tert-butyl N-[[7-chloro-4-oxo-2-(pyrrolidine-1-carbonyl)-1H-quinoline-3-carbonyl]-[(1S)-1-pyridin-2-ylethyl]amino]carbamate | 681270-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl N-[[7-chloro-4-oxo-2-(pyrrolidine-1-carbonyl)-1H-quinoline-3-carbonyl]-[(1S)-1-pyridin-2-ylethyl]amino]carbamate
• CAS: 681270-22-4
• 化学式: C₂₇H₃₀ClN₅O₅
• 分子量: 540.019
• InChiKey: JNNZCPSEPYRVHO-INIZCTEOSA-N

物化性质

• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲烷磺酸 、 tert-butyl N-[[7-chloro-4-oxo-2-(pyrrolidine-1-carbonyl)-1H-quinoline-3-carbonyl]-[(1S)-1-pyridin-2-ylethyl]amino]carbamate 以 四氢呋喃 为溶剂， 以56%的产率得到7-Chloro-2-((S)-1-pyridin-2-yl-ethyl)-2,3-dihydro-5H-pyridazino[4,5-b]quinoline-1,4,10-trione; compound with methanesulfonic acid
  参考文献：
  名称：

  Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain

  摘要：

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.

  DOI：

  10.1021/jm060212s
• 作为产物：
  描述：

  3-carbomethoxy-2-pyrrolidinocarbamide-7-chloro-4-hydroxyquinoline 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.08h， 生成 tert-butyl N-[[7-chloro-4-oxo-2-(pyrrolidine-1-carbonyl)-1H-quinoline-3-carbonyl]-[(1S)-1-pyridin-2-ylethyl]amino]carbamate
  参考文献：
  名称：

  Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain

  摘要：

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.

  DOI：

  10.1021/jm060212s

文献信息

• Synthesis of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5- b ]quinoline-1,4,10(5 H )-triones as NMDA glycine-site antagonists
  作者：Dean G. Brown、Rebecca A. Urbanek、Thomas M. Bare、Frances M. McLaren、Carey L. Horchler、Megan Murphy、Gary B. Steelman、James R. Empfield、Janet M. Forst、Keith J. Herzog、Wenhua Xiao、Martin C. Dyroff、Chi-Ming C. Lee、Shephali Trivedi、Kathy L. Neilson、Richard A. Keith

  DOI：10.1016/s0960-894x(03)00750-9

  日期：2003.10

  Several members of the 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones (2) have been identified as being potent and selective NMDA glycine-site antagonists. Increasing size of the alkyl substituent on the alpha-carbon led to a progressive decrease in binding affinity. Some of these analogues possess improved drug-like properties such as cellular permeability, solubility and oral absorption. (C) 2003 Elsevier Ltd. All rights reserved.