ethyl 5-methoxy-1-cyanomethylindole-2-carboxylate | 126718-06-7

• 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: ethyl 5-methoxy-1-cyanomethylindole-2-carboxylate
• 英文别名: 1-cyanomethyl-5-methoxy-1H-indole-2-carboxylic acid ethyl ester；ethyl 1-(cyanomethyl)-5-methoxy-1H-indole-2-carboxylate；1-cyanomethyl-5-methoxy-indole-2-carboxylic acid ethyl ester；ethyl 1-(cyanomethyl)-5-methoxyindole-2-carboxylate
• CAS: 126718-06-7
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: UEJYOXZZJAMGRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-methoxy-1-cyanomethylindole-2-carboxylate 在 palladium 10% on activated carbon 盐酸 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 乙酸乙酯 、 水 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 反应 7.0h， 以75%的产率得到8-methoxy-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one
  参考文献：
  名称：

  [a]-FUSED INDOLE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES

  摘要：

  该发明涉及Formula II的[a]-融合吲哚化合物，或其药用可接受的盐，其中组成变量如本文所定义。该发明还涉及包含Formula II化合物的组合物，以及制备和使用这些化合物的方法。

  公开号：

  US20090192147A1
• 作为产物：
  描述：

  5-甲氧基吲哚-2-羧酸 在 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 ethyl 5-methoxy-1-cyanomethylindole-2-carboxylate
  参考文献：
  名称：

  吲哚并六氢吡嗪并喹唑啉酮类抗肿瘤化合物及 其制备方法

  摘要：

  本发明涉及医药技术领域，具体涉及一类吲哚并六氢吡嗪并喹唑啉酮类抗肿瘤化合物及其制备方法。本发明的吲哚并六氢吡嗪并喹唑啉酮类化合物，其化学结构式如通式I或通式II所示，该类化合物是通过对吴茱萸碱进行了系统的骨架跃迁设计与合成得到一类吴茱萸碱新骨架化合物，是新发现的一类全新结构的拓扑异构酶I/微管蛋白双重抑制剂，具有明显抗肿瘤活性。本发明还提供了该类化合物在制备拓扑异构酶I/微管蛋白双重抑制剂和抗肿瘤药物中的应用。

  公开号：

  CN103992326B

文献信息

• Tricyclic compounds, a process for their preparation and pharmaceutical compositions containing them
  申请人：Casara Patrick

  公开号：US20080188460A1

  公开（公告）日：2008-08-07

  Compounds of formula (I): wherein A represents a 5, 6 or 7-membered (hetero)aromatic or non-aromatic ring, n and n′ represent 0, 1 or 2 X represents an alkylene chain as defined in the description, R 3 represents an aryl or heteroaryl group, one of the groups R 1 and R 2 represents a hydrogen atom and the other represents a group of formula (II) as defined in the description. Medicinal products containing the same which are useful in treating conditions involving a defect in apoptosis.

  式(I)的化合物： 其中 A代表一个5、6或7-成员的(杂)芳香族或非芳香族环， n和n′代表0、1或2 X代表描述中定义的烷基链， R3代表芳基或杂芳基团， R1和R2中的一个代表氢原子，另一个代表描述中定义的式(II)的团。 含有这些化合物的药物，对治疗涉及凋亡缺陷的疾病有用。
• Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer
  作者：Lei Wang、Kun Fang、Junfei Cheng、Yu Li、Yahui Huang、Shuqiang Chen、Guoqiang Dong、Shanchao Wu、Chunquan Sheng

  DOI：10.1021/acs.jmedchem.9b01626

  日期：2020.1.23

  Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.
• Evaluation of isotryptamine derivatives at 5-HT2 serotonin receptors
  作者：Jean Chang-Fong、James Addo、Małgorzata Dukat、Carol Smith、Nicholas A. Mitchell、Katharine Herrick-Davis、Milt Teitler、Richard A. Glennon

  DOI：10.1016/s0960-894x(01)00713-2

  日期：2002.1

  On the basis that meta-chlorophenylpiperazine (mCPP: 1) is a nonselective 5-HT2C agonist. that benz-fused tryptamines (e.g., 5) display enhanced 5-HT2 affinity, and that certain isotryptamines 3 reportedly bind with enhanced affinity and selectivity at 5-HT2C receptors, we prepared and examined a series of isotryptamine-related analogues as potentially selective 5-HT2C agonists. None of the compounds displayed selectivity for 5-HT2C versus 5-HT2A receptors. Detailed re-examination of a compound previously reported to display 100-fold 5-HT2C selectivity [i.e.. S(+)-5,6-aifluoro-alpha-methylisotryptamine] revealed that its selectivity versus 5-HT2A receptors was, at best. only 10-fold. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Rajur; Merwade; Hendi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 12, p. 1065 - 1068
  作者：Rajur、Merwade、Hendi、Basanagoudar

  DOI：——

  日期：——
• RAJUR, SHARANABASAVA B.;MERWADE, A. Y.;HENDI, S. B.;BASANAGOUDAR, L. D., INDIAN J. JHEM. B, 28,(1989) N2, C. 1065-1068
  作者：RAJUR, SHARANABASAVA B.、MERWADE, A. Y.、HENDI, S. B.、BASANAGOUDAR, L. D.

  DOI：——

  日期：——