3-bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione | 447408-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 3-bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione
• 英文别名: 3-bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrole-2,5-dione；3-bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyrid-3-yl)-1H-pyrrole-2,5-dione
• CAS: 447408-23-3
• 化学式: C₁₂H₈BrN₃O₂
• 分子量: 306.118
• InChiKey: OYODXVBXJCSFQG-UHFFFAOYSA-N

物化性质

• 熔点：
  >200 °C
• 密度：
  1.841±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione 在 四丁基氟化铵 、 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 14.0h， 生成 1-methyl-3,4-bis(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
• 作为产物：
  描述：

  7-氮杂吲哚 在 乙基溴化镁 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 3-bromo-1-methyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of 7-azaindolocarbazoles

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)00691-9

文献信息

• [3,4-a:3,4-c]carbazole compounds
  申请人：——

  公开号：US20040077672A1

  公开（公告）日：2004-04-22

  A compound selected from those of formula (I): 1 wherein: W 1 represents, together with carbon to which it is bonded, phenyl, pyridyl, Z represents a group of formula U—V as defined in the description, Q 1 represents oxygen, NR 2 as defined in the description, Q 2 represents oxygen, NR′ 2 as defined in the description, X 1 , X 2 , X′ 1 and X′ 2 each represents hydrogen, hydroxy, alkoxy, mercapto or alkylthio, Y 1 , Y 2 , Y′ 1 and Y′ 2 each represents hydrogen, or X 1 and Y 1 , X 2 and Y 2 , X′ 1 and Y′ 1 , X′ 2 and Y′ 2 with carbon carrying them, together form carbonyl or thiocarbonyl, R 1 is as defined in the description, its isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.

  从式（I）中选择的一种化合物： 其中： W1表示与其结合的碳一起，苯基，吡啶基， Z表示如描述中定义的U—V式的基团， Q1表示氧，如描述中定义的NR2， Q2表示氧，如描述中定义的NR′2， X1，X2，X′1和X′2分别表示氢，羟基，烷氧基，巯基或烷基硫基， Y1，Y2，Y′1和Y′2分别表示氢， 或者X1和Y1，X2和Y2，X′1和Y′1，X′2和Y′2与携带它们的碳一起形成羰基或硫代羰基， R1如描述中定义，其异构体，以及与药学上可接受的酸或碱形成的加合盐，以及含有这种化合物的治疗癌症的药物。
• 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 activities of isogranulatimide analogues
  作者：Bernadette Hugon、Fabrice Anizon、Christian Bailly、Roy M. Golsteyn、Alain Pierré、Stéphane Léonce、John Hickman、Bruno Pfeiffer、Michelle Prudhomme

  DOI：10.1016/j.bmc.2007.05.073

  日期：2007.9.1

  The synthesis of new isogranulatimide analogues, their inhibitory activities toward the Checkpoint 1 kinase (Chk1), and their in vitro cytotoxicities toward four tumor cell lines (one murine L1210 leukemia, and three human cell lines: DU145 prostate carcinoma, A549 non-small cell lung carcinoma, and HT29 colon carcinoma) are described. The affinity for DNA of some representative compounds and their

  新异烟酰胺基类似物的合成，对Checkpoint 1激酶（Chk1）的抑制活性以及对四种肿瘤细胞系（一种鼠L1210白血病和三种人类细胞系的体外细胞毒性）：DU145前列腺癌，A549非小细胞肺癌和HT29结肠癌）。已经检查了一些代表性化合物对DNA的亲和力及其诱导由拓扑异构酶I介导的DNA切割的能力。在一些新合成的化合物中，异戊拉米肽的咪唑杂环被吡咯取代和/或吲哚单元被7-氮杂吲哚取代。还已经制备了其中糖部分连接至7-氮杂吲哚部分的化合物。一些新合成的化合物是比格拉那肽更有效的Chk1抑制剂。已经使用各种激酶评估了两种有效的Chk1抑制剂24和26的选择性。发现对Chk1的抑制作用最强。
• Pyrrolo (3,4-c) carbazole and pyrido (2,3-b) pyrrolo (3,4-e) indole derivatives, preparation method and pharmaceutical compositions containing same
  申请人：Prudhomme Michelle

  公开号：US20060004428A1

  公开（公告）日：2006-01-05

  A compound selected from those of formula (I): wherein: Z represents a group of the formula U-V as defined in the description, W 1 represents together with carbon to which it is bonded, phenyl, pyridyl, W 2 is as defined in the description, X 1 , X 2 each represents hydrogen, hydroxy, alkoxy, mercapto or alkylthio, Y 1 , Y 2 each represents hydrogen, or X 1 and Y 1 , X 2 and Y 2 with carbon carrying them, together form carbonyl or thiocarbonyl, R 1 is as defined in the description, Q represents oxygen, a group NR 2 as defined in the description, its isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.

  从式（I）中选择的化合物：其中：Z代表公式U-V所定义的基团，W1与其结合的碳原子一起代表苯基、吡啶基，W2如描述中所定义，X1、X2各自代表氢、羟基、烷氧基、巯基或烷硫基，Y1、Y2各自代表氢，或者X1和Y1、X2和Y2与它们所连接的碳原子一起形成羰基或硫代羰基，R1如描述中所定义，Q代表氧、氮原子上的基团NR2，其异构体和与药学上可接受的酸或碱形成的加合物，以及含有这些化合物的药物产品，用于治疗癌症。
• Use of maleimide derivatives for preventing and treating cancer
  申请人：CENTOGENE AG

  公开号：US10420754B2

  公开（公告）日：2019-09-24

  The present invention is related to a compound of formula (I): a pharmaceutically acceptable salt thereof, a hydrate thereof, a solvate thereof, a metabolite thereof or a prodrug thereof; for use in a method for the treatment and/or prevention of cancer, wherein X is selected from the group consisting of N—R1, O and S; R1 is selected from the group consisting of alkyl, cycloalkyl, aryl, arylalkyl and hydrogen; R2 is selected from the group consisting of indolyl, substituted indolyl, azaindolyl and substituted azaindolyl; and R3 is selected from the group consisting of aryl, substituted aryl, unsubstituted heteroaryl, heterocyclyl and substituted heterocyclyl.

  本发明涉及一种式（I）化合物： 其药学上可接受的盐、其水合物、其溶液、其代谢物或其原药； 用于治疗和/或预防癌症的方法，其中 X选自由N-R1、O和S组成的组； R1 选自由烷基、环烷基、芳基、芳烷基和氢组成的组； R2 选自由吲哚基、取代的吲哚基、偶氮吲哚基和取代的偶氮吲哚基组成的组；和 R3 选自由芳基、取代的芳基、未取代的杂芳基、杂环基和取代的杂环基组成的组。