3-[(S)-2-(4,5-Diphenyl-oxazol-2-yl)-cyclohex-2-enylmethyl]-phenol | 652976-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[(S)-2-(4,5-Diphenyl-oxazol-2-yl)-cyclohex-2-enylmethyl]-phenol
• 英文别名: 3-[[(1S)-2-(4,5-Diphenyl-2-oxazolyl)-2-cyclohexen-1-yl]methyl]phenol；3-[[(1S)-2-(4,5-diphenyl-1,3-oxazol-2-yl)cyclohex-2-en-1-yl]methyl]phenol
• CAS: 652976-37-9
• 化学式: C₂₈H₂₅NO₂
• 分子量: 407.512
• InChiKey: JZGPILNRGRMGHO-QHCPKHFHSA-N

物化性质

• 沸点：
  590.7±52.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[(S)-2-(4,5-Diphenyl-oxazol-2-yl)-cyclohex-2-enylmethyl]-phenol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 Sodium [3-[[(1S)-2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl]phenoxy]acetate
  参考文献：
  名称：

  A simple stereoselective synthesis and biological evaluation of FR181157: orally active prostacyclin mimetic

  摘要：

  Synthetic method of novel prostaglandin (PG) mimetic: FR181175 without PG skeleton are described. The key to success is creation of a chiral epoxide using Sharpless AD reaction with high ee yield. FR181157 shows high potency and agonist efficacy at the IP receptor and has good bioavailability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.054
• 作为产物：
  描述：

  (1R,2S)-1-(4,5-diphenyl-oxazol-2-yl)-1,2-epoxycyclohexane 在 三溴化硼 、 对甲苯磺酸 、 copper(I) bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 3-[(S)-2-(4,5-Diphenyl-oxazol-2-yl)-cyclohex-2-enylmethyl]-phenol
  参考文献：
  名称：

  A simple stereoselective synthesis and biological evaluation of FR181157: orally active prostacyclin mimetic

  摘要：

  Synthetic method of novel prostaglandin (PG) mimetic: FR181175 without PG skeleton are described. The key to success is creation of a chiral epoxide using Sharpless AD reaction with high ee yield. FR181157 shows high potency and agonist efficacy at the IP receptor and has good bioavailability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.054

文献信息

• Discovery of Diphenyloxazole and Nδ-Z-Ornithine Derivatives as Highly Potent and Selective Human Prostaglandin EP₄ Receptor Antagonists
  作者：Kouji Hattori、Akira Tanaka、Naoaki Fujii、Hisashi Takasugi、Yoshiyuki Tenda、Masayuki Tomita、Shoko Nakazato、Keiko Nakano、Yasuko Kato、Yutaka Kono、Hidetsugu Murai、Kazuo Sakane

  DOI：10.1021/jm050085k

  日期：2005.5.1

  Two novel classes of diphenyloxazole and Ndelta-Z-ornithine derivatives as highly potent and selective EP(4) antagonists have been discovered. The optimized diphenyloxzole 8 and Ndelta-Z-ornithine 11 effectively competed with [(3)H]PGE(2) binding to human recombinant EP(4), with K(i) values of 0.30 nM and 0.91 nM, respectively, and were selective for all members of the human prostanoid receptor family

  已发现两类新型的二苯基恶唑和Ndelta-Z-鸟氨酸衍生物作为高效和选择性的EP（4）拮抗剂。优化的二苯并恶唑8和Ndelta-Z-鸟氨酸11有效竞争与[（3）H] PGE（2）绑定到人类重组EP（4），K（i）值分别为0.30 nM和0.91 nM，分别为对人类前列腺素受体家族的所有成员具有选择性。8已显示在大鼠和狗中表现出良好的药代动力学特性，并且对体外PGE（2）促进的IgE合成具有强大的抑制活性。