6-bromo-2,4-dimethyl-1H-benzimidazole | 215239-69-3

• 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: 6-bromo-2,4-dimethyl-1H-benzimidazole
• 英文别名: 6-bromo-2,4-dimethyl-1(3)H-benzimidazole；6-Brom-2,4-dimethyl-1(3)H-benzimidazol
• CAS: 215239-69-3
• 化学式: C₉H₉BrN₂
• 分子量: 225.088
• InChiKey: GXRBMCDGVSZJHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-2,4-dimethyl-1H-benzimidazole 在 N-甲基吗啉 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 molybdenum hexacarbonyl 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.59h， 生成 1-(2,4-dimethyl-1H-benzo[d]imidazole-6-carbonyl)-2'-ethyl-3'-methyl-2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazol]-7'(6'H)-one
  参考文献：
  名称：

  Maximizing Lipophilic Efficiency: The Use of Free-Wilson Analysis in the Design of Inhibitors of Acetyl-CoA Carboxylase

  摘要：

  This paper describes the design and synthesis of a novel series of dual inhibitors of acetyl-CoA carboxylase 1 and 2 (ACC1 and ACC2). Key findings include the discovery of an initial lead that was modestly potent and subsequent medicinal chemistry optimization with a focus on lipophilic efficiency (LipE) to balance overall druglike properties. Free-Wilson methodology provided a clear breakdown of the contributions of specific structural elements to the overall LipE, a rationale for prioritization of virtual compounds for synthesis, and a highly successful prediction of the LipE of the resulting analogues. Further preclinical assays, including in vivo malonyl-CoA reduction in both rat liver (ACC1) and rat muscle (ACC2), identified an advanced analogue that progressed to regulatory toxicity studies.

  DOI：

  10.1021/jm201503u
• 作为产物：
  描述：

  4-溴-2-甲基-6-硝基苯胺 在 水 、 铁粉 、 氯化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.0h， 生成 6-bromo-2,4-dimethyl-1H-benzimidazole
  参考文献：
  名称：

  [EN] BENZIMIDAZOLE COMPOUNDS HAVING HYPOGLYCEMIC ACTIVITY
  [FR] COMPOSES DE BENZIMIDAZOLE

  摘要：

  公开号：

  WO2004108686A3

文献信息

• [EN] USE OF BENZIMIDAZOLE-PROLINE DERIVATIVES<br/>[FR] UTILISATION DE DÉRIVÉS DE BENZIMIDAZOLE-PROLINE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2015083094A1

  公开（公告）日：2015-06-11

  The present invention relates to compounds of the formula (I), wherein Ar1 and Ar2 are as described in the description and to their use as pharmaceuticals for the treatment of sundown syndrome. The invention also relates to the preparation of such compounds and of pharmaceutically acceptable salts thereof.

  本发明涉及式(I)的化合物，其中Ar1和Ar2如描述中所述，并且它们作为治疗日落综合征的药物的用途，该发明还涉及制备这种化合物及其药用盐的方法。
• [EN] PYRAZOLOSPIROKETONE ACETYL-C0A CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PYRAZOLOSPIROCÉTONE ACÉTL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2009144554A1

  公开（公告）日：2009-12-03

  The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供了式(1)的化合物或所述化合物的药用可接受盐，其中R1、R2和R3如本文所述；其药物组合物；以及用于治疗通过抑制动物中的乙酰辅酶A羧化酶酶活性来调节的疾病、病症或障碍的使用方法。
• CYCLIN DEPENDENT KINASE INHIBITORS
  申请人：Pfizer Inc.

  公开号：US20190330196A1

  公开（公告）日：2019-10-31

  This invention relates to compounds of Formula (I) or a pharmaceutically acceptable salt thereof, in which R-groups R 1 to R 23 , A, Q, U, V, W, X, Y, Z, n, p and q are as defined herein, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer, in a subject.

  这项发明涉及式（I）的化合物或其药学上可接受的盐，其中R基团R1至R23，A，Q，U，V，W，X，Y，Z，n，p和q如本文所定义，以及包含这种化合物和盐的药物组合物，以及使用这种化合物、盐和组合物治疗受试者的异常细胞生长，包括癌症的方法。
• USE OF BENZIMIDAZOLE-PROLINE DERIVATIVES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：US20170001985A1

  公开（公告）日：2017-01-05

  The present invention relates to compounds of the formula (I), wherein Ar 1 and Ar 2 are as described in the description and to their use as pharmaceuticals for the treatment of sundown syndrome. The invention also relates to the preparation of such compounds and of pharmaceutically acceptable salts thereof.

  本发明涉及式(I)化合物，其中Ar1和Ar2如说明书所述，并且它们的用途是作为治疗日落综合症的药物。本发明还涉及这种化合物的制备以及其药学上可接受的盐的制备。
• Benzimidazole compounds
  申请人：Hayashida Hisashi

  公开号：US20050014812A1

  公开（公告）日：2005-01-20

  The present invention provides novel benzimidazole compounds of the formula (I): wherein each symbol is as defined in the specification, salts thereof and prodrugs thereof, which are useful in treating, for example, the diseases curable through decrease in blood sugar level.

  本发明提供了一种新的苯并咪唑化合物，其化学式为(I)：其中每个符号如规范中所定义，其盐和前药，可用于治疗例如通过降低血糖水平可治愈的疾病。