1-(3-hydroxyphenyl)-2-(α-(tert-butoxycarbonylamino)propionyl)-6-chloro-2,3,4,9-tetrahydrocarboline | 1236397-66-2

• 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-(α-(tert-butoxycarbonylamino)propionyl)-6-chloro-2,3,4,9-tetrahydrocarboline
• 英文别名: tert-butyl N-[1-[6-chloro-1-(3-hydroxyphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl]-1-oxopropan-2-yl]carbamate
• CAS: 1236397-66-2
• 化学式: C₂₅H₂₈ClN₃O₄
• 分子量: 469.968
• InChiKey: KSKXNDYUBGGFMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-hydroxyphenyl)-2-(α-(tert-butoxycarbonylamino)propionyl)-6-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54.1%的产率得到1-(3-hydroxyphenyl)-2-(α-aminopropionyl)-6-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：

  3-(6-chloro-2,3,4,4a,9,9a-hexahydro-1H-b-carbolin-1-yl)phenol hydrochloride 、 N-t-butyloxycarbonyl-DL-alanine 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69.3%的产率得到1-(3-hydroxyphenyl)-2-(α-(tert-butoxycarbonylamino)propionyl)-6-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

文献信息

• Tetrahydrocarboline compounds as anticancer agents
  申请人：Wang Weibo

  公开号：US20050215580A1

  公开（公告）日：2005-09-29

  Tetrahydrocarboline compounds, pharmaceutically acceptable salts, and prodrugs thereof; compositions that include a pharmaceutically acceptable carrier and one or more of the tetrahydrocarboline compounds, either alone or in combination with at least one additional therapeutic agent. Methods of using the tetrahydrocarboline compounds, either alone or in combination with at least one additional therapeutic agent, in the prophylaxis or treatment of proliferative diseases.

  四氢吲哚烷类化合物，药用可接受盐和前药；包括药用可接受载体和一种或多种四氢吲哚烷类化合物的组合物，可以单独使用或与至少一种其他治疗剂联合使用。使用四氢吲哚烷类化合物的方法，可以单独使用或与至少一种其他治疗剂联合使用，用于预防或治疗增殖性疾病。
• US7855295B2
  申请人：——

  公开号：US7855295B2

  公开（公告）日：2010-12-21