N-[(S)-6-Cyano-1-(3-methyl-3H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinolin-3-yl]-benzenesulfonamide | 851759-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[(S)-6-Cyano-1-(3-methyl-3H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinolin-3-yl]-benzenesulfonamide
• CAS: 851759-02-9
• 化学式: C₂₁H₂₁N₅O₂S
• 分子量: 407.496
• InChiKey: PWWOCBOJXZIMPZ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-溴甲基噻吩 、 N-[(S)-6-Cyano-1-(3-methyl-3H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinolin-3-yl]-benzenesulfonamide 在 base 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(3S)-6-cyano-1-[(3-methylimidazol-4-yl)methyl]-3,4-dihydro-2H-quinolin-3-yl]-N-(thiophen-3-ylmethyl)benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of tetrahydroquinoline-based farnesyltransferase inhibitors

  摘要：

  Tetrahydroquinoline-based small molecule inhibitors of farnesyltransferase (FT) have been identified. Lead compounds were shown to have nanomolar to sub-nanomolar activity in biochemical assays with excellent potency in a Ras-mutated cellular reversion assay. BMS-316810 (9e), a 0.7 nM FT inhibitor, was orally-active in a nude mouse tumor allograft efficacy study. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.004
• 作为产物：
  描述：

  3-氨基喹啉 在 palladium on activated charcoal 三乙基硅烷 、 四(三苯基膦)钯 、 氢气 、 sodium hexamethyldisilazane 、 三溴化磷 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-[(S)-6-Cyano-1-(3-methyl-3H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinolin-3-yl]-benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of tetrahydroquinoline-based farnesyltransferase inhibitors

  摘要：

  Tetrahydroquinoline-based small molecule inhibitors of farnesyltransferase (FT) have been identified. Lead compounds were shown to have nanomolar to sub-nanomolar activity in biochemical assays with excellent potency in a Ras-mutated cellular reversion assay. BMS-316810 (9e), a 0.7 nM FT inhibitor, was orally-active in a nude mouse tumor allograft efficacy study. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.004