(1R,2S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,2-dihydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester | 173008-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,2-dihydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester
• 英文别名: ethyl (1R,2S)-5-[tert-butyl(diphenyl)silyl]oxy-1,2-dihydroxy-3,4-dihydro-1H-naphthalene-2-carboxylate
• CAS: 173008-82-7
• 化学式: C₂₉H₃₄O₅Si
• 分子量: 490.671
• InChiKey: UTHBPDUXWLLPGP-UHSQPCAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,2-dihydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S)-5-[tert-butyl(diphenyl)silyl]oxy-2-hydroxy-3,4-dihydro-1H-naphthalen-2-yl]methyl N,N-diphenylcarbamate
  参考文献：
  名称：

  Discovery of diphenylcarbamate derivatives as highly potent and selective IP receptor agonists: Orally active prostacyclin mimetics. Part 3

  摘要：

  The new classes of diphenylcarbamate derivatives with a tetrahydronaphthalene skeleton as highly potent and selective IP agonists have been discovered. The optimized diphenylcarbamate type compound FK-788: (R)-4 exhibited potent antiaggregative potency with an IC50 of 18 nM and high binding affinity for the human recombinant IP receptor with K-i values of 20 nM and selectivity for human IP over all other members of the human prostanoid receptor family. Compound (R)-4 was shown to exhibit good pharmacokinetic properties in rats and dogs, and also good bioavailability in healthy volunteers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.047
• 作为产物：
  描述：

  2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthalene 在 AD-mix-α 、 水 作用下， 以 叔丁醇 为溶剂， 生成 (S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester 、 (R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester 、 (1S,2R)-1,2-dihydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene 、 (1R,2S)-5-(tert-Butyl-diphenyl-silanyloxy)-1,2-dihydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of diphenylcarbamate derivatives as highly potent and selective IP receptor agonists: Orally active prostacyclin mimetics. Part 3

  摘要：

  The new classes of diphenylcarbamate derivatives with a tetrahydronaphthalene skeleton as highly potent and selective IP agonists have been discovered. The optimized diphenylcarbamate type compound FK-788: (R)-4 exhibited potent antiaggregative potency with an IC50 of 18 nM and high binding affinity for the human recombinant IP receptor with K-i values of 20 nM and selectivity for human IP over all other members of the human prostanoid receptor family. Compound (R)-4 was shown to exhibit good pharmacokinetic properties in rats and dogs, and also good bioavailability in healthy volunteers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.047

文献信息

• Discovery of diphenylcarbamate derivatives as highly potent and selective IP receptor agonists: Orally active prostacyclin mimetics. Part 3
  作者：Kouji Hattori、Akira Tanaka、Osamu Okitsu、Seiichiro Tabuchi、Kiyoshi Taniguchi、Mie Nishio、Satoshi Koyama、Masahide Higaki、Jiro Seki、Kazuo Sakane

  DOI：10.1016/j.bmcl.2005.04.047

  日期：2005.6

  The new classes of diphenylcarbamate derivatives with a tetrahydronaphthalene skeleton as highly potent and selective IP agonists have been discovered. The optimized diphenylcarbamate type compound FK-788: (R)-4 exhibited potent antiaggregative potency with an IC50 of 18 nM and high binding affinity for the human recombinant IP receptor with K-i values of 20 nM and selectivity for human IP over all other members of the human prostanoid receptor family. Compound (R)-4 was shown to exhibit good pharmacokinetic properties in rats and dogs, and also good bioavailability in healthy volunteers. (c) 2005 Elsevier Ltd. All rights reserved.