3-acetoxymethyl-β-carboline | 88932-14-3

• 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: 3-acetoxymethyl-β-carboline
• 英文别名: 9H-β-carbolin-3-ylmethyl acetate；3-acetyloxymethyl-β-carboline；9H-beta-carbolin-3-ylmethyl acetate；9H-pyrido[3,4-b]indol-3-ylmethyl acetate
• CAS: 88932-14-3
• 化学式: C₁₄H₁₂N₂O₂
• 分子量: 240.261
• InChiKey: URMCKFOELFIFSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetoxymethyl-β-carboline 以89%的产率得到[9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methyl acetate
  参考文献：
  名称：

  Non-peptide antagonists of GLP-1 receptor and methods of use

  摘要：

  非肽类化合物作为肠道激素胰高血糖素样肽1（GLP-1）的拮抗剂，具有一个9H-b-咔啉中心基团。这些化合物具有有利的物理、化学和生物特性，能够抑制GLP-1肽与GLP-1受体的结合，或者阻止受体通过结合的GLP-1而被激活。该发明还涉及一种抑制GLP-1与GLP-1受体结合的方法，以及一种抑制GLP-1受体激活的方法。还描述了用于制备非肽类GLP-1受体拮抗剂的中间体化合物。

  公开号：

  US06469021B1
• 作为产物：
  描述：

  3-羟甲基-β-咔啉 以 乙酸酐 为溶剂， 以82 mg (68%)的产率得到3-acetoxymethyl-β-carboline
  参考文献：
  名称：

  Non-peptide antagonists of GLP-1 receptor and methods of use

  摘要：

  非肽类化合物作为肠道激素胰高血糖素样肽1（GLP-1）的拮抗剂，具有一个9H-b-咔啉中心基团。这些化合物具有有利的物理、化学和生物特性，能够抑制GLP-1肽与GLP-1受体的结合，或者阻止受体通过结合的GLP-1而被激活。该发明还涉及一种抑制GLP-1与GLP-1受体结合的方法，以及一种抑制GLP-1受体激活的方法。还描述了用于制备非肽类GLP-1受体拮抗剂的中间体化合物。

  公开号：

  US06469021B1

文献信息

• HARMINE DERIVATIVES, INTERMEDIATES USED IN THEIR PREPARATION, PREPARATION PROCESSES AND USE THEREOF
  申请人：Xinjiang Huashidan Pharmaceutical Research Co., Ltd.

  公开号：EP1634881B1

  公开（公告）日：2011-07-27
• Design, synthesis and in vitro and in vivo antitumor activities of novel β-carboline derivatives
  作者：R. Cao、H. Chen、W. Peng、Y. Ma、X. Hou、H. Guan、X. Liu、A. Xu

  DOI：10.1016/j.ejmech.2005.04.008

  日期：2005.10

  To further our SAR study on the chemistry and antitumor activity/neurotoxicity of beta-carboline alkaloids. several series of beta-carboline derivatives with various substituents were designed and synthesized from the starting material L-tryptophan on the basis of harmine chemical structure. Cytotoxic activities of these compounds were investigated in vitro. The results showed that some beta-carboline derivatives had significant cytotoxic activities against human tumor cell lines. Among all the synthesized beta-carboline derivatives, the compounds 27, 28 and 32, having a benzyl substituent at both position-2 and 9, respectively, were found to be the most potent compounds with IC50 value lower than 50 mu M against all human tumor cell lines examined. Acute toxicities and antitumor activities of the selected beta-carboline derivatives in mice were also evaluated. The results demonstrated that a benzyl substituent at position-2 increased the antitumor activity as well as acute toxicity significantly. However an (ethoxycarbonyl)amino substituent at position-3 reduced the acute toxicity as well as antitumor activity remarkedly. These data suggested that (1) the antitumor potencies of beta-carboline derivatives were enhanced by the introduction of benzyl substituent into the position-2; (2) the acute toxicity of beta-carboline derivatives reduced dramatically by the introduction of an appropriate substituent into the position-3 and 9; (3) the beta-carboline structure might be an important basis for the design and synthesis of new antitumor drugs with significant antitumor activity and low toxicity. (c) 2005 Elsevier SAS. All rights reserved.
• NON-PEPTIDE ANTAGONISTS OF GLP-1 RECEPTOR AND METHODS OF USE
  申请人：AGOURON PHARMACEUTICALS, INC.

  公开号：EP1137413A2

  公开（公告）日：2001-10-04
• EP1137413A4
  申请人：——

  公开号：EP1137413A4

  公开（公告）日：2002-06-26
• US6469021B1
  申请人：——

  公开号：US6469021B1

  公开（公告）日：2002-10-22