2-Aethyl-7-hydroxy-5-methylchromon | 62036-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-Aethyl-7-hydroxy-5-methylchromon
• 英文别名: 2-ethyl-7-hydroxy-5-methyl-chromen-4-one；2-Aethyl-7-hydroxy-5-methyl-chromen-4-on；2-Ethyl-7-hydroxy-5-methyl-4H-chromen-4-one；2-ethyl-7-hydroxy-5-methylchromen-4-one
• CAS: 62036-42-4
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: DBAQTPJYPSIYMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Aethyl-7-hydroxy-5-methylchromon 在 吡啶 、 4-二甲氨基吡啶 、 potassium osmate(VI) dihydrate 、 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 、 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 [(9R,10R)-2-ethyl-5,8,8-trimethyl-4-oxo-9-[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]oxy-9,10-dihydropyrano[2,3-h]chromen-10-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Anti-AIDS agents 89. Identification of DCX derivatives as anti-HIV and chemosensitizing dual function agents to overcome P-gp-mediated drug resistance for AIDS therapy

  摘要：

  In this study, 19 dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-dihydropyranoxanth-one (DCX) derivatives, previously discovered as novel anti-HIV agents, were evaluated for their potential to reverse multi-drug resistance (MDR) in a cancer cell line over-expressing P-glycoprotein (P-gp). Seven compounds fully reversed resistance to vincristine (VCR) at 4 mu M, a 20-fold enhancement compared to the first generation chemosensitizer, verapamil (4 mu M). The mechanism of action of DCPs and DCXs was also resolved, since the most active compounds (3, 4, and 7) significantly increased intracellular drug accumulation due, in part, to inhibiting the P-gp mediated drug efflux from cells. We conclude that DCPs (3 and 4) and DCXs (7, 11, and 17) can exhibit polypharmacologic behavior by acting as dual inhibitors of HIV replication and chemoresistance mediated by P-gp. As such, they may be useful in combination therapy to overcome P-gp-associated drug resistance for AIDS treatment. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.037
• 作为产物：
  描述：

  1-(2,4-二羟基-6-甲基苯基)乙酮 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 19.0h， 生成 2-Aethyl-7-hydroxy-5-methylchromon
  参考文献：
  名称：

  一种5-甲基色酮及其制备方法和应用

  摘要：

  本发明提供一种5‑甲基色酮及其制备方法和应用，所述5‑甲基色酮具有下述结构：其中R1和R2为烷基。取代后的色酮具有抑制酪氨酸酶的生物活性。制备方法以3,5‑二羟基甲苯为原料，经过酰基化、酯化、重排和环化反应等合成2‑C位不同基团取代的色酮。本发明R1为‑CH2CH2CH3，R2为‑CH2CH3及R1为‑C(CH3)3，R2为H者为全新的化合物。所有化合物对酪氨酸酶具有明显的抑制活性，可应用于制备酪氨酸酶抑制剂或美白剂。

  公开号：

  CN112174922A

文献信息

• Sethna; Shah, Journal of the Indian Chemical Society, 1940, vol. 17, p. 487,490
  作者：Sethna、Shah

  DOI：——

  日期：——
• Anti-AIDS agents 89. Identification of DCX derivatives as anti-HIV and chemosensitizing dual function agents to overcome P-gp-mediated drug resistance for AIDS therapy
  作者：Ting Zhou、Emika Ohkoshi、Qian Shi、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2012.03.037

  日期：2012.5

  In this study, 19 dicamphanoyl-dihydropyranochromone (DCP) and dicamphanoyl-dihydropyranoxanth-one (DCX) derivatives, previously discovered as novel anti-HIV agents, were evaluated for their potential to reverse multi-drug resistance (MDR) in a cancer cell line over-expressing P-glycoprotein (P-gp). Seven compounds fully reversed resistance to vincristine (VCR) at 4 mu M, a 20-fold enhancement compared to the first generation chemosensitizer, verapamil (4 mu M). The mechanism of action of DCPs and DCXs was also resolved, since the most active compounds (3, 4, and 7) significantly increased intracellular drug accumulation due, in part, to inhibiting the P-gp mediated drug efflux from cells. We conclude that DCPs (3 and 4) and DCXs (7, 11, and 17) can exhibit polypharmacologic behavior by acting as dual inhibitors of HIV replication and chemoresistance mediated by P-gp. As such, they may be useful in combination therapy to overcome P-gp-associated drug resistance for AIDS treatment. (C) 2012 Elsevier Ltd. All rights reserved.
• 一种5-甲基色酮及其制备方法和应用
  申请人：海南医学院

  公开号：CN112174922A

  公开（公告）日：2021-01-05

  本发明提供一种5‑甲基色酮及其制备方法和应用，所述5‑甲基色酮具有下述结构：其中R1和R2为烷基。取代后的色酮具有抑制酪氨酸酶的生物活性。制备方法以3,5‑二羟基甲苯为原料，经过酰基化、酯化、重排和环化反应等合成2‑C位不同基团取代的色酮。本发明R1为‑CH2CH2CH3，R2为‑CH2CH3及R1为‑C(CH3)3，R2为H者为全新的化合物。所有化合物对酪氨酸酶具有明显的抑制活性，可应用于制备酪氨酸酶抑制剂或美白剂。