4-methyl-6-(tert-butyl)-7-mercapto-2H-chromen-2-one | 827024-64-6

• 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: 4-methyl-6-(tert-butyl)-7-mercapto-2H-chromen-2-one
• 英文别名: 6-tert-Butyl-4-methyl-7-sulfanyl-2H-1-benzopyran-2-one；6-tert-butyl-4-methyl-7-sulfanylchromen-2-one
• CAS: 827024-64-6
• 化学式: C₁₄H₁₆O₂S
• 分子量: 248.346
• InChiKey: YTOBCFKWRZLCQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-6-(tert-butyl)-7-mercapto-2H-chromen-2-one 在 potassium carbonate 、 N,N-二乙基苯胺 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 2H,8H-Thiopyrano[2,3-h]-1-benzopyran-2-one,6-(1,1-dimethylethyl)-4-methyl-
  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：

  羟甲香豆素 在 4-二甲氨基吡啶 、 磷酸酐 、 磷酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 147.0h， 生成 4-methyl-6-(tert-butyl)-7-mercapto-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

文献信息

• Anti-AIDS agents. Part 56: Synthesis and anti-HIV activity of 7-thia-di-O-(−)-camphanoyl-(+)-cis-khellactone (7-thia-DCK) analogs
  作者：Ying Chen、Qian Zhang、Beina Zhang、Peng Xia、Yi Xia、Zheng-Yu Yang、Nicole Kilgore、Carl Wild、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2004.09.038

  日期：2004.12

  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.