3-溴-6-甲氧基-1,5-萘啶-4-醇 | 1075259-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-溴-6-甲氧基-1,5-萘啶-4-醇
• 英文名称: 3-bromo-6-methoxy-1,5-naphthyridin-4-ol
• 英文别名: 3-bromo-6-methoxy-1H-1,5-naphthyridin-4-one
• CAS: 1075259-68-5
• 化学式: C₉H₇BrN₂O₂
• 分子量: 255.071
• InChiKey: UTGCNXFYKIPNJM-UHFFFAOYSA-N

物化性质

• 沸点：
  335.7±37.0 °C(Predicted)
• 密度：
  1.716±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴-6-甲氧基-1,5-萘啶-4-醇 在 potassium carbonate 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (6R)-3-bromo-6-(hydroxymethyl)-5,6-dihydro-8H-[1,4]oxazino[2,3,4-ij]-1,5-naphthyridin-8-one
  参考文献：
  名称：

  WO2008/128953

  摘要：

  公开号：
• 作为产物：
  描述：

  5-氨基-2-甲氧基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 5.17h， 生成 3-溴-6-甲氧基-1,5-萘啶-4-醇
  参考文献：
  名称：

  [EN] NEW COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS

  摘要：

  这项发明涉及新的萘啉衍生物化合物，包括所述化合物的药物组合物，制备所述化合物的方法以及利用所述化合物治疗疾病，例如癌症。

  公开号：

  WO2013061077A1

文献信息

• [EN] TRICYCLIC ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES TRICYCLIQUES
  申请人：BASILEA PHARMACEUTICA AG

  公开号：WO2011073378A1

  公开（公告）日：2011-06-23

  Compound of formula (I): wherein A1 represents -O-, -S- or -N-R3; A2 represents -CH2-, -O-, -N-R4, -C(=O)- or -CH(O-R4)-; A3 represents C3-C8cycloalkylene; saturated and unsaturated 4 to 8-membered heterocyclodiyl with 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, which group A3 is unsubstituted or substituted; A4 represents C1-C4alkylene, C2-C4alkenylene, >C=O or a group selected from - C2H4NH-, -C2H4O-, and -C2H4S- being linked to the adjacent NR5-group via the carbon atom; and G represents aryl or heteroaryl, which is unsubstituted or substituted and R1 and R2 independently of one another, represent hydrogen or a substituent selected from hydroxy, halogen, mercapto, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylcarbonyloxy, C1-C6alkylsulfonyloxy, C1-C6heteroalkylcarbonyloxy, C5-C6heterocyclylcarbonyloxy, C1-C6heteroalkoxy, wherein heteroalkyl, heteroalkoxy groups or heterocyclyl comprise 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, in which substituents the alkyl moieties are unsubstituted or further substituted; R3, R4 and R5 independently of one another, represent hydrogen or C1-C6alkyl; X1 and X2 independently of one another, represent a nitrogen atom or CR2, with the proviso that at least one of Xl and X2 represents a nitrogen atom; m is 1; and the (CH2)m moiety is optionally substituted by C1-C4alkyl; halogen, carboxy, hydroxy, C1-C4alkoxy, C1-C4-alkylcarbonyloxy, amino, mono- or di-(C1-C4alkyl)amino or acylamino n is 0, 1 or 2 or pharmaceutically acceptable salt thereof are valuable for use as a medicament for the treatment of bacterial infections.

  化合物的化学式（I）：其中A1代表-O-，-S-或-N-R3；A2代表-CH2-，-O-，-N-R4，-C（=O）-或-CH（O-R4）-；A3代表C3-C8环烷基；饱和和不饱和的含有1、2或3个氮、氧和硫杂原子的4至8元杂环二基，其中该基A3未取代或取代；A4代表C1-C4烷基，C2-C4烯基，>C=O或从-C2H4NH-，-C2H4O-和-C2H4S-中选择的一个基团，通过碳原子与相邻的NR5基团连接；G代表芳基或杂芳基，未取代或取代，R1和R2相互独立地代表氢或从羟基，卤素，巯基，氰基，硝基，C1-C6烷基，C1-C6烷氧基，C1-C6烷硫基，C1-C6烷基羰氧基，C1-C6烷基磺酰氧基，C1-C6杂烷基羰氧基，C5-C6杂环烷基羰氧基，C1-C6杂烷氧基中选择的取代基，其中杂烷基，杂烷氧基或杂环烷基包括1、2或3个从氮、氧和硫中选择的杂原子，在这些取代基中，烷基基未取代或进一步取代；R3，R4和R5相互独立地代表氢或C1-C6烷基；X1和X2相互独立地代表氮原子或CR2，但至少X1和X2中的一个代表氮原子；m为1；（CH2）m基团可选地通过C1-C4烷基，卤素，羧基，羟基，C1-C4烷氧基，C1-C4-烷基羰氧基，氨基，单烷基或双烷基氨基或酰胺基n为0，1或2或其药学上可接受的盐，适用于作为治疗细菌感染的药物。
• [EN] NOVEL BICYCLIC ANTIBIOTICS<br/>[FR] NOUVEAUX ANTIBIOTIQUES BICYCLIQUES
  申请人：BASILEA PHARMACEUTICA AG

  公开号：WO2010084152A1

  公开（公告）日：2010-07-29

  Compounds of formula (I) wherein X1, X3; X4 and X6, each independently of the others, represents a nitrogen atom or CR2, with the proviso that at least one of X1, X3; X4 and X6 represents a nitrogen atom; X2 represents C-H, C-(C1-C6alkyl), C-(C1-C6alkoxy), C-halogen, C-COOH; X5 represents C-H or C-(C1-C6alkyl), C-halogen; R1 and R2, independently of one another, represent hydrogen or a substituent selected from hydroxy, halogen, carboxy, amino, C1-C6alkylamino, di(C1-C6alkyl)amino, mercapto, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylamino- carbonyloxy, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkylcarbonyloxy, C1-C6alkyl- sulfonyloxy, C1 -C6heteroalkylcarbonyloxy, C5-C6heterocyclylcarbonyloxy, C1-C6heteroalkyl, C1-C6heteroalkoxy, wherein heteroalkyl, heteroalkoxy groups or heterocyclyl comprise 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, in which substituents the alkyl moieties are unsubstituted or further substituted by halogeno, cyano, hydroxy, C1-C4alkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, unsubstituted or substituted phenoxy or phenylcarbonyl, unsubstituted or substituted C5-C6heterocyclyl or carboxy; A1 represents a divalent group of one of the formulae -O-(CH2)m-(CH2)-, -S-(CH2)m-(CH2)- or -(C=O)O-(CH2)m-(CH2)-, wherein the (CH2)m moiety is optionally substituted by C1-C4alkyl, C2-C4alkenyl, C3-C6cycloalkyl, C3-C6cycloalkylmethyl, morpholinomethyl, halogen, carboxy, hydroxy, C1-C4alkoxy; C1 -C4alkoxyC1 -C4alkyl, C1 -C4alkoxy(C1 -C4alkylenoxy)C1 -C4alkyl, benzyloxyC1 - C4alkyl, amino, mono- or di-(C1-C4alkyl)amino or acylamino, in which substituents the alkyl moieties can be further substituted by 1 or more fluoro atoms m is 0, 1 or 2, provided that the number of atoms in the direct chain between the two terminal valencies of A1 is at least 3, which group A1 is linked to A2 via the terminal (CH2)-moiety; A2 is a group selected from C3-C8cycloalkylene; saturated and unsaturated 4 to 8- membered heterocyclodiyl with 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, which group A2 is unsubstituted or substituted; R4 represents hydrogen or C1 -C4alkyl; A3 represents C1-C4alkylene, C2-C4alkenylene, >C=O, -C(O)C1-C3alkylene-, -C(=O)NH-, or a group selected from -C2H4NH-, -C2H4O-, and -C2H4S- being linked to the adjacent NR4-group via the carbon atom; and G represents aryl or heteroaryl, which is unsubstituted or substituted and n is 0, 1 or 2; or a pharmaceutically acceptable salts, hydrates or solvates thereof are valuable antibacterial agents.

  式(I)中的化合物，其中X1、X3、X4和X6，每个独立地代表氮原子或CR2，但X1、X3、X4和X6中至少有一个代表氮原子；X2代表C-H、C-(C1-C6烷基)、C-(C1-C6烷氧基)、C-卤素、C-COOH；X5代表C-H或C-(C1-C6烷基)、C-卤素；R1和R2独立地代表氢或从羟基、卤素、羧基、氨基、C1-C6烷基氨基、二(C1-C6烷基)氨基、巯基、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基氧基羰氧、C2-C6烯基、C2-C6炔基、C1-C6烷基羰氧、C1-C6烷基磺酰氧、C1-C6杂烷基羰氧、C5-C6杂环烷基羰氧、C1-C6杂烷基、C1-C6杂烷氧基中选择的取代基；A1代表以下式之一的二价基团：-O-(CH2)m-(CH2)-、-S-(CH2)m-(CH2)-或-(C=O)O-(CH2)m-(CH2)-，其中(CH2)m基团可选择地由C1-C4烷基、C2-C4烯基、C3-C6环烷基、C3-C6环烷基甲基、吗啉基甲基、卤素、羧基、羟基、C1-C4烷氧基；C1-C4烷氧基C1-C4烷基、C1-C4烷氧基(C1-C4烷氧基)C1-C4烷基、苄氧基C1-C4烷基、氨基、单或二-(C1-C4烷基)氨基或酰胺基取代，其中取代基的烷基基团可以进一步由1个或多个氟原子取代；m为0、1或2，前提是A1的两个末端价的直链中的原子数至少为3，该基团A1通过末端(CH2)-基团与A2连接；A2是选择自C3-C8环烷基烯；饱和和不饱和的含氮、氧和硫的1、2或3个杂原子的4至8环杂环二基团，该基团A2未取代或取代；R4代表氢或C1-C4烷基；A3代表C1-C4亚烷基、C2-C4烯亚烷基、>C=O、-C(O)C1-C3烷基-、-C(=O)NH-，或选择自-C2H4NH-、-C2H4O-和-C2H4S-的基团，通过碳原子与相邻的NR4基团连接；G代表芳香族或杂芳基，未取代或取代，n为0、1或2；或其药学上可接受的盐、水合物或溶剂合物是有价值的抗菌剂。
• TRICYCLIC NITROGEN CONTAINING HETEROCYCLES AS ANTIBACTERIAL AGENTS
  申请人：Brown Pamela

  公开号：US20100087424A1

  公开（公告）日：2010-04-08

  Tricyclic nitrogen containing compounds and their use as antibacterials.

  三环氮含有化合物及其作为抗菌剂的用途。
• Novel Bicyclic Antibiotics
  申请人：Gaucher Berangere

  公开号：US20120040957A1

  公开（公告）日：2012-02-16

  Compounds of formula (I) wherein X1, X3; X4 and X6, each independently of the others, represents a nitrogen atom or CR2, with the proviso that at least one of X1, X3; X4 and X6 represents a nitrogen atom; X2 represents C—H, C—(C1-C6alkyl), C—(C1-C6alkoxy), C-halogen, C—COOH; X5 represents C—H or C—(C1-C6alkyl), C-halogen; R1 and R2, independently of one another, represent hydrogen or a substituent selected from hydroxy, halogen, carboxy, amino, C1-C6alkylamino, di(C1-C6alkyl)amino, mercapto, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylamino-carbonyloxy, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkylcarbonyloxy, C1-C6alkyl-sulfonyloxy, C1-C6heteroalkylcarbonyloxy, C5-C6heterocyclyl-carbonyloxy, C1-C6heteroalkyl, C1-C6heteroalkoxy, wherein heteroalkyl, heteroalkoxy groups or heterocyclyl comprise 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, in which substituents the alkyl moieties are unsubstituted or further substituted by halogeno, cyano, hydroxy, C1-C4alkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, unsubstituted or substituted phenoxy or phenylcarbonyl, unsubstituted or substituted C5-C6heterocyclyl or carboxy; A1 represents a divalent group of one of the formulae —O—(CH 2 ) m —(CH 2 )—, —S—(CH 2 ) m —(CH 2 )— or —(C═O)O—(CH 2 ) m —(CH 2 )—, wherein the (CH 2 ) m moiety is optionally substituted by C1-C4alkyl, C2-C4alkenyl, C3-C6cycloalkyl, C3-C6cycloalkylmethyl, morpholinomethyl, halogen, carboxy, hydroxy, C1-C4alkoxy; C1-C4alkoxyC1-C4alkyl, C1-C4alkoxy(C1-C4alkylenoxy)C1-C4alkyl, benzyloxyC1-C4alkyl, amino, mono- or di-(C1-C4alkyl)amino or acylamino, in which substituents the alkyl moieties can be further substituted by 1 or more fluoro atoms m is 0, 1 or 2, provided that the nunber of atoms in the direct chain between the two terminal valencies of A 1 is at least 3, which group A 1 is linked to A 2 via the terminal (CH 2 )-moiety; A 2 is a group selected from C 3 -C 8 cycloalkylene; saturated and unsaturated 4 to 8 -membered heterocyclodiyl with 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, which group A 2 is unsubstituted or substituted; R 4 represents hydrogen or C 1 -C 4 alkyl; A 3 represents C 1 -C 4 alkylene, C 2 -C 4 alkenylene, >C═O, —C(O)C 1 -C 3 alkylene-, —C(═O)NH—, or a group selected from —C 2 H 4 NH—, —C 2H 4 O—, and —C 2 H 4 S— being linked to the adjacent NR 4 -group via the carbon atom; and G represents aryl or heteroaryl, which is unsubstituted or substituted and n is 0, 1 or 2; or a pharmaceutically acceptable salts, hydrates or solvates thereof are valuable antibacterial agents.

  化合物式(I)中，其中X1、X3、X4和X6分别独立地表示氮原子或CR2，但至少其中一个表示氮原子；X2表示C-H、C-(C1-C6烷基)、C-(C1-C6烷氧基)、C-卤素、C-COOH；X5表示C-H或C-(C1-C6烷基)、C-卤素；R1和R2独立地表示氢或从羟基、卤素、羧基、氨基、C1-C6烷基氨基、二(C1-C6烷基)氨基、巯基、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6烷基硫基、C1-C6烷基氨基羰氧基、C2-C6烯基、C2-C6炔基、C1-C6烷基羰氧基、C1-C6烷基磺酰氧基、C1-C6杂烷基羰氧基、C5-C6杂环基羰氧基、C1-C6杂烷基、C1-C6杂烷氧基中选择的取代基，其中杂烷基、杂烷氧基或杂环基包括1、2或3个从氮、氧和硫选择的杂原子，在这些取代基中，烷基基团未取代或进一步取代为卤代、氰基、羟基、C1-C4烷氧基、C1-C4烷基羧基、C1-C4烷氧羰基、未取代或取代的苯氧基或苯基羧基、未取代或取代的C5-C6杂环基或羧基；A1表示一个二价基团，其中之一为式之一的基团-O-(CH2)m-(CH2)-、-S-(CH2)m-(CH2)-或-(C═O)O-(CH2)m-(CH2)-，其中(CH2)m基团可以选择地被C1-C4烷基、C2-C4烯基、C3-C6环烷基、C3-C6环烷基甲基、吗啉基甲基、卤素、羧基、羟基、C1-C4烷氧基取代；C1-C4烷氧基C1-C4烷基、C1-C4烷氧基(C1-C4烷氧基)C1-C4烷基、苄氧基C1-C4烷基、氨基、单取代或双取代(C1-C4烷基)氨基或酰基氨基，在这些取代基中，烷基基团可以进一步取代1个或多个氟原子，m为0、1或2，前提是A1的两个端面价之间的直链原子数至少为3，该基团A1通过端面(CH2)基团与A2相连；A2是选择自C3-C8环烷基、饱和和不饱和的1、2或3个从氮、氧和硫选择的杂环二基，该基团A2未取代或取代；R4表示氢或C1-C4烷基；A3表示C1-C4烷基、C2-C4烯基、>C═O、-C(O)C1-C3烷基、-C(═O)NH-或选择自-C2H4NH-、-C2H4O-和-C2H4S-的基团，通过碳原子与相邻的NR4基团相连；G表示未取代或取代的芳基或杂芳基，其中n为0、1或2；或其药学上可接受的盐、水合物或溶剂。这些化合物是有价值的抗菌剂。
• TRICYCLIC ANTIBIOTICS
  申请人：Gaucher Bérangère

  公开号：US20120245345A1

  公开（公告）日：2012-09-27

  Compound of formula (I): wherein A1 represents —O—, —S— or —N—R3; A2 represents —CH 2 —, —O—, —N—R4, —C(═O)— or —CH(O—R4)—; A3 represents C 3 -C 8 cycloalkylene; saturated and unsaturated 4 to 8-membered heterocyclodiyl with 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, which group A3 is unsubstituted or substituted; A4 represents C 1 -C 4 alkylene, C 2 -C 4 alkenylene, >C═O or a group selected from —C 2 H 4 NH—, —C 2 H 4 O—, and —C 2 H 4 S— being linked to the adjacent NR5-group via the carbon atom; and G represents aryl or heteroaryl, which is un-substituted or substituted and R1 and R2 independently of one another, represent hydrogen or a substituent selected from hydroxy, halogen, mercapto, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 heteroalkylcarbonyloxy, C5-C 6 heterocyclylcarbonyloxy, C 1 -C 6 heteroalkoxy, wherein heteroalkyl, heteroalkoxy groups or heterocyclyl comprise 1, 2 or 3 heteroatoms selected from nitrogen, oxygen and sulphur, in which substituents the alkyl moieties are unsubstituted or further substituted; R3, R4 and R5 independently of one another, represent hydrogen or C 1 -C 6 alkyl; X1 and X2 independently of one another, represent a nitrogen atom or CR2, with the proviso that at least one of X1 and X2 represents a nitrogen atom; m is 1; and the (CH2)m moiety is optionally substituted by C 1 -C 4 alkyl; halogen, carboxy, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 -alkylcarbonyloxy, amino, mono- or di-(C 1 -C 4 alkyl)amino or acylamino n is 0, 1 or 2 or pharmaceutically acceptable salt thereof are valuable for use as a medicament for the treatment of bacterial infections.

  化合物的公式（I）：其中A1代表—O—、—S—或—N—R3；A2代表—CH2—、—O—、—N—R4、—C（═O）—或—CH（O—R4）—；A3代表C3-C8环烷基、饱和和不饱和的4至8元杂环二基，其中1、2或3个杂原子选自氮、氧和硫，该基团A3未取代或取代；A4代表C1-C4烷基、C2-C4烯基、>C═O或从—C2H4NH—、—C2H4O—和—C2H4S—中选择的基团，通过碳原子与相邻的NR5基团连接；G代表芳基或杂芳基，未取代或取代，R1和R2独立地代表氢或来自羟基、卤素、硫醇基、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫氧基、C1-C6烷基羰酸酯氧基、C1-C6烷基磺酸酯氧基、C1-C6杂烷基羰酸酯氧基、C5-C6杂环烷基羰酸酯氧基、C1-C6杂烷氧基，其中杂烷基、杂烷氧基或杂环烷基包含1、2或3个选自氮、氧和硫的杂原子，在这些取代基中，烷基基团未取代或进一步取代；R3、R4和R5独立地代表氢或C1-C6烷基；X1和X2独立地代表氮原子或CR2，但至少其中之一代表氮原子；m为1；（CH2）m基团可选择地被C1-C4烷基、卤素、羧基、羟基、C1-C4烷氧基、C1-C4烷基羰酸酯氧基、氨基、单或双-(C1-C4烷基)氨基或酰胺基取代；n为0、1或2或其药学上可接受的盐，用作治疗细菌感染的药物。