(+/-)-7-bromo-1,11a-dihydro-3H,5H,11H-thiazolo[4,3-c][1,4]benzothiazepine-5,11-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: (+/-)-7-bromo-1,11a-dihydro-3H,5H,11H-thiazolo[4,3-c][1,4]benzothiazepine-5,11-dione
• 英文别名: 8-bromo-3,3a-dihydro-1H-[1,3]thiazolo[4,3-c][1,4]benzothiazepine-4,10-dione
• 化学式: C₁₁H₈BrNO₂S₂
• 分子量: 330.226
• InChiKey: BSMXFJKVNOUMID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴-2-[(4-溴-2-羧基苯基)二硫烷基]苯甲酸 在 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 sodium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (+/-)-7-bromo-1,11a-dihydro-3H,5H,11H-thiazolo[4,3-c][1,4]benzothiazepine-5,11-dione
  参考文献：
  名称：

  Thiazolothiazepine Inhibitors of HIV-1 Integrase

  摘要：

  A series of thiazolothiazepines were prepared and tested against purified human immunodeficiency virus type-1 integrase (HIV-1 IN) and viral replication. Structure-activity studies reveal that the compounds possessing the pentatomic moiety SC(O)CNC(O) with two carbonyl groups are in general more potent against purified IN than those containing only one carbonyl group. Substitution with electron-donating or -withdrawing groups did not enhance nor abolish potency against purified IN. By contrast, compounds with a naphthalene ring system showed enhanced potency, suggesting that a hydrophobic pocket in the IN active site might accommodate an aromatic system rather than a halogen. The position of sulfur in the thiazole ring appears important for potency against IN, as its replacement with an oxygen or carbon abolished activity. Further extension of the thiazole ring diminished potency. Compounds 1, 19, and 20 showed antiviral activity and inhibited IN within similar concentrations. These compounds inhibited IN when Mn2+ or Mg2+ was used as cofactor. None of these compounds showed detectable activities against HIV-1 reverse transcriptase, protease, virus attachment, or nucleocapsid protein zinc fingers. Therefore, thiazolothiazepines are potentially important lead compounds for development as inhibitors of IN and HIV replication.

  DOI：

  10.1021/jm990047z

文献信息

• THIAZEPINE INHIBITORS OF HIV-1 INTEGRASE
  申请人：THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1187837B1

  公开（公告）日：2007-07-18
• US7015212B1
  申请人：——

  公开号：US7015212B1

  公开（公告）日：2006-03-21