(9R,10R)-9,10-dihydroxy-4-methyl-8H,9H,10H-thiopyrano[6,5-h]-2H-chromen-2-one | 827024-69-1

• 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: (9R,10R)-9,10-dihydroxy-4-methyl-8H,9H,10H-thiopyrano[6,5-h]-2H-chromen-2-one
• CAS: 827024-69-1
• 化学式: C₁₃H₁₂O₄S
• 分子量: 264.302
• InChiKey: BPIRAGGBVFFJCG-UFBFGSQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  70.67
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (9R,10R)-9,10-dihydroxy-4-methyl-8H,9H,10H-thiopyrano[6,5-h]-2H-chromen-2-one 、 (1S)-(-)-莰烷酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95.2%的产率得到(9R,10R)-9,10-dicamphanoyloxy-4-methyl-8H,9H,10H-thiopyrano[6,5-h]-2H-chromen-2-one
  参考文献：
  名称：

  Anti-AIDS agents. Part 56: Synthesis and anti-HIV activity of 7-thia-di-O-(−)-camphanoyl-(+)-cis-khellactone (7-thia-DCK) analogs

  摘要：

  Two thia-DCK analogs (3a,b) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. Compound 3a showed potent anti-HIV activity with an EC50 value of 0.14 muM and a therapeutic index of 1110. However, the corresponding 6-tert-butyl-substituted compound (3b) showed no suppression. The bioassay results indicated that thia-DCK analogs merit attention as potential HIV-1 inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.038
• 作为产物：
  描述：

  4-甲基-7-(2-丙炔-1-基硫基)-2H-苯并吡喃-2-酮 在 Hydroquinone 1,4-phthalazinediyl diether potassium osmate(VI) 、 potassium carbonate 、 N,N-二乙基苯胺 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 37.0h， 生成 (9R,10R)-9,10-dihydroxy-4-methyl-8H,9H,10H-thiopyrano[6,5-h]-2H-chromen-2-one
  参考文献：
  名称：

  Anti-AIDS agents. Part 56: Synthesis and anti-HIV activity of 7-thia-di-O-(−)-camphanoyl-(+)-cis-khellactone (7-thia-DCK) analogs

  摘要：

  Two thia-DCK analogs (3a,b) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. Compound 3a showed potent anti-HIV activity with an EC50 value of 0.14 muM and a therapeutic index of 1110. However, the corresponding 6-tert-butyl-substituted compound (3b) showed no suppression. The bioassay results indicated that thia-DCK analogs merit attention as potential HIV-1 inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.038