4-(2-furyl)-6-oxo-2-methylsulfanyl-1,6-dihydropyrimidine-5-carbonitrile | 137447-00-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(2-furyl)-6-oxo-2-methylsulfanyl-1,6-dihydropyrimidine-5-carbonitrile
• 英文别名: 6-(2-furyl)-3,4-dihydro-2-methylthio-4-oxo-5-pyrimidine carbonitrile；6-(2-furyl)-2-methylthio-4-oxo-3,4-dihydropyrimidine-5-carbonitrile；5-cyano-6-(2-furyl)-2-(methylthio)pyrimidin-4(3H)-one；4-(furan-2-yl)-2-methylsulfanyl-6-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 137447-00-8
• 化学式: C₁₀H₇N₃O₂S
• mdl: MFCD20483345
• 分子量: 233.25
• InChiKey: VFRHETWIJGNSLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-furyl)-6-oxo-2-methylsulfanyl-1,6-dihydropyrimidine-5-carbonitrile 在 一水合肼 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 正丁醇 为溶剂， 反应 6.0h， 生成 4-(furan-2-yl)-2,6-dihydrazinylpyrimidine-5-carbonitrile
  参考文献：
  名称：

  Ahmed, Gamal A.; El-Bahai, Said; Nasser, Bollettino Chimico Farmaceutico, 2003, vol. 142, # 2, p. 72 - 75

  摘要：

  DOI：
• 作为产物：
  描述：

  糠醛 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-(2-furyl)-6-oxo-2-methylsulfanyl-1,6-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  具有细胞凋亡作用的新型细胞毒性嘧啶和吡唑并嘧啶衍生物的合成及体外研究。

  摘要：

  已经合成了一系列新颖的肼基嘧啶，吡唑基嘧啶和3-氨基[3,4-d]吡唑并嘧啶衍生物，并通过NCI测试了它们对60种肿瘤细胞系的体外细胞毒性活性。确定了活性最高的化合物在体外对结肠KM12细胞系（5d，7c和7d），乳腺癌MCF-7（6a）和黑素瘤-MDA-MB-435（6h）的体外细胞毒性IC50值。氟尿嘧啶（5-FU）作为阳性对照。发现衍生物5d和7c是对KM12细胞系最有效的衍生物（分别为IC50 = 1.73和1.21 µM），与5-FU（IC50 = 12.26）相比，具有较高的选择性指数（SI）（分别为18.82和35.49）。 µM，SI = 1.93）。进一步研究化合物5d和7c在KM12细胞系中的凋亡行为。研究表明，caspase 3/9和促凋亡因子Bax上调。另一方面，抗凋亡因子Bcl-2的表达及其在纳摩尔浓度下的抑制被下调。此外，使用膜联蛋白V-FITC染色法检测了KM12细胞中衍生物5d和7c的凋亡作用。

  DOI：

  10.1016/j.bioorg.2020.103621

文献信息

• THIENOPYRIMIDINES
  申请人：Hoelzemann Guenter

  公开号：US20110028472A1

  公开（公告）日：2011-02-03

  Novel thienopyrimidines of the formula (I), in which R 1 , R 2 and X have the meanings indicated in Claim 1 , are inhibitors of TGF-beta receptor kinase, and can be employed, inter alia, for the treatment of tumours.

  化合物(I)的新噻吩嘧啶类化合物，在其中R1、R2和X具有权利要求书中指示的含义，是TGF-beta受体激酶的抑制剂，可用于治疗肿瘤。
• 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。
• Chloropyrimidines as a new class of antimicrobial agents
  作者：Nidhi Agarwal、Pratibha Srivastava、Sandeep K Raghuwanshi、D.N Upadhyay、Sudhir Sinha、P.K Shukla、Vishnu Ji Ram

  DOI：10.1016/s0968-0896(01)00374-1

  日期：2002.4

  In the course of our investigations of pyrimidines as antimycotic agents, we have identified a sub-class, with significant in vitro activity against mycobacteria. The salient feature of these pyrimidine derivatives (3a-o and 7a,b) is their appended aryl, heteroaryl and alkylthio substituent at position 6 and also alkylthio substituent at position 2. The rational design, synthesis, and evaluation of the in vitro antibacterial activity against six pathogenic bacteria including virulent and non-virulent strains of Mycobacterium tuberculosis is described. Some of the synthesized compounds (3c, 3h, 3i, 3o) have displayed only potent in vitro antimycobacterial activity with MIC of 0.75 mug/mL except 3i which also demonstrated activity against Escherichia coli at 12.5 mug/ mL concentration. Only two compounds, 3a and 3b, demonstrated antibacterial activity against Pseudomonas aeruginosa and E. coli with MIC 12.5 mug/mL. All the synthesized compounds were also evaluated for their antimycotic activity against five pathogenic fungi but only some of them 3j-n and 7a,b were found most potent against Aspergillus fumigatus and Trichophyton mentagrophytes. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Ram, Vishnu Ji; Haque, Navedul; Guru, P. Y., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 10, p. 962 - 965
  作者：Ram, Vishnu Ji、Haque, Navedul、Guru, P. Y.、Shoeb, A.

  DOI：——

  日期：——
• Glucopyranosides Derived From 6-Aryl-5-Cyano-2-(Methylthio)Pyrimidin-4(3<i>H</i>)Ones
  作者：Ibrahim M. Abdou、Adel M. Attia、Lucjan Strekowski

  DOI：10.1081/ncn-120006527

  日期：2002.4.15

  The reaction of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide with a 6-aryl-5-cyano-2-(methylthio)pyrimidin-4(3H)one in aqueous acetone in the presence of KOH furnishes a 4-(beta-D-glucopyranosyloxy)pyrimidine and a 3-(beta-D-glucopyranosyl)pyrimidine as the major and minor product, respectively.