2-甲硫基-4-氯-6-(2-呋喃基)-5-嘧啶甲腈 | 137447-07-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-甲硫基-4-氯-6-(2-呋喃基)-5-嘧啶甲腈
• 英文名称: 4-chloro-6-(2-furyl)-2-methylsulfanyl-pyrimidine-5-carbonitrile
• 英文别名: 2-methylthio-4-chloro-6-(2-furyl)-5-pyrimidine carbonitrile；4-chloro-6-(2-furyl)-2-methylthiopyrimidine-5-carbonitrile；4-chloro-6-furan-2-yl-2-methylsulfanylpyrimidine-5-carbonitrile；4-Chloro-6-(2-furyl)-2-methylsulfanylpyrimidine-5-carbonitrile；4-chloro-6-(furan-2-yl)-2-methylsulfanylpyrimidine-5-carbonitrile
• CAS: 137447-07-5
• 化学式: C₁₀H₆ClN₃OS
• 分子量: 251.696
• InChiKey: ORQKYNZYPVDJGX-UHFFFAOYSA-N

物化性质

• 沸点：
  448.4±45.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  88
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲硫基-4-氯-6-(2-呋喃基)-5-嘧啶甲腈 在 一水合肼 作用下， 以 正丁醇 为溶剂， 反应 2.0h， 以39%的产率得到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：

  6-(2-呋喃基)-4-氧代-2-硫代-1,2,3,4-四氢嘧啶-5-腈 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-甲硫基-4-氯-6-(2-呋喃基)-5-嘧啶甲腈
  参考文献：
  名称：

  Chloropyrimidines as a new class of antimicrobial agents

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00374-1

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。
• Synthesis and in vitro investigation of novel cytotoxic pyrimidine and pyrazolopyrimidne derivatives showing apoptotic effect
  作者：Fatma A. Ragab、Yassin M. Nissan、Emad M. Seif、Ahmed Maher、Reem K. Arafa

  DOI：10.1016/j.bioorg.2020.103621

  日期：2020.3

  A series of novel derivatives of hydrazinylpyrimidines, pyrazolylpyrimidines and 3-amino[3,4-d]pyrazolopyrimidines have been synthesized and tested for their in vitro cytotoxic activity against 60 tumor cell lines by NCI. The in vitro cytotoxic IC50 values for the most active compounds were determined against the colon-KM12 cell line (5d, 7c and 7d), breast-MCF-7 (6a) and melanoma-MDA-MB-435 (6h) using

  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。
• [EN] SUBSTITUTED PYRIMIDINE FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION<br/>[FR] PYRIMIDINE SUBSTITUÉE POUR LE TRAITEMENT ET LA PROPHYLAXIE D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021063852A1

  公开（公告）日：2021-04-08

  The present invention provides novel compounds having the general formula: wherein R1 to R4, L1, L2 and X are as described herein, compositions including the compounds and methods of using the compounds.

  本发明提供具有通式的新化合物：其中R1至R4、L1、L2和X如本文所述，包括这些化合物的组合物和使用这些化合物的方法。
• 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：——
• THIENOPYRIMIDINE
  申请人：Merck Patent GmbH

  公开号：EP2260044A2

  公开（公告）日：2010-12-15