4,5-Dihydro-4-<(4-oxo-4H-1-benzopyran-3-yl)methylene>-2-phenyloxazol-5-one | 62484-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4,5-Dihydro-4-<(4-oxo-4H-1-benzopyran-3-yl)methylene>-2-phenyloxazol-5-one
• 英文别名: 4-(4-oxo-4H-chromen-3-ylmethylene)-2-phenyl-4H-oxazol-5-one；4-[(4-Oxo-4H-1-benzopyran-3-yl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one；4-[(4-oxochromen-3-yl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 62484-59-7
• 化学式: C₁₉H₁₁NO₄
• 分子量: 317.301
• InChiKey: XRVLEKJAXIKBIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-Dihydro-4-<(4-oxo-4H-1-benzopyran-3-yl)methylene>-2-phenyloxazol-5-one 在 二乙胺 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以45%的产率得到methyl 4-(2-hydroxybenzoyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Ghosh, Chandra Kanta; Bandyopadhyay, Chandrakanta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 11, p. 1048 - 1053

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 sodium acetate 、 乙酸酐 、 三氯氧磷 作用下， 反应 5.0h， 生成 4,5-Dihydro-4-<(4-oxo-4H-1-benzopyran-3-yl)methylene>-2-phenyloxazol-5-one
  参考文献：
  名称：

  Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives

  摘要：

  Four series of sulfonamides incorporating chromone moieties were synthesized and assessed for their cytotoxic activity against MCF-7 and A-549 cell lines, considering the fact that some of these tumors overexpress isoforms of carbonic anhydrase (CA, EC 4.2.1.1) which is inhibited by sulfonamides. Most new sulfonamides showed weak inhibitory activity against the offtarget, cytosolic isoforms hCA I, II but effectively inhibited the tumor-associated hCA IX and XII. The most active compounds featured a primary SO2NH2 group and were active in the low micromolar range against MCF-7 and A-549 cell lines. Compound 4a showed IC50 of 0.72 and 0.50 mu M against MCF-7 and A-549 cell lines, respectively, and was further evaluated for its proapoptotic activity which proved enhanced in both tumor types. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.033

文献信息

• Aminolysis and hydrolysis of chromonyl oxazolones and some condensation reactions of 2-methylchromone leading to novel chromones
  作者：Winton D. Jones

  DOI：10.1039/p19810000344

  日期：——

  The aminolysis of 4-[(4-oxo-4H-1-benzopyran-3-yl)methylene]-2-phenyl-1,3-oxazol-5(4H)-one with diethylamine gave N-[1-(diethylamino)-1-oxo-3-(4-oxo-4H-1-benzopyran-3-yl)prop-2-en-2-yl] benzamide. The hydrolysis of 2-methyl-4-[(4-oxo-4H-1-benzopyran-3-yl)methylene]-1,3-oxazol-5(4H)-one gave the α-keto-acid, which could be converted into amino-acid derivatives. Condensation of 2-methylchromone with diethyl

  4-[（4-氧代-4 H -1-苯并吡喃-3-基）亚甲基] -2-苯基-1,3-恶唑-5（4 H）-与二乙胺的氨解反应得到N- [1- （二乙氨基）-1-氧代-3-（4-氧代-4 H -1-苯并吡喃-3-基）丙-2-烯-2-基]苯甲酰胺。2-甲基-4-[（4-氧代-4 H -1-苯并吡喃-3-基）亚甲基] -1,3-恶唑-5（4 H）-的水解得到α-酮酸，可以转化为氨基酸衍生物。2-甲基色酮与草酸二乙酯，2-甲酰基-NN-二乙基苯甲酰胺和2-甲酰基苯甲酸的缩合得到α-酮酸，（E）-NN-二乙基-2- [2-（4-氧代-4 H -1-苯并吡喃-2-基）乙烯基]苯甲酰胺和（E）-2-[（（4-氧代-4 H -1-苯并吡喃-2-基）乙烯基]苯甲酸。
• Ghosh; Bandyopadhyay; Biswas, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 814 - 818
  作者：Ghosh、Bandyopadhyay、Biswas

  DOI：——

  日期：——
• Conversion of 3-Formylchromones into Pyrrole and Thiophene Derivatives
  作者：Alan O. FITTON、Jonathan R. FROST、Hans SUSCHITZKY、Peter G. HOUGHTON

  DOI：10.1055/s-1977-24298

  日期：——