7-nitro-1-(propylsulfonyl)-1,2,3,4-tetrahydroquinoline | 1215819-42-3

• 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: 7-nitro-1-(propylsulfonyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 7-nitro-1-propylsulfonyl-3,4-dihydro-2H-quinoline
• CAS: 1215819-42-3
• 化学式: C₁₂H₁₆N₂O₄S
• 分子量: 284.336
• InChiKey: CQFZSFIBQLEJSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  7-硝基-1,2,3,4-四氢喹啉	7-nitro-1,2,3,4-tetrahydro-quinoline	30450-62-5	C9H10N2O2	178.191

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-methyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide	946226-70-6	C19H24N2O4S2	408.543
  ——	4-isopropyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide	946353-07-7	C21H28N2O4S2	436.596
  3-甲基-N-(1-(丙基磺酰基)-1,2,3,4-四氢喹啉-7-基)苯磺酰胺	3-methyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide	1021117-32-7	C19H24N2O4S2	408.543
  ——	3,5-dimethyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide	1581710-50-0	C20H26N2O4S2	422.569
  ——	N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)-[1,1'-biphenyl]-4-sulfonamide	946249-63-4	C24H26N2O4S2	470.613
  ——	N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)thiophene-2-sulfonamide	946300-76-1	C16H20N2O4S3	400.544
  ——	2-methyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide	1581710-48-6	C19H24N2O4S2	408.543
  ——	2,4-dimethyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide	946352-91-6	C20H26N2O4S2	422.569
  ——	2-fluoro-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide	946226-59-1	C18H21FN2O4S2	412.506
  ——	2,3,4,5,6-pentamethyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl) benzenesulfonamide	946300-85-2	C23H32N2O4S2	464.65

反应信息

• 作为反应物：
  描述：

  7-nitro-1-(propylsulfonyl)-1,2,3,4-tetrahydroquinoline 在 吡啶 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 10.34h， 生成 3,5-dimethyl-N-(1-(propylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide
  参考文献：
  名称：

  Facile Synthesis and Preliminary Structure–Activity Analysis of New Sulfonamides Against Trypanosoma brucei

  摘要：

  The high throughput screening of a library of over 87,000 drug-like compounds against the African sleeping sickness parasite resulted in the discovery of hits with a wide range of molecular diversity. We report here the medicinal chemistry development of one such hit, a tetrahydroisoquinoline disulfonamide, with the synthesis and testing of 26 derivatives against the trypanosome subspecies. Activities in the 2-4 mu M range were revealed with a selectivity index suitable for further development.

  DOI：

  10.1021/ml400487t
• 作为产物：
  描述：

  丙基磺酰氯 、 7-硝基-1,2,3,4-四氢喹啉 在 吡啶 作用下， 反应 24.17h， 以80%的产率得到7-nitro-1-(propylsulfonyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Facile Synthesis and Preliminary Structure–Activity Analysis of New Sulfonamides Against Trypanosoma brucei

  摘要：

  The high throughput screening of a library of over 87,000 drug-like compounds against the African sleeping sickness parasite resulted in the discovery of hits with a wide range of molecular diversity. We report here the medicinal chemistry development of one such hit, a tetrahydroisoquinoline disulfonamide, with the synthesis and testing of 26 derivatives against the trypanosome subspecies. Activities in the 2-4 mu M range were revealed with a selectivity index suitable for further development.

  DOI：

  10.1021/ml400487t

文献信息

• Facile Synthesis and Preliminary Structure–Activity Analysis of New Sulfonamides Against <i>Trypanosoma brucei</i>
  作者：Adel A. Rashad、Amy J. Jones、Vicky M. Avery、Jonathan Baell、Paul A. Keller

  DOI：10.1021/ml400487t

  日期：2014.5.8

  The high throughput screening of a library of over 87,000 drug-like compounds against the African sleeping sickness parasite resulted in the discovery of hits with a wide range of molecular diversity. We report here the medicinal chemistry development of one such hit, a tetrahydroisoquinoline disulfonamide, with the synthesis and testing of 26 derivatives against the trypanosome subspecies. Activities in the 2-4 mu M range were revealed with a selectivity index suitable for further development.