2,8-bis(4-chlorophenyl)-4H,6H-pyrano[3,2-g]chromene-4,6-dione | 1385717-77-0

• 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: 2,8-bis(4-chlorophenyl)-4H,6H-pyrano[3,2-g]chromene-4,6-dione
• 英文别名: 2,8-Bis(4-chlorophenyl)-4h,6h-pyrano[3,2-g]chromene-4,6-dione；2,8-bis(4-chlorophenyl)pyrano[3,2-g]chromene-4,6-dione
• CAS: 1385717-77-0
• 化学式: C₂₄H₁₂Cl₂O₄
• 分子量: 435.263
• InChiKey: WSSIEDYHZQWYDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,1'-(4,6-二羟基苯)二乙酮 在 碘 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 生成 2,8-bis(4-chlorophenyl)-4H,6H-pyrano[3,2-g]chromene-4,6-dione
  参考文献：
  名称：

  新型黄酮类化合物的设计、合成和体内抗焦虑活性

  摘要：

  全世界有数百万人患有心理障碍，其中焦虑是主要和常见的问题之一。了解焦虑的统计报告，本研究的重点是通过分子对接设计新的类黄酮衍生物，使用薛定谔（Maestro 10.5 v），这是一种基于配体 - 蛋白质相互作用的著名计算软件。具有强效的Glide评分的最有效的类黄酮衍生物（IC 50）值-化合物3A（-6.824），3B（-7.215），3E（-6.239），3F（-6.679） ，和3J(–7.123) – 被选择用于在微波辐射下在两步反应中合成，包括 Claisen-Schmidth 缩合形成查耳酮和氧化环化形成黄酮类化合物。然后，使用高架十字迷宫测试模型在成年瑞士白化小鼠中研究合成衍生物的体内抗焦虑活性。地西泮 (2 mg/kg, IP) 用作标准药物。化合物3b对 GABA A受体表现出最显着的抗焦虑活性，但与地西泮相比，其他化合物在 100 和 200 mg/kg 剂量的小鼠中也显示出显着的抗焦虑作用。

  DOI：

  10.1007/s11094-021-02514-w

文献信息

• Synthesis and antimicrobial activity of bischalcone derivatives
  作者：Asif Husain、Aftab Ahmad、Ibraheem Ahmed I. Mkhalid、Ravinesh Mishra、Mohd Rashid

  DOI：10.1007/s00044-012-0137-4

  日期：2013.4

  Several bischalcones (2a-h and 5a-e) and flavones (3a-f) were synthesized and evaluated for their antimicrobial actions. Bischalcones were prepared by condensing 1,1'-(4,6-dimethyl-1,3-phenylene)diethanone (1) or 1-(5-acetyl-2,4-dimethoxyphenyl)-1-ethanone (4) with arylaldehydes. Bischalcones were cyclized in presence of iodine to give corresponding flavones (3a-f). An alternative route to synthesize the flavones consisted in preparing the diester derivatives (6a-f) of (1) with different aromatic acids, which could be converted to beta-diketones followed by cyclization to give the corresponding flavones. However, all the attempts in this direction were unsuccessful and it could not be possible to proceed beyond diester stage; six diester derivatives (6a-f) were synthesized. The structures of the synthesized compounds were assigned on the basis of H-1 NMR, mass spectral data and microanalyses results. The antimicrobial screening was performed at a concentration of 100 mu g/mL by cup plate method; the compounds inhibiting growth of one or more of the microorganisms were further tested for their minimum inhibitory concentration (MIC) by turbidity method. Preliminary antimicrobial results revealed that the compounds 2a-h and 3a-f were significant in their antibacterial and antifungal activities. MICs results showed that the compound 2f exhibited very good activity against E. coli, P. aeruginosa, and C. albicans with MIC-12.5 mu g/mL. Similar type of activity was shown the compound 3a against S. aureus and C. albicans with MIC-12.5 mu g/mL. Another compound, 3f, was active against P. aeruginosa and C. albicans with MIC-12.5 mu g/mL. Methylation of the two chelated hydroxyls (5a-e) significantly reduced the activity. However, oxidative cyclization of bischalcones resulted in compounds (3a-f) which were found to be considerably active. Diesters (6a-f) were insignificant in their antimicrobial activities.
• Design, Synthesis and In Vivo Anxiolytic Activity of Novel Flavonoids
  作者：P. M. Sabale、L. C. Potey

  DOI：10.1007/s11094-021-02514-w

  日期：2021.12

  focused on design of new flavonoid derivatives through molecular docking by using Schrödinger (Maestro 10.5 v), the well-known computational software on the basis of ligand – protein interaction. The most effective flavonoid derivatives with potent Glide score (IC50) values – compounds 3a (–6.824), 3b (–7.215), 3e (–6.239), 3f (-6.679), and 3j (–7.123) – were selected for the synthesis under microwave irradiation

  全世界有数百万人患有心理障碍，其中焦虑是主要和常见的问题之一。了解焦虑的统计报告，本研究的重点是通过分子对接设计新的类黄酮衍生物，使用薛定谔（Maestro 10.5 v），这是一种基于配体 - 蛋白质相互作用的著名计算软件。具有强效的Glide评分的最有效的类黄酮衍生物（IC 50）值-化合物3A（-6.824），3B（-7.215），3E（-6.239），3F（-6.679） ，和3J(–7.123) – 被选择用于在微波辐射下在两步反应中合成，包括 Claisen-Schmidth 缩合形成查耳酮和氧化环化形成黄酮类化合物。然后，使用高架十字迷宫测试模型在成年瑞士白化小鼠中研究合成衍生物的体内抗焦虑活性。地西泮 (2 mg/kg, IP) 用作标准药物。化合物3b对 GABA A受体表现出最显着的抗焦虑活性，但与地西泮相比，其他化合物在 100 和 200 mg/kg 剂量的小鼠中也显示出显着的抗焦虑作用。