N-[(2R)-1-{[(2S,3R,4S)-1-环己基-4-环丙基-3,4-二羟基-2-丁烷基]氨基}-1-氧代-3-(1,3-噻唑-4-基)-2-丙基]-1H-苯并咪唑-2-甲酰胺 | 134362-79-1

• 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
• 中文名称: N-[(2R)-1-{[(2S,3R,4S)-1-环己基-4-环丙基-3,4-二羟基-2-丁烷基]氨基}-1-氧代-3-(1,3-噻唑-4-基)-2-丙基]-1H-苯并咪唑-2-甲酰胺
• 英文名称: Ro 0437526
• 英文别名: Ro 0437626；Ro-0437626；Ro0437626；N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]-2-oxo-1-(thiazol-4-ylmethyl)ethyl]-1H-benzo[D]imidazole-2-carboxamide；N-[(2R)-1-[[(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-1H-benzimidazole-2-carboxamide
• CAS: 134362-79-1
• 化学式: C₂₇H₃₅N₅O₄S
• 分子量: 525.672
• InChiKey: JHRSGCIIDRWHCD-UARRHKHWSA-N

物化性质

• 溶解度：
  在 DMSO 中溶解度为 100 mM，在乙醇中溶解度为 100 mM

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-cyclohexyl-3-(S)-ethoxycarbonylamino-2-(R)-hydroxybutyric acid 在 氢氧化钾 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙酰氧基硼氢化钠 、 三乙胺 、 三氟乙酸 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 44.75h， 生成 N-[(2R)-1-{[(2S,3R,4S)-1-环己基-4-环丙基-3,4-二羟基-2-丁烷基]氨基}-1-氧代-3-(1,3-噻唑-4-基)-2-丙基]-1H-苯并咪唑-2-甲酰胺
  参考文献：
  名称：

  Discovery and synthesis of a novel and selective drug-like P2X1 antagonist

  摘要：

  Although there is extensive literature to indicate that many different types of P2 purinoceptors are present in the lower urinary tract, the physiological role of these receptors in micturition is still uncertain. In part, this uncertainty has been caused by a lack of P2 subtype selective ligands. In this paper we report the discovery, gram scale synthesis, and binding results for 1, the first potent, drug-like, selective P2X(1) receptor antagonist described. Compound 1 was shown to be more than 30-fold selective over other purinergic receptor subtypes. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2005.04.049

文献信息

• NOVEL CELLULAR TARGETS FOR HIV INFECTION
  申请人：ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY

  公开号：US20150057331A1

  公开（公告）日：2015-02-26

  Methods and compositions are provided for treating HIV infection and for inhibiting HIV infection, and for identifying purinergic receptor antagonists or Panx 1 hemi-channel blockers useful therefor. The invention provides a method of treating a mammalian subject having an HIV infection, or suspected of having been exposed to HIV, comprising administering to the mammalian subject an amount of (i) an antagonist of a Panx 1 hemichannel, or (ii) of an inhibitor of a purinergic receptor, effective to inhibit (a) HIV fusion with a target cell, or (b) HIV replication, or (c) HIV entry into a target cell, or two or more of (a), (b) and (c).
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF PULMONARY ARTERIAL HYPERTENSION
  申请人：The Regents of the University of Michigan

  公开号：US20190160029A1

  公开（公告）日：2019-05-30

  Provided herein are compositions and methods for the treatment of pulmonary arterial hypertension. In particular, compositions and methods are provided that address purinergic dysregulation, the causes thereof, and/or the effect of downstream targets.
• Discovery and synthesis of a novel and selective drug-like P2X1 antagonist
  作者：S. Jaime-Figueroa、R. Greenhouse、F. Padilla、M.P. Dillon、J.R. Gever、A.P.D.W. Ford

  DOI：10.1016/j.bmcl.2005.04.049

  日期：2005.7

  Although there is extensive literature to indicate that many different types of P2 purinoceptors are present in the lower urinary tract, the physiological role of these receptors in micturition is still uncertain. In part, this uncertainty has been caused by a lack of P2 subtype selective ligands. In this paper we report the discovery, gram scale synthesis, and binding results for 1, the first potent, drug-like, selective P2X(1) receptor antagonist described. Compound 1 was shown to be more than 30-fold selective over other purinergic receptor subtypes. (c) 2005 Published by Elsevier Ltd.