6-(methylthio)-4-oxo-4H-quinazoline-3-propanoic acid | 84118-02-5

• 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: 6-(methylthio)-4-oxo-4H-quinazoline-3-propanoic acid
• 英文别名: 3-(6-Methylsulfanyl-4-oxoquinazolin-3-yl)propanoic acid
• CAS: 84118-02-5
• 化学式: C₁₂H₁₂N₂O₃S
• 分子量: 264.305
• InChiKey: WTUAUXINAMLMSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氯-2-硝基苯甲酸 在 palladium on activated charcoal 盐酸 、 sodium sulfide 、 ammonium hydroxide 、 sodium hydroxide 、 氢气 、 sodium hydride 作用下， 以 甲醇 为溶剂， 50.0~145.0 ℃ 、344.73 kPa 条件下， 反应 49.5h， 生成 6-(methylthio)-4-oxo-4H-quinazoline-3-propanoic acid
  参考文献：
  名称：

  (E)-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acids, a new series of antiallergy agents

  摘要：

  A series of substituted (E)-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acids was prepared and evaluated in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity. Alkoxy, alkylthio, and isopropyl substituents at the 6- or 8-positions provided highly potent compounds. Conversion to the Z isomer, reduction of the side chain double bond, or reduction of the quinazoline ring resulted in substantial loss of activity. Among the analogues that exhibited oral activity in the PCA test, (E)-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid (5i) was the most potent.

  DOI：

  10.1021/jm00357a018

文献信息

• LEMAHIEU, R. A.;CARSON, M.;NASON, W. C.;PARRISH, D. R.;WELTON, A. F.;BARU+, J. MED. CHEM., 1983, 26, N 3, 420-425
  作者：LEMAHIEU, R. A.、CARSON, M.、NASON, W. C.、PARRISH, D. R.、WELTON, A. F.、BARU+

  DOI：——

  日期：——
• (E)-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acids, a new series of antiallergy agents
  作者：Ronald A. LeMahieu、Mathew Carson、William C. Nason、David R. Parrish、Ann F. Welton、Herman W. Baruth、Bohdan Yaremko

  DOI：10.1021/jm00357a018

  日期：1983.3

  A series of substituted (E)-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acids was prepared and evaluated in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity. Alkoxy, alkylthio, and isopropyl substituents at the 6- or 8-positions provided highly potent compounds. Conversion to the Z isomer, reduction of the side chain double bond, or reduction of the quinazoline ring resulted in substantial loss of activity. Among the analogues that exhibited oral activity in the PCA test, (E)-3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid (5i) was the most potent.