Aureol N,N-dimethyl thiocarbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Aureol N,N-dimethyl thiocarbamate
• 英文别名: O-[[(1S,10R,11S,14S)-10,11,15,15-tetramethyl-2-oxatetracyclo[8.8.0.01,14.03,8]octadeca-3(8),4,6-trien-6-yl]] N,N-dimethylcarbamothioate
• 化学式: C₂₄H₃₅NO₂S
• 分子量: 401.613
• InChiKey: DRTPUUQCYHYPIT-FOEAQLGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Aureol 、 二甲氨基硫代甲酰氯 在 锌 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以60%的产率得到Aureol N,N-dimethyl thiocarbamate
  参考文献：
  名称：

  New Antiinfective and Human 5-HT2 Receptor Binding Natural and Semisynthetic Compounds from the Jamaican Sponge Smenospongia aurea

  摘要：

  In addition to the sesquiterpene-phenol aureols (1), 6'-chloroaureol (2), and aureol acetate (3), eight indole alkaloids including the new N-3'-ethylaplysinopsin (9) have been isolated from the Jamaican sponge Smenospongia aurea. Makaluvamine 0 (10), a new member of the pyrroloiminoquinone class, was also isolated. The structures were characterized by spectroscopic methods, and two new derivatives of aureol were prepared to optimize the biological activity. Aureol N,N-dimethyl thiocarbamate (1a) and 6-bromoaplysinopsin (7) exhibit significant antimalarial and antimycobacterial activity in vitro. Compound 6 showed activity against the Plasmodium enzyme plasmepsin II. The 6-bromo-2'-de-N-methylaplysinopsin (6), 6-bromoaplysinopsin (7), and N-3'-ethylaplysinopsin (9) displaced high-affinity [3H] antagonist ligands from cloned human serotonin 5-HT2 receptor subtypes, whereas the other compounds tested did not. Remarkably, the 6-bromo-2'-de-N-methylaplysinopsin (6) showed a >40-fold selectivity for the 5-HT2C subtype over the 5-HT2A subtype.

  DOI：

  10.1021/np010471e

文献信息

• New Antiinfective and Human 5-HT2 Receptor Binding Natural and Semisynthetic Compounds from the Jamaican Sponge <i>Smenospongia </i><i>a</i><i>urea</i>
  作者：Jin-Feng Hu、John A. Schetz、Michelle Kelly、Jiang-Nan Peng、Kenny K. H. Ang、Horst Flotow、Chung Yan Leong、Siew Bee Ng、Antony D. Buss、Scott P. Wilkins、Mark T. Hamann

  DOI：10.1021/np010471e

  日期：2002.4.1

  In addition to the sesquiterpene-phenol aureols (1), 6'-chloroaureol (2), and aureol acetate (3), eight indole alkaloids including the new N-3'-ethylaplysinopsin (9) have been isolated from the Jamaican sponge Smenospongia aurea. Makaluvamine 0 (10), a new member of the pyrroloiminoquinone class, was also isolated. The structures were characterized by spectroscopic methods, and two new derivatives of aureol were prepared to optimize the biological activity. Aureol N,N-dimethyl thiocarbamate (1a) and 6-bromoaplysinopsin (7) exhibit significant antimalarial and antimycobacterial activity in vitro. Compound 6 showed activity against the Plasmodium enzyme plasmepsin II. The 6-bromo-2'-de-N-methylaplysinopsin (6), 6-bromoaplysinopsin (7), and N-3'-ethylaplysinopsin (9) displaced high-affinity [3H] antagonist ligands from cloned human serotonin 5-HT2 receptor subtypes, whereas the other compounds tested did not. Remarkably, the 6-bromo-2'-de-N-methylaplysinopsin (6) showed a >40-fold selectivity for the 5-HT2C subtype over the 5-HT2A subtype.