(2S)-2-<4-(trans-(1S,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid | 83648-77-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-2-<4-(trans-(1S,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
• 英文别名: (S)-2-(4-(((1S,2R)-2-hydroxycyclopentyl)methyl)phenyl)propanoic acid；(2S)-2-[4-[[(1S,2R)-2-hydroxycyclopentyl]methyl]phenyl]propanoic acid
• CAS: 83648-77-5
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: SHAHPWSYJFYMRX-LEWSCRJBSA-N

物化性质

• 熔点：
  87-88 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  418.6±20.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-<4-(trans-(1S,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2S)-2-<4-(cis-(1S,2S)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
  参考文献：
  名称：

  HR1405-01, a Safe intravenous NSAID with superior anti-inflammatory and analgesic activities in preclinical trials

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114258
• 作为产物：
  描述：

  洛索洛芬 在 4-二甲氨基吡啶 、 1-环已基-2-吗啉乙基碳二亚胺对甲苯磺酸盐 、 sodium cyanoborohydride 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 (2S)-2-<4-(trans-(1S,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
  参考文献：
  名称：

  Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2

  摘要：

  Loxoprofen, its trans-alcohol and cis-alcohol metabolites were evaluated for selectivity of inhibition of COX-2 over COX-1. The (2S,1'R,2'S)-trans-alcohol derivative was found to be the most active metabolite and to be a potent and nonselective inhibitor of COX-2 and COX-1 in both enzyme and human whole blood assays. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.047

文献信息

• Synthesis of the eight possible optically active isomers of 2-(4-(2-hydroxycyclopentylmethyl)phenyl)propionic acid.
  作者：SHUNJI NARUTO、ATSUSUKE TERADA

  DOI：10.1248/cpb.31.4319

  日期：——

  A recently synthesized compound, (±)-2-[4-(2-oxocyclopentylmethyl) phenyl] propionic acid, had good anti-inflammatory and analgesic activities. One of the metabolites of this compound showed more potent prostaglandin synthetase inhibitory activity than the parent acid. For the structural determination and absolute configurational assignment of the metabolites, we synthesized the eight possible title alcohols and carried out stereochemical assignment of these alcohols.

  最近合成的一种化合物(±)-2-[4-(2-氧代环戊基甲基)苯基]丙酸具有良好的抗炎和镇痛活性。与母酸相比，该化合物的一种代谢物具有更强的前列腺素合成酶抑制活性。为了确定代谢物的结构和绝对构型分配，我们合成了 8 种可能的标题醇，并对这些醇进行了立体化学分配。
• TERADA, ATSUSUKE;MISAKA, EIICHI
  作者：TERADA, ATSUSUKE、MISAKA, EIICHI

  DOI：——

  日期：——
• NARUTO, SHUNJI;TERADA, ATSUSUKE, CHEM. AND PHARM. BULL., 1983, 31, N 12, 4319-4323
  作者：NARUTO, SHUNJI、TERADA, ATSUSUKE

  DOI：——

  日期：——
• Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2
  作者：Denis Riendeau、Myriam Salem、Angela Styhler、Marc Ouellet、Joseph A Mancini、Chun Sing Li

  DOI：10.1016/j.bmcl.2003.12.047

  日期：2004.3

  Loxoprofen, its trans-alcohol and cis-alcohol metabolites were evaluated for selectivity of inhibition of COX-2 over COX-1. The (2S,1'R,2'S)-trans-alcohol derivative was found to be the most active metabolite and to be a potent and nonselective inhibitor of COX-2 and COX-1 in both enzyme and human whole blood assays. (C) 2004 Elsevier Ltd. All rights reserved.
• HR1405-01, a Safe intravenous NSAID with superior anti-inflammatory and analgesic activities in preclinical trials
  作者：Hai Ye、Tian Lv、Tao Min、Di Mao、Xingran Chen、Boxiang Ding、Can Zhang

  DOI：10.1016/j.ejmech.2022.114258

  日期：2022.5