5-amino-3-methyl-1-(2-methylphenyl)-1H-pyrazole-4-carbonitrile | 870189-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-3-methyl-1-(2-methylphenyl)-1H-pyrazole-4-carbonitrile
• 英文别名: 5-amino-3-methyl-1-o-tolyl-1H-pyrazole-4-carbonitrile；5-amino-3-methyl-1-(2-methylphenyl)pyrazole-4-carbonitrile
• CAS: 870189-32-5
• 化学式: C₁₂H₁₂N₄
• 分子量: 212.254
• InChiKey: QSNXAGNYGHUEAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-3-methyl-1-(2-methylphenyl)-1H-pyrazole-4-carbonitrile 在 tris-(dibenzylideneacetone)dipalladium(0) racemic-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 、 硫酸 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 66.0h， 生成 5-methoxy-2-(5-methyl-4-oxazol-2-yl-2-o-tolyl-2H-pyrazol-3-ylamino )-benzoic acid methyl ester
  参考文献：
  名称：

  [EN] 5-ANILINO-4-HETEROARYLPYRAZOLE DERIVATIVES USEFUL FOR THE TREATMENT OF DIABETES
  [FR] DÉRIVÉS DE 5-ANILINO-4-HÉTÉROARYLPYRAZOLE UTILES POUR LE TRAITEMENT DU DIABETE

  摘要：

  公开号：

  WO2005112923A3
• 作为产物：
  描述：

  (2-甲基苯基)肼 、 2-(1-乙氧基亚乙基)丙二腈 以 乙醇 为溶剂， 生成 5-amino-3-methyl-1-(2-methylphenyl)-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  Structure–activity relationship study of phenylpyrazole derivatives as a novel class of anti-HIV agents

  摘要：

  The structure-activity relationship of phenylpyrazole derivative 1 was investigated for the development of novel anti-HIV agents. Initial efforts revealed that the diazenyl group can be replaced by an aminomethylene group. In addition, we synthesized various derivatives by the reductive amination of benzaldehydes with 5-aminopyrazoles and carried out parallel structural optimization on the benzyl group and the pyrazole ring. This optimization led to a six-fold more potent derivative 32j than the lead compound 1, and this derivative has a 3',4'-dichloro-(1,1'-biphenyl)-3-yl group. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.026

文献信息

• 5-Anilino-4-Heteroarylpyrazole Derivatives Useful for the Treatment of Diabetes
  申请人：Cantin David Louis

  公开号：US20080009531A1

  公开（公告）日：2008-01-10

  The present invention relates to 5-anilino-4-heteroarylpyrazole compounds, pharmaceutical compositions, and methods for treating diabetes and related disorders.

  本发明涉及5-苯胺基-4-杂环芳基吡唑化合物、制药组合物以及治疗糖尿病及相关疾病的方法。
• 5-ANILINO-4-HETEROARYLPYRAZOLE DERIVATIVES USEFUL FOR THE TREATMENT OF DIABETES
  申请人：Bayer Pharmaceuticals Corporation

  公开号：EP1750698A2

  公开（公告）日：2007-02-14
• [EN] 5-ANILINO-4-HETEROARYLPYRAZOLE DERIVATIVES USEFUL FOR THE TREATMENT OF DIABETES<br/>[FR] DÉRIVÉS DE 5-ANILINO-4-HÉTÉROARYLPYRAZOLE UTILES POUR LE TRAITEMENT DU DIABETE
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2005112923A3

  公开（公告）日：2006-09-14
• Structure–activity relationship study of phenylpyrazole derivatives as a novel class of anti-HIV agents
  作者：Tsukasa Mizuhara、Takayuki Kato、Atsushi Hirai、Hideki Kurihara、Yasuhiro Shimada、Masahiko Taniguchi、Hideki Maeta、Hiroaki Togami、Kazuya Shimura、Masao Matsuoka、Shiho Okazaki、Tomoki Takeuchi、Hiroaki Ohno、Shinya Oishi、Nobutaka Fujii

  DOI：10.1016/j.bmcl.2013.06.026

  日期：2013.8

  The structure-activity relationship of phenylpyrazole derivative 1 was investigated for the development of novel anti-HIV agents. Initial efforts revealed that the diazenyl group can be replaced by an aminomethylene group. In addition, we synthesized various derivatives by the reductive amination of benzaldehydes with 5-aminopyrazoles and carried out parallel structural optimization on the benzyl group and the pyrazole ring. This optimization led to a six-fold more potent derivative 32j than the lead compound 1, and this derivative has a 3',4'-dichloro-(1,1'-biphenyl)-3-yl group. (C) 2013 Elsevier Ltd. All rights reserved.