4-chloro-3-nitrobenzoic acid 2'-acetylphenyl ester | 92426-76-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-chloro-3-nitrobenzoic acid 2'-acetylphenyl ester
• 英文别名: 2-<4-Chlor-3-nitro-benzoyloxy>-acetophenon；(2-Acetylphenyl) 4-chloro-3-nitrobenzoate
• CAS: 92426-76-1
• 化学式: C₁₅H₁₀ClNO₅
• 分子量: 319.701
• InChiKey: APPSHELEVZSYFO-UHFFFAOYSA-N

物化性质

• 沸点：
  529.6±50.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-3-nitrobenzoic acid 2'-acetylphenyl ester 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 硫酸 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 10.67h， 生成 2-(1-ethyl-2-ethoxycarbonylmethyl-1H-benzimidazol-5-yl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and antiaggregator activity of some new derivatives of 4H-1-benzopyran-4-one

  摘要：

  A series of 2-[2-alkyl-1H-benzimidazol-5(6)-yl]-4H-1 analogues 7a-7e was synthesized by the reaction with 3',4'-diaminoflavone and aliphatic carboxylic acids. 3',4'-Diaminoflavone 6 was prepared via the reduction of 2-(4-amino-3-nitrophenyl)-4H-1-benzopyran-4-one 5a. The compounds 7a-e and 14a-f were tested in vitro for their inhibitory activities against human platelet aggregation induced by collagen, ADP and A23187. The compound with a COOR group as a side chain, 2-(2-alkyloxycarbonyl-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-1-benzopyran-4-one 14a-f, has potent activity, and so compound 13 was also prepared as an analogue of series 14 and tested for its antiaggregator activity.

  DOI：

  10.1016/0223-5234(96)88270-5
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 吡啶 、 五氯化磷 作用下， 生成 4-chloro-3-nitrobenzoic acid 2'-acetylphenyl ester
  参考文献：
  名称：

  Synthesis of B-ring substituted flavones and evaluation of their antitumor and antioxidant activities

  摘要：

  A series of flavones, substituted at the ring B, were synthesized using either Claisen-Schimdt Condensation or Baker-Venkataraman rearrangement. The synthesized compounds were tested for in vitro cytotoxic activity by sulforhodamine B assay against three cell lines of different origin, viz. HepG2, MCF-7, and MOLT-4. The compounds were also tested for a possible antioxidant activity by determination of inhibition of lipid peroxidation. Quercetin was taken as a standard for antioxidant activity. Compound 1c showed the highest cytotoxic activity against MCF-7 (GI50 < 0.1 mu M) and MOLT-4 (GI50 < 0.1 mu M) cell lines and was comparable to adriamycin, the standard used. Compounds 1b, 1g, and 1h also showed promising activity against MCF-7 and MOLT-4 cell lines. In the absence of a hydroxyl group, one or more methoxy groups present on the B-ring (compounds 1c-1e) were major determinants of inhibition of lipid peroxidation.

  DOI：

  10.1007/s00044-012-0423-1

文献信息

• Jucker,E.; Vogel,A., Helvetica Chimica Acta, 1963, vol. 46, p. 727 - 741
  作者：Jucker,E.、Vogel,A.

  DOI：——

  日期：——
• Synthesis and antiaggregator activity of some new derivatives of 4H-1-benzopyran-4-one
  作者：H Göker、G Ayhan、M Tunçbilek、R Ertan、G Leoncini、R Garzoglio、M Mazzei

  DOI：10.1016/0223-5234(96)88270-5

  日期：1995.1

  A series of 2-[2-alkyl-1H-benzimidazol-5(6)-yl]-4H-1 analogues 7a-7e was synthesized by the reaction with 3',4'-diaminoflavone and aliphatic carboxylic acids. 3',4'-Diaminoflavone 6 was prepared via the reduction of 2-(4-amino-3-nitrophenyl)-4H-1-benzopyran-4-one 5a. The compounds 7a-e and 14a-f were tested in vitro for their inhibitory activities against human platelet aggregation induced by collagen, ADP and A23187. The compound with a COOR group as a side chain, 2-(2-alkyloxycarbonyl-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-1-benzopyran-4-one 14a-f, has potent activity, and so compound 13 was also prepared as an analogue of series 14 and tested for its antiaggregator activity.
• Synthesis of B-ring substituted flavones and evaluation of their antitumor and antioxidant activities
  作者：Akshada J. Joshi、Manoj K. Gadhwal、Urmila J. Joshi、Priscilla D’Mello、Ragini Sinha、Girjesh Govil

  DOI：10.1007/s00044-012-0423-1

  日期：2013.9

  A series of flavones, substituted at the ring B, were synthesized using either Claisen-Schimdt Condensation or Baker-Venkataraman rearrangement. The synthesized compounds were tested for in vitro cytotoxic activity by sulforhodamine B assay against three cell lines of different origin, viz. HepG2, MCF-7, and MOLT-4. The compounds were also tested for a possible antioxidant activity by determination of inhibition of lipid peroxidation. Quercetin was taken as a standard for antioxidant activity. Compound 1c showed the highest cytotoxic activity against MCF-7 (GI50 < 0.1 mu M) and MOLT-4 (GI50 < 0.1 mu M) cell lines and was comparable to adriamycin, the standard used. Compounds 1b, 1g, and 1h also showed promising activity against MCF-7 and MOLT-4 cell lines. In the absence of a hydroxyl group, one or more methoxy groups present on the B-ring (compounds 1c-1e) were major determinants of inhibition of lipid peroxidation.