6-Trifluoromethyl-2,3,4,9-tetrahydro-β-carbolin-1-one | 111492-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-Trifluoromethyl-2,3,4,9-tetrahydro-β-carbolin-1-one
• 英文别名: 6-(Trifluoromethyl)-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
• CAS: 111492-80-9
• 化学式: C₁₂H₉F₃N₂O
• 分子量: 254.211
• InChiKey: ITRZTXKEIGQBJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Trifluoromethyl-2,3,4,9-tetrahydro-β-carbolin-1-one 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,4,9-四氢-6-(三氟甲基)-1H-吡啶并[3,4-b]吲哚
  参考文献：
  名称：

  Novel IKK inhibitors: β-carbolines

  摘要：

  Inhibitors of IkappaB kinase (IKK) have long been sought as specific regulators of NF-kappaB. A screening effort of the endogenous IKK complex allowed us to identify 5-bromo-6-methoxy-beta-carboline as a nonspecific IKK inhibitor. Optimization of this beta-carboline natural product derivative resulted in a novel class of selective IKK inhibitors with IC(50)s in the nanomolar range. In addition. we show that one of these beta-carboline analogues inhibits the phosphorylation of IkappaBalpha and subsequent activation of NF-kappaB in whole cells, as well as blocking TNF-alpha release in LPS-challenged mice. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00408-6
• 作为产物：
  描述：

  3-[(4-Trifluoromethyl-phenyl)-hydrazono]-piperidin-2-one 以 甲酸 为溶剂， 反应 1.0h， 生成 6-Trifluoromethyl-2,3,4,9-tetrahydro-β-carbolin-1-one
  参考文献：
  名称：

  Substituted beta-carbolines

  摘要：

  式I的化合物适用于生产用于预防和治疗在其过程中涉及IκB激酶活性增加的疾病的药物。

  公开号：

  EP1209158A1

文献信息

• Herdeis, Claus; Bissinger, Gerhard, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1987, vol. 42, # 6, p. 785 - 790
  作者：Herdeis, Claus、Bissinger, Gerhard

  DOI：——

  日期：——
• Synthesis and cytotoxic activity of novel quinazolino-β-carboline-5-one derivatives
  作者：Bipul Baruah、Kavitha Dasu、Balasubramanian Vaitilingam、Premkumar Mamnoor、Prasanthi Penubaka Venkata、Sriram Rajagopal、Koteswar Rao Yeleswarapu

  DOI：10.1016/j.bmc.2004.03.005

  日期：2004.5

  A novel series of quinazolino-beta-carbolinone derivatives was synthesized and evaluated for their in vitro and in vivo anticancer activity. Many compounds have shown good in vitro activity in the range 1-8 muM concentration. Three of the compounds were further tested in nude mice bearing HT-29 colon cancer xenografts. (C) 2004 Elsevier Ltd. All rights reserved.
• HERDEIS, CLAUS;BISSINGER, GERHARD, Z. NATURFORSCH., 42,(1987) N 6, 785-790
  作者：HERDEIS, CLAUS、BISSINGER, GERHARD

  DOI：——

  日期：——
• US4272539A
  申请人：——

  公开号：US4272539A

  公开（公告）日：1981-06-09
• US4336256A
  申请人：——

  公开号：US4336256A

  公开（公告）日：1982-06-22