[(4-羟基-2-喹唑啉基)硫基]乙酸 | 16431-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: [(4-羟基-2-喹唑啉基)硫基]乙酸
• 英文名称: 2-((4-oxo-3,4-dihydroquinazolin-2-yl)thio)acetic acid
• 英文别名: (4-Hydroxy-quinazolin-2-ylsulfanyl)-acetic acid；2-[(4-oxo-3H-quinazolin-2-yl)sulfanyl]acetic acid
• CAS: 16431-29-1
• 化学式: C₁₀H₈N₂O₃S
• mdl: MFCD00845240
• 分子量: 236.251
• InChiKey: MVJSWCZVASBMCH-UHFFFAOYSA-N

物化性质

• 熔点：
  223 °C
• 沸点：
  477.2±47.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  [(4-羟基-2-喹唑啉基)硫基]乙酸 在 吡啶 、 乙酸酐 作用下， 反应 0.5h， 以51%的产率得到5H-thiazolo<2,3-b>qunazoline-3,5(2H)-dione
  参考文献：
  名称：

  Chaurasia, Munnu Ram; Sharma, Ajay Kumar, Heterocycles, 1983, vol. 20, # 8, p. 1549 - 1558

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯甲酸乙酯 在 水 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 5.0h， 生成 [(4-羟基-2-喹唑啉基)硫基]乙酸
  参考文献：
  名称：

  New Syntheses of 2-Alkylthio-4-oxo-3,4-dihydroquinazolines, 2 - Alkylthio - quinazolines, as well as Their Hetero Analogues

  摘要：

  N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-yl-sulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-di-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with. amines.

  DOI：

  10.3987/com-00-8954

文献信息

• [EN] QUINAZOLINONE COMPOUNDS AND DERIVATIVES THEREOF<br/>[FR] COMPOSÉS QUINAZOLINONES ET LEURS DÉRIVÉS
  申请人：AMGEN INC

  公开号：WO2014036022A1

  公开（公告）日：2014-03-06

  Compounds of Formula I are useful inhibitors of tankyrase. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  公式I的化合物是坦克酶的有用抑制剂。公式I的化合物具有以下结构：其中变量的定义在此提供。
• Synthesis of Novel 2-(4-Oxo-3,4- Dihydroquinazolin-2-Ylsulfinylmethyl)-3<i>H</i>-Quinazolin-4-One
  作者：B. Srinivasa Reddy、A. Naidu、P. K. Dubey

  DOI：10.1080/10426507.2011.634466

  日期：2012.5

  acid (2) that with anthranilamide (3) gave 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfanylmethyl)-3H-quinazolin-4-one (4). Oxidation of 4 with sodium hypochlorite in alkaline medium gave the novel product, 2-(4-oxo-3,4- dihydroquinazolin-2-ylsulfinyl methyl)-3H -quinazolin-4-one) (5). The entire sequences of reactions in this work have been carried out using eco-friendly solvents and green conditions.

  摘要 2-mercapto-3H-quinazolin-4-one (1) 与氯乙酸缩合得到 4-oxo-3,4-dihydroquinazoline-2-yl-sulfanyl)-乙酸 (2)，再与邻氨基苯甲酰胺 (3) 缩合得到2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfanylmethyl)-3H-quinazolin-4-one (4)。在碱性介质中用次氯酸钠氧化 4 得到新产品，2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfinylmethyl)-3H-quinazolin-4-one) (5)。这项工作中的整个反应序列都是使用环保溶剂和绿色条件进行的。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Quinazolinone Compounds and Derivatives Thereof
  申请人：AMGEN INC.

  公开号：US20150225396A1

  公开（公告）日：2015-08-13

  Compounds of Formula I are useful inhibitors of tankyrase. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  公式I的化合物是坦克酰酶的有用抑制剂。公式I的化合物具有以下结构：其中变量的定义在此提供。
• Development of Novel Dual Binders as Potent, Selective, and Orally Bioavailable Tankyrase Inhibitors
  作者：Zihao Hua、Howard Bregman、John L. Buchanan、Nagasree Chakka、Angel Guzman-Perez、Hakan Gunaydin、Xin Huang、Yan Gu、Virginia Berry、Jingzhou Liu、Yohannes Teffera、Liyue Huang、Bryan Egge、Renee Emkey、Erin L. Mullady、Steve Schneider、Paul S. Andrews、Lisa Acquaviva、Jennifer Dovey、Ankita Mishra、John Newcomb、Douglas Saffran、Randy Serafino、Craig A. Strathdee、Susan M. Turci、Mary Stanton、Cindy Wilson、Erin F. DiMauro

  DOI：10.1021/jm401317z

  日期：2013.12.27

  Tankyrases (TNKS1 and TNKS2) are proteins in the poly ADP-ribose polymerase (PARP) family. They have been shown to directly bind to axin proteins, which negatively regulate the Wnt pathway by promoting β-catenin degradation. Inhibition of tankyrases may offer a novel approach to the treatment of APC-mutant colorectal cancer. Hit compound 8 was identified as an inhibitor of tankyrases through a combination of substructure searching of the Amgen compound collection based on a minimal binding pharmacophore hypothesis and high-throughput screening. Herein we report the structure- and property-based optimization of compound 8 leading to the identification of more potent and selective tankyrase inhibitors 22 and 49 with improved pharmacokinetic properties in rodents, which are well suited as tool compounds for further in vivo validation studies.
• Synthesis of 2-alkylthioquinazol-4-ones
  作者：L. M. Yun、S. Yangibaev、Kh. M. Shakhidoyatov、V. Ya. Alekseeva、K. A. V'yunov

  DOI：10.1007/bf00663865

  日期：1987.2