4-(4-methylbenzyl)-1H-pyrazole-3,5-diamine | 109547-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-methylbenzyl)-1H-pyrazole-3,5-diamine
• 英文别名: 4-[(4-methylphenyl)methyl]-1H-pyrazole-3,5-diamine
• CAS: 109547-61-7
• 化学式: C₁₁H₁₄N₄
• mdl: MFCD00265985
• 分子量: 202.259
• InChiKey: YISMUTXHXRJKES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-methylbenzyl)-1H-pyrazole-3,5-diamine 在 哌啶 、 W₂-Raney Ni 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 2-acetylamino-8-methoxy-3-(4-methylbenzyl)-6H-indeno<2,1-e>pyrazolo<1,5-a>pyrimidine
  参考文献：
  名称：

  Ram, Vishnu J.; Nath, Mahendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 5, p. 416 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-甲基苄基)丙二腈 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以70%的产率得到4-(4-methylbenzyl)-1H-pyrazole-3,5-diamine
  参考文献：
  名称：

  The Reactions of Benzylmalononitriles with Hydrazine and Hydroxylamine. Synthesis of Pyrazoles, Isoxazoles, and Pyrazolo[1,5-a]-pyrimidine Derivatives

  摘要：

  苄基丙二腈与肼或羟胺反应，分别生成 4-取代的 3,5-二氨基吡唑或异噁唑。 在温和的条件下，这些吡唑与一些 2,3-二取代的丙烯腈（包括亚苄基丙二腈）反应，制备出吡唑并[1,5-a]嘧啶衍生物。

  DOI：

  10.1055/s-1987-27831

文献信息

• The Reactions of Benzylmalononitriles with Hydrazine and Hydroxylamine. Synthesis of Pyrazoles, Isoxazoles, and Pyrazolo[1,5-<i>a</i>]-pyrimidine Derivatives
  作者：Juan J. Vaquero、Luis Fuentes、Juan C. Del Castillo、María I. Pérez、José L. García、José L. Soto

  DOI：10.1055/s-1987-27831

  日期：——

  Benzylmalononitriles react with hydrazine or hydroxylamine to give 4-substituted 3,5-diaminopyrazoles or isoxazoles, respectively. Pyrazolo[1,5-a]pyrimidine derivatives are prepared by reaction of these pyrazoles with some 2,3-disubstituted propenenitriles (including benzylidenemalononitrile) under mild conditions.

  苄基丙二腈与肼或羟胺反应，分别生成 4-取代的 3,5-二氨基吡唑或异噁唑。 在温和的条件下，这些吡唑与一些 2,3-二取代的丙烯腈（包括亚苄基丙二腈）反应，制备出吡唑并[1,5-a]嘧啶衍生物。
• Discovery of mixed type thymidine phosphorylase inhibitors endowed with antiangiogenic properties: Synthesis, pharmacological evaluation and molecular docking study of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones. Part II
  作者：Hriday Bera、Probir kumar Ojha、Bee Jen Tan、Lingyi Sun、Anton V. Dolzhenko、Wai-Keung Chui、Gigi Ngar Chee Chiu

  DOI：10.1016/j.ejmech.2014.03.063

  日期：2014.5

  In our drug discovery program, a series of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones were designed, synthesized and evaluated for their TP inhibitory potential. All the synthesized analogues conferred a varying degree of TP inhibitory activity, comparable or better than positive control, 7-deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). A systematic approach to the lead optimization identified compounds 3c and 4a as the most promising TP inhibitors, exhibiting mixed mode of enzyme inhibition. Moreover, selected compounds demonstrated the ability to attenuate the expression of the angiogenic markers (viz. MMP-9 and VEGF) in MDA-MB-231 cells at sublethal concentrations. In addition, molecular docking studies revealed the plausible binding orientation of these inhibitors towards TP, which was in accordance with the experimental results. Taken as a whole, these compounds would constitute a new direction for the design of novel TP inhibitors with promising antiangiogenic properties. (C) 2014 Elsevier Masson SAS. All rights reserved.
• VAQUERO J. J.; FUENTES L.; DEL CASTILLO J. C.; PEREZ M. I.; GARCIA J. L.;+, SYNTHESIS,(1987) N 1, 33-35
  作者：VAQUERO J. J.、 FUENTES L.、 DEL CASTILLO J. C.、 PEREZ M. I.、 GARCIA J. L.、+

  DOI：——

  日期：——
• Ram, Vishnu J.; Nath, Mahendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 5, p. 416 - 422
  作者：Ram, Vishnu J.、Nath, Mahendra

  DOI：——

  日期：——
• Synthesis of New Bis(pyrazolo[1,5‐<i>a</i>]pyrimidines) Linked to Different Spacers as Potential MurB Inhibitors
  作者：Sherif M. H. Sanad、Alshimaa A. M. Abdelsalam、Aya A. Gamal Eldin、Esraa H. Abdelfattah、Fatma R. M. Hussein、Nada G. Mohammed、Nariman A. S. Taha、Ahmed E. M. Mekky

  DOI：10.1002/cbdv.202300546

  日期：2023.6

  efficient protocol was adopted to efficiently prepare three new series of bis(pyrazolo[1,5-a]pyrimidines) linked to different spacers. The new bis(pyrazolo[1,5-a]pyrimidines) were prepared in 80–90 % yields by reacting the respective bis(enaminones) and 4-(4-substituted benzyl)-1H-pyrazole-3,5-diamines in pyridine at reflux temperature for 5–7 h. The new products showed a wide spectrum of antibacterial activity

  采用有效的方案有效地制备了连接到不同间隔基的三个新系列的双(吡唑并[1,5- a ]嘧啶)。通过使相应的双(烯胺酮)和4-(4-取代的苄基)-1 H-吡唑-3,5-二胺反应，制备了新的双(吡唑并[1,5- a ]嘧啶)，产率为80-90%在吡啶中回流5-7小时。新产品对六种不同的细菌菌株表现出广泛的抗菌活性。一般来说，丙烷和丁烷连接的双(吡唑并[1,5- a]嘧啶），连接到3-（4-甲基-或4-甲氧基苄基）单位，具有最好的抗菌活性，最低抑菌浓度（MIC）和最低杀菌浓度（MBC）值分别高达2.5和5.1 μM 。此外，之前的产品表现出良好的 MurB 抑制活性，IC 50值高达 7.2 μM。