2-(R)-amino-N-[(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R),3-(S)-dihydroxypropyl)amino]-3-thiazol-4-yl-propionamide | 134362-77-9

• 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: 2-(R)-amino-N-[(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R),3-(S)-dihydroxypropyl)amino]-3-thiazol-4-yl-propionamide
• CAS: 134362-77-9
• 化学式: C₁₉H₃₁N₃O₃S
• 分子量: 381.539
• InChiKey: DKOVBLRZBDPGKK-VSZNYVQBSA-N

物化性质

• 沸点：
  661.3±55.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  108.47
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(R)-amino-N-[(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R),3-(S)-dihydroxypropyl)amino]-3-thiazol-4-yl-propionamide 、 1H-苯并咪唑-2-甲酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以51%的产率得到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
• 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 36.75h， 生成 2-(R)-amino-N-[(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R),3-(S)-dihydroxypropyl)amino]-3-thiazol-4-yl-propionamide
  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