di(4-oxo-4H-1-benzopyran-3-yl)methane | 52852-91-2

• 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: di(4-oxo-4H-1-benzopyran-3-yl)methane
• 英文别名: 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one；Bis-3-chromonyl-methan；3,3'-methanediyl-bis-chromen-4-one；bis-(4-oxo-4H-chromen-3-yl)-methane；Bis-(4-oxo-4H-chromen-3-yl)-methan；3,3'-Methylenebischromone；3-[(4-oxochromen-3-yl)methyl]chromen-4-one
• CAS: 52852-91-2
• 化学式: C₁₉H₁₂O₄
• 分子量: 304.302
• InChiKey: DOFIUCSVGPULKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  在 palladium on carbon 、 三氟化硼乙醚 、 氢气 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~50.0 ℃ 、275.8 kPa 条件下， 反应 8.0h， 生成 di(4-oxo-4H-1-benzopyran-3-yl)methane
  参考文献：
  名称：

  Synthesis and SAR studies of bis-chromenone derivatives for anti-proliferative activity against human cancer cells

  摘要：

  A novel family of 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one (bis-chromone) derivatives were designed, synthesized and studied for their anti-cancer activity using the XTT assay for the growth inhibition against various human cancer cells. Among them, 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-methoxy-4H-chromen-4-one and 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-hydroxy-4H-chromen-4-one showed micromolar level of in vitro anti-proliferative activity against human cancer cell lines. The SAR studies indicated bis-chromone as a basic scaffold to design anticancer agents. The 5-cyclohexylmethoxy on the first chromenone ring and electron donating group such as CH3, OCH3 or hydrogen bonding group (OH) on the other chromenone ring of bis-chromone increased the activity. However, saturation of one of chromenone to chromanone in bis-chromones decreased the activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.057

文献信息

• ANTIMICROBIAL AND CYTOTOXIC COMPOUNDS AND METHODS FOR TREATING CANCER, A BACTERIAL INFECTION, AND/OR A FUNGAL INFECTION
  申请人：King Abdulaziz University

  公开号：US20180201598A1

  公开（公告）日：2018-07-19

  Small molecules and methods of treating cancer, a bacterial infection, and/or a fungal infection. The small molecules are chromenone derivatives. They have antimicrobial properties and are cytotoxic towards colon, liver, and breast cancer cell lines.

  小分子及其治疗癌症、细菌感染和/或真菌感染的方法。这些小分子是香豆素衍生物。它们具有抗微生物和细胞毒性，可以对结肠、肝脏和乳腺癌细胞株产生作用。
• Antimicrobial and cytotoxic compounds and methods for treating cancer, a bacterial infection, and/or a fungal infection
  申请人：King Abdulaziz University

  公开号：US10266510B2

  公开（公告）日：2019-04-23

  Small molecules and methods of treating cancer, a bacterial infection, and/or a fungal infection. The small molecules are chromenone derivatives. They have antimicrobial properties and are cytotoxic towards colon, liver, and breast cancer cell lines.

  治疗癌症、细菌感染和/或真菌感染的小分子和方法。这些小分子是铬酮衍生物。它们具有抗菌特性，对结肠癌、肝癌和乳腺癌细胞株具有细胞毒性。
• Mentzer et al., Bulletin de la Societe Chimique de France, 1945, vol. <5> 12, p. 430,436
  作者：Mentzer et al.

  DOI：——

  日期：——
• Bandyopadhyay, Chandrakanta; Sur, Kumar Ranabir; Das, Hemanta Kumar, Journal of Chemical Research, Miniprint, 1999, # 10, p. 2561 - 2568
  作者：Bandyopadhyay, Chandrakanta、Sur, Kumar Ranabir、Das, Hemanta Kumar

  DOI：——

  日期：——
• Synthesis and SAR studies of bis-chromenone derivatives for anti-proliferative activity against human cancer cells
  作者：Eeda Venkateswararao、Vinay K. Sharma、Manoj Manickam、Jieun Yun、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2014.09.057

  日期：2014.11

  A novel family of 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one (bis-chromone) derivatives were designed, synthesized and studied for their anti-cancer activity using the XTT assay for the growth inhibition against various human cancer cells. Among them, 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-methoxy-4H-chromen-4-one and 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-hydroxy-4H-chromen-4-one showed micromolar level of in vitro anti-proliferative activity against human cancer cell lines. The SAR studies indicated bis-chromone as a basic scaffold to design anticancer agents. The 5-cyclohexylmethoxy on the first chromenone ring and electron donating group such as CH3, OCH3 or hydrogen bonding group (OH) on the other chromenone ring of bis-chromone increased the activity. However, saturation of one of chromenone to chromanone in bis-chromones decreased the activity. (C) 2014 Elsevier Ltd. All rights reserved.