2,5-Dimethyl-4-(4-nitrophenyl)-3-pyrrolcarbonsaeure-ethylester | 95838-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-Dimethyl-4-(4-nitrophenyl)-3-pyrrolcarbonsaeure-ethylester
• 英文别名: ethyl 2,5-dimethyl-4-(4-nitrophenyl)-1H-pyrrole-3-carboxylate
• CAS: 95838-64-5
• 化学式: C₁₅H₁₆N₂O₄
• 分子量: 288.303
• InChiKey: FJLLCFOEVGFGGY-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C(Solv: methanol (67-56-1))
• 沸点：
  483.8±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-Dimethyl-4-(4-nitrophenyl)-3-pyrrolcarbonsaeure-ethylester 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (2,5-dimethyl-4-(4-nitrophenyl)-1H-pyrrol-3-yl)methanol
  参考文献：
  名称：

  EP1466902

  摘要：

  公开号：
• 作为产物：
  描述：

  1-硝基-4-[(1E)-2-硝基-1-丙烯-1-基]苯 在 盐酸 、 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.25h， 生成 2,5-Dimethyl-4-(4-nitrophenyl)-3-pyrrolcarbonsaeure-ethylester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 4-phenylpyrrole derivatives as novel androgen receptor antagonists

  摘要：

  A series of 4-phenylpyrrole derivatives D were designed, synthesized, and evaluated for their potential as novel orally available androgen receptor antagonists therapeutically effective against castration-resistant prostate cancers. 4-Phenylpyrrole compound 1 exhibited androgen receptor (AR) antagonistic activity against T877A and W741C mutant-type ARs as well as wild-type AR. An arylmethyl group incorporated into compound 1 contributed to enhancement of antagonistic activity. Compound 4n, 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile exhibited inhibitory effects on tumor cell growth against the bicalutamide-resistant LNCaP-cxD2 cell line as well as the androgen receptor-dependent JDCaP cell line in a mouse xenograft model. These results demonstrate that this series of pyrrole compounds are novel androgen receptor antagonists with efficacy against prostate cancer cells, including castration-resistant prostate cancers such as bicalutamide-resistant prostate cancer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.067

文献信息

• Androgen receptor antagonists
  申请人：Furuya Shuichi

  公开号：US20050101657A1

  公开（公告）日：2005-05-12

  The present invention provides an androgen receptor antagonistic agent and a superior prophylactic or therapeutic agent for hormone-sensitive cancer, which contain a compound of the formula: wherein, R 1 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, R 2 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, R 3 is a hydrogen atom, a hydrocarbon group which may have substituent(s), an acyl group or a heterocyclic group which may have substituent(s), R 4 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, and R 5 is a cyclic group which may have substituent(s); or a salt thereof, or its prodrug.

  本发明提供了一种雄激素受体拮抗剂，以及一种优越的预防或治疗激素敏感性癌症的药物，其含有式中的化合物：其中，R1是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团，R2是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团，R3是氢原子、可能具有取代基的碳氢基团、酰基或可能具有取代基的杂环基团，R4是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团，R5是可能具有取代基的环状基团；或其盐或前药。
• ANDROGEN RECEPTOR ANTAGONISTS
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1466902A1

  公开（公告）日：2004-10-13

  The present invention provides an androgen receptor antagonistic agent and a superior prophylactic or therapeutic agent for hormone-sensitive cancer, which contain a compound of the formula: wherein, R1 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom; R2 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, R3 is a hydrogen atom, a hydrocarbon group which may have substituent (s) , an acyl group or a heterocyclic group which may have substituent(s), R4 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, and R5 is a cyclic group which may have substituent(s); or a salt thereof, or its prodrug.

  本发明提供了一种雄激素受体拮抗剂和一种激素敏感性癌症的高级预防或治疗剂，其中含有一种式化合物： 其中，R1 是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团；R2 是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合 的基团或通过硫原子结合的基团； R3 是氢原子、烃基，该烃基可能具有取代基（s）、R4 是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团，R5 是可能带有取代基的环状基团；或其盐或其原药。
• MUTATED ANDROGEN RECEPTOR, CANCER CELLS EXPRESSING THE SAME, METHOD OF CONSTRUCTING THE SAME AND USE THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1550720A1

  公开（公告）日：2005-07-06

  The present invention provides a mutant androgen receptor (AR) useful for screening an agent for the prophylaxis/treatment of androgen-independent cancer and the like, DNA encoding the AR and the like. It also provides a method of producing a mutant AR expressing cancer cell line in vitro, a method of screening for an anti-antiandrogen drug using the mutant AR expressing cancer cell line obtained by this method, a method of classifying anti-androgen drugs, a cocktail therapy agent comprising a combination of anti-androgen drugs classified by this method and the like.

  本发明提供了一种可用于筛选预防/治疗雄激素依赖性癌症等药物的突变雄激素受体（AR）、编码该AR的DNA等。本发明还提供了一种体外制备突变型 AR 表达癌细胞系的方法、一种利用通过该方法获得的突变型 AR 表达癌细胞系筛选抗雄激素药物的方法、一种抗雄激素药物分类方法、一种由通过该方法分类的抗雄激素药物组合组成的鸡尾酒疗法制剂等。
• Mutant androgen receptor, cancer cells expressing the same, method of constructing the same and use thereof
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2090656A1

  公开（公告）日：2009-08-19

  The present invention provides a mutant androgen receptor (AR) useful for screening an agent for the prophylaxis/treatment of androgen-independent cancer and the like, DNA encoding the AR and the like. It also provides a method of producing a mutant AR expressing cancer cell line in vitro, a method of screening for an anti-antiandrogen drug using the mutant AR expressing cancer cell line obtained by this method, a method of classifying anti-androgen drugs, a cocktail therapy agent comprising a combination of anti-androgen drugs classified by this method and the like.

  本发明提供了一种可用于筛选预防/治疗雄激素依赖性癌症等药物的突变雄激素受体（AR）、编码该AR的DNA等。本发明还提供了一种体外制备突变型 AR 表达癌细胞系的方法、一种利用通过该方法获得的突变型 AR 表达癌细胞系筛选抗雄激素药物的方法、一种抗雄激素药物分类方法、一种由通过该方法分类的抗雄激素药物组合组成的鸡尾酒疗法制剂等。
• Mutant androgen receptor, cancer cells expressing the same, a method of producing them and use thereof
  申请人：Hara Takahito

  公开号：US20050181462A1

  公开（公告）日：2005-08-18

  The present invention provides a mutant androgen receptor (AR) useful for screening an agent for the prophylaxis/treatment of androgen-independent cancer and the like, DNA encoding the AR and the like. It also provides a method of producing a mutant AR expressing cancer cell line in vitro, a method of screening for an anti-antiandrogen drug using the mutant AR expressing cancer cell line obtained by this method, a method of classifying anti-androgen drugs, a cocktail therapy agent comprising a combination of anti-androgen drugs classified by this method and the like.

  本发明提供了一种可用于筛选预防/治疗雄激素依赖性癌症等药物的突变雄激素受体（AR）、编码该AR的DNA等。本发明还提供了一种体外制备突变型 AR 表达癌细胞系的方法、一种利用通过该方法获得的突变型 AR 表达癌细胞系筛选抗雄激素药物的方法、一种抗雄激素药物分类方法、一种由通过该方法分类的抗雄激素药物组合组成的鸡尾酒疗法制剂等。