4-Methyl-6,7-dihydroxanthyletin | 39112-66-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-Methyl-6,7-dihydroxanthyletin
• 英文别名: 4,8,8-trimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one；2,2,6-trimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS: 39112-66-8
• 化学式: C₁₅H₁₆O₃
• mdl: MFCD06492885
• 分子量: 244.29
• InChiKey: UYWBIHHNIMDFDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-6,7-dihydroxanthyletin 在 selenium(IV) oxide 、 双氧水 、 溶剂黄146 作用下， 以 xylene 为溶剂， 反应 84.0h， 生成 4-Carboxy-6,7-dihydroxanthyletin
  参考文献：
  名称：

  Waykole, Pratibha; Shaikh, Salim; Usgaonkar, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 3, p. 238 - 240

  摘要：

  DOI：
• 作为产物：
  描述：

  间苯二酚 在 ascorbic acid 、 硫酸 、 柠檬酸 作用下， 反应 22.25h， 生成 4-Methyl-6,7-dihydroxanthyletin
  参考文献：
  名称：

  Pancreatic α-amylase inhibition and free radical scavenging activity of substituted pyranochromenone derivatives

  摘要：

  Pyranochromenone derivatives 3a-d, 6a-j and 2H-chromenones 8a-b were synthesized and screened for their in vitro alpha-amylase inhibitory and ABTS(aEuro cent+) [2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)] free radical scavenging activities. Compounds 3a, 3c, and 6d displayed dual function of ABTS(aEuro cent+) radical scavenging as well as alpha-amylase inhibition. Compound 6h was found to be most potent alpha-amylase inhibitor in present series of compounds. Docking studies suggest that these compounds occupy active site of the human pancreatic alpha-amylase similar to that of acarbose which inhibits enzyme by hydrophobic interactions. These compounds have potential to be developed as therapeutics targeted against diet-induced hyperglycemia in diabetes.Series of pyranochromenone derivatives 3a-d, 6a-j, and 8a-b were synthesized, among these compound 6h shown potent intestinal alpha-amylase inhibitory activity. Compounds 3a, 3c, and 6d were shown dual properties such as alpha-amylase inhibitory and antioxidant activities. These derivatives may serve as a model compounds for design and development of therapeutics based agents.

  DOI：

  10.1007/s00044-013-0867-y

文献信息

• Novel syntheses of dihydroxanthyletin and dihydroseselin derivatives
  作者：Michele M. Jetter、Ned D. Heindel、Jeffrey D. Laskin

  DOI：10.1002/jhet.5570270433

  日期：1990.5

  In a one-step alkylation, ring-closure 7-hydroxycoumarins are condensed in acid media with allyl and homoallyl halides or alcohols to linear 6,7-dihydro-2H,8H-benzo[1,2–6:5,4-b']dipyran-2-ones. If both carbon-6 and carbon-8 are unsubstituted in the original coumarin, cyclization to angular isomers 9,10-dihydro-2H,8H-benzo[1,2–6:3,4-b']dipyran-2-ones competes. These compounds are higher ring homologs

  在一步式烷基化中，将闭环的7-羟基香豆素在酸介质中与烯丙基和高烯丙基卤化物或醇缩合成线性6,7-二氢-2 H，8 H-苯并[1,2–6：5,4 - b” ] dipyran -2-酮。如果原始香豆素中的碳6和碳8都未被取代，则环化成角异构体9,10-dihydro-2 H，8 H-苯并[1,2-6：3,4- b' ] dipyran-2 -竞争。这些化合物是通常用于皮肤疾病的光疗中的补骨脂素和当归素的较高环同系物。
• Kanvinde, M.N.; Kulkarni, S.A.; Paradkar, M.V., Synthetic Communications, 1990, vol. 20, # 21, p. 3259 - 3264
  作者：Kanvinde, M.N.、Kulkarni, S.A.、Paradkar, M.V.

  DOI：——

  日期：——
• Pathak, S. D.; Mujumdar, A. S.; Usgaonkar, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, p. 767 - 768
  作者：Pathak, S. D.、Mujumdar, A. S.、Usgaonkar, R. N.

  DOI：——

  日期：——
• Reaction of 2,2-Dimethylchromans with 2,3-Dichloro-5,6-dicyanobenzoguinone (DDQ)
  作者：V. K. Ahluwalia、R. S. Jolly

  DOI：10.1055/s-1982-29707

  日期：——
• SHAIKH S.; USAONKAR R. N., INDIAN J. CHEM., 1979, B 18, NO 5, 405-408
  作者：SHAIKH S.、 USAONKAR R. N.

  DOI：——

  日期：——