7-(3-bromo-4-fluoro-phenyl)-5-ethyl-1,1-dioxo-2,3,4,7-tetrahydro-1H-1λ6-thieno[3,2-b]pyridine-6-carboxylic acid methyl ester | 927672-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 7-(3-bromo-4-fluoro-phenyl)-5-ethyl-1,1-dioxo-2,3,4,7-tetrahydro-1H-1λ6-thieno[3,2-b]pyridine-6-carboxylic acid methyl ester
• CAS: 927672-12-6
• 化学式: C₁₇H₁₇BrFNO₄S
• 分子量: 430.295
• InChiKey: DOHMXYSBUMCKEA-UHFFFAOYSA-N

物化性质

• 沸点：
  574.1±50.0 °C(predicted)
• 密度：
  1.61±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-(3-bromo-4-fluoro-phenyl)-5-ethyl-1,1-dioxo-2,3,4,7-tetrahydro-1H-1λ6-thieno[3,2-b]pyridine-6-carboxylic acid methyl ester 在 吡啶 、 pyridinium hydrobromide perbromide 作用下， 以 氯仿 为溶剂， 反应 0.58h， 以7%的产率得到trans-8-(3-bromo-4-fluorophenyl)-5-methyl-1,1-dioxo-1,2,3,4,5,8-hexahydro-6-oxa-1λ⁶-4-aza-s-indacen-7-one
  参考文献：
  名称：

  Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener

  摘要：

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.

  DOI：

  10.1021/jm060549u
• 作为产物：
  描述：

  3-氧代戊酸甲酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 7-(3-bromo-4-fluoro-phenyl)-5-ethyl-1,1-dioxo-2,3,4,7-tetrahydro-1H-1λ6-thieno[3,2-b]pyridine-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2,6-dioxa-4- azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener

  摘要：

  Structure-activity relationships were investigated on the tricyclic dihydropyridine ( DHP) K-ATP openers 9-(3-bromo-4-fluorophenyl)-5,9- dihydro-3H, 4H-2,6-dioxa-4-azacyclopenta[ b] naphthalene-1,8-dione ( 6) and 10( 3-bromo-4-fluorophenyl)-9,10-dihydro-1H, 8H-2,7-dioxa-9-azaanthracene-4,5-dione ( 65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk-cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.

  DOI：

  10.1021/jm060549u