(+/-)-4-oxo-5-phenyl-4,5-dihydro-11H-pyrrolo[2,1-d][1,5]benzothiazocine | 189883-86-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (+/-)-4-oxo-5-phenyl-4,5-dihydro-11H-pyrrolo[2,1-d][1,5]benzothiazocine
• 英文别名: 9-Phenyl-10-thia-3-azatricyclo[9.4.0.03,7]pentadeca-1(15),4,6,11,13-pentaen-8-one
• CAS: 189883-86-1
• 化学式: C₁₉H₁₅NOS
• 分子量: 305.4
• InChiKey: FNIRMTXQSBIYNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-4-oxo-5-phenyl-4,5-dihydro-11H-pyrrolo[2,1-d][1,5]benzothiazocine 、 二甲氨基甲酰氯 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以20%的产率得到(+/-)-4-[(dimethylcarbamoyl)oxy]-5-phenyl-11H-pyrrolo[2,1-d][1,5]benzothiazocine
  参考文献：
  名称：

  New pyrrolobenzothiazepine derivatives as molecular probes of the ‘peripheral-type’ benzodiazepine receptor (PBR) binding site

  摘要：

  A number of new pyrrolobenzothiazepine derivatives and a pyrrolobenzothiazocine derivative have been synthesized and evaluated for their affinity towards the 'peripheral-type' benzodiazepine receptor (PER). The new compounds were tested in rat cortex, a tissue expressing a high density of mitochondrial PER. Some of the pyrrolobenzothiazepines exhibited IC50 values in the low nanomolar range as measured by the displacement of [H-3]PK 11195 binding. Compound 4i was found to be the most potent ligand for this receptor in the pyrrolobenzothiazepine subgroup with an IC50 practically identical to that determined for PK 11195. Structure-affinity relationships (SARs) have been developed to elucidate the topology of the PER binding site.

  DOI：

  10.1016/s0223-5234(97)83975-x
• 作为产物：
  描述：

  alpha-溴苯乙酸 在 五氯化磷 、 sodium ethanolate 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 (+/-)-4-oxo-5-phenyl-4,5-dihydro-11H-pyrrolo[2,1-d][1,5]benzothiazocine
  参考文献：
  名称：

  New pyrrolobenzothiazepine derivatives as molecular probes of the ‘peripheral-type’ benzodiazepine receptor (PBR) binding site

  摘要：

  A number of new pyrrolobenzothiazepine derivatives and a pyrrolobenzothiazocine derivative have been synthesized and evaluated for their affinity towards the 'peripheral-type' benzodiazepine receptor (PER). The new compounds were tested in rat cortex, a tissue expressing a high density of mitochondrial PER. Some of the pyrrolobenzothiazepines exhibited IC50 values in the low nanomolar range as measured by the displacement of [H-3]PK 11195 binding. Compound 4i was found to be the most potent ligand for this receptor in the pyrrolobenzothiazepine subgroup with an IC50 practically identical to that determined for PK 11195. Structure-affinity relationships (SARs) have been developed to elucidate the topology of the PER binding site.

  DOI：

  10.1016/s0223-5234(97)83975-x