1-(3-hydroxyphenyl)-2-(β-(tert-butoxycarbonylamino)propionyl)-8-chloro-2,3,4,9-tetrahydrocarboline | 1236397-68-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(3-hydroxyphenyl)-2-(β-(tert-butoxycarbonylamino)propionyl)-8-chloro-2,3,4,9-tetrahydrocarboline
• CAS: 1236397-68-4
• 化学式: C₂₅H₂₈ClN₃O₄
• 分子量: 469.968
• InChiKey: JVRKXSLQFXUOQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxyphenyl)-2-(β-(tert-butoxycarbonylamino)propionyl)-8-chloro-2,3,4,9-tetrahydrocarboline 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以67%的产率得到1-(3-hydroxyphenyl)-2-(β-aminopropionyl)-8-chloro-1,2,3,4-tetrahydro-β-carboline hydrochloride
  参考文献：
  名称：

  Discovery of tetrahydro-β-carbolines as inhibitors of the mitotic kinesin KSP

  摘要：

  Inhibitors of kinesin spindle protein (KSP) are a promising class of anticancer agents that cause mitotic arrest in cells from a failure to form functional bipolar mitotic spindles. Here, we report the synthesis and biological evaluation of a novel series of tetrahydro-beta-carboline analogs based on the structure of the known KSP inhibitor HR22C16. Preferred compounds 11b, 12a and 19b were identified as potent inhibitors in a KSP ATPase assay with good anti-proliferative activity in A549 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.024
• 作为产物：
  描述：

  Boc-beta-丙氨酸 、 1-(3-hydroxyphenyl)-8-chloro-1,2,3,4-tetrahydro-β-carboline hydrochloride 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以72.7%的产率得到1-(3-hydroxyphenyl)-2-(β-(tert-butoxycarbonylamino)propionyl)-8-chloro-2,3,4,9-tetrahydrocarboline
  参考文献：
  名称：

  Discovery of tetrahydro-β-carbolines as inhibitors of the mitotic kinesin KSP

  摘要：

  Inhibitors of kinesin spindle protein (KSP) are a promising class of anticancer agents that cause mitotic arrest in cells from a failure to form functional bipolar mitotic spindles. Here, we report the synthesis and biological evaluation of a novel series of tetrahydro-beta-carboline analogs based on the structure of the known KSP inhibitor HR22C16. Preferred compounds 11b, 12a and 19b were identified as potent inhibitors in a KSP ATPase assay with good anti-proliferative activity in A549 cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.024