3-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran | 31273-64-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran
• 英文别名: 3-(4-methoxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one；3-(4-methoxyphenyl)-8,8-dimethylpyrano[2,3-f]chromen-4(8H)-one；4-Methoxy-8,8-dimethylpyrano<2,3:7,8>-isoflavone；Calopogonium isoflavone A；calopogoniumisoflavone A；3-(4-methoxy-phenyl)-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one；3-(4-methoxyphenyl)-8,8-dimethylpyrano[2,3-f]chromen-4-one
• CAS: 31273-64-0
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: QLPJSBWLIFSIMS-UHFFFAOYSA-N

物化性质

• 沸点：
  508.9±50.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,1-二乙氧基-3-甲基-2-丁烯 在 3-甲基吡啶 、 palladium on activated charcoal 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 5,5-dimethyl-1,3-cyclohexadiene 、 水 为溶剂， 反应 25.0h， 生成 3-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-benzo[1,2-b:3,4-b']dipyran
  参考文献：
  名称：

  高选择性基于氨基甲酸酯的丁酰胆碱酯酶抑制剂，其源自天然存在的吡喃异黄酮。

  摘要：

  这项当前的研究描述了一系列基于天然吡喃异黄酮的衍生物的设计和合成，该衍生物是从粟米草的种子中获得的，在我们之前的研究中显示出有吸引力的BChE抑制作用和高选择性。评价了所有衍生物对两种胆碱酯酶的抑制潜力。只有少数化合物在测试浓度下显示出AChE抑制活性，而26种化合物显示出对BChE的显着抑制作用（IC50值从9.34μM到0.093μM不等），其中大多数对BChE病区具有选择性。预测了7种活性最高的化合物的ADME性质。其中9g（IC50 = 222 nM）和9h（IC50 = 93 nM）被发现是最有效的BChE抑制剂，对AChE的选择性极好（SI比分别为1339和836）。动力学分析表明它们都充当混合型BChE抑制剂，而分子对接结果表明它们与催化活性位点的两个残基都相互作用。对PC12细胞的细胞毒性测试表明，9g和9h的治疗安全范围均与他克林相似。总体而言，结果表明9h可能是BChE抑制剂的良好候选者。

  DOI：

  10.1016/j.bioorg.2019.102949

文献信息

• Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents
  作者：Zhe Wei、Youzhe Yang、Caifeng Xie、Chunyan Li、Guangcheng Wang、Liang Ma、Mingli Xiang、Jian Sun、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.fitote.2014.06.002

  日期：2014.9

  In this paper, barbigerone (1a) and its twenty-seven related structural analogues were synthesized via complementary synthetic routes and their anti-inflammatory effects on the expression of TNF-α in LPS-stimulated splenocytes were evaluated. Among these compounds, 1a, 1d, 1f and 1g were found to remarkably inhibit TNF-α production. Furthermore, 1g showed the most potent and dose-dependent manner inhibitory effect on TNF-α release, with better IC50 value (3.58 μM) than barbigerone (8.46 μM). Oral administration of 1g at 20 mg/kg/day for two weeks obviously demonstrated protective effect in adjuvant-induced arthritis models as evaluated by clinical score of paws, and histological examination of joint tissues from rats. Mechanism studies on mRNA and protein level suggested that 1g inhibited the TNF-α production via depressing TNF-α converting enzyme (TACE) mRNA expression. In conclusion, these data show 1g with potential therapeutic effects as an anti-inflammatory agent.
• Synthesis, structure–activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents
  作者：Guangcheng Wang、Fang Wang、Dong Cao、Yibin Liu、Ronghong Zhang、Haoyu Ye、Xiuxia Li、Lin He、Zhuang Yang、Liang Ma、Aihua Peng、Mingli Xiang、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmcl.2014.04.121

  日期：2014.7

  A series of barbigerone analogues (7a-7w, 13a-13x) were designed, synthesized and biologically evaluated for their anti-proliferative and anti-angiogenic activities. Among these compounds, compound 13a exhibited the most potent inhibitory effect on the proliferation of HUVECs, HepG2, A375, U251, B16, and HCT116 cells (IC50 = 3.80, 0.28, 1.58, 3.50, 1.09 and 0.68 mu M, respectively). Compound 13a inhibited the angiogenesis in zebrafish embryo assay in a concentration-dependent manner. Furthermore, 13a also effectively inhibited the migration and capillary like tube formation of human umbilical vein endothelial cell in vitro. These results support the further investigation of this class of compounds as potential anti-proliferative and anti-angiogenesis agents. (C) 2014 Published by Elsevier Ltd.
• Jain, A. C.; Gupta, S.; Gupta, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 609 - 613
  作者：Jain, A. C.、Gupta, S.、Gupta, A.、Bambah, P.

  DOI：——

  日期：——
• Highly selective carbamate-based butyrylcholinesterase inhibitors derived from a naturally occurring pyranoisoflavone
  作者：Chuanhai Wu、Yan-bei Tu、Ziyuan Li、Yan-fang Li

  DOI：10.1016/j.bioorg.2019.102949

  日期：2019.7

  obtained from the seeds of Millettia pachycarpa and displayed attractive BChE inhibition and high selectivity in our previous study. The inhibitory potential of all derivatives against two cholinesterases was evaluated. Only a few compounds demonstrated AChE inhibitory activity at the tested concentrations, while 26 compounds showed significant inhibition on BChE (the IC50 values varied from 9.34 μM

  这项当前的研究描述了一系列基于天然吡喃异黄酮的衍生物的设计和合成，该衍生物是从粟米草的种子中获得的，在我们之前的研究中显示出有吸引力的BChE抑制作用和高选择性。评价了所有衍生物对两种胆碱酯酶的抑制潜力。只有少数化合物在测试浓度下显示出AChE抑制活性，而26种化合物显示出对BChE的显着抑制作用（IC50值从9.34μM到0.093μM不等），其中大多数对BChE病区具有选择性。预测了7种活性最高的化合物的ADME性质。其中9g（IC50 = 222 nM）和9h（IC50 = 93 nM）被发现是最有效的BChE抑制剂，对AChE的选择性极好（SI比分别为1339和836）。动力学分析表明它们都充当混合型BChE抑制剂，而分子对接结果表明它们与催化活性位点的两个残基都相互作用。对PC12细胞的细胞毒性测试表明，9g和9h的治疗安全范围均与他克林相似。总体而言，结果表明9h可能是BChE抑制剂的良好候选者。

表征谱图