苯并[g]喹啉-4-醇 | 38455-38-8

• 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: 苯并[g]喹啉-4-醇
• 英文名称: 4-Hydroxy-benzochinolin
• 英文别名: Benzo[g]quinolin-4-ol；1H-benzo[g]quinolin-4-one
• CAS: 38455-38-8
• 化学式: C₁₃H₉NO
• mdl: MFCD18448621
• 分子量: 195.221
• InChiKey: IJSYZVOZJVJMIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯并[g]喹啉-4-醇 在 三氯氧磷 作用下， 生成 苯并[g]喹啉-4-胺
  参考文献：
  名称：

  Albert et al., Journal of the Chemical Society, 1948, p. 1284,1290

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氢苯并[g]喹啉-4(1H)-酮 在 manganese dioxide 氮气 作用下， 以 四氢呋喃 为溶剂， 以to afford 445 mg of relatively clean benzo[g]quinolin-4-ol (6) in 90% yield的产率得到苯并[g]喹啉-4-醇
  参考文献：
  名称：

  Benzoquinoline derivatives useful as antibacterial agents

  摘要：

  本发明涉及具有公式（I）至（V）的苯并喹啉衍生物的制药组合物和制剂，其中公式（I）为：X选自O，S，CH2，CH2-CH2，C═O或NRB组成的群，Y为C或N; R1，R2，R3和R4独立地选自氢，卤素，线性或支链低级烷基，烯基，炔基，烷氧基或酰基; X-RA和R3或R3和R4可选择地连接在一起形成C3-C4烷基桥，其中X为CH2或C═O; 前提是：当X为NRB时，那么(a)RB为氢，RA为线性或支链低级烷基，芳基，杂环芳基，环烷基或环烯基，可选择地通过至少一个杂原子中断，所述烷基，烯基，炔基，芳基，杂环芳基，环烷基或环烯基可选择地被一个线性或支链低级烷基，烯基，炔基，酰基，烷氧基或环烷基中断，可选择地被一个线性或支链低级烷基，烯基，炔基，酰基或烷氧基或一个线性或支链低级烷基单烷基或双烷基氨基，（线性或支链低级烷基N-单烷基或N，N-双烷基氨基）（低级烷基），（线性或支链低级烷基N-单烷基或N，N-双烷基）氨基甲酰基，芳基或杂环芳基; 或(b) X，RA和RB共同形成一个包含约五个至十二个链接碳原子的环系统，该系统可选择地通过至少一个杂原子中断，可选择地单烯或多不饱和，并可选择地被一个线性或支链低级烷基，烯基，炔基，酰基或烷氧基，一个线性或支链低级烷基N-单烷基或N，N-双烷基氨基，卤素，氰基，三氟甲基，硝基，芳基或杂环芳基取代，当X为O，S，CH2，CH2-CH2或C═O时，那么(a) RA为氢或线性或支链低级烷基，烯基，炔基，芳基或杂环芳基，所述烷基，烯基，炔基，芳基或杂环芳基可选择地被一个线性或支链低级烷基，烯基，炔基，酰基或烷氧基，一个线性或支链低级烷基N-单烷基或N，N-双烷基氨基，（线性或支链低级烷基N-单烷基或N，N-双烷基）（低级烷基），卤素，氰基，三氟甲基，硝基，芳基或杂环芳基; 和(b) R3是通过羟基苯基或线性或支链低级烷氧基苯基取代的线性或支链低级烷基，可选择地被CH2NRCRD取代，其中N，RC和RD共同形成一个包含约五个至十二个链接碳原子的环系统，该系统可选择地通过至少一个杂原子中断，可选择地单烯或多不饱和，并可选择地被一个线性或支链低级烷基，酰基或烷氧基，一个线性或支链低级烷基N-单烷基或N，N-双烷基氨基，（线性或支链低级烷基N-单烷基或N，N-双烷基）（低级烷基），卤素，氰基，三氟甲基，硝基，芳基或杂环芳基取代; 或其盐，以及药学上可接受的载体或稀释剂。还公开了抑制细菌生长的方法，包括给予含有公式（I）至（V）的化合物的制剂的管理。

  公开号：

  US06274596B1

文献信息

• US6274596B1
  申请人：——

  公开号：US6274596B1

  公开（公告）日：2001-08-14
• [EN] BENZOQUINOLINE DERIVATIVES USEFUL AS ANTIBACTERIAL AGENTS<br/>[FR] DERIVES DE BENZOQUINOLINE UTILES COMME ANTIBACTERIENS
  申请人：SCRIPTGEN PHARM INC

  公开号：WO2000024389A2

  公开（公告）日：2000-05-04

  Disclosed are pharmaceutical compositions and formulations comprising benzoquinoline derivatives having formulas (I) to (V). In formula (I), X i selected from the group consisting of O, S, CH2, CH2-CH2, C=O or NR8; Z is C or N; R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen, linear or branched chain lower alkyl, alkenyl, alkynyl, alkoxy or acyl; X-RA and R3, or R3 and R4 are optionally linked together to form a ring or a salt thereof, and a pharmaceutically acceptable carrier or diluent. Also disclosed are methods of inhibiting bacterial growth, comprising the administration of formulations comprising the compounds of formulas (I) to (V).
• Albert et al., Journal of the Chemical Society, 1948, p. 1284,1290
  作者：Albert et al.

  DOI：——

  日期：——
• Benzoquinoline derivatives useful as antibacterial agents
  申请人：Anadys Pharmaceuticals, Inc.

  公开号：US06274596B1

  公开（公告）日：2001-08-14

  Disclosed are pharmaceutical compositions and formulations comprising benzoquinoline derivatives having the formula (I) to (V), wherein formula (I) is: X is selected from the group consisting of O, S, CH2, CH2-CH2, C═O or NRB; Y is C or N; R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, linear or branched chain lower alky, alkenyl, alkynyl, alkoxy or acyl; X-RA and R3, or R3 and R4, are optionally linked together to form a C3-C4 alkylene bridge, where X is CH2 or C═O; provided that: when X is NRB, then (a) RB is hydrogen, and RA is a linear or branched chain lower alkyl, aryl, heteroaryl, cycloalkyl or cycloalkenyl optionally interrupted by at least one heteroatom, said alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl or cycloalkenyl being optionally substituted singly or plurally by at least one of a linear or branched chain lower alkyl, alkenyl, alkynyl, acyl, alkoxy, or cycloalkyl optionally interrupted by at least one heteroatom and optionally substituted by at least one linear or branched chain lower alkyl, alkenyl, alkynyl, acyl, or alkoxy, or a linear or branched chain lower alkyl mono- or dialkylamino, (linear or branched chain lower alkyl N-mono- or N,N-dialkylamino)(lower alkyl), (linear or branched chain lower alkyl N-mono- or N,N-dialkyl)carbamyl, aryl or heteroaryl; or (b) X, RA and RB together form a ring system comprising from about five to about twelve linked carbon atoms, said system being optionally interrupted by at least one heteroatom, optionally mono- or polyunsaturated and optionally substituted singly or plurally by at least one of a linear or branched chain lower alkyl, alkenyl, alkynyl, acyl, or alkoxy, a linear or branched chain lower alkyl N-mono- or N,N-dialkylamino, (linear or branched chain lower alkyl N-mono- or N,N-dialkylarnino)(lower alkyl), halogen, cyano, trifluoromethyl, nitro, aryl or heteroaryl; and when X is O, S, CH2, CH2-CH2 or C═O, then (a) RA is hydrogen or a linear or branched chain lower alkyl, alkenyl, alkynyl, aryl or heteroaryl, said alkyl, alkenyl, alkynyl, aryl or heteroaryl being optionally substituted singly or plurally by at least one of a linear or branched chain lower alkyl, alkenyl, alkynyl, acyl, or alkoxy, a linear or branched chain lower alkyl N-mono- or N,N-dialkylamino, (linear or branched chain lower alkyl N-mono- or N,N-dialkylamino)(lower alkyl), halogen, cyano, trifluoromethyl, nitro, aryl or heteroaryl; and (b) R3 is a linear or branched chain lower alkyl substituted by hydroxyphenyl or linear or branched chain lower alkoxyphenyl singly or plurally substituted by CH2NRCRD wherein N, RC and RD together form a ring system comprising from about five to about twelve linked carbon atoms, said system being optionally interrupted by at least one heteroatom, optionally mono- or polyunsaturated and optionally substituted singly or plurally by at least one of a linear or branched chain lower alkyl, acyl, or alkoxy, a linear or branched chain lower alkyl N-mono- or N,N-dialkylamino, (linear or branched chain lower alkyl N-mono- or N,N-dialkylamino)(lower alkyl), halogen, cyano, trifluoromethyl, nitro, aryl or heteroaryl; or a salt thereof, and a pharmaceutically acceptable carrier or diluent. Also disclosed are methods of inhibiting bacterial growth, comprising the administration of formulations comprising the compounds of formulas (I) to (V).

  本发明涉及含有苯并喹啉衍生物的药物组合物和制剂，其具有公式（I）至（V），其中公式（I）为：X选自O、S、CH2、CH2-CH2、C═O或NRB的群；Y为C或N；R1、R2、R3和R4独立地选自氢、卤素、线性或支链低碳基、烯基、炔基、烷氧基或酰基的群；X-RA和R3，或R3和R4，可选择地连接在一起形成一个C3-C4烷基桥，其中X为CH2或C═O；前提是：当X为NRB时，那么（a）RB为氢，RA为线性或支链低碳基、芳基、杂环芳基、环烷基或环烯基，可选择地由至少一个杂原子中断，所述的烷基、烯基、炔基、芳基、杂环芳基、环烷基或环烯基可选择地由至少一个线性或支链低碳基、烯基、炔基、酰基、烷氧基或环烷基中断，可选择地由至少一个线性或支链低碳基、烯基、炔基、酰基或烷氧基取代，或者线性或支链低碳基单烷基或双烷基氨基、（线性或支链低碳基N-单烷基或N，N-双烷基氨基）（低碳基）、（线性或支链低碳基N-单烷基或N，N-双烷基）氨基甲酰基、芳基或杂环芳基；或（b）X、RA和RB共同形成一个环系统，包含约5到约12个连接的碳原子，该系统可选择地由至少一个杂原子中断，可选择地单或多不饱和，并可选择地由至少一个线性或支链低碳基、烯基、炔基、酰基、烷氧基、线性或支链低碳基N-单烷基或N，N-双烷基氨基、（线性或支链低碳基N-单烷基或N，N-双烷基）（低碳基）、卤素、氰基、三氟甲基、硝基、芳基或杂环芳基取代；当X为O、S、CH2、CH2-CH2或C═O时，那么（a）RA为氢或线性或支链低碳基、烯基、炔基、芳基或杂环芳基，所述的烷基、烯基、炔基、芳基或杂环芳基可选择地由至少一个线性或支链低碳基、烯基、炔基、酰基、烷氧基、线性或支链低碳基N-单烷基或N，N-双烷基氨基、（线性或支链低碳基N-单烷基或N，N-双烷基）（低碳基）、卤素、氰基、三氟甲基、硝基、芳基或杂环芳基取代；（b）R3为线性或支链低碳基，由羟基苯基或线性或支链低烷氧基苯基单独或多次取代，取代基为CH2NRCRD，其中N、RC和RD共同形成一个环系统，包含约5到约12个连接的碳原子，该系统可选择地由至少一个杂原子中断，可选择地单或多不饱和，并可选择地由至少一个线性或支链低碳基、酰基或烷氧基、线性或支链低碳基N-单烷基或N，N-双烷基氨基、（线性或支链低碳基N-单烷基或N，N-双烷基）（低碳基）、卤素、氰基、三氟甲基、硝基、芳基或杂环芳基取代；或其盐，以及药学上可接受的载体或稀释剂。还公开了抑制细菌生长的方法，包括给予公式（I）至（V）的化合物组成的制剂的管理。