ethyl (S)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenoxy}acetate | 171045-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (S)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenoxy}acetate
• 英文别名: ethyl 2-[3-[[(1S)-2-(4,5-diphenyl-1,3-oxazol-2-yl)cyclohex-2-en-1-yl]methyl]phenoxy]acetate
• CAS: 171045-79-7
• 化学式: C₃₂H₃₁NO₄
• 分子量: 493.602
• InChiKey: RWGCRGCIOXFLTL-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (S)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenoxy}acetate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 生成 Sodium; {3-[(1S,2R)-2-(4,5-diphenyl-oxazol-2-yl)-cyclohexylmethyl]-phenoxy}-acetate
  参考文献：
  名称：

  Replacing the cyclohexene-linker of FR181157 leading to novel IP receptor agonists: Orally active prostacyclin mimetics. Part 6

  摘要：

  The synthesis and biological activity of novel derivatives of our previously reported IP receptor agonist FR181157 is described. SAR studies to replace the cyclohexene-linker of FR181157 led to the discovery of compound 1i (FR207845) as a potent non-prostanoid PGI(2) mimetic with good oral bioavailability. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.076
• 作为产物：
  描述：

  (1R,2S)-1-(4,5-diphenyl-oxazol-2-yl)-1,2-epoxycyclohexane 在 三溴化硼 、 potassium carbonate 、 对甲苯磺酸 、 copper(I) bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 ethyl (S)-{3-{[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

文献信息

• Oxazole compounds useful as PGE2 agonists and antagonists
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06245790B1

  公开（公告）日：2001-06-12

  Azole compounds of the formula: wherein R1 is lower alkyl substituted with carboxy, etc., R2 is hydrogen or lower alkyl, R3 is aryl, etc. R4 is aryl, etc. Q is  etc., and X is O, NH or S, and its salt, which are useful as medicament.

  Azole化合物具有以下公式： 其中R1是取代有羧基的低级烷基等， R2是氢或低级烷基， R3是芳基等。 R4是芳基等。 Q是  等，以及 X是O，NH或S， 及其盐，可用作药物。
• 4,5-diaryloxazole compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06297267B1

  公开（公告）日：2001-10-02

  A compound of the formula: wherein R1 is a hydrogen atom or a carboxy protective group, R2, R5, R6 and R7 are each a hydrogen atom or a hydroxy group, R3 and R4 are each a hydrogen atom, or are combined together to form an epoxy group or a single bond. R8 and R9 are each an optionally substituted aryl group, and X is a single bond or a methylene group, in addition to the above definitions. R2 and R3 may be combined together to form a single bond; provided that when R2, R5, R6 and R7 are each a hydrogen atom, then R3 and R4 are combined together to form an epoxy group; when R3 and R4 are combined together to form a single bond, then at least one of R2, R5, R6 and R7 is a hydroxy group and the others are hydrogen; and when R3 and R4 are each a hydrogen atom, then at least one of R2, R5, R6 and R7 is a hydroxy group and the others are hydrogen, and X is a methylene group, or its salt.

  一个化合物的化学式：其中R1是氢原子或羧基保护基，R2、R5、R6和R7分别是氢原子或羟基，R3和R4分别是氢原子，或结合在一起形成环氧基团或单键。R8和R9分别是可选择取代的芳基，X是一个单键或亚甲基，除了上述定义。R2和R3可以结合在一起形成单键；条件是当R2、R5、R6和R7分别是氢原子时，那么R3和R4结合在一起形成环氧基团；当R3和R4结合在一起形成单键时，那么R2、R5、R6和R7中至少有一个是羟基，其余是氢；当R3和R4分别是氢原子时，那么R2、R5、R6和R7中至少有一个是羟基，其余是氢，X是亚甲基，或其盐。
• Replacing the cyclohexene-linker of FR181157 leading to novel IP receptor agonists: Orally active prostacyclin mimetics. Part 6
  作者：Akira Tanaka、Kouji Hattori、Kiyoshi Taniguchi、Osamu Okitsu、Seiichiro Tabuchi、Mie Nishio、Yasunori Nagakura、Noriaki Maeda、Hidetsugu Murai、Jiro Seki

  DOI：10.1016/j.bmcl.2006.06.076

  日期：2006.9

  The synthesis and biological activity of novel derivatives of our previously reported IP receptor agonist FR181157 is described. SAR studies to replace the cyclohexene-linker of FR181157 led to the discovery of compound 1i (FR207845) as a potent non-prostanoid PGI(2) mimetic with good oral bioavailability. (c) 2006 Elsevier Ltd. All rights reserved.
• A simple stereoselective synthesis and biological evaluation of FR181157: orally active prostacyclin mimetic
  作者：Kouji Hattori、Seiichiro Tabuchi、Osamu Okitsu、Kiyoshi Taniguchi

  DOI：10.1016/j.bmcl.2003.09.054

  日期：2003.12

  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.