4-(4-methylpyridin-3-yl)-1H-benzo[d]imidazole | 1370001-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(4-methylpyridin-3-yl)-1H-benzo[d]imidazole
• 英文别名: 4-(4-methylpyridin-3-yl)-1H-benzimidazole
• CAS: 1370001-91-4
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: PIJLCLKZXHEQLP-UHFFFAOYSA-N

物化性质

• 沸点：
  485.1±30.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-methylpyridin-3-yl)-1H-benzo[d]imidazole 在 caesium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 10.5h， 生成 (3-(1-(2,2,2-trifluoroethyl)-1H-benzo[d]imidazol-4-yl)pyridin-4-yl)methyl acetate
  参考文献：
  名称：

  [EN] SUBSTITUTED BENZIMIDAZOLE AND IMIDAZOPYRIDINE COMPOUNDS USEFUL AS CYP17 MODULATORS
  [FR] COMPOSÉS SUBSTITUÉS DE BENZIMIDAZOLE ET D'IMIDAZOPYRIDINE UTILES COMME MODULATEURS DE CYP17

  摘要：

  揭示了Formula (I)、(I)的杂环芳基化合物或其药用盐，其中Z为CH或N；W为CR3或N；R1、R2和R3在此处被定义。还公开了使用这些化合物治疗至少一种CYP17相关疾病的方法，例如癌症，并包括这些化合物的药物组合物。

  公开号：

  WO2012044537A1
• 作为产物：
  描述：

  4-甲基-3-溴吡啶 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 25.0h， 生成 4-(4-methylpyridin-3-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Discovery of the Selective CYP17A1 Lyase Inhibitor BMS-351 for the Treatment of Prostate Cancer

  摘要：

  Efforts to identify a potent, reversible, non steroidal CYP17A1 lyase inhibitor with good selectivity over CYP17A1 hydroxylase and CYPs 11B1 and 21A2 for the treatment of castration-resistant prostate cancer (CRPC) culminated in the discovery of BMS-351 (compound 18), a pyridyl biaryl benzimidazole with an excellent in vivo profile. Biological evaluation of BMS-351 at a dose of 1.5 mg in castrated cynomolgus monkeys revealed a remarkable reduction in testosterone levels with minimal glucocorticoid and mineralcorticoid perturbation. Based on a favorable profile, BMS-351 was selected as a candidate for further preclinical evaluation.

  DOI：

  10.1021/acsmedchemlett.5b00310

文献信息

• SUBSTITUTED BENZIMIDAZOLE AND IMIDAZOPYRIDINE COMPOUNDS USEFUL AS CYP17 MODULATORS
  申请人：Huang Audris

  公开号：US20130310393A1

  公开（公告）日：2013-11-21

  Disclosed are heteroaryl compounds of Formula (I), (I), or pharmaceutically acceptable salts thereof, wherein Z is CH or N; W is CR 3 or N; and R 1 , R 2 , and R 3 are defined herein. Also disclosed are methods of using such compounds in the treatment of at least one CYP17 associated condition, such as, for example, cancer, and pharmaceutical compositions comprising such compounds.

  本发明涉及公式（I）的杂环化合物，或其药学上可接受的盐，其中Z为CH或N；W为CR3或N；R1、R2和R3在此定义。本发明还涉及使用这种化合物治疗至少一种CYP17相关疾病的方法，例如癌症，并包括这种化合物的制药组合物。
• Substituted benzimidazole and imidazopyridine compounds useful as CYP17 modulators
  申请人：Huang Audris

  公开号：US09133160B2

  公开（公告）日：2015-09-15

  Disclosed are heteroaryl compounds of Formula (I), (I), or pharmaceutically acceptable salts thereof, wherein Z is CH or N; W is CR3 or N; and R1, R2, and R3 are defined herein. Also disclosed are methods of using such compounds in the treatment of at least one CYP17 associated condition, such as, for example, cancer, and pharmaceutical compositions comprising such compounds.

  本发明揭示了式（I）或（II）的杂环芳基化合物，或其药学上可接受的盐，其中Z为CH或N; W为CR3或N; R1，R2和R3在此被定义。本发明还揭示了使用这些化合物治疗至少一种CYP17相关疾病的方法，例如癌症，并且包括这些化合物的制药组合物。
• US9133160B2
  申请人：——

  公开号：US9133160B2

  公开（公告）日：2015-09-15
• Discovery of the Selective CYP17A1 Lyase Inhibitor BMS-351 for the Treatment of Prostate Cancer
  作者：Audris Huang、Lata Jayaraman、Aberra Fura、Gregory D. Vite、George L. Trainor、Marco M. Gottardis、Thomas E. Spires、Vanessa M. Spires、Cheryl A. Rizzo、Mary T. Obermeier、Paul A. Elzinga、Gordon Todderud、Yi Fan、John A. Newitt、Sophie M. Beyer、Yongxin Zhu、Bethanne M. Warrack、Angela K. Goodenough、Andrew J. Tebben、Arthur M. Doweyko、David L. Gold、Aaron Balog

  DOI：10.1021/acsmedchemlett.5b00310

  日期：2016.1.14

  Efforts to identify a potent, reversible, non steroidal CYP17A1 lyase inhibitor with good selectivity over CYP17A1 hydroxylase and CYPs 11B1 and 21A2 for the treatment of castration-resistant prostate cancer (CRPC) culminated in the discovery of BMS-351 (compound 18), a pyridyl biaryl benzimidazole with an excellent in vivo profile. Biological evaluation of BMS-351 at a dose of 1.5 mg in castrated cynomolgus monkeys revealed a remarkable reduction in testosterone levels with minimal glucocorticoid and mineralcorticoid perturbation. Based on a favorable profile, BMS-351 was selected as a candidate for further preclinical evaluation.
• [EN] SUBSTITUTED BENZIMIDAZOLE AND IMIDAZOPYRIDINE COMPOUNDS USEFUL AS CYP17 MODULATORS<br/>[FR] COMPOSÉS SUBSTITUÉS DE BENZIMIDAZOLE ET D'IMIDAZOPYRIDINE UTILES COMME MODULATEURS DE CYP17
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012044537A1

  公开（公告）日：2012-04-05

  Disclosed are heteroaryl compounds of Formula (I), (I), or pharmaceutically acceptable salts thereof, wherein Z is CH or N; W is CR3 or N; and R1, R2, and R3 are defined herein. Also disclosed are methods of using such compounds in the treatment of at least one CYP17 associated condition, such as, for example, cancer, and pharmaceutical compositions comprising such compounds.

  揭示了Formula (I)、(I)的杂环芳基化合物或其药用盐，其中Z为CH或N；W为CR3或N；R1、R2和R3在此处被定义。还公开了使用这些化合物治疗至少一种CYP17相关疾病的方法，例如癌症，并包括这些化合物的药物组合物。