4-(phenylhydrazinylidene)pyrazole-3,5-diamine | 3656-02-8

• 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-(phenylhydrazinylidene)pyrazole-3,5-diamine
• 英文别名: 3,5-diamino-4-(phenyl)azo-pyrazole
• CAS: 3656-02-8
• 化学式: C₉H₁₀N₆
• 分子量: 202.219
• InChiKey: BLXRKDXUWQFGAW-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  105.44
• 氢给体数：
  3.0
• 氢受体数：
  5.0

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  4-(phenylhydrazinylidene)pyrazole-3,5-diamine 、 依达拉奉 以70%的产率得到
  参考文献：
  名称：

  ABED, NOSRAT, MUSTAFA;HAFEZ, EBTISAM, ABDEL, AZIZ;IBRAHIM, NADIA, SOBHY;M+, MONATSH. CHEM., 1985, 116, N 2, 223-228

  摘要：

  DOI：
• 作为产物：
  描述：

  (苯基亚肼基)丙二腈 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 4-(phenylhydrazinylidene)pyrazole-3,5-diamine
  参考文献：
  名称：

  4-Arylazo-3,5-diamino-1H-pyrazole CDK Inhibitors:  SAR Study, Crystal Structure in Complex with CDK2, Selectivity, and Cellular Effects

  摘要：

  In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl] phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.

  DOI：

  10.1021/jm0605740

文献信息

• [EN] 4-ARYLAZO-3,5-DIAMINO-PYRAZOLE COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSES DE 4-ARYLAZO-3,5-DIAMINO-PYRAZOLE ET LEUR UTILISATION
  申请人：INST OF EX BOTANY OF THE ACADE

  公开号：WO2006024858A1

  公开（公告）日：2006-03-09

  A series of mono- and binuclear 4-arylazo-3,5-diamino-pyrazoles which are useful for inhibition of cyclin-dependent kinases (preferably CDK9). Hence they can be used as antimitotic-, pro-apoptotic and antünflammatory drugs, in particular, in chemotherapy of cancer and asthma, therapy of psoriasis and parasitoses as those caused by fungi or protists, treatment of Alzheimer's disease or as antineurodegenerative drugs, or to suppress immunostimulation. These compounds are useful in a variety of utilities, including as intermediates in the preparation of flame-retardants, diagnostic reagents and therapeutics, including antivirals and immunosuppressors.

  一系列单核和双核的4-芳基偶氮-3,5-二氨基吡唑醇，可用于抑制细胞周期依赖性激酶（优选为CDK9）。因此，它们可以用作抗有丝分裂、促凋亡和抗炎药物，特别是在癌症和哮喘化疗、牛皮癣和由真菌或原生动物引起的寄生虫病的治疗中，阿尔茨海默病的治疗或作为抗神经退行性药物，或用于抑制免疫刺激。这些化合物在各种用途中都很有用，包括作为制备阻燃剂、诊断试剂和治疗药物的中间体，包括抗病毒药物和免疫抑制剂。
• POTENTIAL PURINE ANALOGUE ANTAGONISTS: SYNTHESIS OF NOVEL CYCLOALKANE RING-FUSED PYRAZOLO[1,5-<i>A</i>]PYRIMIDINES
  作者：Galal H. Elgemeie、Hany A. Ali

  DOI：10.1081/scc-120002010

  日期：2002.1

  ABSTRACT A convenient route for the synthesis of new variety of pyrazolo[1,5-a]pyrimidine derivatives by the reaction of 5-aminopyrazoles with suitable unsaturated keto compounds. The structure of the reaction products were established based on the elemental analysis, spectral data (IR, 1H NMR, MS) and X-ray diffraction analysis.

  摘要 通过 5-氨基吡唑与合适的不饱和酮化合物反应合成新型吡唑并 [1,5-a] 嘧啶衍生物的便捷途径。基于元素分析、光谱数据（IR、1H NMR、MS）和X射线衍射分析确定了反应产物的结构。
• TARGETING NAD BIOSYNTHESIS IN BACTERIAL PATHOGENS
  申请人：Mackerell, JR. Alexander

  公开号：US20120190708A1

  公开（公告）日：2012-07-26

  The emergence of multidrug-resistant pathogens necessitates the search for new antibiotics acting on previously unexplored targets. Nicotinate mononucleotide adenylyltransferase of the NadD family, an essential enzyme of NAD biosynthesis in most bacteria, was selected as a target for structure-based inhibitor development. To this end, the inventors have identified small molecule compounds that inhibit bacterial target enzymes by interacting with a novel inhibitory binding site on the enzyme while having no effect on functionally equivalent human enzymes.

  多重耐药病原体的出现需要寻找作用于先前未被开发的靶标的新抗生素。Nicotinate单核苷酸腺苷转移酶（NadD家族），是大多数细菌NAD生物合成的必需酶，被选为基于结构的抑制剂开发的目标。为此，发明人已经鉴定出小分子化合物，通过与酶上的新型抑制性结合位点相互作用来抑制细菌靶标酶，而对功能相当的人类酶没有影响。
• WRUBEL, Y.;MAYER, R., Z. CHEM., 1984, 24, N 7, 256-257
  作者：WRUBEL, Y.、MAYER, R.

  DOI：——

  日期：——
• ELNAGDI M. H.; KANDEEL E. M.; ZAYED E. M.; KANDIL Z. E., J. PRAKT. CHEMIE, 1978, 320, NO 4, 533-538
  作者：ELNAGDI M. H.、 KANDEEL E. M.、 ZAYED E. M.、 KANDIL Z. E.

  DOI：——

  日期：——