ethyl 2-bromo-4-(3-bromopropyl)phenylcarbamate | 866403-63-6

• 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: ethyl 2-bromo-4-(3-bromopropyl)phenylcarbamate
• 英文别名: ethyl N-[2-bromo-4-(3-bromopropyl)phenyl]carbamate
• CAS: 866403-63-6
• 化学式: C₁₂H₁₅Br₂NO₂
• 分子量: 365.065
• InChiKey: AGGKQWFKRGMOCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-4-(3-bromopropyl)phenylcarbamate 在 四(三苯基膦)钯 磷酸酐 、 sodium carbonate 、 三氯氧磷 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 7.5h， 生成 2-(3-bromopropyl)phenanthridin-6(5H)-one
  参考文献：
  名称：

  Discovery of potent and selective PARP-1 and PARP-2 inhibitors: SBDD analysis via a combination of X-ray structural study and homology modeling

  摘要：

  We disclose herein our efforts aimed at discovery of selective PARP-1 and PARP-2 inhibitors. We have recently discovered several novel classes of quinazolinones, quinazolidinones, and quinoxalines as potent PARP-1 inhibitors, which may represent attractive therapeutic candidates. In PARP enzyme assays using recombinant PARP-1 and PARP-2, the quinazolinone derivatives displayed relatively high selectivity for PARP-1 and quinoxaline derivatives showed superior selectivity for PARP-2, and the quinazolidinone derivatives did not have selectivity for PARP-1/2. Structure-based drug design analysis via a combination of X-ray structural study utilizing the complexes of inhibitors and human PARP-1 catalytic domain, and homology modeling using murine PARP-2 suggested distinct interactions of inhibitors with PARP-1 and PARP-2. These findings provide a new structural framework for the design of selective inhibitors for PARP-1 and PARP-2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.061
• 作为产物：
  描述：

  [2-Bromo-4-(3-hydroxy-propyl)-phenyl]-carbamic acid ethyl ester 在 三溴化磷 作用下， 以 乙酸乙酯 为溶剂， 以66%的产率得到ethyl 2-bromo-4-(3-bromopropyl)phenylcarbamate
  参考文献：
  名称：

  4-Phenyl-1,2,3,6-tetrahydropyridine, an excellent fragment to improve the potency of PARP-1 inhibitors

  摘要：

  We have shown that a 4-phenyl-1,2,3,6-tetrahydropyridine fragment plays an important role in improving inhibitory potency against poly(ADP-ribose) polymerise-1 (PARP-1). Various benzamide analogues linked with this fragment via alkyl spacers have been prepared and evaluated. As a result, some of them have been found to be highly potent PARP-1 inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.094

文献信息

• Phenanthridinones as parp inhibitors
  申请人：Yamamoto Hirofumi

  公开号：US20050171101A1

  公开（公告）日：2005-08-04

  A compound of the formula (I): wherein ring A is a carbocyclic group, R1 is hydrogen or a halogen atom or a lower alkyl group, R2 is a di(lower)alkylamino group or N-containing heterocyclic group, among which the N-containing heterocyclic group may be substituted with one or more substituent(s), Y is an oxygen or sulfur atom, n is an integer from 0 to 2, and m is an integer from 0 to 4, or its prodrug, or their salt which has poly(adenosine 5′-diphospho-ribose)polymerase inhibiting activity.

  化合物的式子(I)如下：其中环A是一个碳环基团，R1是氢原子或卤素原子或低碳基团，R2是二(低)烷基氨基团或含N的杂环基团，其中含N的杂环基团可以被一个或多个取代基取代，Y是氧原子或硫原子，n是0到2之间的整数，m是0到4之间的整数，或其前药，或其具有聚腺苷酸二磷酸核糖酶抑制活性的盐。
• PHENANTHRIDINONES AS PARP INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1487800A1

  公开（公告）日：2004-12-22
• [EN] PHENANTHRIDINONES AS PARP INHIBITORS<br/>[FR] PHENANTHRIDINONES UTILISEES COMME INHIBITEURS DE PARP
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2003080581A1

  公开（公告）日：2003-10-02

  A compound of the formula (I):whereinring A is a carbocyclic group, R1 is hydrogen or a halogen atom or a lower alkyl group,R2 is a di(lower)alkylamino group or N-containing heterocyclic group, among which the N-containing heterocyclic group may be substituted with one or more substituent(s),Y is an oxygen or sulfur atom, n is an integer from 0 to 2, andm is an integer from 0 to 4,or its prodrug, or their salt.which has poly(adenosine 5'-diphospho-ribose)polymerase inhibiting activity.
• Discovery of potent and selective PARP-1 and PARP-2 inhibitors: SBDD analysis via a combination of X-ray structural study and homology modeling
  作者：Junya Ishida、Hirofumi Yamamoto、Yoshiyuki Kido、Kazunori Kamijo、Kenji Murano、Hiroshi Miyake、Mitsuru Ohkubo、Takayoshi Kinoshita、Masaichi Warizaya、Akinori Iwashita、Kayoko Mihara、Nobuya Matsuoka、Kouji Hattori

  DOI：10.1016/j.bmc.2005.09.061

  日期：2006.3

  We disclose herein our efforts aimed at discovery of selective PARP-1 and PARP-2 inhibitors. We have recently discovered several novel classes of quinazolinones, quinazolidinones, and quinoxalines as potent PARP-1 inhibitors, which may represent attractive therapeutic candidates. In PARP enzyme assays using recombinant PARP-1 and PARP-2, the quinazolinone derivatives displayed relatively high selectivity for PARP-1 and quinoxaline derivatives showed superior selectivity for PARP-2, and the quinazolidinone derivatives did not have selectivity for PARP-1/2. Structure-based drug design analysis via a combination of X-ray structural study utilizing the complexes of inhibitors and human PARP-1 catalytic domain, and homology modeling using murine PARP-2 suggested distinct interactions of inhibitors with PARP-1 and PARP-2. These findings provide a new structural framework for the design of selective inhibitors for PARP-1 and PARP-2. (c) 2005 Elsevier Ltd. All rights reserved.
• 4-Phenyl-1,2,3,6-tetrahydropyridine, an excellent fragment to improve the potency of PARP-1 inhibitors
  作者：Junya Ishida、Kouji Hattori、Hirofumi Yamamoto、Akinori Iwashita、Kayoko Mihara、Nobuya Matsuoka

  DOI：10.1016/j.bmcl.2005.06.094

  日期：2005.10

  We have shown that a 4-phenyl-1,2,3,6-tetrahydropyridine fragment plays an important role in improving inhibitory potency against poly(ADP-ribose) polymerise-1 (PARP-1). Various benzamide analogues linked with this fragment via alkyl spacers have been prepared and evaluated. As a result, some of them have been found to be highly potent PARP-1 inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.