2-(1-methylethyl)-3H-quinazoline-4-thione | 13193-53-8

• 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-(1-methylethyl)-3H-quinazoline-4-thione
• 英文别名: 2-isopropyl-3H-quinazolin-4-thione；2-isopropyl-3,4-dihydroquinazolin-4-thione；2-(1-methylethyl)-3,4-dihydroquinazolin-4-thione；2-isopropyl-3H-quinazoline-4-thione；2-Isopropyl-3H-chinazolin-4-thion；2-propan-2-yl-1H-quinazoline-4-thione
• CAS: 13193-53-8
• 化学式: C₁₁H₁₂N₂S
• mdl: MFCD03713577
• 分子量: 204.296
• InChiKey: JQFZNBGEAOFSEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 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-(1-methylethyl)-3H-quinazoline-4-thione 在 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以50%的产率得到2-(1-methylethyl)-4-(4-hydrazino)quinazoline
  参考文献：
  名称：

  El-Hashash; Rizk, Egyptian Journal of Chemistry, 2011, vol. 54, # 4, p. 411 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-2-异丙基喹唑啉 在 劳森试剂 作用下， 以 甲苯 为溶剂， 生成 2-(1-methylethyl)-3H-quinazoline-4-thione
  参考文献：
  名称：

  Phosphodiesterase inhibitory properties of losartan. design and synthesis of new lead compounds

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(98)00058-4

文献信息

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

  DOI：——

  日期：——
• 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.
• [EN] COMPOUNDS AND USE THEREOF AS HDAC6 INHIBITORS<br/>[FR] COMPOSÉS ET LEUR UTILISATION COMME INHIBITEURS D'HDAC6
  申请人：[en]AUGUSTINE THERAPEUTICS

  公开号：WO2023118507A2

  公开（公告）日：2023-06-29

  The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, wherein Y1is a 9- or 10-membered bicyclic heteroaryl, Y2is a 5-membered heteroaryl, Z1is selected from (C=O)-R9, S(O)-R9and S(O2)-R9, L is an alkyl-, cycloalkyl- or heterocycloalkyl-based linker, and R1and R9may be various groups. The present invention further relates to a compound of formula (I) as HDAC6 inhibitor, typically for use in the treatment and/or the prevention of an HDAC6-associated disease, such as cancers, neurodegenerative diseases, neuropathies or cardiovascular diseases.
• Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors
  作者：Ana I. Sánchez、Valentín Martínez-Barrasa、Carolina Burgos、Juan J. Vaquero、Julio Alvarez-Builla、Emma Terricabras、Víctor Segarra

  DOI：10.1016/j.bmc.2013.01.067

  日期：2013.4

  The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7. (C) 2013 Elsevier Ltd. All rights reserved.