3-benzamido-5-methyl-1H-pyrazole | 52566-42-4

• 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: 3-benzamido-5-methyl-1H-pyrazole
• 英文别名: N-(5-methyl-1(2)H-pyrazol-3-yl)-benzamide；N-(5-methyl-1H-pyrazol-3-yl)benzamide
• CAS: 52566-42-4
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: RBFPHINFSBMIFN-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C
• 沸点：
  310.4±30.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

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：
  0.09
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzamido-5-methyl-1H-pyrazole 在 盐酸 、 氢氧化钾 、 potassium nitrite 作用下， 生成 3-methyl-4-diazo-5-benzamido-1H-pyrazole
  参考文献：
  名称：

  Antimicrobial and antineoplastic activities of new 4-diazopyrazole derivatives

  摘要：

  Several new 4-diazopyrazole derivatives were prepared by the reaction of 3-methyl-5(substituted-benzamido)pyrazoles with an excess of nitrous acid in acetic acid solution. The compounds were tested for antiretroviral activity in HIV-1 infected MT-4 cells and antiproliferative effects against a panel of human leukemia, lymphoma and solid tumor cell lines. They were also tested for activity against representative gram-negative (Shigella, Salmonella) and gram-positive (S. aureus, D group Streptococcus) bacteria as well as fungi (C. albicans, C. paratropicalis, C. neoformans and A. fumigatus). Compounds were devoid of anti HIV-1 and antimicotic activities, whereas they were active against tumor cell lines, with inhibitory activity (IC50) in the range 2.4-20 mu M and bacteria. The highest microbial susceptibility was shown by gram-positive bacteria, with minimum inhibitory concentrations in the range 0.8-12.5 mu M. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80004-4
• 作为产物：
  描述：

  6-甲基-2-苯基-1,3-恶嗪-4-酮 以74%的产率得到
  参考文献：
  名称：

  YAMAMOTO Y.; AZUMA Y.; MIYAKAWA K., CHEM. AND PHARM. BULL., 1978, 26, NO 6, 1825-1831

  摘要：

  DOI：

文献信息

• 3-Aminopyrazole Inhibitors of CDK2/Cyclin A as Antitumor Agents. 1. Lead Finding
  作者：Paolo Pevarello、Maria Gabriella Brasca、Raffaella Amici、Paolo Orsini、Gabriella Traquandi、Luca Corti、Claudia Piutti、Pietro Sansonna、Manuela Villa、Betsy S. Pierce、Maurizio Pulici、Patrizia Giordano、Katia Martina、Edward L. Fritzen、Richard A. Nugent、Elena Casale、Alexander Cameron、Marina Ciomei、Fulvia Roletto、Antonella Isacchi、GianPaolo Fogliatto、Enrico Pesenti、Wilma Pastori、Aurelio Marsiglio、Karen L. Leach、Paula M. Clare、Francesco Fiorentini、Mario Varasi、Anna Vulpetti、Martha A. Warpehoski

  DOI：10.1021/jm031145u

  日期：2004.6.1

  targeting complexes between cyclin-dependent kinases (CDK) and cyclins, such as CDK2/cyclin A and CDK2/cyclin E, and inhibiting their kinase activity are regarded as promising antitumor agents to complement the existing therapies. From a high-throughput screening effort, we identified a new class of CDK2/cyclin A/E inhibitors. The hit-to-lead expansion of this class is described. X-ray crystallographic

  由正常细胞周期机制的破坏介导的异常增殖实际上是所有癌细胞的标志。靶向针对细胞周期蛋白依赖性激酶（CDK）与细胞周期蛋白之间的复合物（例如CDK2 / cyclin A和CDK2 / cyclin E）并抑制其激酶活性的化合物被认为是有前途的抗肿瘤药物，可补充现有疗法。通过高通量筛选工作，我们确定了一类新的CDK2 / cyclin A / E抑制剂。描述了此类的从头到尾的扩展。该系列中早期化合物的X射线晶体学数据以及为快速达到体内功效而进行的体外试验，导致了CDK2 / cyclin A（N-（5-环丙基-1H-吡唑-3- yl）-2-（2-萘基）乙酰胺（41），PNU-292137，IC50 = 37 nM），具有体内抗肿瘤活性（TGI>
• Diamino pyrazols, their synthesis, keratin fibre dyeing compositions
  申请人：L'Oreal

  公开号：US06118008A1

  公开（公告）日：2000-09-12

  The invention discloses new 5-substituted 3,4-diamino pyrazols, their methods of preparation, compositions for keratin fiber oxidation dyeing containing them as an oxidizing base, and the dyeing methods using same.

  本发明公开了新型5-取代的3,4-二氨基吡唑、其制备方法、含有它们作为氧化基质的角蛋白纤维氧化染料组合物，以及使用这些染料的染色方法。
• Straightforward transformation of isoxazoles into pyrazoles: renewed and improved
  作者：Sergey I. Sviridov、Andrei A. Vasil'ev、Sergey V. Shorshnev

  DOI：10.1016/j.tet.2007.09.046

  日期：2007.12

  or carbamoyl groups were transformed into the corresponding pyrazoles in high yields by the treatment with hydrazine in methanol in the presence of a hydrogenation catalyst, e.g., Raney nickel, at ambient temperature. For the synthesis of N-substituted pyrazoles, hydrogenolysis of isoxazole followed by the treatment with substituted hydrazine was required. 3(5)-Aryl- or acylamido-substituted isoxazoles

  通过在环境温度下在氢化催化剂例如阮内镍的存在下用肼在甲醇中处理，将具有烷基或氨基甲酰基的异恶唑高产率地转化成相应的吡唑。为了合成N-取代的吡唑，需要将异恶唑氢解，然后用取代的肼处理。3（5）-芳基或酰基酰胺基取代的异恶唑不太适合这种转化。
• NOUVEAUX DIAMINO PYRAZOLES, LEUR SYNTHESE, COMPOSITIONS DE TEINTURE DES FIBRES KERATINIQUES LES CONTENANT, PROCEDES DE TEINTURE DES FIBRES KERATINIQUES
  申请人：L'OREAL

  公开号：EP0900206A1

  公开（公告）日：1999-03-10
• US6118008A
  申请人：——

  公开号：US6118008A

  公开（公告）日：2000-09-12