4-[(prop-2-en-1-yl)sulfanyl]quinazoline | 33238-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-[(prop-2-en-1-yl)sulfanyl]quinazoline
• 英文别名: 4-(S-Allyl)-mercapto-chinazolin；4-Allylthio-chinazolin；4-Allylthioquinazoline；4-allylsulfanyl-quinazoline；4-Allylsulfanylquinazoline；4-prop-2-enylsulfanylquinazoline
• CAS: 33238-78-7
• 化学式: C₁₁H₁₀N₂S
• 分子量: 202.28
• InChiKey: GVPYNGMXQRALGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(prop-2-en-1-yl)sulfanyl]quinazoline 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-(bromomethyl)-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium tribromide
  参考文献：
  名称：

  Synthesis and Heterocyclization of 4-(Alkenylsulfanyl)quinazolines

  摘要：

  Alkylation of quinazoline-4(3H)-thione with 3-chloro-2-methylpropene and 2,3-dibromopropene afforded previously unknown 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline and 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline, respectively. 4-[(Prop-2-en-1-yl)sulfanyl]quinazoline reacted with bromine to give bromocyclization product and product of bromine addition to the exocyclic double bond. The reaction of 4-[(2-methylprop-2-en-1-yl)sulfanyl]quinazoline with halogens involved thiazole ring fusion. 5-Bromo-3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium bromide was isolated in the reaction of 4-[(2-bromoprop-2-en-1-yl)sulfanyl]quinazoline with bromine, and the reaction of the same substrate with iodine gave a mixture of 3-bromo-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium and 3-methylidene-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium iodides. 4-[(2-Methylprop-2-en-1-yl)sulfanyl]quinazoline reacted with 2 equiv of iodine to produce 3-methyl-3-iodomethyl-2,3-dihydro[1,3]thiazolo[3,2-c]quinazolinium triiodide and pentaiodide; the structure of the latter was studied by X-ray diffraction.

  DOI：

  10.1134/s1070428020090018
• 作为产物：
  描述：

  4-羟基喹唑啉 在 吡啶 、 氢氧化钾 、 tetraphosphorus decasulfide 、 四丁基溴化铵 作用下， 以 环己烷 为溶剂， 反应 20.0h， 生成 4-[(prop-2-en-1-yl)sulfanyl]quinazoline
  参考文献：
  名称：

  Quinazoline derivatives with antitubercular activity

  摘要：

  4-Quinazolinol was prepared by the reaction of anthranilic acid and formamide. The hydroxy group was converted into the thiol function by treatment with phosphorus(V)sulfide, and the subsequent alkylation of the thiol group was carried out with alkylhalides under the conditions of phase-transfer catalysis. The structure of the substances was confirmed by H-1, C-13 NMR, IR, and MS. Most of the synthesized compounds exhibited antimycobacterial activity against the strains of Mycobacterium tuberculosis, Mycobacerium avium, Mycobacterium fortuitum, Mycobacterium kansasii and Mycobacterium intracellulare. 4-(S-Butylthio)quinazoline (3c) was even more active than isoniazide against atypical strains of mycobacteria. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00100-2

文献信息

• Synthesis and bioactivity of 4-alkyl(aryl)thioquinazoline derivatives
  作者：Song Yang、Zhi Li、Linhong Jin、Baoan Song、Gang Liu、Jiang Chen、Zhuo Chen、Deyu Hu、Wei Xue、Ruiqing Xu

  DOI：10.1016/j.bmcl.2007.01.101

  日期：2007.4

  Some S'-substituted 4-alkyl(aryl)thioquinazoline derivatives were synthesized through thioetherification reaction of 4-chloroquinazolines 2 and thiol compounds 1 refluxed in acetone in the presence of K(2)CO(3). Their structures were verified by elemental analysis, IR, (1)H NMR, and (13)C NMR. The compounds were evaluated for their anti-proliferative activities against some cancer cells in vitro by

  通过4-氯喹唑啉2和在K（2）CO（3）存在下在丙酮中回流的硫醇化合物1的硫醚化反应，合成了一些S'-取代的4-烷基（芳基）硫代喹唑啉衍生物。通过元素分析，IR，（1）H NMR和（13）C NMR验证了它们的结构。通过MTT法评价了这些化合物在体外对某些癌细胞的抗增殖活性。其中，3c，3a，3d，3f和3l对PC3细胞非常有效，而3a-3m对Bcap37和BGC823细胞则显示弱活性。3c，3a，3d，3f和31l对PC3细胞的IC（50）值分别为1.8、5.6、8.1、8.7和8.9 microM。
• Synthesis of 4-Thioquinazoline Compounds in Aqueous Media Catalyzed by Indium
  作者：G. Liu、W.Q. Ma、H.G. Chen、C.P. Liu、S.G. Xu、X.G. Liu、C.N. Ji、X.Y. Liu

  DOI：10.14233/ajchem.2013.15685

  日期：——

  An efficient and facile reaction of 4-chloroquinazoline and thiols was achieved under indium mediation in water, providing a simple method for the synthesis of substituted 4-thioquinazoline compounds in good yield. The structures of the title compounds were characterized by elemental analyses as well as IR, 1H and 13C NMR spectroscopies. Preliminary biological tests showed that compound 3d exhibited good antifungal activity against Fusarium oxysporum with EC50 = 17.08 μg/mL.

  在铟的介导下，4-氯喹唑啉和硫醇在水中发生了高效而简便的反应，为合成取代的 4-硫代喹唑啉化合物提供了一种简单的方法，而且收率很高。通过元素分析以及红外光谱、1H 和 13C NMR 光谱，对标题化合物的结构进行了表征。初步生物测试表明，化合物 3d 对恶孢镰刀菌具有良好的抗真菌活性，EC50 = 17.08 μg/mL。
• AMINO QUINAZOLINES AS KINASE INHIBITORS
  申请人：Bury Michael Jonathan

  公开号：US20140206688A1

  公开（公告）日：2014-07-24

  Disclosed are compounds having the formula (Formula I)): wherein R 1 , R 2 , R 3 and Z are as defined herein, and methods of making and using the same.

  公开了具有以下公式（公式I）的化合物：其中R1，R2，R3和Z的定义如本文所述，并公开了制备和使用这些化合物的方法。
• SINGH H.; KUMAR A.; KUMAR K. S.; LAL K. B., INDIAN J. CHEM. <IJOC-AP>, 1975, 13, NO 9, 983-985
  作者：SINGH H.、 KUMAR A.、 KUMAR K. S.、 LAL K. B.

  DOI：——

  日期：——
• US9604938B2
  申请人：——

  公开号：US9604938B2

  公开（公告）日：2017-03-28