(+/-)-4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylic acid tert-butyl ester | 335165-67-8

• 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: (+/-)-4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: (+/-)-4-[3-(3,6-Dibromocarbazol-9-yl)-2-hydroxy-propyl]-piperazine-1-carboxylic tert-butyl ester；tert-butyl 4-[3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate；tert-butyl 4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylate
• CAS: 335165-67-8
• 化学式: C₂₄H₂₉Br₂N₃O₃
• 分子量: 567.321
• InChiKey: QURQMIHUXXYJIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 Bax channel blocker
  参考文献：
  名称：

  3,6-Dibromocarbazole Piperazine Derivatives of 2-Propanol as First Inhibitors of Cytochrome c Release via Bax Channel Modulation

  摘要：

  There is compelling evidence that Bax channel activity stimulates cytochrome c release leading ultimately to cell death, which is a key event in ischemic injuries and neurodegenerative diseases. Here 3,6-dibromocarbazole piperazine derivatives of 2-propanol are described as the first small and potent modulators of the cytochrome c release triggered by Bid-induced Bax activation in a mitochondrial assay. Furthermore, a mechanism of action is proposed, and fluorescent derivatives allowing the localization of such inhibitors are reported.

  DOI：

  10.1021/jm034107j
• 作为产物：
  描述：

  3,6-二溴咔唑 以72%的产率得到(+/-)-4-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  9-(Piperazinylalkyl)carbazoles as Bax-modulators

  摘要：

  本发明涉及哌嗪衍生物的咔唑，特别用作药用活性化合物，以及含有这种哌嗪衍生物的咔唑的药物配方。所述的哌嗪衍生物的咔唑是有效的调节剂，特别是Bax功能和/或激活的抑制剂。本发明还涉及新型哌嗪衍生物的咔唑以及其制备方法。

  公开号：

  EP1094063A1

文献信息

• [EN] 9- (PIPERAZINYLALKYL) CARBAZOLES AS BAX-MODULATORS<br/>[FR] 9- (PIPERAZINYLALKYL) CARBAZOLES UTILES EN TANT QUE MODULATEURS DE BAX
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2001029028A1

  公开（公告）日：2001-04-26

  The present invention is related to piperazine derivatives of carbazole of formula (I) notably for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such piperazine derivatives of carbazole. Said piperazine derivatives of carbazole are efficient modulators, in particular efficient inhibitors, of the Bax function and/or activation. The present invention is furthermore related to novel piperazine derivatives of carbazole as well as methods of their preparation.

  本发明涉及式(I)的嘧啶二酰胺衍生物，特别是作为药物活性化合物的使用，以及含有这种嘧啶二酰胺衍生物的制药配方。所述嘧啶二酰胺衍生物是高效的调节剂，特别是高效的抑制剂，对Bax功能和/或激活具有作用。本发明还涉及新的嘧啶二酰胺衍生物以及其制备方法。
• 9-(PIPERAZINYLALKYL) CARBAZOLES AS BAX-MODULATORS
  申请人：HALAZY Serge

  公开号：US20120040933A1

  公开（公告）日：2012-02-16

  piperazine compounds for use as pharmaceutically active compounds and in pharmaceutical formulations that are useful for the treatment of disorders associated with apoptosis, including neurodegenerative disorders, diseases associated with polyglutamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders, renal hypoxia, hepatitis and AIDS, where the piperazine compounds are represented by formula (I) and the terms R 0 , R 1 , R 2 , R 3 , k, l, m, n, and X are defined herein:

  使用哌嗪化合物作为药物活性化合物和制药配方，可用于治疗与凋亡相关的疾病，包括神经退行性疾病、多谷氨酸链相关疾病、癫痫、缺血、不育症、心血管疾病、肾脏缺氧、肝炎和艾滋病等。其中，哌嗪化合物由公式（I）表示，其中R0，R1，R2，R3，k，l，m，n和X的定义如下：
• 9-(piperazinylalkyl) carbazoles as bax-modulators
  申请人：Merck Serono SA

  公开号：US08053436B1

  公开（公告）日：2011-11-08

  The present invention is related to piperazine derivatives of carbazole of formula (I) notably for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such piperazine derivatives of carbazole. Said piperazine derivatives of carbazole are efficient modulators, in particular efficient inhibitors, of the Bax function and/or activation. The present invention is furthermore related to novel piperazine derivatives of carbazole as well as methods of their preparation.

  本发明涉及公式(I)的咪唑衍生物的咔唑，特别是用作药物活性化合物的咪唑衍生物的咔唑，以及含有这种咪唑衍生物的咔唑的制药配方。所述的咪唑衍生物的咔唑是高效的调节因子，特别是高效的抑制剂，可用于Bax功能和/或激活。本发明还涉及新型咪唑衍生物的咔唑以及其制备方法。
• 9-(piperazinylalkyl) carbazoles as Bax-modulators
  申请人：Halazy Serge

  公开号：US08410110B2

  公开（公告）日：2013-04-02

  Piperazine compounds for use as pharmaceutically active compounds and in pharmaceutical formulations that are useful for the treatment of disorders associated with apoptosis, including neurodegenerative disorders, diseases associated with polyglutamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders, renal hypoxia, hepatitis and AIDS, where the piperazine compounds are represented by formula (I) and the terms R0, R1, R2, R3, k, l, m, n, and X are defined herein:

  Piperazine化合物可用作药物活性化合物和制药配方，对于与凋亡有关的疾病的治疗有用，包括神经退行性疾病、与多谷氨酸氨基酸序列相关的疾病、癫痫、缺血、不孕症、心血管疾病、肾脏缺氧、肝炎和艾滋病，其中Piperazine化合物由公式（I）表示，术语R0、R1、R2、R3、k、l、m、n和X在此定义：
• 9-(PIPERAZINYLALKYL)CARBAZOLES AS BAX-MODULATORS
  申请人：Laboratoires Serono SA

  公开号：EP1237887B1

  公开（公告）日：2008-06-04