7-氟-2,3-二氢喹啉-4-酮 | 114417-35-5

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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
• 中文名称: 7-氟-2,3-二氢喹啉-4-酮
• 英文名称: 7-fluoro-2,3-dihydro-1H-quinolin-4-one
• 英文别名: 7-Fluoro-2,3-dihydroquinolin-4(1H)-one
• CAS: 114417-35-5
• 化学式: C₉H₈FNO
• mdl: MFCD13179234
• 分子量: 165.167
• InChiKey: PYOQBYNTTOIUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P264,P270,P301+P310+P330,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301

反应信息

• 作为反应物：
  描述：

  7-氟-2,3-二氢喹啉-4-酮 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 苄基三乙基氯化铵 、 氢气 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 70.0 ℃ 、196.5 kPa 条件下， 反应 29.67h， 生成 N,N-diethyl-3-fluoro-11H-indolo<3,2-c>quinolin-11-ethanamine 5-oxide
  参考文献：
  名称：

  Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]

  摘要：

  Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo[3,2-c]quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.

  DOI：

  10.1016/0223-5234(93)90036-e
• 作为产物：
  描述：

  1-(3-fluorophenyl)azetidin-2-one 在 三氟甲磺酸 、 碳酸氢钠 作用下， 以 1,2-二氯乙烷 、 水 为溶剂， 反应 18.0h， 生成 7-氟-2,3-二氢喹啉-4-酮
  参考文献：
  名称：

  Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof

  摘要：

  对VR1受体拮抗剂，其化学式为(I)或其药用可接受的盐、前药或前药的盐，其中A1、A2、A3、A4、R7、R8、R9、X、Y、Z、L、n和m的定义如本文所述，并且在通过抑制VR1受体预防或改善的疾病中具有用处。

  公开号：

  US20060128689A1

文献信息

• Compound having 11β-HSD1 inhibitory activity
  申请人：Taisho Pharmaceutical Co., Ltd

  公开号：US08222417B2

  公开（公告）日：2012-07-17

  The present invention provides compounds having excellent 11β-HSD1 inhibitory activity. A compound represented by the following formula (I): [wherein X1 represents an oxygen atom, or the formula —(CR11R12)p—, etc., Y1 represents a hydrogen atom, a hydroxyl group, etc., Z1 represents an oxygen atom or the formula —(NR14)—, R1 represents a hydrogen atom, a halogen atom, a cyano group, a C1-4 alkyl group, a C1-4 alkyl group substituted with 1 to 3 halogen atoms, a C1-4 alkoxy group, a C1-4 alkoxycarbonyl group, a carboxyl group, a carbamoyl group, or an amino group, and m represents an integer of 1 or 2, and R2 represents a hydrogen atom or a C1-4 alkyl group, and n represents an integer of 1 or 2].

  本发明提供了具有优异11β-HSD1抑制活性的化合物。一种由以下式子（I）表示的化合物：[其中X1表示氧原子，或者式子—（CR11R12）p—等，Y1表示氢原子，羟基等，Z1表示氧原子或式子—（NR14）—，R1表示氢原子，卤素原子，氰基，C1-4烷基，1至3个卤素原子取代的C1-4烷基，C1-4烷氧基，C1-4烷氧羰基，羧基，氨基或氨基甲酰基，m表示1或2的整数，R2表示氢原子或C1-4烷基，n表示1或2的整数]。
• COMPOUND HAVING 11BETA-HSD1 INHIBITORY ACTIVITY
  申请人：Suzuki Ryo

  公开号：US20100179325A1

  公开（公告）日：2010-07-15

  The present invention provides compounds having excellent 11β-HSD1 inhibitory activity. A compound represented by the following formula (I): [wherein X 1 represents an oxygen atom, or the formula —(CR 11 R 12 ) p —, etc., Y 1 represents a hydrogen atom, a hydroxyl group, etc., Z 1 represents an oxygen atom or the formula —(NR 14 )—, R 1 represents a hydrogen atom, a halogen atom, a cyano group, a C 1-4 alkyl group, a C 1-4 alkyl group substituted with 1 to 3 halogen atoms, a C 1-4 alkoxy group, a C 1-4 alkoxycarbonyl group, a carboxyl group, a carbamoyl group, or an amino group, and m represents an integer of 1 or 2, and R 2 represents a hydrogen atom or a C 1-4 alkyl group, and n represents an integer of 1 or 2].

  本发明提供了具有优异的11β-HSD1抑制活性的化合物。其中一种化合物的结构式为(I)：[其中，X1表示氧原子，或者公式—(CR11R12)p—等；Y1表示氢原子，羟基等；Z1表示氧原子或者公式—(NR14)—等；R1表示氢原子，卤素原子，氰基，C1-4烷基，1至3个卤素原子取代的C1-4烷基，C1-4烷氧基，C1-4烷氧羰基，羧基，氨基或者氨基取代的羰基；m表示1或2的整数；R2表示氢原子或者C1-4烷基；n表示1或2的整数。]
• COMPOUND HAVING 11 ß-HSD1 INHIBITORY ACTIVITY
  申请人：Taisho Pharmaceutical Co. Ltd.

  公开号：EP2172453A1

  公开（公告）日：2010-04-07

  The present invention provides compounds having excellent 11β-HSD1 inhibitory activity. A compound represented by the following formula (I): [wherein X1 represents an oxygen atom, or the formula -(CR11R12)p-, etc., Y1 represents a hydrogen atom, a hydroxyl group, etc., Z1 represents an oxygen atom or the formula -(NR14)-, R1 represents a hydrogen atom, a halogen atom, a cyano group, a C1-4 alkyl group, a C1-4 alkyl group substituted with 1 to 3 halogen atoms, a C1-4 alkoxy group, a C1-4 alkoxycarbonyl group, a carboxyl group, a carbamoyl group, or an amino group, and m represents an integer of 1 or 2, and R2 represents a hydrogen atom or a C1-4 alkyl group, and n represents an integer of 1 or 2].

  本发明提供了具有优异 11β-HSD1 抑制活性的化合物。 由下式（I）代表的化合物： 其中 X1代表氧原子，或式-(CR11R12)p-等、 Y1 代表氢原子、羟基等、 Z1 代表氧原子或式-(NR14)-、 R1 代表氢原子、卤素原子、氰基、C1-4 烷基、被 1 至 3 个卤素原子取代的 C1-4 烷基、C1-4 烷氧基、C1-4 烷氧羰基、羧基、氨基甲酰基或氨基，且 m 代表 1 或 2 的整数，且 R2 代表氢原子或 C1-4 烷基，n 代表 1 或 2 的整数]。
• Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists
  作者：Robert G. Schmidt、Erol K. Bayburt、Steven P. Latshaw、John R. Koenig、Jerome F. Daanen、Heath A. McDonald、Bruce R. Bianchi、Chengmin Zhong、Shailen Joshi、Prisca Honore、Kennan C. Marsh、Chih-Hung Lee、Connie R. Faltynek、Arthur Gomtsyan

  DOI：10.1016/j.bmcl.2011.01.056

  日期：2011.3

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and diuretic activity of 2,3-dihydro-4(1H)-quinolinone 4-oxime-O-sulfonic acid derivatives
  作者：Kazumi Nishijima、Tomoaki Shinkawa、Yoshiaki Yamashita、Naofumi Sato、Hidemitsu Nishida、Kazuo Kato、Yoshiaki Onuki、Masahiro Mizota、Kikuo Ohtomo、Soutarou Miyano

  DOI：10.1016/s0223-5234(98)80061-5

  日期：1998.4

  The diuretic activity of 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime 1 (M12285) was previously shown to derive from a 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime-O-sulfonic acid salt as a rat metabolite. Thus, in the present study, the potassium salt 2 (M17000) was synthesized to unambiguously establish the structure as well as the stereochemistry of the oxime. The structural features of compounds 1 and 2 were compared with those of conventional diuretics by electrostatic potential maps. Using compound 2 as a lead compound, various quinolinone oxime sulfonic acid derivatives were synthesized and the diuretic activity for elucidation of the structure-activity relationships examined. Among the compounds synthesized, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 3 (M17055) showed a particularly high activity. (C) Elsevier, Paris.