(+/-)-1-{[(2-ethoxycarbonylmethyl)thio]phenyl}pyrrolidin-5-one-2-carboxylic acid ethyl ester | 189883-84-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-1-{[(2-ethoxycarbonylmethyl)thio]phenyl}pyrrolidin-5-one-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-[2-(2-ethoxy-2-oxoethyl)sulfanylphenyl]-5-oxopyrrolidine-2-carboxylate
• CAS: 189883-84-9
• 化学式: C₁₇H₂₁NO₅S
• 分子量: 351.423
• InChiKey: IMLGCFJXGACQAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-1-{[(2-ethoxycarbonylmethyl)thio]phenyl}pyrrolidin-5-one-2-carboxylic acid ethyl ester 在 盐酸 、 磺酰氯 、 sodium 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 10.5h， 生成 (+/-)-6-chloro-7,10-dioxo-6,7,7a,8,9,10-hexahydropyrrolo[2,1-d][1,5]benzothiazepine
  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：

  Bis<2-<2-(ethoxycarbonyl)-5-oxo-1-pyrrolidinyl>phenyl> Disulphide 、 溴乙酸乙酯 在 sodium tetrahydroborate 作用下， 生成 (+/-)-1-{[(2-ethoxycarbonylmethyl)thio]phenyl}pyrrolidin-5-one-2-carboxylic acid ethyl ester
  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

文献信息

• New pyrrolobenzothiazepine derivatives as molecular probes of the ‘peripheral-type’ benzodiazepine receptor (PBR) binding site
  作者：G Campiani、V Nacci、I Fiorini、MP De Filippis、A Garofalo、SM Ciani、G Greco、E Novellino、C Manzoni、T Mennini

  DOI：10.1016/s0223-5234(97)83975-x

  日期：1997.1

  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.