3-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione | 447408-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione
• 英文别名: 1-methyl-3-[1-(phenylsulphonyl)-1H-pyrrolo[2,3-b]pyrid-3-yl]-4-(1H-pyrrolo[2,3-b]pyrid-3-yl)-1H-pyrrole-2,5-dione；3-[1-(benzenesulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione
• CAS: 447408-26-6
• 化学式: C₂₅H₁₇N₅O₄S
• 分子量: 483.507
• InChiKey: FXPDOKSKWGVOGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione 在 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 17.5h， 生成 1-methyl-3-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Syntheses and antiproliferative activities of rebeccamycin analogues bearing two 7-azaindole moieties

  摘要：

  As a part of structure activity relationship studies on rebeccamycin analogues, compounds containing two aza-indole moieties were synthesized bearing either a methyl group or a hydrogen atom on the imide nitrogen. The azaindole substructures were expected to enhance the cytotoxicity toward tumor cell lines through stronger hydrogen bonding with the target enzyme(s). The cytotoxicities of compounds 8, 10 and 19 against a panel of tumor cell lines were examined and compared with those of rebeccamycin, dechlorinated rebeccamycin 2 and N-methylated analogue A. Their effect on the L1210 cell cycle was also evaluated. Compound 19, having an imide NH function had the strongest cytotoxicity towards L1210 cells and induced the largest accumulation of cells in the G2 + M phases of the cell cycle. In contrast to their non-aza analogues, which were cytotoxic for all the cell lines tested, diaza compounds 10 and 19 showed selectivity for some cell lines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00532-1
• 作为产物：
  描述：

  3-bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione 在 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 3-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  First synthesis of symmetrical and non-symmetrical aza indolocarbazoles derivatives

  摘要：

  A new family of aza-indolocarbazoles 2-3 was built from protected 3-(3-indolyl)-4-bromo-N-methylmaleimide in a few efficient steps. Symmetrical and non-symmetrical products were obtained. Regioselectivity of anionic condensation was controlled. A possible selective deprotection between an N-Boc and N-benzenesulphonyl group using mild basic conditions was confirmed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00315-5

文献信息

• Pyrido-pyrido-pyrrolo pyrrolo-indole and pyrido-pyrrolo pyrrolo carbazole derivatives, method for the production thereof and pharmaceutical compositions containing said derivatives
  申请人：——

  公开号：US20040152721A1

  公开（公告）日：2004-08-05

  Compounds of formula (I): 1 wherein: W 1 and W 2 , together with the carbon atoms to which they are bonded, represent a phenyl group or a pyridyl group, and at least one of the groups W 1 or W 2 represents a pyridyl group, R 1 and R 2 each represent a group of formula U-V as defined in the description, X and X 1 each represent a hydrogen atom or a hydroxy, alkoxy, mercapto or alkylthio group, Y and Y 1 each represent a hydrogen atom, or X and Y, X 1 and Y 1 , together with the carbon atom carrying them, represent a carbonyl or thiocarbonyl group, R 4 and R 5 are as defined in the description, Q 1 , Q 2 represent a hydrogen atom, or Q 1 and Q 2 , together with the carbon atoms carrying them, form an aromatic bond. Medicaments.

  式(I)的化合物：其中：W1和W2与它们连接的碳原子一起表示苯基或吡啶基，且W1或W2中至少一个表示吡啶基，R1和R2分别表示如描述中所定义的U-V式的基团，X和X1分别表示氢原子或羟基、烷氧基、巯基或烷硫基，Y和Y1分别表示氢原子，或X和Y、X1和Y1连同携带它们的碳原子表示羰基或硫代羰基，R4和R5如描述中所定义，Q1、Q2表示氢原子，或Q1和Q2连同携带它们的碳原子形成芳香键。药物。
• Synthesis and biological evaluation of 7-azaindolocarbazoles
  作者：Sylvain Routier、Nathalie Ayerbe、Jean-Yves Mérour、Gérard Coudert、Christian Bailly、Alain Pierré、Bruno Pfeiffer、Daniel-Henri Caignard、Pierre Renard

  DOI：10.1016/s0040-4020(02)00691-9

  日期：2002.8

  In the course of a program aimed at designing antitumor agents containing an indolocarbazole framework, an efficient synthetic scheme based on the use of 3,4-dibromo-N-methylmaleimide and 7-azaindole has been developed to elaborate a series of mono- and di-aza derivatives of arcyriaflavin. The procedure was further exploited to introduce a hydroxyl group at different positions on the indole moiety of the non-symmetrical compounds. The DNA binding capacity and cytotoxic potential of these 7-azaindolocarbazole derivatives was evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• DERIVES DE PYRIDO-PYRIDO-PYRROLO PYRROLO-INDOLE ET PYRIDO-PYRROLO PYRROLO CARBAZOLE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：LES LABORATOIRES SERVIER

  公开号：EP1409486A1

  公开（公告）日：2004-04-21
• US7001906B2
  申请人：——

  公开号：US7001906B2

  公开（公告）日：2006-02-21
• [EN] PYRIDO-PYRIDO-PYRROLO PYRROLO-INDOLE AND PYRIDO-PYRROLO PYRROLO CARBAZOLE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAID DERIVATIVES<br/>[FR] DERIVES DE PYRIDO-PYRIDO-PYRROLO PYRROLO-INDOLE ET PYRIDO-PYRROLO PYRROLO CARBAZOLE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：SERVIER LAB

  公开号：WO2003002563A1

  公开（公告）日：2003-01-09

  Composés de formule (I): dans laquelle: - WI et W2 représentent avec les atomes de carbone auxquels ils sont liés, un groupement phényle ou un groupement pyridinyle, et au moins un des groupements W1 ou W2 représente un groupement pyridinyle, - R1 et R2 représentent chacun un groupement de formule U-V telle que définie dans la description, - X et X1 représentent chacun un atome d'hydrogène, un groupement hydroxy, alkoxy, mercapto ou alkylthio, - Y et Y1 représentent chacun un atome d'hydrogène, - ou X et Y, X1 et Y1 représentent ensemble avec l'atome de carbone qui les portent, un groupement carbonyle ou thiocarbonyle, - R4 et R5 sont tels que définis dans la description, - Q1, Q2 représentent un atome d'hydrogène, ou Q1 et Q2 forment ensemble, avec les atomes de carbone qui les portent, une liaison aromatique. Médicaments.