Ethyl 3(S)-(quinolin-3-yl)-3-(2-oxo-3(R)-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-pyrrolidin-1-yl)-propionate | 227939-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: Ethyl 3(S)-(quinolin-3-yl)-3-(2-oxo-3(R)-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-pyrrolidin-1-yl)-propionate
• 英文别名: ethyl (3S)-3-[(3R)-2-oxo-3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrrolidin-1-yl]-3-quinolin-3-ylpropanoate
• CAS: 227939-65-3
• 化学式: C₂₉H₃₄N₄O₃
• 分子量: 486.614
• InChiKey: COQXIYQRQNWJFD-RLWLMLJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 3(S)-(quinolin-3-yl)-3-(2-oxo-3(R)-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-pyrrolidin-1-yl)-propionate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (3S)-3-{(3R)-2-oxo-3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrrolidin-1-yl}-3-quinolin-3-ylpropanoic acid
  参考文献：
  名称：

  Non-peptide α v β 3 antagonists: Identification of potent, chain-shortened RGD mimetics that incorporate a central pyrrolidinone constraint

  摘要：

  Antagonists of the integrin receptor alpha(nu)beta(3) are expected to have utility in the treatment of osteoporosis through inhibition of bone resorption. A series of potent, chain-shortened, pyrrolidinone-containing alpha(nu)beta(3) receptor antagonists is described. Two sets of diasteromeric pairs of high-affinity antagonists demonstrated marked differences in log P values, which translated into differing dog pharmacokinctic properties. One member of this set was demonstrated to be effective in reducing bone resorption in rats. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.055
• 作为产物：
  描述：

  5-乙酰基戊酸 在 palladium on activated charcoal 氢气 、 三乙酰氧基硼氢化钠 、 对甲苯磺酸 、 臭氧 、 三乙胺 、 DL-脯氨酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 Ethyl 3(S)-(quinolin-3-yl)-3-(2-oxo-3(R)-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-pyrrolidin-1-yl)-propionate
  参考文献：
  名称：

  Non-peptide α v β 3 antagonists: Identification of potent, chain-shortened RGD mimetics that incorporate a central pyrrolidinone constraint

  摘要：

  Antagonists of the integrin receptor alpha(nu)beta(3) are expected to have utility in the treatment of osteoporosis through inhibition of bone resorption. A series of potent, chain-shortened, pyrrolidinone-containing alpha(nu)beta(3) receptor antagonists is described. Two sets of diasteromeric pairs of high-affinity antagonists demonstrated marked differences in log P values, which translated into differing dog pharmacokinctic properties. One member of this set was demonstrated to be effective in reducing bone resorption in rats. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.055

文献信息

• US6066648A
  申请人：——

  公开号：US6066648A

  公开（公告）日：2000-05-23
• US6268378B1
  申请人：——

  公开号：US6268378B1

  公开（公告）日：2001-07-31
• Non-peptide α v β 3 antagonists: Identification of potent, chain-shortened RGD mimetics that incorporate a central pyrrolidinone constraint
  作者：James J Perkins、L.T Duong、Carmen Fernandez-Metzler、George D Hartman、Donald B Kimmel、Chih-Tai Leu、Joseph J Lynch、Thomayant Prueksaritanont、Gideon A Rodan、Sevgi B Rodan、Mark E Duggan、Robert S Meissner

  DOI：10.1016/j.bmcl.2003.09.055

  日期：2003.12

  Antagonists of the integrin receptor alpha(nu)beta(3) are expected to have utility in the treatment of osteoporosis through inhibition of bone resorption. A series of potent, chain-shortened, pyrrolidinone-containing alpha(nu)beta(3) receptor antagonists is described. Two sets of diasteromeric pairs of high-affinity antagonists demonstrated marked differences in log P values, which translated into differing dog pharmacokinctic properties. One member of this set was demonstrated to be effective in reducing bone resorption in rats. (C) 2003 Elsevier Ltd. All rights reserved.