3-羟基-1-(4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮 | 142596-71-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 3-羟基-1-(4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮
• 英文名称: pongamol
• 英文别名: 3-Hydroxy-1-(4-methoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one
• CAS: 142596-71-2
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: IHWPQGIYXJKCOV-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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羟基-1-(4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 lanceolatin B
  参考文献：
  名称：

  Furanoflavones pongapin and lanceolatin B blocks the cell cycle and induce senescence in CYP1A1-overexpressing breast cancer cells

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2018.11.013
• 作为产物：
  描述：

  4-羟基-2-甲氧基苯甲醛 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-dibenzylbenzimidazolium chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3-羟基-1-(4-甲氧基-1-苯并呋喃-5-基)-3-苯基丙-2-烯-1-酮
  参考文献：
  名称：

  新型 3, 4-二氢嘧啶-2(1H)-硫酮基 pongamol 抗菌剂的合成与评价

  摘要：

  Pongamol，一种存在于 karanj ( Pongamia glabra ) 树不同部分的呋喃查耳酮，已在本次调查中与硫脲和对位取代的苯甲醛发生 Biginelli 反应。在盐酸的催化下，这三组分在乙酸中的环缩合反应形成了一系列新的 4-甲氧基苯并呋喃-5-酰基共轭 3,4-二氢嘧啶-2(1 H)-硫酮( 4a至4g )。合成的新衍生物通过 NMR（ 1 H 和13 C）和质量（HRESI-MS）表征。对一些选定细菌菌株的抗菌活性筛选表明，衍生物4a，4b、4c和4f对植物克雷伯菌表现出优异的抗菌活性。衍生物4c还显示出对大肠杆菌和藤黄微球菌的效力。基于这一有希望的结果，进一步筛选了这四种化合物的最低杀菌浓度 (MBC) 和抗生物膜活性。化合物4c和4f分别对 M. luteus 和K. planticola具有优异的杀菌活性（MBC，1.9 μg/mL） ，与参比药物环丙沙星相当。

  DOI：

  10.1007/s00044-023-03059-1

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 evaluation of novel 3, 4-dihydropyrimidin-2(1H)- thione based pongamol conjugates as antibacterial agents
  作者：Anjaneyulu Eanti、Rajesh Gujju、Sunil Misra、Siddaiah Vidavalur、Sanjit Kanjilal

  DOI：10.1007/s00044-023-03059-1

  日期：2023.6

  three component cyclo-condensation reaction in acetic acid catalyzed by hydrochloric acid resulted in the formation of a new series of 4-methoxybenzofuran-5-oyl conjugated 3,4-dihydropyrimidin-2(1H)-thiones (4a to 4g). Synthesized new derivatives were characterized by NMR (1H and 13C) and mass (HRESI-MS). Screening of the antibacterial activity against some selected bacterial strains showed that the derivatives

  Pongamol，一种存在于 karanj ( Pongamia glabra ) 树不同部分的呋喃查耳酮，已在本次调查中与硫脲和对位取代的苯甲醛发生 Biginelli 反应。在盐酸的催化下，这三组分在乙酸中的环缩合反应形成了一系列新的 4-甲氧基苯并呋喃-5-酰基共轭 3,4-二氢嘧啶-2(1 H)-硫酮( 4a至4g )。合成的新衍生物通过 NMR（ 1 H 和13 C）和质量（HRESI-MS）表征。对一些选定细菌菌株的抗菌活性筛选表明，衍生物4a，4b、4c和4f对植物克雷伯菌表现出优异的抗菌活性。衍生物4c还显示出对大肠杆菌和藤黄微球菌的效力。基于这一有希望的结果，进一步筛选了这四种化合物的最低杀菌浓度 (MBC) 和抗生物膜活性。化合物4c和4f分别对 M. luteus 和K. planticola具有优异的杀菌活性（MBC，1.9 μg/mL） ，与参比药物环丙沙星相当。