2-chloro-4,5-dimethyl-1H-benzimidazole | 1093231-04-9

• 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: 2-chloro-4,5-dimethyl-1H-benzimidazole
• CAS: 1093231-04-9
• 化学式: C₉H₉ClN₂
• 分子量: 180.637
• InChiKey: DPZKIQWKLGXXOG-UHFFFAOYSA-N

物化性质

• 沸点：
  358.1±45.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-chloro-4,5-dimethyl-1H-benzimidazole 在 一水合肼 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 1-(4,5-dimethyl-1H-benzimidazol-2-yl)-3-methyl-4-(phenylmethyl)-1H-pyrazol-5-ol
  参考文献：
  名称：

  Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

  摘要：

  A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5-methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H- pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.008
• 作为产物：
  描述：

  3,4-二甲基-O-苯二胺 在 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-chloro-4,5-dimethyl-1H-benzimidazole
  参考文献：
  名称：

  Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

  摘要：

  A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5-methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H- pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.008

文献信息

• [EN] BENZOIMIDAZOLES AS PROLYL HYDROXYLASE INHIBITORS<br/>[FR] BENZOIMIDAZOLES COMME INHIBITEURS DE LA PROLYL HYDROXYLASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2009134750A1

  公开（公告）日：2009-11-05

  The present invention is directed to benzoimidazole compounds of the formula (1) and enantiomers, diastereomers, racemates, and pharmaceutically acceptable salts thereof. Compounds of the present invention are useful in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions modulated by prolyl hydroxylase activity.

  本发明涉及公式（1）的苯并咪唑化合物及其对映体、二对映体、消旋体和药学上可接受的盐。本发明的化合物在制药组合物和治疗由脯氨酸羟化酶活性调节的疾病状态、紊乱和条件的方法中是有用的。
• [EN] INDOLE/BENZIMIDAZOLE COMPOUNDS AS mTOR KINASE INHIBITORS<br/>[FR] COMPOSÉS D'INDOLE OU BENZIMIDAZOLE CONVENANT COMME INHIBITEURS DE LA KINASE MTOR
  申请人：AMGEN INC

  公开号：WO2010096314A1

  公开（公告）日：2010-08-26

  The present invention provides compounds that are kinase inhibitors, specifically PIK kinase inhibitors, more specifically, mTOR inhibitors and are therefore useful for the treatment of diseases treatable by inhibition of kinases, specifically PIK kinase inhibitors, more specifically, mTOR such as cancer. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本发明提供了一种激酶抑制剂化合物，具体来说是PIK激酶抑制剂，更具体地说是mTOR抑制剂，因此适用于治疗通过抑制激酶治疗的疾病，特别是PIK激酶抑制剂，更具体地说是mTOR抑制剂，例如癌症。还提供了含有这些化合物的药物组合物和制备这些化合物的方法。
• NOVEL BENZIMIDAZOLE DERIVATIVE AND USE THEREOF
  申请人：HYOGO COLLEGE OF MEDICINE

  公开号：US20150011600A1

  公开（公告）日：2015-01-08

  The present invention aims to provide a compound capable of inhibiting PCA-1 that can be a target for a novel treatment method of various diseases, and pharmaceutical use of the compound. A compound represented by the formula (I): wherein each symbol is as defined in the DESCRIPTION, or a pharmaceutically acceptable salt thereof.

  本发明旨在提供一种能够抑制PCA-1的化合物，该化合物可作为各种疾病的新型治疗方法的靶点，并且可用于制药的该化合物。一种由以下化学式（I）表示的化合物：其中每个符号如描述中定义的，或其药用盐。
• BENZOIMIDAZOLES AS PROLYL HYDROXYLASE INHIBITORS
  申请人：Hocutt Frances Meredith

  公开号：US20110046132A1

  公开（公告）日：2011-02-24

  The present invention is directed to benzoimidazole compounds of the formula (1) and enantiomers, diastereomers, racemates, and pharmaceutically acceptable salts thereof. Compounds of the present invention are useful in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions modulated by prolyl hydroxylase activity.

  本发明涉及公式（1）的苯并咪唑化合物及其对映体、二对映异构体、外消旋体和药学上可接受的盐。本发明化合物在制药组合物和治疗疾病状态、紊乱和通过脯氨酸羟化酶活性调节的疾病条件的方法中是有用的。
• Indole/Benzimidazole Compounds as mTOR Kinase Inhibitors
  申请人：Boezio Alessandro

  公开号：US20120165334A1

  公开（公告）日：2012-06-28

  The present invention provides compounds that are kinase inhibitors, specifically PIK kinase inhibitors, more specifically, mTOR inhibitors and are therefore useful for the treatment of diseases treatable by inhibition of kinases, specifically PIK kinase inhibitors, more specifically, mTOR such as cancer. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本发明提供了一种激酶抑制剂，具体地说是PIK激酶抑制剂，更具体地说是mTOR抑制剂，因此适用于治疗通过抑制激酶，特别是PIK激酶抑制剂，更具体地说是mTOR抑制剂可治疗的疾病，例如癌症。还提供了含有这种化合物的药物组合物和制备这种化合物的方法。