5-amino-1-benzyl-1H-pyrazole-4-carbohydrazide | 132835-00-8

• 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-1-benzyl-1H-pyrazole-4-carbohydrazide
• 英文别名: 5-amino-1-benzylpyrazole-4-carbohydrazide
• CAS: 132835-00-8
• 化学式: C₁₁H₁₃N₅O
• mdl: MFCD01408841
• 分子量: 231.257
• InChiKey: QQRCQUWTDHLMKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  99
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-1-benzyl-1H-pyrazole-4-carbohydrazide 以 甲醇 为溶剂， 反应 8.0h， 生成 1-benzyl-5-(benzylideneamino)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  Synthesis of imine-pyrazolopyrimidinones and their mechanistic interventions on anticancer activity

  摘要：

  Design, synthesis and anticancer activity of a series of imine-pyrazolopyrimidinones is reported for the first time. Compounds 9d, 9n and 9o in the series show encouraging in vitro anticancer activity with low micromolar IC50 values against prostate (PC3) and breast (MCF7) cancer cell lines. Some notions about structure-activity relationships and plausible mechanism of biological activity are presented. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.016
• 作为产物：
  描述：

  5-氨基-1-苄基吡唑-4-甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 以73%的产率得到5-amino-1-benzyl-1H-pyrazole-4-carbohydrazide
  参考文献：
  名称：

  1-取代的4,5-二氨基吡唑类化合物的简便合成及其在吡唑并[3,4- b ]吡嗪类化合物中的应用

  摘要：

  由适当的5-氨基吡唑-4-羧酸酯制备1-取代的5-氨基吡唑-4-羰基叠氮化物。酰基叠氮化物经历Curtius重排，然后用醇淬灭以形成相应的氨基甲酸酯。通过催化氢解解封1-取代的5-氨基-4-苄氧基羰基氨基吡唑，得到所需的4，5-二氨基吡唑。立即将这些4，5-二氨基吡唑与乙二醛缩合，得到1-取代的吡唑并[3，4- b ]吡嗪。

  DOI：

  10.1016/j.tetlet.2004.03.142

文献信息

• Synthesis of imine-pyrazolopyrimidinones and their mechanistic interventions on anticancer activity
  作者：Ashish T. Baviskar、Uttam C. Banerjee、Mukesh Gupta、Rajveer Singh、Sunil Kumar、Manish K. Gupta、Sanjeev Kumar、Satish K. Raut、Madhu Khullar、Sandeep Singh、Raj Kumar

  DOI：10.1016/j.bmc.2013.07.016

  日期：2013.9

  Design, synthesis and anticancer activity of a series of imine-pyrazolopyrimidinones is reported for the first time. Compounds 9d, 9n and 9o in the series show encouraging in vitro anticancer activity with low micromolar IC50 values against prostate (PC3) and breast (MCF7) cancer cell lines. Some notions about structure-activity relationships and plausible mechanism of biological activity are presented. (C) 2013 Elsevier Ltd. All rights reserved.
• Facile synthesis of 1-substituted 4,5-diaminopyrazoles and its application toward the synthesis of pyrazolo[3,4- b ]pyrazines
  作者：Tun-Cheng Chien、Ronald A. Smaldone、Leroy B. Townsend

  DOI：10.1016/j.tetlet.2004.03.142

  日期：2004.5

  5-aminopyrazole-4-carboxylates. The acyl azides undergo a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates. The 1-substituted 5-amino-4-benzyloxycarbonylaminopyrazoles were unblocked by catalytic hydrogenolysis to give the desired 4,5-diaminopyrazoles. These 4,5-diaminopyrazoles were immediately condensed with glyoxal to afford 1-substituted pyrazolo[3,4-b]pyrazines.

  由适当的5-氨基吡唑-4-羧酸酯制备1-取代的5-氨基吡唑-4-羰基叠氮化物。酰基叠氮化物经历Curtius重排，然后用醇淬灭以形成相应的氨基甲酸酯。通过催化氢解解封1-取代的5-氨基-4-苄氧基羰基氨基吡唑，得到所需的4，5-二氨基吡唑。立即将这些4，5-二氨基吡唑与乙二醛缩合，得到1-取代的吡唑并[3，4- b ]吡嗪。