ethyl (R)-2-(2-naphthamido)pent-4-ynoate | 884048-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl (R)-2-(2-naphthamido)pent-4-ynoate
• CAS: 884048-29-7
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: PQNNYUGNMHAEEW-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (R)-2-(2-naphthamido)pent-4-ynoate 在 (-)-α-蒎烯 、 dimethyl sulfide borane 、 乙醛 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-(4-(2-naphthamido)-5-ethoxy-5-oxopent-1-en-1-yl)boronic acid
  参考文献：
  名称：

  Structure-based design of novel human Pin1 inhibitors (II)

  摘要：

  Following the discovery of a novel series of phosphate-containing small molecular Pin1 inhibitors, the drug design strategy shifted to replacement of the phosphate group with an isostere with potential better pharmaceutical properties. The initial loss in potency of carboxylate analogs was likely due to weaker charge-charge interactions in the putative phosphate binding pocket and was subsequently recovered by structure-based optimization of ligand-protein interactions in the proline binding site, leading to the discovery of a sub-micromolar non-phosphate small molecular Pin1 inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.033
• 作为产物：
  描述：

  ethyl (2R)-2-aminopent-4-ynoate;hydrochloride 、 2-萘甲酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到ethyl (R)-2-(2-naphthamido)pent-4-ynoate
  参考文献：
  名称：

  Structure-based design of novel human Pin1 inhibitors (II)

  摘要：

  Following the discovery of a novel series of phosphate-containing small molecular Pin1 inhibitors, the drug design strategy shifted to replacement of the phosphate group with an isostere with potential better pharmaceutical properties. The initial loss in potency of carboxylate analogs was likely due to weaker charge-charge interactions in the putative phosphate binding pocket and was subsequently recovered by structure-based optimization of ligand-protein interactions in the proline binding site, leading to the discovery of a sub-micromolar non-phosphate small molecular Pin1 inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.033

文献信息

• [EN] BENZIMIDAZOLE OR INDOLE AMIDES AS INHIBITORS OF PIN1<br/>[FR] AMIDES DE BENZIMIDAZOLE OU D'INDOLE EN TANT QU'INHIBITEURS DE PIN1
  申请人：PFIZER

  公开号：WO2006040646A1

  公开（公告）日：2006-04-20

  The invention relates to compounds of the formula (1) and to pharmaceutically acceptable salts and solvates thereof, wherein the variables are defined herein. The invention also relates to methods of treating abnormal cell growth in mammals by administering the compounds of formula (1) and to pharmaceutical compositions for treating such disorders that contain the compounds of formula (1). The invention also relates to methods of preparing the compounds of formula (1).

  这项发明涉及公式（1）的化合物，以及其药学上可接受的盐和溶剂化合物，其中变量在此处定义。该发明还涉及通过给予公式（1）的化合物来治疗哺乳动物中的异常细胞生长的方法，以及用于治疗包含公式（1）化合物的这类疾病的药物组合物。该发明还涉及制备公式（1）化合物的方法。