3-(4-methoxybenzofuran-5-yl)-5-phenylisoxazole | 864745-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(4-methoxybenzofuran-5-yl)-5-phenylisoxazole
• 英文别名: 3-(4-methoxy-1-benzofuran-5-yl)-5-phenyl-1,2-oxazole
• CAS: 864745-80-2
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: LIDVCGVURBDYCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxybenzofuran-5-yl)-5-phenylisoxazole 在 镍 氢气 、 silica gel 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 34.0h， 生成 pongamol
  参考文献：
  名称：

  An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones

  摘要：

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.111
• 作为产物：
  描述：

  methyl 4-methoxybenzofuran-5-carboxylate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 chloroamine-T 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 3-(4-methoxybenzofuran-5-yl)-5-phenylisoxazole
  参考文献：
  名称：

  An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones

  摘要：

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.111

文献信息

• Furanoflavones pongapin and lanceolatin B blocks the cell cycle and induce senescence in CYP1A1-overexpressing breast cancer cells
  作者：Rajni Sharma、Ibidapo S. Williams、Linda Gatchie、Vinay R. Sonawane、Bhabatosh Chaudhuri、Sandip B. Bharate

  DOI：10.1016/j.bmc.2018.11.013

  日期：2018.12

  Expression of cytochrome P450-1A1 (CYP1A1) is suppressed under physiologic conditions but is induced (a) by polycyclic aromatic hydrocarbons (PAHs) which can be metabolized by CYP1A1 to carcinogens, and (b) in majority of breast cancers. Hence, phytochemicals or dietary flavonoids, if identified as CYP1A1 inhibitors, may help in preventing PAH-mediated carcinogenesis and breast cancer. Herein, we have investigated the cancer chemopreventive potential of a flavonoid-rich Indian medicinal plant, Pongamia pinnata (L.) Pierre. Methanolic extract of its seeds inhibits CYP1A1 in CYP1A1-overexpressing normal human HEK293 cells, with IC50 of 0.6 mu g/mL. Its secondary metabolites, the furanoflavonoids pongapin/lanceolatin B, inhibit CYP1A1 with IC50 of 20 nM. Although the furanochalcone pongamol inhibits CYP1A1 with IC50 of only 4.4 mu M, a semisynthetic pyrazole-derivative P5b, has similar to 10-fold improved potency (IC50, 0.49 mu M). Pongapin/lanceolatin B and the methanolic extract of P. pinnata seeds protect CYP1A1-overexpressing HEK293 cells from B[a] P-mediated toxicity. Remarkably, they also block the cell cycle of CYP1A1-overexpressing MCF-7 breast cancer cells, at the G(0)-G(1) phase, repress cyclin D1 levels and induce cellular-senescence. Molecular modeling studies demonstrate the interaction pattern of pongapin/lanceolatin B with CYP1A1. The results strongly indicate the potential of methanolic seed-extract and pongapin/lanceolatin B for further development as cancer chemopreventive agents.
• Synthesis and anticancer effects of pongamol derivatives on mitogen signaling and cell cycle kinases
  作者：R. Ranga Rao、Vishal Chaturvedi、K. Suresh Babu、P. Prabhakar Reddy、V. Rama Subba Rao、P. Sreekanth、A. S. Sreedhar、J. Madhusudana Rao

  DOI：10.1007/s00044-011-9563-y

  日期：2012.5

  A series of oxazole and pyrazole derivatives of pongamol (1) were designed and synthesized to examine their anti-cancer activity. The cytotoxicity of these compounds was examined in three different human tumor cell lines, IMR-32, HeLa and Jurkat. Although all compounds tested were quite effective than the pongamol against all the three different types of cancer cell lines examined, the compounds (2), (5), and (6) were found to be the most active compounds of this series.
• An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones
  作者：Prem P. Yadav、Ghufran Ahmad、Rakesh Maurya

  DOI：10.1016/j.tetlet.2005.06.111

  日期：2005.8

  An efficient route for the syntheses of beta-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from Claisen aroylation of an ester and subsequent acid cyclization, or from isoxazolines via DDQ-mediated dehydrogenation, were subjected to catalytic hydrogenation followed by hydrolysis to afford 1-phenyl-3-(benzofuran-5-yl)-1,3-diketone and 1-phenyl-3(benzothiophene-5-yl)-1,3-diketones in very good yields. (c) 2005 Elsevier Ltd. All rights reserved.