ethyl 5-amino-3-methyl-1H-indole-2-carboxylate | 95979-79-6

• 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-amino-3-methyl-1H-indole-2-carboxylate
• CAS: 95979-79-6
• 化学式: C₁₂H₁₄N₂O₂
• mdl: MFCD20229203
• 分子量: 218.255
• InChiKey: PPLPTNVCVSBQBM-UHFFFAOYSA-N

物化性质

• 沸点：
  416.2±40.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-3-methyl-1H-indole-2-carboxylate 在 2,6-二甲基吡啶 、 甲醇 、 ammonium hydroxide 、 sodium tetrahydroborate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 nickel dichloride 、 lithium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 N-(2-(aminomethyl)-3-methyl-1H-indol-5 -yl)butane-1-sulfonamide
  参考文献：
  名称：

  A Preclinical Candidate Targeting Mycobacterium tuberculosis KasA

  摘要：

  Published Mycobacterium tuberculosis beta-ketoacyl-ACP synthase KasA inhibitors lack sufficient potency and/or pharmacokinetic properties. A structure-based approach was used to optimize existing KasA inhibitor DG167. This afforded indazole JSF-3285 with a 30-fold increase in mouse plasma exposure. Biochemical, genetic, and X-ray studies confirmed JSF-3285 targets KasA. JSF-3285 offers substantial activity in an acute mouse model of infection and in the corresponding chronic infection model, with efficacious reductions in colony-forming units at doses as low as 5 mg/kg once daily orally and improvement of the efficacy of front-line drugs isoniazid or rifampicin. JSF-3285 is a promising preclinical candidate for tuberculosis.

  DOI：

  10.1016/j.chembiol.2020.02.007
• 作为产物：
  描述：

  1-(5-氨基-2-溴苯基)乙酮 在 copper(l) iodide 、 caesium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 ethyl 5-amino-3-methyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  [EN] THERAPEUTIC INDOLES
  [FR] INDOLES THÉRAPEUTIQUES

  摘要：

  公开号：

  WO2019046465A3

文献信息

• 苯并杂环衍生物、其制备方法及其在医药上的 应用
  申请人：江苏恒瑞医药股份有限公司

  公开号：CN107619384B

  公开（公告）日：2020-07-28

  本发明涉及苯并杂环衍生物、其制备方法及其在医药上的应用。特别地，本发明涉及一类如通式(I)所示的化合物，该类化合物具有抗肿瘤的用途，抑制血管生成的作用以及作为HIF‑1α抑制剂在医学上的应用。其中通式(I)中的各取代基与说明书中的定义相同。
• Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process
  作者：Qian Cai、Zhengqiu Li、Jiajia Wei、Chengyong Ha、Duanqing Pei、Ke Ding

  DOI：10.1039/b918345k

  日期：——

  A straightforward synthesis of indole-2-carboxylic esters was developed through a ligand-free copper-catalysed condensation/coupling/deformylation cascade process from 2-halo aryl aldehydes or ketones with ethyl isocyanoacetate. The reactions proceeded well for most of the 2-iodo-, bromo-, and chloro-substrates under room temperature or mild conditions.

  通过无配体的铜催化的2-卤代芳基醛或酮与异氰基乙酸乙酯的合成，开发了吲哚-2-羧酸酯的直接合成方法。在室温或温和条件下，大多数2-碘，溴和氯底物的反应进展顺利。
• 1-(CYCLOALKYL-CARBONYL)PROLINE DERIVATIVE
  申请人：SUMITOMO DAINIPPON PHARMA CO., LTD.

  公开号：US20150210640A1

  公开（公告）日：2015-07-30

  A compound represented by formula (1) (in the formula: ring-D represents a three- to eight-membered hydrocarbon ring; R a represents an optionally substituted amino C 1-6 alkyl group or the like; R b1 and R b2 each independently represent a hydrogen atom, a halogen atom, or the like; R c represents an optionally substituted C 6-10 aryl group or the like; R d represents a hydrogen atom or the like; and ring-Q represents a (hetero)aryl group or the like which may be substituted with a carboxyl group or the like) or a pharmaceutically acceptable salt thereof exhibits an excellent FXIa inhibitory activity, and is useful as a therapeutic agent against thrombosis or the like.

  化合物的化学式为（1）（其中，环D代表3-8个碳原子的碳氢环；R代表可选择性取代的氨基C1-6烷基或类似物；Rb1和Rb2各自独立地代表氢原子、卤素原子或类似物；Rc代表可选择性取代的C6-10芳基或类似物；Rd代表氢原子或类似物；环Q代表（杂）芳基或类似物，可被羧基或类似物取代），或其药学上可接受的盐，具有出色的FXIa抑制活性，可用作治疗血栓或类似疾病的治疗剂。
• CONDENSED 5-OXAZOLIDINONE DERIVATIVE
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：EP3095786A1

  公开（公告）日：2016-11-23

  Provided are condensed 5-oxazolidinone derivatives and pharmaceutically permissible salts thereof, which have excellent anticoagulant effects, are well absorbed orally, and are useful as therapeutic drugs for thrombosis, etc. Compounds represented by formula (1) and pharmaceutically permissible salts thereof. [In the formula, L represents a C1-C4 alkylene group that may be substituted; R11 and R12 each independently represent a hydrogen atom or C1-C6 alkyl group, etc. that may be substituted; X1 represents N or CR1; R1 and R2 each independently represent a hydrogen atom, halogen atom, or C1-C6 alkyl group; Ra represents a C4-C7 cycloalkyl group, etc. that may be substituted; and Rb represents a hydrogen atom, etc.]

  本发明提供了缩合 5-恶唑烷酮衍生物及其药学上允许的盐类，它们具有优异的抗凝血效果，口服吸收良好，可用作血栓等的治疗药物。由式（1）代表的化合物及其药学上允许的盐。[式中，L代表可被取代的C1-C4亚烷基；R11和R12各自独立地代表氢原子或可被取代的C1-C6烷基等；X1代表N或CR1；R1和R2各自独立地代表氢原子、卤素原子或C1-C6烷基；Ra代表可被取代的C4-C7环烷基等；Rb代表氢原子等]。
• Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway
  作者：Xiao-li Xu、Ying-rui Yang、Xiao-fei Mo、Jin-lian Wei、Xiao-jin Zhang、Qi-dong You

  DOI：10.1016/j.ejmech.2017.05.042

  日期：2017.9

  Pancreatic ductal adenocarcinoma (PDAC) is one of the most common type of pancreatic cancer, and has still been the medicinal mystery. New drugs and treatment strategies are urgently needed. In this study, 32 benzofuran derivatives are designed, synthesized and evaluated as potential agents against the pancreatic cancer. Among them, compound 9o with the best physicochemical and pharmacokinetic properties exhibited excellent cytotoxicity against many tumor cell lines. In vivo study showed that compound 9o dramatically suppressed the tumor growth of nude mice. Furthermore, compound 9o could affect the hypoxia environment through Hif-1 alpha/VEGF pathway, resulting in the anti-angiogenic activity. These studies indicated that compound 9o was a promising candidate for the treatment of PDAC, deserving further studies. (C) 2017 Elsevier Masson SAS. All rights reserved.