(+/-)-2-isopropenyl-5-methoxy-1,2-dihydro-13-methyl-13H-benzo[b]furo[3,2-h]acridin-6-one | 1082415-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+/-)-2-isopropenyl-5-methoxy-1,2-dihydro-13-methyl-13H-benzo[b]furo[3,2-h]acridin-6-one
• 英文别名: 10-Methoxy-2-methyl-6-prop-1-en-2-yl-7-oxa-2-azapentacyclo[11.8.0.03,11.04,8.015,20]henicosa-1(21),3,8,10,13,15,17,19-octaen-12-one
• CAS: 1082415-60-8
• 化学式: C₂₄H₂₁NO₃
• 分子量: 371.436
• InChiKey: PQQMEVQJLATRLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-2-isopropenyl-5-methoxy-1,2-dihydro-13-methyl-13H-benzo[b]furo[3,2-h]acridin-6-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 96.0h， 生成 (+/-)-(2R*,1'R*)-2-(1,2-dihydroxy-1-methylethyl)-5-methoxy-13-methyl-1,2-dihydro-13H-benzo[b]furo[3,2-h]acridin-6-one 、 (+/-)-(2R*,1'S*)-2-(1,2-dihydroxy-1-methylethyl)-5-methoxy-13-methyl-1,2-dihydro-13H-benzo[b]furo[3,2-h]acridin-6-one
  参考文献：
  名称：

  Synthesis, Cytotoxic Activity, and Mechanism of Action of Furo[2,3-c]acridin-6-one and Benzo[b]furo[3,2-h]acridin-6-one Analogues of Psorospermin and Acronycine

  摘要：

  Compounds possessing the epoxyfuran system present in the natural cytotoxic dihydrofuroxanthone psorospermin (4) fused onto the acridone or benzo[b]acridone chromophores present in the antitumor acronycine (1) and S23906-1 (3) were prepared. The basic furoacridone and benzofuroacridone cores bearing an isopropenyl substituent at a convenient position were synthesized by condensation of 1,3-dihydroxyacridone (7) or 1,3-dihydroxybenz[b]acridin-12(5H)-one (9) with (E)-1,4-dibromo-2-methylbut-2-ene. In both series, the (2R*,1'S*) epoxides, with the same relative configuration as psorospermin, were the most active compounds, exhibiting cytotoxic properties with IC50 values in the 10-100 nM range. As in the acronycine and psorospermin series, the new compounds act through alkylation of the DNA guanine units. However, a strong difference was noted in the DNA alkylation site between the benzopyranoacridone S23906-1, which alkylates DNA guanine units at position N-2 in the minor groove, and the new 13H-benzo[b]furo[3,2-h]acridin-6-one derived epoxide 21, which alkylates DNA guanine units at position N-7 in the major groove.

  DOI：

  10.1021/jm8009487
• 作为产物：
  描述：

  (+/-)-2-isopropenyl-5-hydroxy-1,2-dihydro-13H-benzo[b]furo[3,2-h]acridin-9-one 、 硫酸二甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以97%的产率得到(+/-)-2-isopropenyl-5-methoxy-1,2-dihydro-13-methyl-13H-benzo[b]furo[3,2-h]acridin-6-one
  参考文献：
  名称：

  Synthesis, Cytotoxic Activity, and Mechanism of Action of Furo[2,3-c]acridin-6-one and Benzo[b]furo[3,2-h]acridin-6-one Analogues of Psorospermin and Acronycine

  摘要：

  Compounds possessing the epoxyfuran system present in the natural cytotoxic dihydrofuroxanthone psorospermin (4) fused onto the acridone or benzo[b]acridone chromophores present in the antitumor acronycine (1) and S23906-1 (3) were prepared. The basic furoacridone and benzofuroacridone cores bearing an isopropenyl substituent at a convenient position were synthesized by condensation of 1,3-dihydroxyacridone (7) or 1,3-dihydroxybenz[b]acridin-12(5H)-one (9) with (E)-1,4-dibromo-2-methylbut-2-ene. In both series, the (2R*,1'S*) epoxides, with the same relative configuration as psorospermin, were the most active compounds, exhibiting cytotoxic properties with IC50 values in the 10-100 nM range. As in the acronycine and psorospermin series, the new compounds act through alkylation of the DNA guanine units. However, a strong difference was noted in the DNA alkylation site between the benzopyranoacridone S23906-1, which alkylates DNA guanine units at position N-2 in the minor groove, and the new 13H-benzo[b]furo[3,2-h]acridin-6-one derived epoxide 21, which alkylates DNA guanine units at position N-7 in the major groove.

  DOI：

  10.1021/jm8009487

文献信息

• Synthesis, Cytotoxic Activity, and Mechanism of Action of Furo[2,3-<i>c</i>]acridin-6-one and Benzo[<i>b</i>]furo[3,2-<i>h</i>]acridin-6-one Analogues of Psorospermin and Acronycine
  作者：Sabrina Boutefnouchet、Nicolas Gaboriaud-Kolar、Nguyen Tuan Minh、Sabine Depauw、Marie-Hélène David-Cordonnier、Bruno Pfeiffer、Stéphane Léonce、Alain Pierré、François Tillequin、Marie-Christine Lallemand、Sylvie Michel

  DOI：10.1021/jm8009487

  日期：2008.11.27

  Compounds possessing the epoxyfuran system present in the natural cytotoxic dihydrofuroxanthone psorospermin (4) fused onto the acridone or benzo[b]acridone chromophores present in the antitumor acronycine (1) and S23906-1 (3) were prepared. The basic furoacridone and benzofuroacridone cores bearing an isopropenyl substituent at a convenient position were synthesized by condensation of 1,3-dihydroxyacridone (7) or 1,3-dihydroxybenz[b]acridin-12(5H)-one (9) with (E)-1,4-dibromo-2-methylbut-2-ene. In both series, the (2R*,1'S*) epoxides, with the same relative configuration as psorospermin, were the most active compounds, exhibiting cytotoxic properties with IC50 values in the 10-100 nM range. As in the acronycine and psorospermin series, the new compounds act through alkylation of the DNA guanine units. However, a strong difference was noted in the DNA alkylation site between the benzopyranoacridone S23906-1, which alkylates DNA guanine units at position N-2 in the minor groove, and the new 13H-benzo[b]furo[3,2-h]acridin-6-one derived epoxide 21, which alkylates DNA guanine units at position N-7 in the major groove.