12-Thiocalanolide B | 183791-90-4

• 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: 12-Thiocalanolide B
• 英文别名: (16S,17S,18S)-10,10,16,17-tetramethyl-6-propyl-18-sulfanyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaen-4-one
• CAS: 183791-90-4
• 化学式: C₂₂H₂₆O₄S
• 分子量: 386.512
• InChiKey: JLDHRKWONIFCQR-OABGYEMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione 在 吡啶 、 sodium tetrahydroborate 、 sodium hydrogensulfide 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 12-Thiocalanolide B
  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.