5,5'-(carbonyldiimino)bis-1H-indole-2-carboxylic acid | 129655-37-4

• 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: 5,5'-(carbonyldiimino)bis-1H-indole-2-carboxylic acid
• 英文别名: 5-[(2-carboxy-1H-indol-5-yl)carbamoylamino]-1H-indole-2-carboxylic acid
• CAS: 129655-37-4
• 化学式: C₁₉H₁₄N₄O₅
• 分子量: 378.344
• InChiKey: ATFRLAFCRGJKAA-UHFFFAOYSA-N

物化性质

• 沸点：
  702.7±55.0 °C(Predicted)
• 密度：
  1.721±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  147
• 氢给体数：
  6
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5'-(carbonyldiimino)bis-1H-indole-2-carboxylic acid 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以82%的产率得到5-[(3-carboxy-1H-indol-5-yl)carbamoylamino]-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Identification of Small-Molecule Enhancers of Arginine Methylation Catalyzed by Coactivator-Associated Arginine Methyltransferase 1

  摘要：

  Arginine methylation, is a common post-translational modification that is crucial in modulating gene expression at multiple critical. levels. The arginine methyltransferases (PRMTs) are envisaged as promising druggable targets,: but their role in physiological and pathological pathways is far from being clear due to the limited number of modulators reported to date. In this effort; enzyme activators can be invaluable tools, useful as gain-of-function reagents to interrogate the biological roles. in cells and in vivo of PRMTs. Yet the identification such molecule's is rarely pursued. Herein we describe a series of aryl ureido acetamido indole carboxylates (dubbed "uracandolates"), able to increase the Methylation of histone (H3) or nonhistone (polyadenylate-bihding protein 1, PABP1) substrates induced by coactivator-associated arginine methyltransferase 1 (CARM1), bath in in vitro and cellular settings. To the best of our knowledge, this is the first report of compounds acting as CARM1 activators.

  DOI：

  10.1021/jm301097p
• 作为产物：
  描述：

  5,5'-(carbonyldiimino)bis-1H-indole-2-carboxylic acid diethyl ester 在 lithium hydroxide 作用下， 以77%的产率得到5,5'-(carbonyldiimino)bis-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  The novel cyclopropapyrroloindole(CPI) bisalkylators bearing methoxycarbonyl and trifluoromethyl groups

  摘要：

  The novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) bisalkylators were synthesized and their antitumor activity was evaluated. Among these derivatives, 7f in which two MCTFCPI moieties are connected with a 5,5'-bis(2-carbonyl-1 H-indole) group, was found to exhibit more prominent cytotoxicity and antitumor activity than U-77,779 (bizelesin) (2). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00235-2

文献信息

• Novel CC-1065 analogs having two CPI subunits
  申请人：THE UPJOHN COMPANY

  公开号：EP0359454A1

  公开（公告）日：1990-03-21

  Chemical compounds of general Formula I wherein CPI, and CPl2, being the same or different, are selected from Formula A or B Rs and R's are selected from a direct bond or a carbonyl acyl group, and T is aminocarbonyl, carbonylamino, carbonyloxy, oxycarbonyl, NR13-T'-NR14-,-CO-het-CO-. The compounds of Formula I are useful as uv light absorbers, antibacterial agents, and are particularly useful as antitumor agents. Representative compounds of Formula I have been shown to possess useful ranges of antitumor activity in standard laboratory animal tests.

  通式 I 的化合物 其中 CPI 和 CPl2 相同或不同，选自式 A 或 B Rs 和 R's 选自直接键或羰基酰基，T 是氨基羰基、羰基氨基、羰基氧基、氧羰基、NR13-T'-NR14-,-CO-he-CO-。 式 I 的化合物可用作紫外线吸收剂、抗菌剂，尤其可用作抗肿瘤剂。在标准的实验室动物试验中，具有代表性的式 I 化合物已被证明具有一定范围的抗肿瘤活性。
• 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。
• Novel Syntheses of Optically Active CC-1065, U-73,975(Adozelesin), U-80,244(Carzelesin), U-77,779 (Bizelesin), KW-2189, and DU-86
  作者：Yasumichi Fukuda、Hirosuke Furuta、Futoshi Shiga、Yoshikazu Asahina、Shiro Terashima

  DOI：10.3987/com-97-7920

  日期：——

  The title syntheses were achieved by the method featuring oxidative cyclization of the enamino esters [(S)-13 and (S)-24] derived from the 5-aminoindoline [(S)-12], acylation with various structural types of indole-2-carboxylic acids, and formation of cyclopropapyrroloindole moieties.
• Synthesis and DNA crosslinking by a rigid CPI dimer
  作者：Mark A. Mitchell、Robert C. Kelly、Nancy A. Wicnienski、Nicole T. Hatzenbuhler、Marta G. Williams、Gary L. Petzold、Jerry L. Slightom、David R. Siemieniak

  DOI：10.1021/ja00023a085

  日期：1991.11
• CC-1065 analogs having two CPI subunits
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0359454B1

  公开（公告）日：2000-12-27