6-异丙基-2-苯基-4H-苯并吡喃-4-酮 | 288401-05-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 6-异丙基-2-苯基-4H-苯并吡喃-4-酮
• 英文名称: 6-Isopropyl-2-phenyl-chromen-4-one
• 英文别名: 2-Phenyl-6-(propan-2-yl)-4H-1-benzopyran-4-one；2-phenyl-6-propan-2-ylchromen-4-one
• CAS: 288401-05-8
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: APJYDAHXYGPDII-UHFFFAOYSA-N

物化性质

• 熔点：
  83-86 °C
• 沸点：
  402.8±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 硫酸 、 溶剂黄146 作用下， 反应 2.0h， 以67%的产率得到6-异丙基-2-苯基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  New synthetic flavone derivatives induce apoptosis of hepatocarcinoma cells

  摘要：

  Natural flavonoids have broad biological activity, including anticancer. In this study, a series of novel flavone derivatives were synthesized with the substitutions of chlorine, isopropyl, methoxy, and nitro groups on the benzene ring of flavone skeleton to develop effective anticancer agents. Antiproliferative assays showed that the synthesized chemicals possess notable activity against hepatocarcinoma cells (HepG-2); in particular, the compound 6f with chlorine and dimethoxy modifications at the two benzene rings showed an IC(50) at 1.1 mu M to HepG-2. The 6f also displayed marked anticancer activity towards a panel of cancer cells, including nasopharyngeal carcinoma cells (CNE-2 and CNE-1), breast adenocarcinoma cell (MCF-7), and epithelial carcinoma cells (Hela). Exposing HepG-2 cells to compound 6f at 10 mu M induced chromatin condensation, nuclear disassembly, and DNA fragmentation. In 6f-treated HepG-2 cells, the sub-G(o) population was remarkably increased; and in these cells, both caspase-8 and caspase-9 activity was significantly increased, which in turn activated caspase-3. In addition, proapoptotic Bax was upregulated by compound 6f while the antiapoptotic Bcl-2 was downregulated. Taken together, our data suggest that the new flavonoid derivative 6f triggers apoptosis through both death-receptor and mitochondria-dependent intrinsic pathways, being a potent therapeutic agent against hepatocarcinoma. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.019

文献信息

• Versatile ligand for palladium-catalyzed meta-C—H functionalizations of aromatic substrates
  申请人：The Scripps Research Institute

  公开号：US10696635B2

  公开（公告）日：2020-06-30

  A class of mono-protected 3-amino-2-hydroxypyridine (MPAHP) ligands that enable the meta-C—H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed, such as in the formation of a reaction product of Formula IA: The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C—H functionalization processes is also illustrated by the development of a meta-C—H amination reaction and a meta-C—H alkynylation reaction.

  本发明公开了一类单保护 3-氨基-2-羟基吡啶（MPAHP）配体，该配体可以使用降冰片烯作为瞬时介质，对苯胺、苯酚、苯乙酸和生物相关杂环化合物进行元-C-H 芳基化反应，例如形成式 IA 的反应产物： 这种元芳基化方法在制药业中的适用性说明了杂芳基底物和杂芳基碘偶联剂的适用性，使用 MPAHP 配体使这一壮举成为可能。通过开发元-C-H 氨基化反应和元-C-H 炔化反应，还说明了 MPAHP 配体在实现其他元-C-H 功能化过程中的促进作用。
• New synthetic flavone derivatives induce apoptosis of hepatocarcinoma cells
  作者：Huachen Liu、Aijun Dong、Chunmei Gao、Chunyan Tan、Zhenhua Xie、Xuyu Zu、Long Qu、Yuyang Jiang

  DOI：10.1016/j.bmc.2010.07.019

  日期：2010.9

  Natural flavonoids have broad biological activity, including anticancer. In this study, a series of novel flavone derivatives were synthesized with the substitutions of chlorine, isopropyl, methoxy, and nitro groups on the benzene ring of flavone skeleton to develop effective anticancer agents. Antiproliferative assays showed that the synthesized chemicals possess notable activity against hepatocarcinoma cells (HepG-2); in particular, the compound 6f with chlorine and dimethoxy modifications at the two benzene rings showed an IC(50) at 1.1 mu M to HepG-2. The 6f also displayed marked anticancer activity towards a panel of cancer cells, including nasopharyngeal carcinoma cells (CNE-2 and CNE-1), breast adenocarcinoma cell (MCF-7), and epithelial carcinoma cells (Hela). Exposing HepG-2 cells to compound 6f at 10 mu M induced chromatin condensation, nuclear disassembly, and DNA fragmentation. In 6f-treated HepG-2 cells, the sub-G(o) population was remarkably increased; and in these cells, both caspase-8 and caspase-9 activity was significantly increased, which in turn activated caspase-3. In addition, proapoptotic Bax was upregulated by compound 6f while the antiapoptotic Bcl-2 was downregulated. Taken together, our data suggest that the new flavonoid derivative 6f triggers apoptosis through both death-receptor and mitochondria-dependent intrinsic pathways, being a potent therapeutic agent against hepatocarcinoma. (C) 2010 Elsevier Ltd. All rights reserved.