6,7,8-Trifluor-chinolin | 5280-09-1

• 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: 6,7,8-Trifluor-chinolin
• 英文别名: 6,7,8-Trifluoroquinoline
• CAS: 5280-09-1
• 化学式: C₉H₄F₃N
• 分子量: 183.133
• InChiKey: HOKAPVMZVHFVPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3,4-三氟苯胺 、 甘油 在 硫酸 、 sodium 3-nitrobenzenesulfonate 作用下， 反应 4.0h， 以77%的产率得到6,7,8-Trifluor-chinolin
  参考文献：
  名称：

  Effects of oligofluorine substitution on the mutagenicity of quinoline: a study with twelve fluoroquinoline derivatives

  摘要：

  A total of 12 variously fluorinated derivatives of quinoline (Q) were tested for their mutagenicity in Salmonella typhimurium TA100 in the presence of S9 mix to investigate the structure-mutagenicity relationship in oligofluorinated quinolines. Nine of them, 3,7-di-, 5,6-di-, 6,7-di-, 6,8-di-, 7,8-di-, 3,5,7-tri-, 5,6,8-tri-, 6,7,8-tri-, and 5,6,7,8-tetrafluoroquinolines (FQs), were newly synthesized for this purpose. Those fluorinated at position 3 were all non-mutagenic. Mutagenicity was enhanced by fluorine-substitution at position 5 or 7, but not in 3-FQs (i.e., 3,5-di-, 3,7-di-, and 3,5,7-triFQs). Some of the 6-fluorinated derivatives showed less maximum induced-revertants with more mutagenic potencies in terms of induced-revertants per dose than quinoline. No marked change occurred by fluorine-substitution at position 8. These results show that the effect of di- and trifluoro-substitution on mutagenicity is generally additive, while that of tetrafluorination approaches the deactivating effect of perfluorination. Our study suggests that 3-fluorine-substitution in the pyridine moiety may be a useful means of antimutagenic structural modification in pyridine-fused aromatic chemicals for medicinal and agricultural use. (C) 1999 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(98)00188-0

文献信息

• REISSERT COMPOUNDS AS ANTI-HIV AGENTS
  申请人：THE UPJOHN COMPANY

  公开号：EP0579695A1

  公开（公告）日：1994-01-26
• US6403587B1
  申请人：——

  公开号：US6403587B1

  公开（公告）日：2002-06-11
• US6673801B1
  申请人：——

  公开号：US6673801B1

  公开（公告）日：2004-01-06
• [EN] REISSERT COMPOUNDS AS ANTI-HIV AGENTS
  申请人：THE UPJOHN COMPANY

  公开号：WO1992016508A1

  公开（公告）日：1992-10-01

  (EN) Disclosed are heterocyclic compounds of formula (I). The compounds of the invention are useful in the treatment of AIDS and AIDS related complex. The compounds of the invention are generally synthesized by following the reactions and conditions used to make Reissert compounds. Compounds included within the scope of formula (I) are 1,2-dihydroquinolines, 1,4-dihydroquinolines, 1,2,3,4-tetrahydroquinolines, 1,2-dihydroquinazolines, and the 1,2-dihydroquinoxalines. Representative compounds include 1-(4-bromobenzoyl)-2-cyano-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-5-fluoro-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-6-fluoro-1,4-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,2,3,4-tetrahydroquinoline, 1-(4-chlorobenzoyl)-2-carboximidamide-8-fluoro-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,4-dihydroquinoxaline, 1-E-(3-(4-chlorophenyl)-1-oxo-2-propenyl)-2-cyano-1,2-dihydroquinoline, and 1-E-(3-(4-chlorophenyl)-1-oxo-2-propenyl)-2-carboximidamide-1,2-dihydroquinoline. Also included within the scope of the invention is a method of treating a human having AIDS or ARC with an effective amount of a compound of the invention.(FR) L'invention se rapporte à des composés hétérocycliques représentés par la formule (I), qui servent au traitement du sida et du syndrome associé au sida. Ces composés sont généralement synthétisés en suivant les réactions et les conditions utilisées pour produire les composés Reissert. Les composés de la formule (I) sont les 1,2-dihydroquinolines, les 1,4-dihydroquinolines, les 1,2,3,4-tétrahydroquinolines, les 1,2-dihydroquinazolines et les 1,2-dihydroquinoxalines. Les composés types sont 1-(4-bromobenzoyl)-2-cyano-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-5-fluoro-1,2-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-6-fluoro-1,4-dihydroquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,2,3,4-tétrahydroquinoline, 1-(4-chlorobenzoyl)-2-carboximidamide-8-fluoro-1,2-dihydroxyquinoline, 1-(4-chlorobenzoyl)-2-cyano-1,4-dihydroquinoxaline, 1-E-(3-(4-chlorophényl)-1-oxo-2-propényl)-2-cyano-1,2-dihydroquinoline et 1-E-(3-(4-chlorophényl)-1-oxo-2-propényl)-2-carboximidamide-1,2-dihydroquinoline. L'invention décrit également un procédé de traitement du sida ou du syndrome associé au sida grâce à une quantité efficace d'un de ces composés.
• Effects of oligofluorine substitution on the mutagenicity of quinoline: a study with twelve fluoroquinoline derivatives
  作者：Taka-aki Kato、Ken-ichi Saeki、Yutaka Kawazoe、Atsushi Hakura

  DOI：10.1016/s1383-5718(98)00188-0

  日期：1999.2

  A total of 12 variously fluorinated derivatives of quinoline (Q) were tested for their mutagenicity in Salmonella typhimurium TA100 in the presence of S9 mix to investigate the structure-mutagenicity relationship in oligofluorinated quinolines. Nine of them, 3,7-di-, 5,6-di-, 6,7-di-, 6,8-di-, 7,8-di-, 3,5,7-tri-, 5,6,8-tri-, 6,7,8-tri-, and 5,6,7,8-tetrafluoroquinolines (FQs), were newly synthesized for this purpose. Those fluorinated at position 3 were all non-mutagenic. Mutagenicity was enhanced by fluorine-substitution at position 5 or 7, but not in 3-FQs (i.e., 3,5-di-, 3,7-di-, and 3,5,7-triFQs). Some of the 6-fluorinated derivatives showed less maximum induced-revertants with more mutagenic potencies in terms of induced-revertants per dose than quinoline. No marked change occurred by fluorine-substitution at position 8. These results show that the effect of di- and trifluoro-substitution on mutagenicity is generally additive, while that of tetrafluorination approaches the deactivating effect of perfluorination. Our study suggests that 3-fluorine-substitution in the pyridine moiety may be a useful means of antimutagenic structural modification in pyridine-fused aromatic chemicals for medicinal and agricultural use. (C) 1999 Elsevier Science B.V. All rights reserved.