5,5'-(carbonyldiimino)bis-1H-indole-2-carboxylic acid diethyl ester | 129680-96-2

• 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 diethyl ester
• 英文别名: ethyl 5-[(2-ethoxycarbonyl-1H-indol-5-yl)carbamoylamino]-1H-indole-2-carboxylate
• CAS: 129680-96-2
• 化学式: C₂₃H₂₂N₄O₅
• 分子量: 434.451
• InChiKey: USSLMJFJRWUITI-UHFFFAOYSA-N

物化性质

• 沸点：
  608.3±50.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  125
• 氢给体数：
  4
• 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 diethyl ester 在 吡啶 、 sodium hydroxide 、 2,4-滴二甲胺盐 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 反应 105.0h， 生成 比折来新
  参考文献：
  名称：

  Synthesis and DNA crosslinking by a rigid CPI dimer

  摘要：

  DOI：

  10.1021/ja00023a085
• 作为产物：
  描述：

  5-氨基吲哚-2-甲酸乙酯 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 以58%的产率得到5,5'-(carbonyldiimino)bis-1H-indole-2-carboxylic acid diethyl ester
  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。
• Identification of Small-Molecule Enhancers of Arginine Methylation Catalyzed by Coactivator-Associated Arginine Methyltransferase 1
  作者：Sabrina Castellano、Astrid Spannhoff、Ciro Milite、Fabrizio Dal Piaz、Donghang Cheng、Alessandra Tosco、Monica Viviano、Abdellah Yamani、Agostino Cianciulli、Marina Sala、Vincent Cura、Jean Cavarelli、Ettore Novellino、Antonello Mai、Mark T. Bedford、Gianluca Sbardella

  DOI：10.1021/jm301097p

  日期：2012.11.26

  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.
• 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
• US5541339A
  申请人：——

  公开号：US5541339A

  公开（公告）日：1996-07-30
• [EN] NOVEL CC-1065 ANALOGS HAVING TWO CPI SUBUNITS
  申请人：THE UPJOHN COMPANY

  公开号：WO1990002746A1

  公开（公告）日：1990-03-22

  (EN) Chemical compounds of formula (I) CPI1 - R5 - T - R'5 - CPI2, wherein CPI1 and CPI2, being the same of different, are selected from formula (A) or (B), R5 and R'5 are selected from a direct bond or a carbonyl acyl group, and T is aminocarbonyl, carbonylamino, carbonyloxy, oxycarbonyl, NR13-T1-NR14-, -CO-het-CO-. The compounds of formula (I) are useful as uv light absorbers, anti-bacterial agents, and are particularly usefus as antitumor agents. Representative compounds of formula (I) have been shown to possess useful ranges of antitumor activity in standard laboratory animal tests.(FR) Composés chimiques de la formule générale (I) CPI1 - R5 - T - R'5 - CPI2 où CPI1 et CPI2 sont identiques ou différents et choisis entre la formule (A) et la formule (B), R5 et R'5 sont sélectionnés parmi un groupe de liaison directe ou un groupe acyle carbonyle; et T est amino carbonyle, carbonylamino, carbonyloxy, oxycarbonyle, NR13-T1-NR14-, CO-het-CO-. Les composés de la formule (I) peuvent servir d'absorbants de lumière UV, d'agents antibactériens, et notamment d'agents antitumoraux. On a montré que des composés représentatifs de la formule (2) ont une activité antitumorale utile à plusieurs niveaux, dans des tests de laboratoire standards sur animaux.