ethyl 4-{(3S)-(pyridin-2-ylamino)piperidin-1-yl}benzoate | 334618-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl 4-{(3S)-(pyridin-2-ylamino)piperidin-1-yl}benzoate
• 英文别名: ethyl 4-[(3S)-3-(pyridin-2-ylamino)piperidin-1-yl]benzoate
• CAS: 334618-89-2
• 化学式: C₁₉H₂₃N₃O₂
• 分子量: 325.411
• InChiKey: LLROGEKJYKIFSG-INIZCTEOSA-N

物化性质

• 沸点：
  519.2±50.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-{(3S)-(pyridin-2-ylamino)piperidin-1-yl}benzoate 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 (2S)-2-(benzenesulfonamido)-3-[[4-[(3S)-3-(pyridin-2-ylamino)piperidin-1-yl]benzoyl]amino]propanoic acid
  参考文献：
  名称：

  Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part III: Synthesis of potent antagonists with αvβ3/αIIbβ3 dual activity and improved water solubility

  摘要：

  In order to optimize our novel integrin alpha(v)beta(3)/alpha(IIb)beta(3) dual antagonists, spatial screening at the N-terminus was performed. The alpha(v)beta(3) antagonistic activity varied depending on the space that was occupied by the N-terminus, but high potency against alpha(IIb)beta(3) was well maintained. The (3S)-aminopiperidine analogue had the strongest activity against alpha(v)beta(3), and the S isomer at piperidine was more potent than the R isomer. Compounds selected on the basis of SAR analysis of a novel lead compound showed acceptable early absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles and sufficient water solubility for use as infusion drugs. Docking studies with the alpha(v)beta(3) receptor were performed to confirm the SAR findings. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.055
• 作为产物：
  描述：

  L-鸟氨酸盐酸盐 在 palladium diacetate lithium aluminium tetrahydride 、 氯化亚砜 、 碳酸氢钠 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 甲苯 为溶剂， 反应 28.5h， 生成 ethyl 4-{(3S)-(pyridin-2-ylamino)piperidin-1-yl}benzoate
  参考文献：
  名称：

  Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part III: Synthesis of potent antagonists with αvβ3/αIIbβ3 dual activity and improved water solubility

  摘要：

  In order to optimize our novel integrin alpha(v)beta(3)/alpha(IIb)beta(3) dual antagonists, spatial screening at the N-terminus was performed. The alpha(v)beta(3) antagonistic activity varied depending on the space that was occupied by the N-terminus, but high potency against alpha(IIb)beta(3) was well maintained. The (3S)-aminopiperidine analogue had the strongest activity against alpha(v)beta(3), and the S isomer at piperidine was more potent than the R isomer. Compounds selected on the basis of SAR analysis of a novel lead compound showed acceptable early absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles and sufficient water solubility for use as infusion drugs. Docking studies with the alpha(v)beta(3) receptor were performed to confirm the SAR findings. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.055

文献信息

• SUBSTITUTED BISINDOLYLMALEIMIDES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1242409A2

  公开（公告）日：2002-09-25
• [EN] SUBSTITUTED PYRROLES<br/>[FR] PYRROLES SUBSTITUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2001046178A2

  公开（公告）日：2001-06-28

  Disclosed are substituted pyrroles having formula (I), wherein R?1, R2, R1' and R2'¿ are as defined in the claims and in the description. These compounds and their pharmaceutically acceptable salts are useful in the treatment and/or control of cell proliferative disorders, in particular cancer. Also disclosed are pharmaceutical compositions containing the foregoing compounds.
• Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part III: Synthesis of potent antagonists with αvβ3/αIIbβ3 dual activity and improved water solubility
  作者：Minoru Ishikawa、Yukiko Hiraiwa、Dai Kubota、Masaki Tsushima、Takashi Watanabe、Shoichi Murakami、Shokichi Ouchi、Keiichi Ajito

  DOI：10.1016/j.bmc.2005.10.055

  日期：2006.4

  In order to optimize our novel integrin alpha(v)beta(3)/alpha(IIb)beta(3) dual antagonists, spatial screening at the N-terminus was performed. The alpha(v)beta(3) antagonistic activity varied depending on the space that was occupied by the N-terminus, but high potency against alpha(IIb)beta(3) was well maintained. The (3S)-aminopiperidine analogue had the strongest activity against alpha(v)beta(3), and the S isomer at piperidine was more potent than the R isomer. Compounds selected on the basis of SAR analysis of a novel lead compound showed acceptable early absorption, distribution, metabolism, excretion, and toxicity (ADMET) profiles and sufficient water solubility for use as infusion drugs. Docking studies with the alpha(v)beta(3) receptor were performed to confirm the SAR findings. (c) 2005 Elsevier Ltd. All rights reserved.