2-ethyl-3H-quinazoline-4-thione | 69729-68-6

• 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: 2-ethyl-3H-quinazoline-4-thione
• 英文别名: 2-ethyl-3H-quinazoline-4-thione；2-Aethyl-3H-chinazolin-4-thion；2-Ethylquinazoline-4(3H)-thione；2-ethyl-1H-quinazoline-4-thione
• CAS: 69729-68-6
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: JHGVAZCNMCJXSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethyl-3H-quinazoline-4-thione 在 正丁基锂 、 重水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以95%的产率得到2-(1-deuterioethyl)-3H-quinazoline-4-thione
  参考文献：
  名称：

  A Simple Procedure for the Side-Chain Substitution of 2-Alkyl-3 H -quinazo­line-4-thiones: Application in Synthesis

  摘要：

  2- 烷基-3H-喹唑啉-4-硫醚在氮和 2-烷基（Me、Et、Pr）的δ-氢处与正丁基锂在-78 °C的无水四氢呋喃中在氮条件下实现了双重石化作用。将得到的二锂试剂与各种亲电体（碘甲烷、碘乙烷、1-溴丁烷、D2O、苯甲醛、4-甲氧基苯甲醛、丁-2-酮、环己酮、二苯甲酮、异硫氰酸苯酯、二硫化四异丙基秋兰姆）反应，可以得到相应的改性 2-取代 3H-喹唑啉-4-硫酮 4-22，收率极高。

  DOI：

  10.1055/s-2004-815923
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 硫化氢 、 氨 作用下， 生成 2-ethyl-3H-quinazoline-4-thione
  参考文献：
  名称：

  Bogert; Breneman; Hand, Journal of the American Chemical Society, 1903, vol. 25, p. 377

  摘要：

  DOI：

文献信息

• Phosphodiesterase inhibitory properties of losartan. design and synthesis of new lead compounds
  作者：Victor Segarra、M. Isabel Crespo、Ferran Pujol、Jorge Beleta、Teresa Doménech、Montserrat Miralpeix、Jose M. Palacios、Ana Castro、Ana Martinez

  DOI：10.1016/s0960-894x(98)00058-4

  日期：1998.3

  A 4-centre PDE 4 pharmacophore search has been carried out in several 3D-databases containing compounds belonging to different therapeutic areas. Losartan, an angiotensin-II antagonist, has been identified as a new lead compound for developping PDE 4 inhibitors. New families of compounds derived from losartan has been synthesized and their PDE inhibition has been measured. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 2-Alkyl(aryl)-quinazolin-4(3<i>H</i>)-thiones, 2-R-(quinazolin-4(3<i>H</i>)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties
  作者：Lyudmyla Antypenko、Sergiy Kovalenko、Yulia Posylkina、Vladyslav Nikitin、Natalia Fedyunina、Vitalii Ivchuk

  DOI：10.3109/14756366.2015.1018243

  日期：2016.3.3

  In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, H-1-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 - leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways.
• SELIM M.; SAMMOUR A.; ABDALLA M.; ELKASABY M., PAKISTAN J. SCI. RES. <PSIR-AA>, 1975, 27, NO 1-4, 67-72
  作者：SELIM M.、 SAMMOUR A.、 ABDALLA M.、 ELKASABY M.

  DOI：——

  日期：——
• Bogert; Breneman; Hand, Journal of the American Chemical Society, 1903, vol. 25, p. 377
  作者：Bogert、Breneman、Hand

  DOI：——

  日期：——
• A Simple Procedure for the Side-Chain Substitution of 2-Alkyl-3<b> <i>H</i> </b>-quinazo­line-4-thiones: Application in Synthesis
  作者：Gamal A. El-Hiti

  DOI：10.1055/s-2004-815923

  日期：——

  Double lithiation of 2-alkyl-3H-quinazoline-4-thiones at nitrogen and at the α-hydrogen of the 2-alkyl group (Me, Et, Pr) has been achieved with n-butyllithium at -78 °C in anhydrous THF under nitrogen. Reactions of the dilithium reagents obtained with various electrophiles (iodomethane, iodoethane, 1-bromobutane, D2O, benzaldehyde, 4-anisaldehyde, butan-2-one, cyclohexanone, benzophenone, phenyl isothiocyanate, tetraisopropylthiuram disulfide) gave the corresponding modified 2-substituted 3H-quinazoline-4-thiones 4-22 in excellent yields.

  2- 烷基-3H-喹唑啉-4-硫醚在氮和 2-烷基（Me、Et、Pr）的δ-氢处与正丁基锂在-78 °C的无水四氢呋喃中在氮条件下实现了双重石化作用。将得到的二锂试剂与各种亲电体（碘甲烷、碘乙烷、1-溴丁烷、D2O、苯甲醛、4-甲氧基苯甲醛、丁-2-酮、环己酮、二苯甲酮、异硫氰酸苯酯、二硫化四异丙基秋兰姆）反应，可以得到相应的改性 2-取代 3H-喹唑啉-4-硫酮 4-22，收率极高。