2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl propionate | 1201807-85-3

• 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-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl propionate
• 英文别名: 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-ylpropionate；[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl] propanoate
• CAS: 1201807-85-3
• 化学式: C₁₈H₁₄O₇
• 分子量: 342.305
• InChiKey: XIMDLCCYNKUUDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-4-oxo-4H-chromen-7-yl propionate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl propionate
  参考文献：
  名称：

  Synthesis of Quercetin and Luteolin Derivatives with Cell Proliferation Inhibitory Activity and Toxicity in B16 Melanoma Cells

  摘要：

  黑色素瘤是一种由黑色素细胞损伤引起的恶性皮肤肿瘤，可扩散到其他器官。因此，人们对防止黑色素瘤扩散进行了各种研究。芹菜素和高良姜素等黄酮类结构物质是抑制黑色素瘤增殖和转移的有效治疗药物。本研究合成了木犀草素、槲皮素及其各自的衍生物。这些化合物抑制了 B16 黑色素瘤细胞的增殖。这些结果证实，槲皮素和木犀草素的衍生物可作为防止黑色素瘤转移的治疗药物。

  DOI：

  10.5012/jkcs.2023.67.3.181

文献信息

• Discovery and synthesis of novel luteolin derivatives as DAT agonists
  作者：Jiange Zhang、Xianbo Liu、Xinsheng Lei、Lei Wang、Lihe Guo、Gang Zhao、Guoqiang Lin

  DOI：10.1016/j.bmc.2010.09.049

  日期：2010.11.15

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Quercetin and Luteolin Derivatives with Cell Proliferation Inhibitory Activity and Toxicity in B16 Melanoma Cells
  作者：Jang, Jongyun、Lee, Seong Uk、Kim, Yoon Hee、Kang, Dong Wook

  DOI：10.5012/jkcs.2023.67.3.181

  日期：——

  Melanoma is a malignant skin tumor caused by damage to melanocytes that can spread to other organs. Hence, various studies have been conducted on preventing the spread of melanoma. Flavonoid-structured substances such as apigenin and galanzin are effective therapeutic agents for inhibiting the proliferation and metastasis of melanoma. In this study, luteolin, quercetin, and their respective derivatives were synthesized. These compounds inhibited cell proliferation of B16 melanoma cells. These results confirmed that the derivatives of quercetin and luteolin may be useful as therapeutic agents to prevent melanoma metastasis.

  黑色素瘤是一种由黑色素细胞损伤引起的恶性皮肤肿瘤，可扩散到其他器官。因此，人们对防止黑色素瘤扩散进行了各种研究。芹菜素和高良姜素等黄酮类结构物质是抑制黑色素瘤增殖和转移的有效治疗药物。本研究合成了木犀草素、槲皮素及其各自的衍生物。这些化合物抑制了 B16 黑色素瘤细胞的增殖。这些结果证实，槲皮素和木犀草素的衍生物可作为防止黑色素瘤转移的治疗药物。