(E)-3-(4-oxo-3,4-dihydroquinazolin-2-yl)acrylic acid | 5584-96-3

• 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: (E)-3-(4-oxo-3,4-dihydroquinazolin-2-yl)acrylic acid
• 英文别名: 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-acrylic acid；3-(4-oxo-3,4-dihydroquinazolin-2-yl)acrylic acid；ME0567；3-(4-oxo-3,4-dihydro-quinazolin-2-yl)-acrylic acid；3-(4-Oxo-3,4-dihydro-chinazolin-2-yl)-acrylsaeure；4-Oxo-3,4-dihydro-2-chinazolin-acrylsaeure；(2E)-3-(4-oxo-3,4-dihydroquinazolin-2-yl)acrylic acid；(E)-3-(4-oxo-3H-quinazolin-2-yl)prop-2-enoic acid
• CAS: 5584-96-3
• 化学式: C₁₁H₈N₂O₃
• 分子量: 216.196
• InChiKey: VSHQCDJWFSXEDO-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-oxo-3,4-dihydroquinazolin-2-yl)acrylic acid 在 sodium acetate 作用下， 以 乙酸酐 为溶剂， 生成 pyrrolo[2,1-b]quinazoline-1,9-dione
  参考文献：
  名称：

  Reaction of anthranilic acid amides with cyclic anhydrides

  摘要：

  Anthranilic acid amide reacts with cyclic anhydrides to give the corresponding N-acyl derivatives at the amino group, while analogous reactions of o-aminobenzohydroxamic acid lead to fori-nation of 3-hydroxy-quinazolin-4-ones under mild conditions. N-Acyl derivatives of anthranilic acid amide undergo intramolecular cyclization to imides on microwave irradiation or on melting, and their treatment with acetic anhydride in the presence of sodium acetate on heating yields quinazolin-4-ones.

  DOI：

  10.1134/s1070428006030079
• 作为产物：
  描述：

  2-(3,3,3-trichloro-2-hydroxy-propyl)-3H-quinazolin-4-one 在 sodium hydroxide 作用下， 生成 (E)-3-(4-oxo-3,4-dihydroquinazolin-2-yl)acrylic acid
  参考文献：
  名称：

  Kulkarni, Journal of the Indian Chemical Society, 1942, vol. 19, p. 180

  摘要：

  DOI：

文献信息

• Chemical Probes to Study ADP-Ribosylation: Synthesis and Biochemical Evaluation of Inhibitors of the Human ADP-Ribosyltransferase ARTD3/PARP3
  作者：Anders E. G. Lindgren、Tobias Karlberg、Torun Ekblad、Sara Spjut、Ann-Gerd Thorsell、C. David Andersson、Ton Tong Nhan、Victor Hellsten、Johan Weigelt、Anna Linusson、Herwig Schüler、Mikael Elofsson

  DOI：10.1021/jm401394u

  日期：2013.12.12

  The racemic 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-[1-(pyridin-2-yl)ethyl]propanamide, 1, has previously been identified as a potent but unselective inhibitor of diphtheria toxin-like ADP-ribosyltransferase 3 (ARTD3). Herein we describe synthesis and evaluation of SS compounds in this class. It was found that the stereochemistry is of great importance for both selectivity and potency and that substituents on the phenyl ring resulted in poor solubility. Certain variations at the meso position were tolerated and caused a large shift in the binding pose. Changes to the ethylene linker that connects the quinazolinone to the amide were also investigated but proved detrimental to binding. By combination of synthetic organic chemistry and structure-based design, two selective inhibitors of ARTD3 were discovered.
• Synthesis and Reactions of some 2-Vinyl-3H-quinazolin-4-ones
  作者：Anette Witt、Jan Bergman

  DOI：10.1016/s0040-4020(00)00595-0

  日期：2000.9

  A simple, high-yielding synthesis of 2-vinyl-3H-quinazolin-4-one, 2-(1-chlorovinyl)-3H-quinazolin-4-one and 2-(1-bromovinyl)-3H-quinazolin-4-one. The 2-vinylquinazolinones 11a and 14 participate readily in nucleophilic addition reactions. Treatment with both carbon and nitrogen nucleophiles results in a clean conversion into a variety of 2-substituted 3H-quinazolin-4-one derivatives. The 2-(1-halovinyl)-3H-quinazolin-4-ones 11b and Ile reacted with carbon nucleophiles to give several derivatives of 2-substituted 3H-quinazolin-4-one, such as dihydrofurancarboxylic ethyl ester 23. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Reaction of anthranilic acid amides with cyclic anhydrides
  作者：L. A. Shemchuk、V. P. Chernykh、O. S. Krys’kiv

  DOI：10.1134/s1070428006030079

  日期：2006.3

  Anthranilic acid amide reacts with cyclic anhydrides to give the corresponding N-acyl derivatives at the amino group, while analogous reactions of o-aminobenzohydroxamic acid lead to fori-nation of 3-hydroxy-quinazolin-4-ones under mild conditions. N-Acyl derivatives of anthranilic acid amide undergo intramolecular cyclization to imides on microwave irradiation or on melting, and their treatment with acetic anhydride in the presence of sodium acetate on heating yields quinazolin-4-ones.
• Kulkarni, Journal of the Indian Chemical Society, 1942, vol. 19, p. 180
  作者：Kulkarni

  DOI：——

  日期：——