1-(1,3-二苯基-1H-吡唑-4-基)甲胺 | 512810-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(1,3-二苯基-1H-吡唑-4-基)甲胺
• 英文名称: C-(1,3-diphenyl-1H-pyrazol-4-yl)methylamine
• 英文别名: 1,3-diphenyl-4-pyrazolylmethylamine；(1,3-diphenyl-1H-pyrazol-4-yl)methylamine；(1,3-diphenylpyrazol-4-yl)methanamine
• CAS: 512810-07-0
• 化学式: C₁₆H₁₅N₃
• mdl: MFCD02656622
• 分子量: 249.315
• InChiKey: LWAPGZAVLLWYAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-(1,3-二苯基-1H-吡唑-4-基)甲胺 、 三光气 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以55%的产率得到4-isocyanatomethyl-1,3-diphenylpyrazole
  参考文献：
  名称：

  4-Functionally-substituted 3-Heterylpyrazoles: XV. 3-Aryl(heteryl)-1-phenyl-4-pyrazolylmethylamines and Heterocumulenes Obtained Therefrom

  摘要：

  在雷尼镍存在下，通过还原 3-芳基（杂基）-1-苯基-4-叠氮基甲基吡唑，或通过肼解 N-[3-芳基（杂基）-1-苯基-4-吡唑基甲基]邻苯二甲酰亚胺，得到 4-吡唑基甲基胺，与碳酸二（三氯甲基）酯反应，得到 3-芳基-（杂基）-1-苯基-4-吡唑基甲基异氰酸酯、与二硫化碳反应可得到 3-芳基-(杂)-1-苯基-4-吡唑甲基异氰酸酯。

  DOI：

  10.1007/s11178-005-0150-x
• 作为产物：
  描述：

  在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-(1,3-二苯基-1H-吡唑-4-基)甲胺
  参考文献：
  名称：

  (1,3-Diphenyl-1H-Pyrazol-4-yl)-Methylamine Analogues as Inhibitors of Dipeptidyl Peptidases

  摘要：

  AbstractA number of pyrazole compounds reported in literatures elicit anti‐hyperglycemic effects. By modifying the side chain of the heterocyclic skeleton, a new chemical class of DPP‐IV inhibitors structurally derived from the (pyrazol‐4‐yl)‐methylamine scaffold have been discovered and evaluated the biological activities of these inhibitors against DPP‐IV, DPP8, DPP‐II and FAP. The SAR studies showed the (1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐methylamines with 2,4‐dichloro substituents at the 3‐phenyl ring selectively preferred as DPP‐IV inhibitors, whereas with difluoro substituents at the 3‐phenyl ring selectively preferred as DPP8 inhibitors. The binding mode of representative compound 15h at the active site of DPP‐IV was predicted by computer model. In additional, 15h exhibited the ability to significantly decrease the glucose excursion in mice.

  DOI：

  10.1002/jccs.200900152

文献信息

• (1,3-Diphenyl-1<i>H</i>-Pyrazol-4-yl)-Methylamine Analogues as Inhibitors of Dipeptidyl Peptidases
  作者：Tsu Hsu、Chiung-Tong Chen、Ting-Yueh Tsai、Jai-Hong Cheng、Su-Ying Wu、Chung-Nien Chang、Chia-Hui Chien、Kai-Chia Yeh、Yu-Wen Huang、Chen-Lung Huang、Chung-Yu Huang、Ssu-Hui Wu、Yi-Kun Chiang、Min-Hsien Wang、Yu-Sheng Chao、Xin Chen、Weir-Torn Jiaang

  DOI：10.1002/jccs.200900152

  日期：2009.10

  AbstractA number of pyrazole compounds reported in literatures elicit anti‐hyperglycemic effects. By modifying the side chain of the heterocyclic skeleton, a new chemical class of DPP‐IV inhibitors structurally derived from the (pyrazol‐4‐yl)‐methylamine scaffold have been discovered and evaluated the biological activities of these inhibitors against DPP‐IV, DPP8, DPP‐II and FAP. The SAR studies showed the (1,3‐diphenyl‐1H‐pyrazol‐4‐yl)‐methylamines with 2,4‐dichloro substituents at the 3‐phenyl ring selectively preferred as DPP‐IV inhibitors, whereas with difluoro substituents at the 3‐phenyl ring selectively preferred as DPP8 inhibitors. The binding mode of representative compound 15h at the active site of DPP‐IV was predicted by computer model. In additional, 15h exhibited the ability to significantly decrease the glucose excursion in mice.
• 4-Functionally-substituted 3-Heterylpyrazoles: XV. 3-Aryl(heteryl)-1-phenyl-4-pyrazolylmethylamines and Heterocumulenes Obtained Therefrom
  作者：M. K. Bratenko、O. I. Panimarchuk、N. V. Mel’nichenko、M. V. Vovk

  DOI：10.1007/s11178-005-0150-x

  日期：2005.2

  By reduction of 3-aryl(heteryl)-1-phenyl-4-azidomethyl-pyrazoles in the presence of Raney nickel or by hydrazinolysis of N-[3-aryl(heteryl)-1-phenyl-4-pyrazolylmethyl]phthalimides 4-pyrazolylmethylamines were obtained that in reaction with bis(trichloromethyl) carbonate afforded 3-aryl-(heteryl)-1-phenyl-4-pyrazolylmethyl isocyanates, and with carbon disulfide furnished 3-aryl-(heteryl)-1-phenyl-4-pyrazolylmethyl isothiocyanates.

  在雷尼镍存在下，通过还原 3-芳基（杂基）-1-苯基-4-叠氮基甲基吡唑，或通过肼解 N-[3-芳基（杂基）-1-苯基-4-吡唑基甲基]邻苯二甲酰亚胺，得到 4-吡唑基甲基胺，与碳酸二（三氯甲基）酯反应，得到 3-芳基-（杂基）-1-苯基-4-吡唑基甲基异氰酸酯、与二硫化碳反应可得到 3-芳基-(杂)-1-苯基-4-吡唑甲基异氰酸酯。