3'-{3"-[2'"-hydroxybut-3'"-en-1'"-yl]-1",2",4"-thiadiazol-5"-yl}-5',6'-dihydrospiro[indoline-3,2'-thiopyran]-2-one | 1404375-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3'-{3"-[2'"-hydroxybut-3'"-en-1'"-yl]-1",2",4"-thiadiazol-5"-yl}-5',6'-dihydrospiro[indoline-3,2'-thiopyran]-2-one
• 英文别名: 5'-[3-(2-hydroxybut-3-enyl)-1,2,4-thiadiazol-5-yl]spiro[1H-indole-3,6'-2,3-dihydrothiopyran]-2-one
• CAS: 1404375-94-5
• 化学式: C₁₈H₁₇N₃O₂S₂
• 分子量: 371.484
• InChiKey: ZERLQFUQGLBCBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-{3"-[2'"-hydroxybut-3'"-en-1'"-yl]-1",2",4"-thiadiazol-5"-yl}-5',6'-dihydrospiro[indoline-3,2'-thiopyran]-2-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 生成 C₂₇H₂₅N₃O₄S₂
  参考文献：
  名称：

  Enantiomers of an Indole Alkaloid Containing Unusual Dihydrothiopyran and 1,2,4-Thiadiazole Rings from the Root of Isatis indigotica

  摘要：

  A pair of enantiomers (la and 1b) of an indole alkaloid containing dihydrothiopyran and 1,2,4-thiadiazole rings was isolated from an aqueous extract of the root of Isatis indigotica. The structures and absolute configurations of the enantiomers were determined by extensive spectroscopic analysis, especially 2D NMR, modified Mosher's method, and electronic CD (ECD). The proposed biosynthetic pathway and preliminary investigations of the biological activity of compounds la and 1b against influenza virus A/Hanfang/359/95 (H3N2) and HSV-1 are also discussed.

  DOI：

  10.1021/ol302660t

文献信息

• Enantiomers of an Indole Alkaloid Containing Unusual Dihydrothiopyran and 1,2,4-Thiadiazole Rings from the Root of <i>Isatis indigotica</i>
  作者：Minghua Chen、Sheng Lin、Li Li、Chenggen Zhu、Xiaoliang Wang、Yanan Wang、Bingya Jiang、Sujuan Wang、Yuhuan Li、Jiandong Jiang、Jiangong Shi

  DOI：10.1021/ol302660t

  日期：2012.11.16

  A pair of enantiomers (la and 1b) of an indole alkaloid containing dihydrothiopyran and 1,2,4-thiadiazole rings was isolated from an aqueous extract of the root of Isatis indigotica. The structures and absolute configurations of the enantiomers were determined by extensive spectroscopic analysis, especially 2D NMR, modified Mosher's method, and electronic CD (ECD). The proposed biosynthetic pathway and preliminary investigations of the biological activity of compounds la and 1b against influenza virus A/Hanfang/359/95 (H3N2) and HSV-1 are also discussed.