5,6-dihydroxy-7-(3-methylbut-2-enyloxy)-2-phenyl-4H-chromen-4-one | 1310461-23-4

• 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: 5,6-dihydroxy-7-(3-methylbut-2-enyloxy)-2-phenyl-4H-chromen-4-one
• 英文别名: 5,6-dihydroxy-7-isoprenoxyflavone；5,6-dihydroxy-7-((3-methylbut-2-en-1-yl)oxy)-2-phenyl-4H-chromen-4-one；5,6-dihydroxy-7-(3-methylbut-2-enoxy)-2-phenylchromen-4-one
• CAS: 1310461-23-4
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: JQLNZAVRUGCPNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  黄芩素	5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one	491-67-8	C15H10O5	270.241
  黄芩苷	baicalin	21967-41-9	C21H18O11	446.367

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5,6-dihydroxy-8,8-dimethyl-2-phenyl-9,10-dihydropyrano[2,3-f]chromen-4(8H)-one	1310461-31-4	C20H18O5	338.36
  ——	5,6-dihydroxy-8,9,9-trimethyl-2-phenyl-8,9-dihydro-4H-furo[2,3-h]chromen-4-one	1310461-30-3	C20H18O5	338.36

反应信息

• 作为反应物：
  描述：

  5,6-dihydroxy-7-(3-methylbut-2-enyloxy)-2-phenyl-4H-chromen-4-one 在 Montmorillonite K₁₀ clay 作用下， 以 氯仿 为溶剂， 反应 0.75h， 以34%的产率得到5,6-dihydroxy-8,8-dimethyl-2-phenyl-9,10-dihydropyrano[2,3-f]chromen-4(8H)-one
  参考文献：
  名称：

  Prenylated derivatives of baicalein and 3,7-dihydroxyflavone: Synthesis and study of their effects on tumor cell lines growth, cell cycle and apoptosis

  摘要：

  Fourteen baicalein and 3,7-dihydroxyflavone derivatives were synthesized and evaluated for their inhibitory activity against the in vitro growth of three human tumor cell lines. The synthetic approaches were based on the reaction with prenyl or geranyl bromide in alkaline medium, followed by cyclization of the respective monoprenylated derivative. Dihydropyranoflavonoids were also obtained by one-pot synthesis, using Montmorillonite K10 clay as catalyst combined with microwave irradiation. In vitro screening of the compounds for cell growth inhibitory activity revealed that the presence of one geranyl group was associated with a remarkable increase in the inhibitory activity. Moreover, for the 3,7-dihydroxyflavone derivatives a marked increase in growth inhibitory effect was also observed for compounds with furan and pyran fused rings. The most active compounds were also studied regarding their effect on cell cycle profile and induction of apoptosis. Overall the results point to the relevant role of the prenylation of flavone scaffold in the growth inhibitory activity of cancer cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.047
• 作为产物：
  描述：

  黄芩苷 在 盐酸 、 potassium hydrogencarbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5,6-dihydroxy-7-(3-methylbut-2-enyloxy)-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model

  摘要：

  Angiogenesis leads to tumor neovascularization by promoting tumor growth and metastatic spread, therefore, angiogenesis is considered as an attractive target for potential small molecule anticancer drug discovery. Herein, we report the structural modification and biological evaluation of baicalein derivatives, among which compound 42 had potent in vivo anti-angiogenic activity and wide security treatment window in transgenic zebrafish model. Further, 42 exhibited the most potent inhibitory activity on HUVEC proliferation, migration and tube formation in vitro. Moreover, 42 significantly inhibited growth of human lung cancer A549 cells and weak influence on human normal fibroblast L929 cells. The present research demonstrated that the significant anti-angiogenic and anticancer effects, which provided the supportive evidence for 42 could be used as a potential compound of cancer therapy.

  DOI：

  10.1016/j.bmc.2018.07.037

文献信息

• Synthesis and biological evaluation of novel 7-O-lipophilic substituted baicalein derivatives as potential anticancer agents
  作者：Shao-Hung Wang、Ching-Hsein Chen、Chih-Yu Lo、Ji-Zhen Feng、Hong-Jhih Lin、Po-Ya Chang、Ling-Ling Yang、Lih-Geeng Chen、Yi-Wen Liu、Cheng-Deng Kuo、Jin-Yi Wu

  DOI：10.1039/c5md00163c

  日期：——

  We synthesized derivatives of baicalein, wogonin, and chrysin through alkylation at the 7-O-position of the A ring with lipophilic terphenyl or long chain n-alkyl groups, and studied the in vitro anticancer activity of the derivatives through the growth inhibition MTT assay. We discovered that baicalein and two of its derivatives were good free radical scavengers. Among the 20 synthesized derivatives

  我们通过在具有亲脂性三联苯或长链正烷基的A环的7- O位上进行烷基化反应，合成了黄ical素，沃戈宁和菊花链素的衍生物，并通过生长抑制MTT分析研究了这些衍生物的体外抗癌活性。我们发现黄ical素及其两个衍生物是良好的自由基清除剂。在20种合成衍生物中，与黄ical苷相比，7- O-法呢基黄ical苷（5d）和7- O-十二烷基黄ical苷（5i）对人结肠癌SW480细胞具有更强的生长抑制作用，最大抑制浓度为一半（IC 50）值分别为1.15和1.57μM。此外，5d和5i剂量和时间依赖性抑制SW480细胞的生长。细胞周期分布分析表明5d和5i通过凋亡机制诱导SW480细胞停滞在S期，这与活性氧的产生增加有关。总之，黄ical素衍生物（5d和5i）的有效抗癌活性表明，这些衍生物是潜在的人类结肠癌抗癌药。
• Effects of a prenyl-baicalein derivative on ER (+) MCF-7 and ER (−) MDA-MB-231 breast tumor cell lines
  作者：Marta Perro Neves、Ana Camões、Maria de São José Nascimento、Honorina Cidade、Maria Emília Sousa、Madalena Maria Magalhães Pinto

  DOI：10.1007/s00044-011-9848-1

  日期：2012.10

  The effect of a prenyl-baicalein derivative in the DNA synthesis of the estrogen-dependent ER (+) MCF-7 and the estrogen-independent ER (-) MDA-MB-231 cell lines was evaluated using both complete and steroid-free medium. The results revealed a biphasic effect in DNA synthesis of ER (+) MCF-7 cells. Moreover, this prenylflavone seemed to reduce the estrogenic effect of 17 beta-estradiol and to increase the antiestrogenic effect of 4-hydroxytamoxifen and fluvestrant on the ER (+) MCF-7 cells.