(R)-2-(2-naphthamido)-5-phenylpent-4-ynoic acid | 1227832-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-(2-naphthamido)-5-phenylpent-4-ynoic acid
• 英文别名: (2R)-2-(naphthalene-2-carbonylamino)-5-phenylpent-4-ynoic acid
• CAS: 1227832-76-9
• 化学式: C₂₂H₁₇NO₃
• 分子量: 343.382
• InChiKey: IIZVJSCXCNYCFJ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到(R)-2-(2-naphthamido)-5-phenylpent-4-ynoic 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

文献信息

• PIN1 inhibitors for use in the prevention and/or treatment of theileriosis, and related applications
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2845588A1

  公开（公告）日：2015-03-11

  The present invention relates to the field of lymphoproliferative Theileriosis, and more particularly to peptidyl-prolyl cis/trans isomerase 1 (PIN1) inhibitors for their use in the prevention and/or treatment of lymphoproliferative Theileriosis. The invention further encompasses screening, diagnostic and therapeutic methods, as well as to kits useful for carrying out said methods.

  本发明涉及淋巴细胞增生性肉芽肿病领域，尤其是肽基脯氨酰顺式/反式异构酶1（PIN1）抑制剂，用于预防和/或治疗淋巴细胞增生性肉芽肿病。本发明还包括筛选、诊断和治疗方法，以及用于实施上述方法的试剂盒。
• [EN] PIN1 INHIBITORS FOR USE IN THE PREVENTION AND/OR TREATMENT OF THEILERIOSIS, AND RELATED APPLICATIONS<br/>[FR] INHIBITEURS DE PIN1 UTILISÉS DANS LA PRÉVENTION ET/OU LE TRAITEMENT DE LA THEILÉRIOSE, ET APPLICATIONS S'Y RAPPORTANT
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2015032998A1

  公开（公告）日：2015-03-12

  The present invention relates to the field of lymphoproliferative Theileriosis, and more particularly to peptidyl-prolyl cis/trans isomerase 1 (PIN1) inhibitors for their use in the prevention and/or treatment of lymphoproliferative Theileriosis. The invention further encompasses screening, diagnostic and therapeutic methods, as well as to kits useful for carrying out said methods.
• Structure-based design of novel human Pin1 inhibitors (II)
  作者：Liming Dong、Joseph Marakovits、Xinjun Hou、Chuangxing Guo、Samantha Greasley、Eleanor Dagostino、RoseAnn Ferre、M. Catherine Johnson、Eugenia Kraynov、James Thomson、Ved Pathak、Brion W. Murray

  DOI：10.1016/j.bmcl.2010.02.033

  日期：2010.4

  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.