2-bromo-N-(3-chloro-4-cyanophenyl)-2-methylpropanamide | 879615-68-6

• 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: 2-bromo-N-(3-chloro-4-cyanophenyl)-2-methylpropanamide
• CAS: 879615-68-6
• 化学式: C₁₁H₁₀BrClN₂O
• 分子量: 301.57
• InChiKey: RMLMIXDFYMETQI-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C
• 沸点：
  456.5±45.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(3-chloro-4-cyanophenyl)-2-methylpropanamide 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 3-[3-(3-chloro-4-cyanophenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Design and synthesis of an androgen receptor pure antagonist (CH5137291) for the treatment of castration-resistant prostate cancer

  摘要：

  A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of castration-resistant prostate cancer. Since CH4933468, which we reported previously, had a problem with agonist metabolites, novel thiohydantoin derivatives were identified by applying two strategies. One was the replacement of the alkylsulfonamide moiety by a phenylsulfonamide to avoid the production of agonist metabolites. The other was the replacement of the phenyl ring with a pyridine ring to improve in vivo potency and reduce hERG affinity. Pharmacological assays indicated that CH5137291 (17b) was a potent AR pure antagonist which did not produce the agonist metabolite. Moreover, CH5137291 completely inhibited in vivo tumor growth of LNCaP-BC2, a castration-resistant prostate cancer model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.023
• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 2-氯-4-氨基苯腈 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到2-bromo-N-(3-chloro-4-cyanophenyl)-2-methylpropanamide
  参考文献：
  名称：

  Design and synthesis of an androgen receptor pure antagonist (CH5137291) for the treatment of castration-resistant prostate cancer

  摘要：

  A series of 5,5-dimethylthiohydantoin derivatives were synthesized and evaluated for androgen receptor pure antagonistic activities for the treatment of castration-resistant prostate cancer. Since CH4933468, which we reported previously, had a problem with agonist metabolites, novel thiohydantoin derivatives were identified by applying two strategies. One was the replacement of the alkylsulfonamide moiety by a phenylsulfonamide to avoid the production of agonist metabolites. The other was the replacement of the phenyl ring with a pyridine ring to improve in vivo potency and reduce hERG affinity. Pharmacological assays indicated that CH5137291 (17b) was a potent AR pure antagonist which did not produce the agonist metabolite. Moreover, CH5137291 completely inhibited in vivo tumor growth of LNCaP-BC2, a castration-resistant prostate cancer model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.023

文献信息

• N-芳香酰胺类化合物及其制备方法和用途
  申请人：深圳恩多凯医药科技有限公司

  公开号：CN110963957B

  公开（公告）日：2021-10-22

  本发明涉及通式(I)和(II)N‑芳香酰胺化合物及其制备方法、含有所述通式(I)或(II)化合物的药物组合物和药物制剂以及所述通式(I)和(II)化合物在制备治疗与雄激素相关疾病的药物方面的应用，通式中R1、R2、R3、R4、R5、R6、W1、W2、W3、W4和W5的定义与说明书中的相同。所述通式(I)和(II)化合物能够与雄激素受体结合，具有抵抗雄激素并且降解雄激素受体活性。所述化合物能够单独或作为组合物用于治疗各种与雄激素相关的疾病，如前列腺癌、前列腺增生、乳腺癌、膀胱癌、卵巢癌等，还能用于粉刺、多毛、脱发等疾病的治疗。
• N-AROMATIC AMIDES COMPOUND AND PREPARATION METHOD AND USE THEREOF
  申请人：Shenzen EDK Pharmaceutical Technology Co., Ltd.

  公开号：EP3858811A1

  公开（公告）日：2021-08-04

  The present invention relates to general formulas (I) and (II) an N-aromatic amide compound and a preparation method therefor, a pharmaceutical composition and a pharmaceutical preparation containing the general formulas (I) and (II), and applications of the general formulas (I) and (II) in preparation of a drug for treating an androgen-related disease. The definitions of R1, R2, R3, R4, R5, R6, W1, W2, W3, W4, and W5 in the general formulas are the same as those in the specification. The compound can be used alone or as a composition for treating various androgen-related diseases such as prostate cancer, prostatic hyperplasia, breast cancer, bladder cancer, and ovarian cancer, and further for the treatment of acne, hirsutism, alopecia, and other diseases. and

  本发明涉及通式(I)和(II)的N-芳香族酰胺化合物及其制备方法、含有通式(I)和(II)的药物组合物和药物制剂，以及通式(I)和(II)在制备治疗雄激素相关疾病药物中的应用。通式中 R1、R2、R3、R4、R5、R6、W1、W2、W3、W4 和 W5 的定义与说明书中的定义相同。该化合物可单独使用或作为组合物用于治疗各种与雄激素有关的疾病，如前列腺癌、前列腺增生症、乳腺癌、膀胱癌和卵巢癌，还可进一步用于治疗痤疮、多毛症、脱发和其他疾病。 和
• [EN] N-AROMATIC AMIDES COMPOUND AND PREPARATION METHOD AND USE THEREOF<br/>[FR] COMPOSÉ AMIDE N-AROMATIQUE ET SON PROCÉDÉ DE PRÉPARATION ET UTILISATION ASSOCIÉE<br/>[ZH] N-芳香酰胺类化合物及其制备方法和用途
  申请人：SHENZHEN EDK PHARMACEUTICAL TECH CO LTD

  公开号：WO2020063407A1

  公开（公告）日：2020-04-02

  本发明涉及通式(I)和(II)N-芳香酰胺化合物及其制备方法、含有所述通式(I)或(II)化合物的药物组合物和药物制剂以及所述通式(I)和(II)化合物在制备治疗与雄激素相关疾病的药物方面的应用，通式中R1、R2、R3、R4、R5、R6、W1、W2、W3、W4和W5的定义与说明书中的相同。所述通式(I)和(II)化合物能够与雄激素受体结合，具有抵抗雄激素并且降解雄激素受体活性。所述化合物能够单独或作为组合物用于治疗各种与雄激素相关的疾病，如前列腺癌、前列腺增生、乳腺癌、膀胱癌、卵巢癌等，还能用于粉刺、多毛、脱发等疾病的治疗。
• EP1790640
  申请人：——

  公开号：——

  公开（公告）日：——
• TW2023/21219
  申请人：——

  公开号：——

  公开（公告）日：——