Carbamothioic acid, dimethyl-,S-[6-(1,1-dimethylethyl)-4-methyl-2-oxo-2H-1-benzopyran-7-yl] ester | 827024-63-5

• 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: Carbamothioic acid, dimethyl-,S-[6-(1,1-dimethylethyl)-4-methyl-2-oxo-2H-1-benzopyran-7-yl] ester
• 英文别名: 4-methyl-6-(tert-butyl)-7-[(N,N-dimethyl)carbamoylthio]-2H-chromen-2-one
• CAS: 827024-63-5
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: GUQMTVYOTLVZCU-UHFFFAOYSA-N

物化性质

• 沸点：
  451.4±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  50.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Carbamothioic acid, dimethyl-,S-[6-(1,1-dimethylethyl)-4-methyl-2-oxo-2H-1-benzopyran-7-yl] ester 在 Hydroquinone 1,4-phthalazinediyl diether potassium osmate(VI) 、 sodium methylate 、 potassium carbonate 、 N,N-二乙基苯胺 、 potassium iodide 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 45.5h， 生成 (9R,10R)-9,10-dihydroxy-4-methyl-6-(tert-butyl)-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-methyl-6-(tert-butyl)-7-hydroxy-2H-chromen-2-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 99.0h， 生成 Carbamothioic acid, dimethyl-,S-[6-(1,1-dimethylethyl)-4-methyl-2-oxo-2H-1-benzopyran-7-yl] ester
  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