2-(4-chloro-3-nitrophenyl)-4H-1-benzopyran-4-one | 92429-17-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-chloro-3-nitrophenyl)-4H-1-benzopyran-4-one
• 英文别名: 2-(4'-chloro-3'-nitrophenyl)-chromen-4-one；4'-Chlor-3'-nitro-flavon；4'-Chloro-3'-nitroflavone；2-(4-Chloro-3-nitrophenyl)chromen-4-one
• CAS: 92429-17-9
• 化学式: C₁₅H₈ClNO₄
• 分子量: 301.686
• InChiKey: YDQBNIDWVWSZQA-UHFFFAOYSA-N

物化性质

• 熔点：
  227 °C(Solv: dichloromethane (75-09-2); acetone (67-64-1))
• 沸点：
  460.6±45.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-3-nitrophenyl)-4H-1-benzopyran-4-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 50.0~80.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 2-(4-ethylamino-3-aminophenyl)-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：

  3-硝基-4-氯苯甲酰氯 在 吡啶 、 硫酸 、 溶剂黄146 、 potassium hydroxide 作用下， 反应 1.0h， 生成 2-(4-chloro-3-nitrophenyl)-4H-1-benzopyran-4-one
  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

• 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.