(6aR)-7-(phenylcarbamoyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid | 1330059-95-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (6aR)-7-(phenylcarbamoyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
• CAS: 1330059-95-4
• 化学式: C₂₂H₁₉N₃O₃
• 分子量: 373.411
• InChiKey: BBADQCZEBHYXRQ-JANGERMGSA-N

物化性质

• 沸点：
  730.4±60.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.43
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 (6aR)-7-(phenylcarbamoyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid 生成 (6aR,9R)-9-(4-methylpiperazine-1-carbonyl)-N-phenyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxamide 、
  参考文献：
  名称：

  Special ergolines efficiently inhibit the chemokine receptor CXCR3 in blood

  摘要：

  The structure-activity relationship of highly potent special ergolines which selectively block the chemokine receptor CXCR3 is reported. The most potent compounds showed IC50 values below 10 nM in both ligand binding and Ca2+-mobilization assays. However, these compounds were poorly active in an assay that measures receptor occupancy in blood. Introduction of polar substituents led to derivatives with IC50 values below 10 nM in this assay. Among them was compound 11a which showed both a favorable PK profile and cross reactivity with rodent CXCR3 making it a promising tool compound to further explore the role of CXCR3 in animal models. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.070
• 作为产物：
  描述：

  9,10-Didehydroergoline-8-carboxylic acid methyl ester 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (6aR)-7-(phenylcarbamoyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
  参考文献：
  名称：

  Special ergolines efficiently inhibit the chemokine receptor CXCR3 in blood

  摘要：

  The structure-activity relationship of highly potent special ergolines which selectively block the chemokine receptor CXCR3 is reported. The most potent compounds showed IC50 values below 10 nM in both ligand binding and Ca2+-mobilization assays. However, these compounds were poorly active in an assay that measures receptor occupancy in blood. Introduction of polar substituents led to derivatives with IC50 values below 10 nM in this assay. Among them was compound 11a which showed both a favorable PK profile and cross reactivity with rodent CXCR3 making it a promising tool compound to further explore the role of CXCR3 in animal models. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.070