3-methyl-2-(methylthio)quinazolin-4(3H)-one | 6437-06-5

• 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: 3-methyl-2-(methylthio)quinazolin-4(3H)-one
• 英文别名: 3-Methyl-2-methylthio-4-quinazolone；3-methyl-2-methylsulfanylquinazolin-4-one
• CAS: 6437-06-5
• 化学式: C₁₀H₁₀N₂OS
• mdl: MFCD00203742
• 分子量: 206.268
• InChiKey: IMNUDUZCMFTLBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-2-(methylthio)quinazolin-4(3H)-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以63%的产率得到2-肼基-3-甲基喹唑啉-4(3h)-酮
  参考文献：
  名称：

  Zahran, Magdy A.-H.; Ali, Omar M.; Zeid, Ibrahim F., Asian Journal of Chemistry, 2012, vol. 24, # 5, p. 2121 - 2124

  摘要：

  DOI：
• 作为产物：
  描述：

  2-巯基-4(3H)-喹唑酮 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 10.0h， 生成 3-methyl-2-(methylthio)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and spectral examination of the position of tautomeric equilibrium in 2-thioxo-4-quinazolone

  摘要：

  DOI：

  10.1007/bf00478134

文献信息

• Synthesis of 2-aminoquinazolinc-4(3<i>H</i>)-one derivatives as potential potassium channel openers
  作者：BÉNÉDicte Erb、Rufine Akue、Benoît Rigo、Bernard Pirotte、Daniel Couturier

  DOI：10.1002/jhet.5570370206

  日期：2000.3

  Starting from 2-thioxoquinazolin-4-one, the synthesis of 2-amino-4(3H)-one derivatives, structurally related to potassium channels openers pinacidil and diazoxide, is described.

  从2-硫代喹唑啉-4-酮开始，描述了2-氨基-4（3 H）-一衍生物的合成，该衍生物在结构上与钾通道开放剂松那地尔和二氮嗪有关。
• Synthesis and histamine H2-antagonist activity of 4-quinazolinone derivatives.
  作者：NOBUO OGAWA、TOSHIHIKO YOSHIDA、TAKAYUKI ARATANI、EIICHI KOSHINAKA、HIDEO KATO、YASUO ITO

  DOI：10.1248/cpb.36.2955

  日期：——

  With the aim of developing new atiulcer agents, a series of 4-quinazolinone derivatives was synthesized and tested for histamine H2-antagonist activity and gastric antisecretory activity. Thus, 2-alkylamino- (8a-d, 10a-s), 2-alkylthio- (15), and 2-alkyl-4-quinazolinones (18a-k) were prepared by the condensation of alkylamines with 2-chloro- or 2-methlthio-4-quinazolinones, the condensation of alkyl bromides with 2-mercapto-4-quinazolinones, and the condensation of alkylcarboxylic acids with anthranilamides, respectively.Several of the 4-quinazolinone derivatives thus synthesized showed potent H2-antagonist activity, and one of them, 2-[3-[3-(1-piperidinylmehyl)phenoxy]propylamino]-4(3H)-quinazo-linone (8d) showed the most potent antisecretory activity. The structure-activity relationships are discussed.

  为了开发新的抗溃疡药物，合成了一系列4-喹唑啉酮衍生物，并测试了其组胺H2拮抗剂活性和胃抗分泌活性。因此，合成了2-烷基氨基（8a-d，10a-s）、2-烷基硫基（15）以及2-烷基-4-喹唑啉酮（18a-k），其方法分别是将烷基胺与2-氯或2-甲硫基-4-喹唑啉酮缩合、将烷基溴化物与2-巯基-4-喹唑啉酮缩合，以及将烷基羧酸与氨基苯甲酸酰胺缩合。合成的几种4-喹唑啉酮衍生物显示出强效的H2拮抗剂活性，其中一种2-[3-[3-(1-哌啶基甲基)苯氧]丙氨基]-4(3H)-喹唑啉酮（8d）表现出最强的抗分泌活性。讨论了结构-活性关系。
• Phase-Transfer Catalyzed Alkylation and Cycloalkylation of 2-Mercaptoquinazolin-4(3<u>H</u>)-One
  作者：A. Kh. Khalil

  DOI：10.1080/104265090929940

  日期：2005.11.1

  Solid/liquid phase-transfer catalyzed alkylation of 2-mercaptoquinazolin-4(3H)-one at 25°C by different organohalogen compounds in the presence of tetrabutylammonium bromide as a catalyst underwent, exclusively, S-monoalkylation or S- and N-, di-, or cycloalkylation, depending on the nature of alkylating agents.

  在四丁基溴化铵作为催化剂存在下，不同有机卤素化合物在 25°C 下固/液相转移催化的 2-巯基喹唑啉-4(3H)-one 烷基化，仅经历了 S-单烷基化或 S-和 N-，二烷基化或环烷基化，取决于烷基化剂的性质。
• Pyrimidine derivatives
  申请人：Sato Michitaka

  公开号：US20070197551A1

  公开（公告）日：2007-08-23

  This invention provides pyrimidine derivatives represented by a formula, in the formula, ring A stands for carbocyclic group or heterocyclic group, X 1 stands for hydrogen, lower alkyl, amino, etc., X 2 stands for hydrogen or lower alkyl, Y stands for a direct bond or sulfur or nitrogen, n stands for an integer of 0-4, and Ar stands for a group of the following formula, or a salt thereof, which concurrently exhibit 5-HT 1A agonistic activity and 5-HT 3 antagonistic activity and are useful for therapy and treatments of diseases such as IBS. The invention furthermore provides a therapeutic method of IBS, characterized by having 5-HT 1A agonistic activity and 5-HT 3 antagonistic activity work simultaneously and cooperatively in vivo, which comprises either administering 5-HT 3 antagonistic agent which concurrently exhibits 5-HT 1A agonistic activity, or administering 5-HT 1A agonistic agent and 5-HT 3 antagonistic agent simultaneously, in sequence or at an interval.

  本发明提供了由下式表示的嘧啶衍生物，其中，环A代表碳环基团或杂环基团，X1代表氢、低碳基、氨基等，X2代表氢或低碳基，Y代表直接键或硫或氮，n代表0-4的整数，Ar代表以下式的基团，或其盐，同时表现出5-HT1A激动活性和5-HT3拮抗活性，并且对治疗诸如肠易激综合征等疾病有用。本发明进一步提供了一种IBS治疗方法，其特征在于在体内同时和协同地发挥5-HT1A激动活性和5-HT3拮抗活性，包括给予同时表现出5-HT1A激动活性和5-HT3拮抗活性的5-HT3拮抗剂，或同时给予5-HT1A激动剂和5-HT3拮抗剂，按顺序或间隔给予。
• PYRIMIDINE DERIVATIVE
  申请人：ASKA Pharmaceutical Co., Ltd.

  公开号：EP1724267B1

  公开（公告）日：2013-11-06