1-(1H-benzo[d]imidazol-2-yl)-3-methyl-1H-pyrazol-5-ol | 516455-57-5

• 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: 1-(1H-benzo[d]imidazol-2-yl)-3-methyl-1H-pyrazol-5-ol
• CAS: 516455-57-5
• 化学式: C₁₁H₁₀N₄O
• mdl: MFCD03759867
• 分子量: 214.227
• InChiKey: OUQGOPKPXOVKDA-UHFFFAOYSA-N

物化性质

• 溶解度：
  二甲基亚砜（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.73
• 氢给体数：
  2.0
• 氢受体数：
  3.0

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为产物：
  描述：

  2-羟基苯并咪唑 在 一水合肼 、 三氯氧磷 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 生成 1-(1H-benzo[d]imidazol-2-yl)-3-methyl-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

文献信息

• 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。
• Enhanced Properties of a Benzimidazole Benzylpyrazole Lysine Demethylase Inhibitor: Mechanism-of-Action, Binding Site Analysis, and Activity in Cellular Models of Prostate Cancer
  作者：David M. Carter、Edgar Specker、Piotr H. Małecki、Jessica Przygodda、Krystyna Dudaniec、Manfred S. Weiss、Udo Heinemann、Marc Nazaré、Ulrich Gohlke

  DOI：10.1021/acs.jmedchem.1c00693

  日期：2021.10.14
• US9212169B2
  申请人：——

  公开号：US9212169B2

  公开（公告）日：2015-12-15
• Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs
  作者：Syuhei Nakao、Miyuki Mabuchi、Tadashi Shimizu、Yoshihiro Itoh、Yuko Takeuchi、Masahiro Ueda、Hiroaki Mizuno、Naoko Shigi、Ikumi Ohshio、Kentaro Jinguji、Yuko Ueda、Masatatsu Yamamoto、Tatsuhiko Furukawa、Shunji Aoki、Kazutake Tsujikawa、Akito Tanaka

  DOI：10.1016/j.bmcl.2014.01.008

  日期：2014.2

  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.