2-hydrazino-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile | 97693-26-0

• 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-phenyl-1,6-dihydropyrimidine-5-carbonitrile
• 英文别名: 2-Hydrazinyl-1-methyl-6-oxo-4-phenylpyrimidine-5-carbonitrile
• CAS: 97693-26-0
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: GXCCIDYKVHLTRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  258 °C(Solv: ethanol (64-17-5))
• 沸点：
  404.8±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 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-phenyl-1,6-dihydropyrimidine-5-carbonitrile 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 以60%的产率得到4-Methyl-5-oxo-7-phenyl-4,5-dihydro-tetrazolo[1,5-a]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Hussain, S. M.; El-Barbary, A. A.; Mansour, S. A., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 169 - 171

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 在 sodium hydroxide 、 sodium acetate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 2-hydrazino-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  Hussain, S. M.; El-Barbary, A. A.; Mansour, S. A., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 169 - 171

  摘要：

  DOI：

文献信息

• Synthesis, biological evaluation and molecular docking studies of some pyrimidine derivatives
  作者：Ahmed M. Fargualy、Nargues S. Habib、Khadiga A. Ismail、Ahmed M.M. Hassan、Marwa T.M. Sarg

  DOI：10.1016/j.ejmech.2013.05.028

  日期：2013.8

  Some novel pyrimidine-5-carbonitrile derivatives bearing various substituent have been synthesized. The structures of target compounds were confirmed by elemental analysis and spectral data. Some selected members of the newly synthesized compounds were investigated for their cytotoxic potency against certain human tumor cell lines. Five representative active anticancer compounds 6a, 6c, 6d, 17a and

  已经合成了一些带有各种取代基的新颖的嘧啶-5-腈衍生物。通过元素分析和光谱数据确认了目标化合物的结构。研究了新合成化合物的某些选定成员对某些人类肿瘤细胞系的细胞毒性。使用MOE程序，对两种酶的3D结构，对五个代表性的活性抗癌化合物6a，6c，6d，17a和18a进行对接。胸苷酸合酶和二氢叶酸还原酶。测试了合成化合物对金黄色葡萄球菌，铜绿假单胞菌的抗菌活性。，志贺志贺菌和白色念珠菌。化合物2c，7a和9c显示了广谱抗菌活性。
• 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。
• Synthesis and Dimroth Rearrangement of 6-Cyano-l,2,4-triazolo- [4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement
  作者：E. S. H. El Ashry、Y. El Kilany、N. Rashed、A. Mousaad、H. Assafir

  DOI：10.1515/znb-1998-1017

  日期：1998.10.1

  4-dihydropyrimidin-4-one (6) with one carbon inserting agents have been confirmed to be of the 1,2,4-triazolo[4,3-a]pyrimidin- 5(8H)-ones type and not the respective 7-ones, by comparing their alkylated derivatives 10a, 11a, 27 and 28 with the product from the cyclization of the 3-methyl and 3-benzyl derivatives of 6. A novel alkylation process was found when triethyl orthoformate was used as a cyclizing

  摘要 5-cyano-2-hydrazino-6-phenyl-3,4-dihydropyrimidin-4-one (6) 与一个碳插入剂的环化产物已被证实为 1,2,4-triazolo [4 , 3-a] 嘧啶- 5 (8H) -ones 类型而不是各自的 7-ones，通过将它们的烷基化衍生物 10a、11a、27 和 28 与 3-甲基和 3-苄基衍生物环化的产物进行比较6. 当使用原甲酸三乙酯作为环化剂时，发现了一种新的烷基化过程。8、14、15、24、34 和 36 与 2% 乙醇 KOH 的 Dimroth 重排分别得到各自的三唑并 [1,5-a] 嘧啶酮 13、18、19、25、38 和 40。使用 10% 乙醇 KOH 导致氰基参与重排，从而 8a 得到 7-亚氨基-5-苯基-1,2,4-三唑并 [1,5-a] 嘧啶 22
• 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.
• 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.