(3S)-ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate | 722550-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (3S)-ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate
• 英文别名: (3S)-Ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate；ethyl (3S)-3-(1,3-benzodioxol-5-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate
• CAS: 722550-06-3
• 化学式: C₂₀H₂₃NO₅S
• 分子量: 389.472
• InChiKey: VCBZISSSMJMEQV-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S)-ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate 在 lithium hydroxide 、 三乙酰氧基硼氢化钠 作用下， 生成 (S)-3-(benzo[d][1,3]dioxol-5-yl)-4-(2-(4-(4-(pyrrolidin-1-yl)pyridin-2-ylamino)butyl)thiazol-4-yl)butanoic acid
  参考文献：
  名称：

  Synthesis of 2,5-thiazole butanoic acids as potent and selective αvβ3 integrin receptor antagonists with improved oral pharmacokinetic properties

  摘要：

  We describe a series of 2,5 thiazole containing compounds, which are potent antagonists of the integrin alpha(V)beta(3) and show selectivity relative to the other integrins, such as alpha(IIB)beta(3) and alpha(V)beta(6). These analogs were demonstrated to have high bioavailability relative to other relative heterocyclic analogs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.017
• 作为产物：
  描述：

  3-<3,4-Methylendioxy-phenyl>-glutarsaeure-anhydrid 在 盐酸 、 N-甲基吲哚酮 、 phosphate buffer 、 四丙基高钌酸铵 、 草酰氯 、 Chirazyme L-2 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 140.0h， 生成 (3S)-ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-oxobutyl)-1,3-thiazol-4-yl]butanoate
  参考文献：
  名称：

  Synthesis of 2,5-thiazole butanoic acids as potent and selective αvβ3 integrin receptor antagonists with improved oral pharmacokinetic properties

  摘要：

  We describe a series of 2,5 thiazole containing compounds, which are potent antagonists of the integrin alpha(V)beta(3) and show selectivity relative to the other integrins, such as alpha(IIB)beta(3) and alpha(V)beta(6). These analogs were demonstrated to have high bioavailability relative to other relative heterocyclic analogs. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.017

文献信息

• [EN] THIAZOLE COMPOUNDS AS INTEGRIN RECEPTOR ANTAGONISTS DERIVATIVES<br/>[FR] COMPOSES DE THIAZOLE EN TANT QUE DERIVES D'ANTAGONISTES DES RECEPTEURS DE L'INTEGRINE
  申请人：PHARMACIA CORP

  公开号：WO2004058760A1

  公开（公告）日：2004-07-15

  The present invention relates to pharmaceutical compositions comprising compounds of the Formula (I), and methods of selectively inhibiting or antagonizing the ανβ3 and/or the ανβ5 integrin without significantly inhibiting the ανβ6 integrin.

  本发明涉及包含式(I)化合物的药物组合物，以及选择性抑制或拮抗ανβ3和/或ανβ5整合素而不显著抑制ανβ6整合素的方法。
• Thiazole compounds as integrin receptor antagonists derivatives
  申请人：Wendt A. John

  公开号：US20050004189A1

  公开（公告）日：2005-01-06

  The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the α v β 3 and/or the α v β 5 integrin without significantly inhibiting the α v β 6 integrin.

  本发明涉及一类由式I表示或其药学上可接受的盐所表示的化合物，包括式I化合物的制药组合物，以及选择性抑制或拮抗αvβ3和/或αvβ5整合素而不显著抑制αvβ6整合素的方法。
• Synthesis of 2,5-thiazole butanoic acids as potent and selective αvβ3 integrin receptor antagonists with improved oral pharmacokinetic properties
  作者：John A. Wendt、Hongwei Wu、Heather G. Stenmark、Mark L. Boys、Victoria L. Downs、Thomas D. Penning、Barbara B. Chen、Yaping Wang、Tiffany Duffin、Mary Beth Finn、Jeffery L. Keene、V. Wayne Engleman、Sandra K. Freeman、Melanie L. Hanneke、Kristen E. Shannon、Maureen A. Nickols、Christina N. Steininger、Marissa Westlin、Jon A. Klover、William Westlin、G. Allen Nickols、Mark A. Russell

  DOI：10.1016/j.bmcl.2005.11.017

  日期：2006.2

  We describe a series of 2,5 thiazole containing compounds, which are potent antagonists of the integrin alpha(V)beta(3) and show selectivity relative to the other integrins, such as alpha(IIB)beta(3) and alpha(V)beta(6). These analogs were demonstrated to have high bioavailability relative to other relative heterocyclic analogs. (c) 2005 Elsevier Ltd. All rights reserved.