dimethylalpinumisoflavone | 34086-56-1

• 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: dimethylalpinumisoflavone
• 英文别名: O,O-dimethylalpinumisoflavone；Alpinumisoflavone dimethyl ether；5-methoxy-7-(4-methoxyphenyl)-2,2-dimethylpyrano[3,2-g]chromen-6-one
• CAS: 34086-56-1
• 化学式: C₂₂H₂₀O₅
• 分子量: 364.398
• InChiKey: WRINUBCCCQLTPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethylalpinumisoflavone 在 甲酸 、 potassium iodide 作用下， 以 乙酸乙酯 为溶剂， 反应 1.83h， 以780 mg的产率得到4'-O-methylalpinumisoflavone
  参考文献：
  名称：

  鸡血藤香豆素类抗真菌先导化合物及其预测作用机制

  摘要：

  尽管努力控制真菌病原体，但它们继续对人类和植物构成挑战。从 Millettia thonningii 中分离出的两种香豆素、robustic acid 和 thonningine-C 显示出对真菌白色念珠菌的有希望的活性，最低杀菌浓度分别为 1.0 和 0.5 mg/mL。针对假定的生物分子靶标羊毛甾醇 14α-脱甲基酶 (CYP51) 的分子建模揭示了活性化合物的合理结合模式，其中羟基与甲硫氨酸骨架羧基结合，阻止进入铁催化位点。这种结合破坏了真菌生存所需的几种重要甾醇的合成。

  DOI：

  10.3390/molecules21101369
• 作为产物：
  描述：

  (E)-7-(benzyloxy)-6-(3-(4-(benzyloxy)phenyl)acryloyl)-5-methoxy-2,2-dimethylchroman-4-one 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 、 三氯化硼 、 potassium carbonate 、 对甲苯磺酸 、 sodium hydrogensulfite 、 thallium(III) nitrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 dimethylalpinumisoflavone
  参考文献：
  名称：

  Synthesis of 4',5- and 3',4',5-Oxygenated Pyranoisoflavones: Alpinumisoflavone and Related Compounds, and a Revised Structure of Derrone

  摘要：

  Alpinumisoflavone (4', 5-dihydroxy-2".2"-dimethylpyrano[5", 6"-g]isoflavone) (1a) was synthesized by regioselective reduction of 7-(4-hydroxyphenyl)-2, 3-dihydro-5-methoxy-2, 2-dimethyl-4H, 6H-benzo[1, 2-b:5, 4-b'] dipyran-4, 6-dione (15a) with NaBH4 and dehydration of the resultant alcohol, followed by demethylation with BC13. Its angular isomer (4', 5-dihydroxy-2", 2"-dimethylpyrano[6", 5"-h]isoflavone) (2a) was synthesized from 3-(4-hydroxyphenyl)-8, 9-dihydro-5-tosyloxy-8, 8-dimethyl-4H,10H-benzo [1, 2-b:3, 4-b']dipyran-4, 10-dione (27a) in a similar manner.

  DOI：

  10.3987/com-91-5918

文献信息

• A pyrano-isoflavone from seeds of Milletia thonningii
  作者：E.Martinez Olivares、W. Lwande、F.Delle Monache、G.B. Marini Bettolo

  DOI：10.1016/s0031-9422(82)85056-5

  日期：1982.1

  Abstract Extraction of the seeds of Milletia thonningii gave alpinumisoflavone, its monomethyl and dimethyl derivatives, robustic acid and a new pyrano-isoflavone. The structure of the latter was established by chemical transformation and spectroscopic means.

  摘要 提取鸡血藤种子得到高山杉木异黄酮、其单甲基和二甲基衍生物、粗野酸和一种新的吡喃异黄酮。后者的结构是通过化学转化和光谱手段确定的。
• Synthesis of alpinum isoflavone, derrone and related pyranoisoflavones
  作者：(Late)K.S.R.Mohan Rao、C.S.Rukmani Iyer、P.R. Iyer

  DOI：10.1016/s0040-4020(01)86841-1

  日期：1987.1

  esters 2 and 3 and decarboxylation of the acids 4 and 5, gave dihydro-4T-0-methyl alpinum isoflavone 6 and 4'-0-methylderrone 7 respectively. Similarly 8 gave 11 which was selectively demthylated to 7. DDQ; dehydrogenation of 6, 7 and 11 gave 14, 15 and 17. Demethylation of 6 and 7 followed by dehydrogenation gave alpinum isofavone 18 and derrone 19.

  苯甲酰基色喃1与乙氧基氯在吡啶中反应，然后水解所得的酯2和3，酸4和5脱羧，分别得到二氢-4 T -0-甲基al异黄酮6和4'-0-甲基derrone。类似地，8得到11，其被选择性地脱甲基化为7。6、7和11的脱氢得到14、15和17。6和7的脱甲基，然后脱氢得到阿尔卑斯异黄酮18和derrone 19。
• Thonningine-A and thonningine-B: two 3-phenylcoumarins from the seeds of Millettia thonningii
  作者：Sami A. Khalid、Peter G. Waterman

  DOI：10.1016/0031-9422(83)85041-9

  日期：——

  The seeds of Millettia thonningii have yielded four isoflavones and three 4-hydroxy-3-phenylcoumarins, of which two are novel. On the basis of spectral analyses the novel compounds have been identified as 4-hydroxy-5,8-dimethoxy-3-(3′,4′-methylenedioxy)phenyl-2″-isopropenylfurano (4″,5″:6,7)coumarin (thonningine-A) and 4-hydroxy-5,8-dimethoxy-3-(4′-methoxy)phenyl-2″-isopropenylfurano(4″, 5″: 6,7)coumarin

  Millettia thonningii 的种子产生了四种异黄酮和三种 4-羟基-3-苯基香豆素，其中两种是新的。根据光谱分析，新化合物已被鉴定为 4-羟基-5,8-二甲氧基-3-(3',4'-亚甲二氧基)苯基-2"-异丙烯基呋喃 (4",5":6,7 )香豆素(thonningine-A)和4-羟基-5,8-二甲氧基-3-(4'-甲氧基)苯基-2″-异丙烯基呋喃(4″，5″：6,7)香豆素(thonningine-B)。
• Synthesis of 4',5- and 3',4',5-Oxygenated Pyranoisoflavones: Alpinumisoflavone and Related Compounds, and a Revised Structure of Derrone
  作者：Masao Tsukayama、Yasuhiko Kawamura、Hideo Tahara

  DOI：10.3987/com-91-5918

  日期：——

  Alpinumisoflavone (4', 5-dihydroxy-2".2"-dimethylpyrano[5", 6"-g]isoflavone) (1a) was synthesized by regioselective reduction of 7-(4-hydroxyphenyl)-2, 3-dihydro-5-methoxy-2, 2-dimethyl-4H, 6H-benzo[1, 2-b:5, 4-b'] dipyran-4, 6-dione (15a) with NaBH4 and dehydration of the resultant alcohol, followed by demethylation with BC13. Its angular isomer (4', 5-dihydroxy-2", 2"-dimethylpyrano[6", 5"-h]isoflavone) (2a) was synthesized from 3-(4-hydroxyphenyl)-8, 9-dihydro-5-tosyloxy-8, 8-dimethyl-4H,10H-benzo [1, 2-b:3, 4-b']dipyran-4, 10-dione (27a) in a similar manner.
• Coumarin Antifungal Lead Compounds from Millettia thonningii and Their Predicted Mechanism of Action
  作者：Daniel Ayine-Tora、Robert Kingsford-Adaboh、William Asomaning、Jerry Harrison、Felix Mills-Robertson、Yahaya Bukari、Patrick Sakyi、Sylvester Kaminta、Jóhannes Reynisson

  DOI：10.3390/molecules21101369

  日期：——

  Fungal pathogens continue to pose challenges to humans and plants despite efforts to control them. Two coumarins, robustic acid and thonningine-C isolated from Millettia thonningii, show promising activity against the fungus Candida albicans with minimum fungicidal concentration of 1.0 and 0.5 mg/mL, respectively. Molecular modelling against the putative bio-molecular target, lanosterol 14α-demethylase

  尽管努力控制真菌病原体，但它们继续对人类和植物构成挑战。从 Millettia thonningii 中分离出的两种香豆素、robustic acid 和 thonningine-C 显示出对真菌白色念珠菌的有希望的活性，最低杀菌浓度分别为 1.0 和 0.5 mg/mL。针对假定的生物分子靶标羊毛甾醇 14α-脱甲基酶 (CYP51) 的分子建模揭示了活性化合物的合理结合模式，其中羟基与甲硫氨酸骨架羧基结合，阻止进入铁催化位点。这种结合破坏了真菌生存所需的几种重要甾醇的合成。