3-(4-乙酰氧基-苯基)-色烯-2-酮 | 2005-94-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 3-(4-乙酰氧基-苯基)-色烯-2-酮
• 英文名称: 3-(4-Acetoxy-phenyl)-cumarin
• 英文别名: 3-p-Acetoxy-phenyl-cumarin；3-(4-acetoxy-phenyl)-chromen-2-one；3-(4-acetoxy-phenyl)-coumarin；4-(2-Oxo-2H-chromen-3-yl)phenyl acetate；[4-(2-oxochromen-3-yl)phenyl] acetate
• CAS: 2005-94-9
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: HLOFWCHOMFXXRP-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C
• 沸点：
  462.9±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-乙酰氧基-苯基)-色烯-2-酮 在 硫酸 作用下， 生成 3-(4'-羟基苯基)香豆素
  参考文献：
  名称：

  Bhandari et al., Journal Of Scientific and Industrial Research, 1949, vol. 8 B, p. 189,190

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酸酐 作用下， 生成 3-(4-乙酰氧基-苯基)-色烯-2-酮
  参考文献：
  名称：

  Bhandari et al., Journal Of Scientific and Industrial Research, 1949, vol. 8 B, p. 189,190

  摘要：

  DOI：

文献信息

• 10.1021/acsmedchemlett.4c00072
  作者：Sallomy, Carita、Awolade, Paul、Rahnasto-Rilla, Minna、Hämäläinen, Mari、Nousiainen, Liisa P.、Johansson, Niklas G.、Hiltunen, Sanna、Turhanen, Petri、Moilanen, Eeva、Lahtela-Kakkonen, Maija、Timonen, Juri M.

  DOI：10.1021/acsmedchemlett.4c00072

  日期：——

  ankyrin 1 (TRPA1) protein plays an important role in the inflammatory response, and it has been associated with different pain conditions and pain-related diseases, making TRPA1 a valid target for painkillers. In this study, we identified potential TRPA1 inhibitors and located their binding sites utilizing computer-aided drug design (CADD) techniques. The designed 3-phenylcoumarin-based TRPA1 inhibitors

  瞬时受体电位锚蛋白 1 (TRPA1) 蛋白在炎症反应中发挥重要作用，并且与不同的疼痛状况和疼痛相关疾病相关，这使得 TRPA1 成为止痛药的有效靶点。在这项研究中，我们鉴定了潜在的 TRPA1 抑制剂，并利用计算机辅助药物设计 (CADD) 技术定位了它们的结合位点。采用微波辅助合成策略成功合成了设计的基于3-苯基香豆素的TRPA1抑制剂。 3-(3-溴苯基)-7-乙酰氧基香豆素 ( 5 )、7-羟基-3-(3-羟基苯基)香豆素 ( 12 ) 和 3-(3-羟基苯基)香豆素 ( 23 )在体外均表现出对 TRPA1 的抑制活性。化合物5还可以减少乳腺癌细胞的大小和形成。因此，靶向 TRPA1 可能是治疗疼痛和炎症的一种有前途的替代方案。
• Bhandari et al., Journal Of Scientific and Industrial Research, 1949, vol. 8 B, p. 189,190
  作者：Bhandari et al.

  DOI：——

  日期：——
• Synthesis and biological evaluation of hydroxylated 3-phenylcoumarins as antioxidants and antiproliferative agents
  作者：Jie Yang、Guo-Yun Liu、Fang Dai、Xiao-Yan Cao、Yan-fei Kang、Li-Mei Hu、Jiang-Jiang Tang、Xiu-Zhuang Li、Yan Li、Xiao-Ling Jin、Bo Zhou

  DOI：10.1016/j.bmcl.2011.08.090

  日期：2011.11

  Based on the observed biological activities of coumarins and resveratrol, we synthesized fourteen hydroxylated 3-phenylcoumarins (stilbene-coumarin hybrids) including six novel ortho-hydroxy-methoxy substituted derivatives, 1-14, by Perkin reaction. We characterized these compounds concerning their antioxidant activity against 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced pBR322 DNA strand breakage, and their antiproliferative effects on human promyelocytic leukemia HL-60 and human lung adenocarcinoma epithelial A549 cells. Structure-activity relationship information suggests that the introduction of ortho-hydroxy-methoxy groups and ortho-dihydroxy groups on the aromatic A ring could efficiently improve antiproliferative activity. Interestingly, a new derivative, 6-methoxy-7-hydroxy-3-(4'-hydroxyphenyl)coumarin, 9, behaved as a poor antioxidant but appeared to be the most potent antiproliferative agent among the compounds examined, and this activity was mediated by deregulation in cell cycle and induction of apoptosis. (C) 2011 Elsevier Ltd. All rights reserved.