.2010.11.042

  日期：2011.1

  Inhibition of the BACE-1 protease enzyme has over the recent decade developed into a promising drug strategy for Alzheimer therapy. In this report, more than 20 new BACE-1 protease inhibitors based on alpha-phenylnorstatine, alpha-benzylnorstatine, iso-serine, and beta-alanine moieties have been prepared. The inhibitors were synthesized by applying Fmoc solid phase methodology and evaluated for their inhibitory properties. The most potent inhibitor, tert-alcohol containing (R)-12 (IC50 = 0.19 mu M) was co-crystallized in the active site of the BACE-1 protease, furnishing a novel binding mode in which the N-terminal amine makes a hydrogen bond to one of the catalytic aspartic acids. (C) 2010 Elsevier Ltd. All rights reserved.