3-氨基-5-甲氧基-1H-吲哚-2-羧酸乙酯 | 89607-80-7

• 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
• 中文名称: 3-氨基-5-甲氧基-1H-吲哚-2-羧酸乙酯
• 英文名称: ethyl 3-amino-5-methoxy-1H-indole-2-carboxylate
• 英文别名: 3-amino-5-methoxy-1H-indole-2-carboxylic acid, ethyl ester
• CAS: 89607-80-7
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: DEKRXQYFEJCJEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-氨基-5-甲氧基-1H-吲哚-2-羧酸乙酯 在 溶剂黄146 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 9-methoxy-6-[2-(4-methylpiperidin-1-yl)-2-oxoethyl]-2,3-dihydro[1,3]thiazolo[3',2':1,2]pyrimido[5,4-b]indol-5(6H)-one
  参考文献：
  名称：

  Overcoming fluconazole resistance in Candida albicans clinical isolates with tetracyclic indoles

  摘要：

  Continuing efforts to discover novel means of combating fluconazole resistance in Candida albicans have identified an indole derivative that sensitizes strains demonstrating resistance to fluconazole. This tetracycle (3, ML229) does not appear to act through established Hsp90 or calcineurin pathways to chemosensitize C. albicans, as determined in Saccharomyces cerevisiae models, and may be a useful probe to uncover alternative resistance pathways. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.035
• 作为产物：
  描述：

  ethyl 2-[(2-cyano-4-methoxyphenyl)amino]acetate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-氨基-5-甲氧基-1H-吲哚-2-羧酸乙酯
  参考文献：
  名称：

  设计，合成和生物评价2-烷氧基羰基-3-苯胺基吲哚作为新型的微管蛋白聚合抑制剂。

  摘要：

  合成了基于2-烷氧基羰基-3-（3'，4'，5'-三甲氧基苯胺基）吲哚分子骨架的新型微管蛋白聚合抑制剂，并评估了其抗增殖活性，抑制微管蛋白聚合和细胞周期的作用。给出的结果表明，甲氧基取代和吲哚核上的位置在抑制细胞生长中起着重要作用，最优选的取代基是在C-6处。另外，期望在吲哚核的2-位具有小尺寸的酯官能团（甲氧基/乙氧基羰基）。同样，被甲基，乙基或正丙基烷基化或在N-1吲哚氮上具有苄基部分的类似物保留的活性与在母体N-1H类似物中观察到的活性相同。

  DOI：

  10.1016/j.bioorg.2020.103665

文献信息

• Acidic tetrazolyl substituted indole compounds and their use as
  申请人：Warner-Lambert Company

  公开号：US04675332A1

  公开（公告）日：1987-06-23

  Novel acidic indole compounds having use as antiallergic agents, methods of synthesis, compositions, and uses are claimed.

  声称具有抗过敏药物作用的新型酸性吲哚化合物，包括合成方法、组合物和用途。
• Design, Optimization, and Study of Small Molecules That Target Tau Pre-mRNA and Affect Splicing
  作者：Jonathan L. Chen、Peiyuan Zhang、Masahito Abe、Haruo Aikawa、Liying Zhang、Alexander J. Frank、Timothy Zembryski、Christopher Hubbs、HaJeung Park、Jane Withka、Claire Steppan、Lucy Rogers、Shawn Cabral、Martin Pettersson、Travis T. Wager、Matthew A. Fountain、Gavin Rumbaugh、Jessica L. Childs-Disney、Matthew D. Disney

  DOI：10.1021/jacs.0c00768

  日期：2020.5.13

  Approximately 95% of human genes are alternatively spliced, and aberrant splicing events can cause disease. One pre-mRNA that is alternatively spliced and linked to neurodegenerative diseases is tau (microtubule-associated protein tau), which can cause frontotemporal dementia and parkinsonism linked to chromosome 17 (FTDP-17) and can contribute to Alzheimer's disease. Here, we describe the design of structure-specific lead small molecules that directly target tau pre-mRNA from sequence. This was followed by hit expansion and analogue synthesis to further improve upon these initial lead molecules. The emergent compounds were assessed for functional activity in a battery of assays, including binding assays and an assay that mimics molecular recognition of tau pre-mRNA by a U1 small nuclear ribonucleoprotein (snRNP) splicing factor. Compounds that emerged from these studies had enhanced potency and selectivity for the target RNA relative to the initial hits, while also having significantly improved drug-like properties. The compounds are shown to directly target tau pre-mRNA in cells, via chemical cross-linking and isolation by pull-down target profiling, and to rescue disease-relevant splicing of tau pre-mRNA in a variety of cellular systems, including primary neurons. More broadly, this study shows that lead, structure-specific compounds can be designed from sequence and then further optimized for their physicochemical properties while at the same time enhancing their activity.
• Synthesis and some properties of 4-oxo-3,4-dihydro- and 2,4-dioxo-1,2,3,4-tetrahydropyrimido[5,4-b]indoles
  作者：S. V. Simakov、V. S. Velezheva、V. V. Dvorkin、N. N. Suvarov

  DOI：10.1007/bf00506067

  日期：1985.5
• Unangst, Paul C.; Connor, David T.; Stabler, S. Russell, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 817 - 820
  作者：Unangst, Paul C.、Connor, David T.、Stabler, S. Russell

  DOI：——

  日期：——
• SIMAKOV, S. V.;VELEZHEVA, V. S.;DVORKIN, V. V.;SUVOROV, N. N., XIMIYA GETEROTSIKL. SOEDIN., 1985, N 5, 635-639
  作者：SIMAKOV, S. V.、VELEZHEVA, V. S.、DVORKIN, V. V.、SUVOROV, N. N.

  DOI：——

  日期：——