2,3-dihydro-5,6-bis<<(N-methylcarbamoyl)oxy>methyl>imidazo<2,1-b>thiazole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3-dihydro-5,6-bis<<(N-methylcarbamoyl)oxy>methyl>imidazo<2,1-b>thiazole
• 英文别名: [5-(methylcarbamoyloxymethyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazol-6-yl]methyl N-methylcarbamate
• 化学式: C₁₁H₁₆N₄O₄S
• 分子量: 300.338
• InChiKey: ZNCKADQUWDFRRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  diethyl 2-mercapto-4,5-imidazoledicarboxylate 在 lithium aluminium tetrahydride 、 dibutyltin diacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2,3-dihydro-5,6-bis<<(N-methylcarbamoyl)oxy>methyl>imidazo<2,1-b>thiazole
  参考文献：
  名称：

  Synthesis, chemical reactivity, and antitumor evaluation of congeners of carmethizole hydrochloride, an experimental acylated vinylogous carbinolamine tumor inhibitor

  摘要：

  A series of analogues of 4,5-bis(((N-methylcarbamoyl)oxy)methyl)-1-methyl-2-(methylthio)-imidazole (1, carmethizole) were synthesized. The chemical reactivities of the analogues (as electrophiles) were evaluated and related to the antitumor activity (in vivo and in vitro). Changes in the alkylthio moiety had a significant effect upon the chemical reactivity. Electron-withdrawing groups on the sulfur decreased chemical reactivity and, in parallel, decreased antitumor activity. Carmethizole sulfoxide (11a) was unreactive as an electrophile and exhibited no antitumor activity either in vivo or in vitro; this led to the conclusion that carmethizole sulfoxide was not acting as a ''carrier form'' of carmethizole, The disulfides 17 and 18 were unreactive as electrophiles but did exhibit antitumor activity. The activity of 17 and 18 was attributed to the thiol 10 that would be generated upon cleavage of the disulfide bond.

  DOI：

  10.1021/jm00075a017

文献信息

• Synthesis, chemical reactivity, and antitumor evaluation of congeners of carmethizole hydrochloride, an experimental acylated vinylogous carbinolamine tumor inhibitor
  作者：Mark A. Jarosinski、Peech S. Reddy、Wayne K. Anderson

  DOI：10.1021/jm00075a017

  日期：1993.11

  A series of analogues of 4,5-bis(((N-methylcarbamoyl)oxy)methyl)-1-methyl-2-(methylthio)-imidazole (1, carmethizole) were synthesized. The chemical reactivities of the analogues (as electrophiles) were evaluated and related to the antitumor activity (in vivo and in vitro). Changes in the alkylthio moiety had a significant effect upon the chemical reactivity. Electron-withdrawing groups on the sulfur decreased chemical reactivity and, in parallel, decreased antitumor activity. Carmethizole sulfoxide (11a) was unreactive as an electrophile and exhibited no antitumor activity either in vivo or in vitro; this led to the conclusion that carmethizole sulfoxide was not acting as a ''carrier form'' of carmethizole, The disulfides 17 and 18 were unreactive as electrophiles but did exhibit antitumor activity. The activity of 17 and 18 was attributed to the thiol 10 that would be generated upon cleavage of the disulfide bond.