2-[2-[(2R)-2-[(3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl]ethylsulfanyl]-1,3-thiazole-5-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-[(2R)-2-[(3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl]ethylsulfanyl]-1,3-thiazole-5-carboxylic acid
• 化学式: C₂₁H₂₄N₂O₄S₂
• 分子量: 432.565
• InChiKey: JJRCQFOJQGXVPO-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(2-((2R)-2-(t-butyldimethylsilyloxymethyl)-5-oxopyrrolidin-1-yl)ethylthio)-1,3-thiazole-4-carboxylic acid ethyl ester 在 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 水 、 三氧化硫吡啶 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙酸乙酯 为溶剂， 生成 2-[2-[(2R)-2-[(3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-oxopyrrolidin-1-yl]ethylsulfanyl]-1,3-thiazole-5-carboxylic acid
  参考文献：
  名称：

  Discovery of a novel EP2/EP4 dual agonist with high subtype-selectivity

  摘要：

  A series of gamma-lactam prostaglandin E(1) analogs bearing a 16-phenyl moiety in the omega-chain and aryl moiety in the alpha-chain were synthesized and biologically evaluated. Among the tested compounds, gamma-lactam PGE analog 3 designed as a structural hybrid of 1 and 2 was discovered as the most optimized EP2/EP4 dual agonist with excellent subtype-selectivity (K(i) values: mEP2 = 9.3 nM, mEP4 = 0.41 nM). A structure-activity relationship study is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.109

文献信息

• Discovery of a novel EP2/EP4 dual agonist with high subtype-selectivity
  作者：Tohru Kambe、Toru Maruyama、Masayuki Nakano、Yoshihiko Nakai、Tadahiro Yoshida、Naoki Matsunaga、Hiroji Oida、Akira Konaka、Takayuki Maruyama、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmcl.2011.10.109

  日期：2012.1

  A series of gamma-lactam prostaglandin E(1) analogs bearing a 16-phenyl moiety in the omega-chain and aryl moiety in the alpha-chain were synthesized and biologically evaluated. Among the tested compounds, gamma-lactam PGE analog 3 designed as a structural hybrid of 1 and 2 was discovered as the most optimized EP2/EP4 dual agonist with excellent subtype-selectivity (K(i) values: mEP2 = 9.3 nM, mEP4 = 0.41 nM). A structure-activity relationship study is presented. (C) 2011 Elsevier Ltd. All rights reserved.