2-hydrazino-1-methyl-6-oxo-4-(4-chlorophenyl)-1,6-dihydropyrimidine-5-carbonitrile | 389614-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-hydrazino-1-methyl-6-oxo-4-(4-chlorophenyl)-1,6-dihydropyrimidine-5-carbonitrile
• 英文别名: 6-(4'-chlorophenyl)-5-cyano-2-hydrazino-3-N-methyl-3,4-dihydropyrimidin-4-one；4-(4-chlorophenyl)-2-hydrazino-1-methyl-5-cyano-6-oxo-1,6-dihydropyrimidine；6-p-chlorophenyl-5-cyano-2-hydrazino-3-N-methyl-3,4-dihydropyrimidin-4-one；4-(4-Chlorophenyl)-2-hydrazinyl-1-methyl-6-oxopyrimidine-5-carbonitrile
• CAS: 389614-64-6
• 化学式: C₁₂H₁₀ClN₅O
• 分子量: 275.697
• InChiKey: RLEQEKFZVMOWIK-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C(Solv: ethanol (64-17-5))
• 沸点：
  428.0±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  94.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydrazino-1-methyl-6-oxo-4-(4-chlorophenyl)-1,6-dihydropyrimidine-5-carbonitrile 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-[3-Chloro-2-(4-chloro-phenyl)-4-oxo-azetidin-1-ylamino]-4-(4-chloro-phenyl)-1-methyl-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Modha; Parmar; Datta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 12, p. 2694 - 2697

  摘要：

  DOI：
• 作为产物：
  描述：

  6-(4-chlorophenyl)-3,4-dihydro-3-methyl-2-methylthio-4-oxopyrimidine-5-carbonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以51%的产率得到2-hydrazino-1-methyl-6-oxo-4-(4-chlorophenyl)-1,6-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  新型二氢嘧啶及其吡唑衍生物：合成与药理筛选

  摘要：

  在本研究中，我们已经合成了新颖的二氢嘧啶（1A - Ĵ），它们的二甲基化加合物（2A - Ĵ），和肼衍生物（3A - Ĵ的）2A - Ĵ并且随后其吡唑衍生物（4A - Ĵ）。元素分析，IR，1 H NMR和质谱数据阐明了新合成化合物的结构。这些新颖的衍生物中的一些表现出中等至有效的体外抗氧化剂，抗炎，抗菌，抗真菌和驱虫活性。

  DOI：

  10.1016/j.ejmech.2011.02.052

文献信息

• Reaction of Pyrimidinonethione Derivatives: Synthesis of N-Methyl-2-Hydrizinopyrimidine-4-One, Thiazolo[3,4-b] N-Methylpyrimidinone; 2-(1-Pyrazolonyl) N-Methylpyrimidine-4-one and 2-Hydrazino-N-Methyl Pyrimidine-4-One Derivatives
  作者：Abdullah A. Al-Karim Al-Shara'ey

  DOI：10.1002/jccs.200400082

  日期：2004.6

  reacted with hydrazine hydrate to give the sulfur free reaction products 3a-c. These reaction products were taken as the starting materials for the synthesis of several new heterocyclic derivatives. Reaction of 3a-c with acetic anhydride and formic acid gave pyrimido triazines 4a-c and 7a-c, respectively. Their reactions with active methylene containing reagents gave the corresponding 2-(1-pyrazonyl)-N-methyl

  6-Aryl-5-cyano-4-pyrimidinone-2-thion 衍生物 1a-c 与碘甲烷 (1:2) 反应生成相应的 2-S,N-二甲基嘧啶-4-one 衍生物 2a-c。化合物2a-c依次与水合肼反应，得到无硫反应产物3a-c。这些反应产物作为合成几种新型杂环衍生物的原料。3a-c 与乙酸酐和甲酸反应分别得到嘧啶基三嗪 4a-c 和 7a-c。它们与含活性亚甲基的试剂反应分别得到相应的 2-(1-吡唑)-N-甲基嘧啶衍生物 9a-c 和 10a-c。它们与芳香醛反应得到相应的 2-腙基嘧啶衍生物 11a-c。
• Novel dihydropyrimidines and its pyrazole derivatives: Synthesis and pharmacological screening
  作者：B. Ramesh、Chetan M. Bhalgat

  DOI：10.1016/j.ejmech.2011.02.052

  日期：2011.5

  In the present study, we have synthesized novel dihydropyrimidines (1a–j), their dimethylated adducts (2a–j), and hydrazine derivatives (3a–j) of 2a–j and subsequently their pyrazole derivatives (4a–j). Elemental analysis, IR, 1H NMR and mass spectral data elucidated structure of newly synthesized compounds. Some of these novel derivatives showed moderate to potent in vitro antioxidant, anti-inflammatory

  在本研究中，我们已经合成了新颖的二氢嘧啶（1A - Ĵ），它们的二甲基化加合物（2A - Ĵ），和肼衍生物（3A - Ĵ的）2A - Ĵ并且随后其吡唑衍生物（4A - Ĵ）。元素分析，IR，1 H NMR和质谱数据阐明了新合成化合物的结构。这些新颖的衍生物中的一些表现出中等至有效的体外抗氧化剂，抗炎，抗菌，抗真菌和驱虫活性。
• Synthesis and biological evaluation of some new 3,4-dihydropyrimidin-4-ones
  作者：Jayesh Modha、Neela Datta、Hansa Parekh

  DOI：10.1016/s0014-827x(01)01118-1

  日期：2001.8

  Condensation of 5-cyano-2-hydrazino-3-N-methyl-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4-one (3a and 3b) with 2 4-bisalkyl/arylamino-6-chloro-s-triazine (4) gave the corresponding 2,4-bisalkyl/arylamino-6-[5'-cyano-3'-N-methyl]-6'-phenyl/p-chlorophenyl-3',4'-dihydropyrimidin-4'-one-2'-yl-hydrazino-s-triazines (5a-n and 6a-n). The compounds 4 have been prepared by the condensation of cyanuric chloride and different alkyl/aryl amines. The reaction between 5-cyano-3-N-methyl-2-methylthio-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4-one (2a and 2b) with hydrazine hydrate furnished 3a and 3b, respectively. The condensation of 6-phenyl/p-chlorophenyl/5-cyano-2-mercapto-3,4-dihydropyrimidin-4-one (1a and 1b) with methyl iodide yielded 2a and 2b, respectively. All the products have been evaluated in vitro for their antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37 Rv. (C) 2001 Elsevier Science S.A. All rights reserved.
• Modha; Parmar; Datta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 12, p. 2694 - 2697
  作者：Modha、Parmar、Datta、Parekh

  DOI：——

  日期：——
• Synthesis of some dihydropyrimidine-based compounds bearing pyrazoline moiety and evaluation of their antiproliferative activity
  作者：Fadi M. Awadallah、Gary A. Piazza、Bernard D. Gary、Adam B. Keeton、Joshua C. Canzoneri

  DOI：10.1016/j.ejmech.2013.10.003

  日期：2013.12

  Two series of 2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitriles 5a-h and 4-(4-chlorophenyl)-2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitriles 6a-h were synthesized via a cydocondensation reaction of the corresponding 2-hydrazinopyrimidines 3a,b with the appropriate 2-propen-1-ones 4a h. The target compounds were screened for their antiproliferative activity against A 549 (lung), HT 29 (colon), MCF 7 and MDA-MB 231 (breast) cell lines. The two most susceptible cell lines were the colon (HT 29) and breast (MDA-MB 231). Generally, the 4-unsubstitutedphenylpyrimidine derivatives 5a h were more active than their 4-chlorophenylpyrimidine analogs 6a h. Compounds 5e and 5g, showed high activity against three of the cell lines. The most active compound 5c possessed IC50 = 1.76 mu M against A 549 cell line. (C) 2013 Elsevier Masson SAS. All rights reserved.