8-fluoro-4-oxo-1,4-dihydro-cinnoline-3-carboxylic acid | 1994-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-fluoro-4-oxo-1,4-dihydro-cinnoline-3-carboxylic acid
• 英文别名: 8-Fluor-4-hydroxy-3-carboxy-cinnolin；8-Fluoro-4-hydroxy-cinnoline-3-carboxylic acid；8-fluoro-4-oxo-1H-cinnoline-3-carboxylic acid
• CAS: 1994-12-3
• 化学式: C₉H₅FN₂O₃
• 分子量: 208.149
• InChiKey: QCUVBXDOBQQZRB-UHFFFAOYSA-N

物化性质

• 沸点：
  421.9±55.0 °C(Predicted)
• 密度：
  1.662±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-二乙基乙二胺 、 8-fluoro-4-oxo-1,4-dihydro-cinnoline-3-carboxylic acid 在 N,N'-羰基二咪唑 作用下， 生成 8-fluoro-4-hydroxy-3-[(2-diethylaminoethyl)]cinnolinecarboxamide
  参考文献：
  名称：

  Stanczak; Lewgowd; Ochocki, Pharmazie, 1997, vol. 52, # 2, p. 91 - 97

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基-8-氟噌啉-3-羧酸 以95.3%的产率得到8-fluoro-4-oxo-1,4-dihydro-cinnoline-3-carboxylic acid
  参考文献：
  名称：

  Stanczak; Lewgowd; Ochocki, Pharmazie, 1997, vol. 52, # 2, p. 91 - 97

  摘要：

  DOI：

文献信息

• [EN] IMMUNOMODULATING HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSES HETEROCYCLIQUES D'IMMUNOMODULATION
  申请人：AVIDEX LTD

  公开号：WO2004081011A1

  公开（公告）日：2004-09-23

  Compounds of formula (I) are inhibitors of CD80 and useful in immunomodulation therapy: wherein R1 and R3 independently represent H; F; CI; Br; -NO2; -CN; C1-C6 alkyl optionally substituted by F or Cl; or C1-C6 alkoxy optionally substituted by F; R4 represents a carboxylic acid group (-COOH) or an ester thereof, or -C(=O)NR6R7, -NR7C(=O)R6, -NR7C(=O)OR6, -NHC(=O)NR7R6 or -NHC(=S)NR7R6 wherein R6 represents H, or a radical of formula - (Alk)m-Q wherein m is 0 or 1, Alk is an optionally substituted divalent straight or branched C1-C12 alkylene, or C2-C12 alkenylene, or C2-C12 alkynylene radical or a divalent C3-C12 carbocyclic radical, any of which radicals may contain one or more -O-, -S- or -N(R8)- links wherein R8 represents H or C1-C4 alkyl, C3-­C4 alkenyl, C3-C4 alkynyl, or C3-C6 cycloalkyl, and Q represents H; -NR9R10 wherein R9 and R10 independently represents H; C1-C4 alkyl; C3-C4 alkenyl; C3-C4 alkynyl; C3-C6 cycloalkyl; an ester group; an optionally substituted carbocyclic or heterocyclic group; or R9 and R10 form a ring when taken together with the nitrogen to which they are attached, which ring is optionally substituted; and R7 represents H or C1-C6 alkyl; or when taken together with the atom or atoms to which they are attached R6 and R7 form an optionally substituted monocyclic heterocyclic ring having 5, 6 or 7 ring atoms; and X represents a bond or a divalent radical of formula - (Z)n-(Alk)- or - (Alk)-(Z)n- ­wherein Z represents -O-, -S- or -NH-, Alk is as defined in relation to R6 and n is 0 or 1.

  化合物的化学式(I)是CD80的抑制剂，在免疫调节疗法中具有用途：其中R1和R3分别代表H; F; CI; Br; -NO2; -CN; 通过F或Cl取代的C1-C6烷基; 或通过F取代的C1-C6烷氧基; R4代表羧酸基(-COOH)或其酯，或-C(=O)NR6R7，-NR7C(=O)R6，-NR7C(=O)OR6，-NHC(=O)NR7R6或-NHC(=S)NR7R6其中R6代表H，或化学式-(Alk)m-Q的基团，其中m为0或1，Alk是一个可选择取代的直链或支链C1-C12烷基，或C2-C12烯基，或C2-C12炔基基团或双价C3-C12碳环基团，其中任何一个基团可能包含一个或多个-O-，-S-或-N(R8)-键，其中R8代表H或C1-C4烷基，C3-C4烯基，C3-C4炔基，或C3-C6环烷基，而Q代表H; -NR9R10其中R9和R10独立地代表H; C1-C4烷基; C3-C4烯基; C3-C4炔基; C3-C6环烷基; 酯基; 可选择取代的碳环或杂环基团; 或当R9和R10与它们连接的氮一起形成一个环时，该环是可选择取代的; R7代表H或C1-C6烷基; 或当R6和R7与它们连接的原子一起形成一个可选择取代的含有5、6或7个环原子的单环杂环环，X代表一个键或化学式-(Z)n-(Alk)-或-(Alk)-(Z)n-其中Z代表-O-，-S-或-NH-，Alk如R6所定义，n为0或1。
• Immunomodulating Heterocyclic Compounds
  申请人：Matthews Richard Ian

  公开号：US20080045527A1

  公开（公告）日：2008-02-21

  Compounds of formula (I) are inhibitors of CD80 and useful in immunomodulation therapy: wherein R 1 and R 3 independently represent H; F; Cl; Br; —NO 2 ; —CN; C 1 -C 6 alkyl optionally substituted by F or Cl; or C 1 -C 6 alkoxy optionally substituted by F; R 4 represents a carboxylic acid group (—COOH) or an ester thereof, or —C(═O)NR 6 R 7 , —NR 7 C(═O)R 6 , —NR 7 C(═O)OR 6 , —NHC(═O)NR 7 R 6 or —NHC(═S)NR 7 R 6 wherein R 6 represents H, or a radical of formula -(Alk) m -Q wherein m is 0 or 1, Alk is an optionally substituted divalent straight or branched C 1 -C 12 alkylene, or C 2 -C 12 alkenylene, or C 2 -C 12 alkynylene radical or a divalent C 3 -C 12 carbocyclic radical, any of which radicals may contain one or more —O—, —S— or —N(R 8 )— links wherein R 8 represents H or C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, or C 3 -C 6 cycloalkyl, and Q represents H; —NR 9 R 10 wherein R 9 and R 10 independently represents H; C 1 -C 4 alkyl; C 3 -C 4 alkenyl; C 3 -C 4 alkynyl; C 3 -C 6 cycloalkyl; an ester group; an optionally substituted carbocyclic or heterocyclic group; or R 9 and R 10 form a ring when taken together with the nitrogen to which they are attached, which ring is optionally substituted; and R 7 represents H or C 1 -C 6 alkyl; or when taken together with the atom or atoms to which they are attached R 6 and R 7 form an optionally substituted monocyclic heterocyclic ring having 5, 6 or 7 ring atoms; and X represents a bond or a divalent radical of formula -(Z) n -(Alk)- or -(Alk)-(Z) n - wherein Z represents —O—, —S— or —NH—, Alk is as defined in relation to R 6 and n is 0 or 1.

  式（I）的化合物是CD80的抑制剂，可用于免疫调节治疗：其中R1和R3分别表示H; F; Cl; Br; -NO2; -CN; C1-C6烷基，其可选地被F或Cl取代; 或C1-C6烷氧基，其可选地被F取代; R4表示羧酸基（-COOH）或其酯，或-C（=O）NR6R7，-NR7C（=O）R6，-NR7C（=O）OR6，-NHC（=O）NR7R6或-NHC（=S）NR7R6，其中R6表示H，或式-(Alk)m-Q的基团，其中m为0或1，Alk为可选地取代的二价直链或支链C1-C12烷基，或C2-C12烯基，或C2-C12炔基基团或二价C3-C12环烷基基团，其中任何基团都可以包含一个或多个-O-，-S-或-N（R8）-链接，其中R8表示H或C1-C4烷基，C3-C4烯基，C3-C4炔基，或C3-C6环烷基; Q表示H; -NR9R10，其中R9和R10独立地表示H; C1-C4烷基; C3-C4烯基; C3-C4炔基; C3-C6环烷基; 酯基; 可选地取代的碳环或杂环基团; 或者R9和R10与它们所连接的氮一起形成一个环，该环可选地被取代; R7表示H或C1-C6烷基; 或者当它们所连接的原子或原子与R6一起形成一个可选地取代的含5,6或7个环原子的单环杂环时; X表示键或式-(Z)n-(Alk)-或-(Alk)-(Z)n-的二价基团，其中Z表示-O-，-S-或-NH-，Alk如在关于R6的定义中所述，n为0或1。
• Immunomodulating heterocyclic compounds
  申请人：Matthews Richard Ian

  公开号：US20070021428A1

  公开（公告）日：2007-01-25

  Compounds of formula (I) are inhibitors of CD80 and useful in immunomodulation therapy: wherein R 1 and R 3 independently represent H; F; CI; Br; —NO 2 ; —CN; C 1 -C 6 alkyl optionally substituted by F or Cl; or C 1 -C 6 alkoxy optionally substituted by F; R 4 represents a carboxylic acid group (—COOH) or an ester thereof, or —C(═O)NR 6 R 7 , —NR 7 C(═O)R 6 , —NR 7 C(═O)OR 6 , —NHC(═O)NR 7 R 6 or —NHC(═S)NR 7 R 6 wherein R 6 represents H, or a radical of formula -(Alk) m -Q wherein m is 0 or 1, Alk is an optionally substituted divalent straight or branched C 1 -C 12 alkylene, or C 2 -C 12 alkenylene, or C 2 -C 12 alkynylene radical or a divalent C 3 -C 12 carbocyclic radical, any of which radicals may contain one or more —O—, —S— or —N(R 8 )— links wherein R 8 , represents H or C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, or C 3 -C 6 cycloalkyl, and Q represents H; —NR 9 R 10 wherein R 9 and R 10 independently represents H; C 1 -C 4 alkyl; C 3 -C 4 alkenyl; C 3 -C 4 alkynyl; C 3 -C 6 cycloalkyl; an ester group; an optionally substituted carbocyclic or heterocyclic group; or R 9 and R 10 form a ring when taken together with the nitrogen to which they are attached, which ring is optionally substituted; and R 7 represents H or C 1 -C 6 alkyl; or when taken together with the atom or atoms to which they are attached R 6 and R 7 form an optionally substituted monocyclic heterocyclic ring having 5, 6 or 7 ring atoms; and X represents a bond or a divalent radical of formula —(Z) n -(Alk)- or -(Alk)-(Z) n — wherein Z represents —O—, —S— or —NH—, Alk is as defined in relation to R 6 , and n is 0 or 1.

  式(I)的化合物是CD80的抑制剂，并且在免疫调节治疗中有用：其中R1和R3分别表示H; F; CI; Br; -NO2; -CN; C1-C6烷基，可选地被F或Cl取代; 或C1-C6烷氧基，可选地被F取代; R4表示羧酸基（-COOH）或其酯，或-C（=O）NR6R7，-NR7C（=O）R6，-NR7C（=O）OR6，-NHC（=O）NR7R6或-NHC（=S）NR7R6，其中R6表示H，或式-(Alk)m-Q的基团，其中m为0或1，Alk为可选取代的二价直链或支链C1-C12烷基，或C2-C12烯基，或C2-C12炔基基团或二价C3-C12环烷基基团，其中任何基团均可能含有一个或多个-O-，-S-或-N（R8）-链接，其中R8表示H或C1-C4烷基，C3-C4烯基，C3-C4炔基或C3-C6环烷基，Q表示H; -NR9R10，其中R9和R10独立地表示H; C1-C4烷基; C3-C4烯基; C3-C4炔基; C3-C6环烷基; 酯基; 可选取代的环烷基或杂环基; 或者当R9和R10与它们所连接的氮一起形成一个环时，该环是可选取代的; R7表示H或C1-C6烷基; 或者当它们所连接的原子或原子与R6和R7一起形成一个可选取代的有5、6或7个环原子的单环杂环时; X表示键或式-(Z)n-(Alk)-或-(Alk)-(Z)n-的二价基团，其中Z表示-O-，-S-或-NH-，Alk如在R6中所定义，n为0或1。
• IMMUNOMODULATING HETEROCYCLIC COMPOUNDS
  申请人：Avidex Limited

  公开号：EP1603917A1

  公开（公告）日：2005-12-14
• US7276505B2
  申请人：——

  公开号：US7276505B2

  公开（公告）日：2007-10-02