ethyl 3-methyl-5-nitro-1H-indole-2-carboxylate | 91559-45-4

• 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 3-methyl-5-nitro-1H-indole-2-carboxylate
• CAS: 91559-45-4
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: AAAIPGCJPYGDAY-UHFFFAOYSA-N

物化性质

• 沸点：
  426.2±40.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 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：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-methyl-5-nitro-1H-indole-2-carboxylate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ethyl 5-(4-bromophenylsulfonamido)-3-methyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2017.05.042
• 作为产物：
  描述：

  2-丁酮酸乙酯 在 polyphosphoric acid 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.0h， 生成 ethyl 3-methyl-5-nitro-1H-indole-2-carboxylate
  参考文献：
  名称：

  苯并杂环衍生物、其制备方法及其在医药上的 应用

  摘要：

  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。

  公开号：

  CN107619384B

文献信息

• Metal and Oxidant Free Construction of Substituted‐ and/or Polycyclic Indoles: A Useful Alternative to Bischler and Related Syntheses
  作者：Giacomo Mari、Lucia De Crescentini、Gianfranco Favi、Stefania Santeusanio、Fabio Mantellini

  DOI：10.1002/ejoc.202000845

  日期：2020.9.7

  wide range of substituted indoles, including complex polycyclic‐architectures were easily assembled by means of a Amberlyst 15H catalyzed synthesis that employs 1,2‐diaza‐1,3‐dienes and anilines. The metal and oxidant free methodology proposed here is characterized by good yields, total and predictable regioselectivity, and the ability to provide electron withdrawing substituted indoles.

  通过使用1,2-二氮杂-1,3-二烯和苯胺的Amberlyst 15H催化合成，可以轻松组装各种取代的吲哚，包括复杂的多环结构。本文提出的无金属和氧化剂的方法的特点是产率高，总的和可预测的区域选择性以及提供吸电子取代的吲哚的能力。
• Triamide-substituted heterobicyclic compounds
  申请人：Bertinato Peter

  公开号：US20050080108A1

  公开（公告）日：2005-04-14

  The invention relates to triamide MTP/ApoB inhibitors of the formula 1 wherein R 1 —R 8 are as defined in the specification, as well as pharmaceutical compositions and uses thereof, and processes for preparing the compounds. The compounds of the invention are useful for the treatment of obesity and lipid disorders.

  本发明涉及公式1中的三酰胺MTP / ApoB抑制剂，其中R1-R8如规范中所定义，以及其制药组合物和用途，以及制备化合物的过程。本发明的化合物对于治疗肥胖和脂质紊乱有用。
• 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]。
• EP2876105
  申请人：——

  公开号：——

  公开（公告）日：——