benzyl (4S)-2-(3,5-dichlorophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate | 936949-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (4S)-2-(3,5-dichlorophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 936949-71-2
• 化学式: C₁₇H₁₃Cl₂NO₃
• 分子量: 350.201
• InChiKey: DLJMLNZLMRNIGQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-2-(3,5-dichlorophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl 2-(3,5-dichlorophenyl)-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Design, synthesis, and evaluation of oxazole transthyretin amyloidogenesis inhibitors

  摘要：

  Ten oxazoles bearing a C(4) carboxyl group were synthesized and evaluated as transthyretin (TTR) amyloid fibril inhibitors. Substituting aryls at the C(2) position of the oxazole ring reveals that a 3,5-dichlorophenyl substituent significantly reduced amyloidogenesis. The efficacy of these inhibitors was enhanced further by installing an ethyl, a propyl, or a CF3 group at the C(5) position. The CF3 substitution at C(5) also improves the TTR binding selectivity over all the other proteins in human blood. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.022
• 作为产物：
  描述：

  3,5-二氯苯甲酰氯 在 伯吉斯试剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 benzyl (4S)-2-(3,5-dichlorophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Design, synthesis, and evaluation of oxazole transthyretin amyloidogenesis inhibitors

  摘要：

  Ten oxazoles bearing a C(4) carboxyl group were synthesized and evaluated as transthyretin (TTR) amyloid fibril inhibitors. Substituting aryls at the C(2) position of the oxazole ring reveals that a 3,5-dichlorophenyl substituent significantly reduced amyloidogenesis. The efficacy of these inhibitors was enhanced further by installing an ethyl, a propyl, or a CF3 group at the C(5) position. The CF3 substitution at C(5) also improves the TTR binding selectivity over all the other proteins in human blood. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.022

文献信息

• Design, synthesis, and evaluation of oxazole transthyretin amyloidogenesis inhibitors
  作者：Hossein Razavi、Evan T. Powers、Hans E. Purkey、Sara L. Adamski-Werner、Kyle P. Chiang、Maria T.A. Dendle、Jeffery W. Kelly

  DOI：10.1016/j.bmcl.2004.12.022

  日期：2005.2

  Ten oxazoles bearing a C(4) carboxyl group were synthesized and evaluated as transthyretin (TTR) amyloid fibril inhibitors. Substituting aryls at the C(2) position of the oxazole ring reveals that a 3,5-dichlorophenyl substituent significantly reduced amyloidogenesis. The efficacy of these inhibitors was enhanced further by installing an ethyl, a propyl, or a CF3 group at the C(5) position. The CF3 substitution at C(5) also improves the TTR binding selectivity over all the other proteins in human blood. (C) 2004 Elsevier Ltd. All rights reserved.