3-(5-Chloromethyl-3-methyl-pyrazol-1-yl)-benzonitrile | 327047-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(5-Chloromethyl-3-methyl-pyrazol-1-yl)-benzonitrile
• 英文别名: 3-[5-(Chloromethyl)-3-methylpyrazol-1-yl]benzonitrile
• CAS: 327047-02-9
• 化学式: C₁₂H₁₀ClN₃
• 分子量: 231.685
• InChiKey: YDHAIJWIEMASOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-Chloromethyl-3-methyl-pyrazol-1-yl)-benzonitrile 在 羟胺 、 乙酸酐 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-{[2-(3-Carbamimidoyl-phenyl)-5-methyl-2H-pyrazol-3-ylmethyl]-methanesulfonyl-amino}-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  3-甲基吡唑-5-甲酸乙酯 在 吡啶 、 lithium aluminium tetrahydride 、 copper diacetate 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-(5-Chloromethyl-3-methyl-pyrazol-1-yl)-benzonitrile
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7

文献信息

• US6534535B1
  申请人：——

  公开号：US6534535B1

  公开（公告）日：2003-03-18
• Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors
  作者：Wenrong Huang、Penglie Zhang、Jingmei F Zuckett、Lingyan Wang、John Woolfrey、Yonghong Song、Zhaozhong J Jia、Lane A Clizbe、Ting Su、Katherine Tran、Brian Huang、Paul Wong、Uma Sinha、Gary Park、Andrea Reed、John Malinowski、Stanley J Hollenbach、Robert M Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)00927-7

  日期：2003.2

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.