3-methoxyseselin | 199393-47-0

• 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: 3-methoxyseselin
• 英文别名: 3-Methoxy-8,8-dimethylpyrano[2,3-f]chromen-2-one
• CAS: 199393-47-0
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: OXCFIFIJGCLQPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-(-)-莰烷酰氯 、 3-methoxyseselin 在 吡啶 、 potassium dioxotetrahydroxoosmate(VI) 、 hydroquinidine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 生成 3-methoxy-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone
  参考文献：
  名称：

  Anti-AIDS agents-XXVIII.1 Synthesis and Anti-HIV activity of methoxy substituted 3′,4′-Di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) analogues

  摘要：

  Four isomeric methoxy substituted DCK analogues (3-6) were asymmetrically synthesized from different starting materials. 5-Methoxy-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (5) exhibited extremely potent anti-HIV activity against HIV-1 replication in H9 lymphocyte cells with EC50 and therapeutic index values of 0.00038 mu M and >402,632, respectively, which are better than those of DCK and AZT in this assay. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10050-6
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 甲氧基乙酸钠 、 potassium carbonate 、 N,N-二乙基苯胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-methoxyseselin
  参考文献：
  名称：

  Anti-AIDS agents-XXVIII.1 Synthesis and Anti-HIV activity of methoxy substituted 3′,4′-Di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) analogues

  摘要：

  Four isomeric methoxy substituted DCK analogues (3-6) were asymmetrically synthesized from different starting materials. 5-Methoxy-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (5) exhibited extremely potent anti-HIV activity against HIV-1 replication in H9 lymphocyte cells with EC50 and therapeutic index values of 0.00038 mu M and >402,632, respectively, which are better than those of DCK and AZT in this assay. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10050-6

文献信息

• Anti-AIDS Agents. 37. Synthesis and Structure−Activity Relationships of (3‘<i>R</i>,4‘<i>R</i>)-(+)-<i>cis</i>-Khellactone Derivatives as Novel Potent Anti-HIV Agents
  作者：Lan Xie、Yasuo Takeuchi、L. Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1021/jm9900624

  日期：1999.7.1

  (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3', 4'-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3-6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3', 4'-substituents

  为了探索作为新型抗HIV药物的（+）-顺式-khellactone衍生物的结构要求，使用24个单取代的3'，4'-di-O-（S）-樟脑酰基-（+）-顺式-khellactone（DCK）衍生物不对称合成。这些化合物包括4个异构的单甲氧基类似物（3-6），4个异构的单甲基类似物（7-10），4个4-烷基/芳基取代的类似物（11-14）和12个4-甲基-（+）-顺式具有3'，4'取代基的khellactone衍生物（15-26）。这些（+）-顺式-khellactone衍生物被筛选针对急性感染的H9淋巴细胞中的HIV-1复制。结果表明，（3'R，4'R）-（+）-顺式-khellactone骨架，3'-和4'-位置的两个（S）-（-）-樟脑酰基和甲基除6-位以外，香豆素环上的α是抗HIV活性的最佳结构部分。3-甲基-（7），4-甲基-（8）和5-甲基-（9）3'，4'-二-O-（S）-樟脑酰基-（3'R，4'R）-
• Anti-AIDS agents-XXVIII.1 Synthesis and Anti-HIV activity of methoxy substituted 3′,4′-Di-O-(−)-camphanoyl-(+)-cis-khellactone (DCK) analogues
  作者：Yasuo Takeuchi、Lan Xie、L.Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(97)10050-6

  日期：1997.10

  Four isomeric methoxy substituted DCK analogues (3-6) were asymmetrically synthesized from different starting materials. 5-Methoxy-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (5) exhibited extremely potent anti-HIV activity against HIV-1 replication in H9 lymphocyte cells with EC50 and therapeutic index values of 0.00038 mu M and >402,632, respectively, which are better than those of DCK and AZT in this assay. (C) 1997 Elsevier Science Ltd.