4,5,6-trimethoxyindole-2-carboxylic acid | 30448-09-0

• 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: 4,5,6-trimethoxyindole-2-carboxylic acid
• 英文别名: 4,5,6-trimethoxy-indole-2-carboxylic acid；4,5,6-Trimethoxyindol-2-carbonsaeure；4,5,6-Trimethoxy-1H-indole-2-carboxylic acid
• CAS: 30448-09-0
• 化学式: C₁₂H₁₃NO₅
• mdl: MFCD02664457
• 分子量: 251.239
• InChiKey: PRUGUKSHOAAIBD-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C (decomp)
• 沸点：
  473.6±40.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 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：
  80.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5,6-trimethoxyindole-2-carboxylic acid 在 氢氧化钾 、 乙醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 1.0h， 生成 5-<(4,5,6-trimethoxy-1H-indol-2-ylcarbonyl)amino>-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Novel Cyclopropapyrroloindole Derivative (AT-3510) Bearing Methoxycarbonyl and Trifluoromethyl Groups

  摘要：

  The seco-Cl 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives dl- and/or (S)-10 carrying various acyl moieties at the NG-position were synthesized along with their prodrugs (S)-12, and their antitumor activity was evaluated. Among these derivatives, AT-3510 [(S)-12m], the novel prodrug MCTFCPI derivative carrying a 5-(7-methoxybenzofuran-2-ylcarbonyl)aminoindole-2-carbonyl group at the NG-position, was found to exhibit more excellent antitumor activity against human tumor xenografts than the clinical trial candidates carzelesin (6) and KW-2189 (7) and cisplatin.

  DOI：

  10.1021/jm980668c
• 作为产物：
  描述：

  4,5,6-trimethoxy-indole-2-carboxylic acid methyl ester 生成 4,5,6-trimethoxyindole-2-carboxylic acid
  参考文献：
  名称：

  Cyclic diamine compound with condensed-ring groups

  摘要：

  公式（1）所示的环状二胺化合物：1 其中R1和R2分别是个别氢原子或甲氧基，条件是当R2是氢原子时R1是甲氧基，或者当R2是甲氧基时R1是氢原子；A是氧原子、硫原子、CH═CH、CH═N或NR3，其中R3是氢原子，或者是低级烷基、羟基低级烷基、低级烷氧基低级烷基、芳基或芳基低级烷基团；B是氮原子、CH或CR4，其中R4是氢原子，或者是低级烷基、羟基低级烷基、低级烷氧基低级烷基、芳基或芳基低级烷基团；m是1或2；n是1到5的数字，其酸加成盐，或其水合物。该化合物具有抑制细胞粘附的作用，并且对于治疗过敏、哮喘、风湿病、动脉硬化以及炎症是有用的。

  公开号：

  US20030060461A1

文献信息

• TRIFLUOROMETHYLPYRROLOINDOLE CARBOXYLIC ESTER DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0656360A1

  公开（公告）日：1995-06-07

  Trifluoromethylpyrroloindole carboxylic ester derivatives represented by general formulae (1) and (2) having an antitumor activity, optically active isomers thereof, and pharmacologically acceptable salts thereof, wherein R represents lower alkyl; R¹ represents an α-amino acid residue, etc.; R² represents hydrogen, a hydroxyl-protecting group, etc.; and Y represents halogen, arylsulfonyloxy, etc.

  通式(1)和(2)代表的具有抗肿瘤活性的三氟甲基吡咯吲哚羧酸酯衍生物、其光学活性异构体及其药理上可接受的盐，其中R代表低级烷基；R¹代表α-氨基酸残基等；R²代表氢、羟基保护基等；Y代表卤素、芳基磺酰氧基等。
• CYCLIC DIAMINE COMPOUNDS HAVING FUSED-RING GROUPS
  申请人：Kowa Co., Ltd.

  公开号：EP1400510A1

  公开（公告）日：2004-03-24

  A cyclic diamine compound of formula (1): wherein R1 and R2 are individually a hydrogen atom or a methoxy group, provided R1 is a methoxy group when R2 is a hydrogen atom, or a hydrogen atom when R2 is a methoxy group; A is an oxygen atom, a sulfur atom, CH=CH, CH=N or NR3, in which R3 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; B is a nitrogen atom, CH or CR4, in which R4 is a hydrogen atom, or a lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl, aryl or aryl lower alkyl group; m is 1 or 2; and n is a number of 1 to 5, an acid-addition salt thereof, or a hydrate thereof. The compound has inhibitory effects on cell adhesion and is useful for treatment of allergy, asthma, rheumatism, arteriosclerosis, and inflammation.

  一种式(1)的环状二胺化合物： 其中 R1 和 R2 分别为氢原子或甲氧基，条件是当 R2 为氢原子时 R1 为甲氧基，或当 R2 为甲氧基时为氢原子；A 为氧原子、硫原子、CH=CH、CH=N 或 NR3，其中 R3 为氢原子，或低级烷基、羟基低级烷基、低级烷氧基低级烷基、芳基或芳基低级烷基；B是氮原子、CH或CR4，其中R4是氢原子、或低级烷基、羟基低级烷基、低级烷氧基低级烷基、芳基或芳基低级烷基；m是1或2；n是1至5的数字、其酸加成盐或其水合物。该化合物对细胞粘附有抑制作用，可用于治疗过敏、哮喘、风湿病、动脉硬化和炎症。
• Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway
  作者：Qing-Kun Shen、Hao Deng、Shi-Ben Wang、Yu-Shun Tian、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2019.04.005

  日期：2019.7

  A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 mu M) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 mu M) and 5-Fu (IC50 = 24.80 mu M) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent. (C) 2019 Elsevier Masson SAS. All rights reserved.
• US5629430A
  申请人：——

  公开号：US5629430A

  公开（公告）日：1997-05-13
• US6632810B2
  申请人：——

  公开号：US6632810B2

  公开（公告）日：2003-10-14