(10S,11R,12R)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-7,8,11,12-tetrahydro-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-2-one

• 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: (10S,11R,12R)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-7,8,11,12-tetrahydro-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-2-one
• 英文别名: (16S,17R,18R)-18-hydroxy-10,10,16,17-tetramethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13)-tetraen-4-one
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: YPUTYHJWWMYIGF-OAVHHTNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (10S,11R,12R)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-7,8,11,12-tetrahydro-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-2-one 生成 (+)-dihydrocalanolide A
  参考文献：
  名称：

  Structure−Activity Modifications of the HIV-1 Inhibitors (+)-Calanolide A and (−)-Calanolide B

  摘要：

  The Delta(7,8) olefinic linkages within (+)-calanolide A (1) and (-)-calanolide B (2) were catalytically reduced to determine impact on the anti-HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.

  DOI：

  10.1021/jm9602827
• 作为产物：
  描述：

  (10S,11R,12R)-12-羟基-6,6,10,11-四甲基-4-丙基-11,12-二氢-2H,6H,10H-二吡喃并[2,3-f:2',3'-h]色烯-2-酮 在 platinum(IV) oxide 、 氨 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (10S,11R,12R)-12-Hydroxy-6,6,10,11-tetramethyl-4-propyl-7,8,11,12-tetrahydro-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-2-one
  参考文献：
  名称：

  Structure−Activity Modifications of the HIV-1 Inhibitors (+)-Calanolide A and (−)-Calanolide B

  摘要：

  The Delta(7,8) olefinic linkages within (+)-calanolide A (1) and (-)-calanolide B (2) were catalytically reduced to determine impact on the anti-HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.

  DOI：

  10.1021/jm9602827

文献信息

• Structure−Activity Modifications of the HIV-1 Inhibitors (+)-Calanolide A and (−)-Calanolide B
  作者：Deborah L. Galinis、Richard W. Fuller、Tawnya C. McKee、John H. Cardellina、Robert J. Gulakowski、James B. McMahon、Michael R. Boyd

  DOI：10.1021/jm9602827

  日期：1996.1.1

  The Delta(7,8) olefinic linkages within (+)-calanolide A (1) and (-)-calanolide B (2) were catalytically reduced to determine impact on the anti-HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.