methyl 2-(cyanomethyl)-3-nitrobenzoate | 90771-65-6

• 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: methyl 2-(cyanomethyl)-3-nitrobenzoate
• 英文别名: <2-Methoxycarbonyl-6-nitro-phenyl>-acetonitril；Methyl 2-(cyanomethyl)-3-nitrobenzoate
• CAS: 90771-65-6
• 化学式: C₁₀H₈N₂O₄
• 分子量: 220.185
• InChiKey: KMPVUBMMIQNEHA-UHFFFAOYSA-N

物化性质

• 熔点：
  90-95.5 °C(Solv: methanol (67-56-1))
• 沸点：
  397.9±32.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(cyanomethyl)-3-nitrobenzoate 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 2-羧基-6-硝基苯乙酸
  参考文献：
  名称：

  合成5-酮-2a，3,4,5-四氢萘苯乙烯苯并[cd]吲哚-瑞和。10.米特隆

  摘要：

  描述了通过4-硝基-茚满酮合成5-酮-2a，3,4,5-四氢萘苯乙烯（3）。

  DOI：

  10.1002/hlca.19610440629
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 水 为溶剂， 反应 10.0h， 生成 methyl 2-(cyanomethyl)-3-nitrobenzoate
  参考文献：
  名称：

  Identification of novel PARP-1 inhibitors: Drug design, synthesis and biological evaluation

  摘要：

  A series of AG014699 derivatives containing a novel scaffold of 2,3-dihydro-1H-[1,2] diazepino[4,5,6-cd] indole-1,4(6H)-dione were synthesized and evaluated for their inhibitory activities toward PARP-1 enzyme and two cell lines, MCF-7 cells and the BRCA1-deficient MDA-MB-436 cells. Our results demonstrated that of all AG014699 derivatives synthesized in this work, compounds 6 and 7 showed strong PARP-1 inhibitory activity (IC50 = 3.5 nM and 2.4 nM, respectively), only four and three times less potent than AG014699. Compound 6 also had significantly cell inhibitory activity against both MCF-7 cells (CC50 = 25.8 mu M) and the BRCA1-deficient MDA-MB-436 cells (CC50 = 5.4 mu M), nearly as good as AG014699, indicating that it can be a promising compound for further evaluation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.060

文献信息

• [EN] ISOQUINOLINONE DERIVATIVES AS PARP INHIBITORS<br/>[FR] DÉRIVÉS D'ISOQUINOLINONE UTILISÉS EN TANT QU'INHIBITEURS DE PARP
  申请人：LUPIN LTD

  公开号：WO2017013593A1

  公开（公告）日：2017-01-26

  Disclosed are compounds of formula (I), their tautomeric forms, stereoisomers, and pharmaceutically acceptable salts thereof, wherein R1-R6, R1a, R2a, R1b, R2b, R1c, R2c, p and q are as defined in the specification, pharmaceutical compositions including a compound, tautomer, stereoisomer, or salt thereof, and methods of treating or preventing diseases or disorders, for example, cancer, that are amenable to treatment or prevention by inhibiting the PARP enzyme of a subject.

  揭示了公式（I）的化合物，它们的互变异构体形式，立体异构体，以及其药用盐，其中R1-R6，R1a，R2a，R1b，R2b，R1c，R2c，p和q如规范中所定义，包括一种化合物、互变异构体、立体异构体或其盐的药物组合物，以及治疗或预防疾病或疾病的方法，例如癌症，这些疾病或疾病可通过抑制受试者的PARP酶来治疗或预防。
• Synthese des 5-Keto-2a,3,4,5-tetrahydro-naphtostyrils Benz[cd]indol-Reihe. 10. Mitteilung
  作者：C. A. Grob、O. Weissbach

  DOI：10.1002/hlca.19610440629

  日期：——

  The synthesis of 5-keto-2a,3,4,5-tetrahydronaphtostyril (3) via 4-nitro-indanone is described.

  描述了通过4-硝基-茚满酮合成5-酮-2a，3,4,5-四氢萘苯乙烯（3）。
• Identification of novel PARP-1 inhibitors: Drug design, synthesis and biological evaluation
  作者：Zhouling Xie、Youli Zhou、Wei Zhao、He Jiao、Yu Chen、Yong Yang、Zhiyu Li

  DOI：10.1016/j.bmcl.2015.08.060

  日期：2015.10

  A series of AG014699 derivatives containing a novel scaffold of 2,3-dihydro-1H-[1,2] diazepino[4,5,6-cd] indole-1,4(6H)-dione were synthesized and evaluated for their inhibitory activities toward PARP-1 enzyme and two cell lines, MCF-7 cells and the BRCA1-deficient MDA-MB-436 cells. Our results demonstrated that of all AG014699 derivatives synthesized in this work, compounds 6 and 7 showed strong PARP-1 inhibitory activity (IC50 = 3.5 nM and 2.4 nM, respectively), only four and three times less potent than AG014699. Compound 6 also had significantly cell inhibitory activity against both MCF-7 cells (CC50 = 25.8 mu M) and the BRCA1-deficient MDA-MB-436 cells (CC50 = 5.4 mu M), nearly as good as AG014699, indicating that it can be a promising compound for further evaluation. (C) 2015 Elsevier Ltd. All rights reserved.