3-methoxy-quinoline-5-carbaldehyde | 881656-52-6

• 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: 3-methoxy-quinoline-5-carbaldehyde
• 英文别名: 3-Methoxyquinoline-5-carbaldehyde；3-methoxyquinoline-5-carbaldehyde
• CAS: 881656-52-6
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: HOPFINDBXLGBEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-quinoline-5-carbaldehyde 在 甲基磺酰胺 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 叔丁醇 为溶剂， 反应 3.5h， 生成 6-({[(3R,6S)-6-[(1S,2R)-1,2-dihydroxy-2-(3-methoxyquinolin-5-yl)ethyl]oxan-3-yl]amino}methyl)-2H,3H,4H-pyrido[3,2-b][1,4]thiazin-3-one
  参考文献：
  名称：

  Design, Synthesis, and Characterization of Novel Tetrahydropyran-Based Bacterial Topoisomerase Inhibitors with Potent Anti-Gram-Positive Activity

  摘要：

  There is an urgent need for new antibacterial drugs that are effective against infections caused by multidrug-resistant pathogens. Novel nonfluoroquinolone inhibitors of bacterial type II topoisomerases (DNA gyrase and topoisomerase IV) have the potential to become such drugs because they display potent antibacterial activity and exhibit no target-mediated cross-resistance with fluoroquinolones. Bacterial topoisomerase inhibitors that are built on a tetrahydropyran ring linked to a bicyclic aromatic moiety through a syn-diol linker show potent anti-Gram-positive activity, covering isolates with clinically relevant resistance phenotypes. For instance, analog 49c was found to be a dual DNA gyrase topoisomerase IV inhibitor, with broad antibacterial activity and low propensity for spontaneous resistance development, but suffered from high hERG K channel block. On the other hand, analog 49e displayed lower hERG K channel block while retaining potent in vitro antibacterial activity and acceptable frequency for resistance development. Furthermore, analog 49e showed moderate clearance in rat and promising in vivo efficacy against Staphylococcus aureus in a murine infection model.

  DOI：

  10.1021/jm400963y
• 作为产物：
  描述：

  3,5-二溴喹啉 在 N,N-二甲基丙烯基脲 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 3-methoxy-quinoline-5-carbaldehyde
  参考文献：
  名称：

  Design, Synthesis, and Characterization of Novel Tetrahydropyran-Based Bacterial Topoisomerase Inhibitors with Potent Anti-Gram-Positive Activity

  摘要：

  There is an urgent need for new antibacterial drugs that are effective against infections caused by multidrug-resistant pathogens. Novel nonfluoroquinolone inhibitors of bacterial type II topoisomerases (DNA gyrase and topoisomerase IV) have the potential to become such drugs because they display potent antibacterial activity and exhibit no target-mediated cross-resistance with fluoroquinolones. Bacterial topoisomerase inhibitors that are built on a tetrahydropyran ring linked to a bicyclic aromatic moiety through a syn-diol linker show potent anti-Gram-positive activity, covering isolates with clinically relevant resistance phenotypes. For instance, analog 49c was found to be a dual DNA gyrase topoisomerase IV inhibitor, with broad antibacterial activity and low propensity for spontaneous resistance development, but suffered from high hERG K channel block. On the other hand, analog 49e displayed lower hERG K channel block while retaining potent in vitro antibacterial activity and acceptable frequency for resistance development. Furthermore, analog 49e showed moderate clearance in rat and promising in vivo efficacy against Staphylococcus aureus in a murine infection model.

  DOI：

  10.1021/jm400963y

文献信息

• 5-Quinoline derivatives having an anti-bacterial activity
  申请人：Dale Glenn

  公开号：US20100324030A1

  公开（公告）日：2010-12-23

  The present invention describes novel anti-bacterial compounds of the formula (I). These compounds are, amongst others, of interest as inhibitors of DNA gyrase and topoisomerases, for example of topoisomerase II and IV.

  本发明描述了通式(I)的新型抗菌化合物。这些化合物,除其他外,作为DNA促旋酶和拓扑异构酶的抑制剂,例如拓扑异构酶II和IV,具有研究价值。
• New Piperidine Antibiotics
  申请人：HUBSCHWERLEN Christian

  公开号：US20070173532A1

  公开（公告）日：2007-07-26

  The invention relates to novel, antibacterially active piperidine derivatives of the formula wherein one of U and V represents N, the other represents N or CH; M represents CH 2 CH 2 , CH═CH, CH(OH)CH(OH), CH(OH)CH 2 , CH(NH 2 )CH 2 , COCH 2 or OCH 2 ; R 1 represents alkyl, haloalkyl, alkoxy, haloalkoxy, halogen or cyano; R 2 represents hydrogen or halogen; R 3 represents carboxy, carboxamido, alkylaminocarbonyl, hydroxy, aminocarbonyloxy, 2-tetrazolyl or 3-methyl-1,2,4-oxadiazol-5-yl; R 4 represents alkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, haloalkyl, alkenyl, arylalkyl, aryl-S(O) m -alkyl, heteroarylalkyl, heteroarylaminocarbonylalkyl, heteroaryl-S(O) m -alkyl, CH 2 —CH═CH-aryl or cycloalkyl-S(O) m -alkyl; n is an integer from 0 to 3; and m is 0 or 2.

  该发明涉及一种新的具有抗菌活性的哌啶衍生物，其化学式如下： 其中U和V中的一个代表N，另一个代表N或CH； M代表CH2CH2，CH═CH，CH(OH)CH(OH)，CH(OH)CH2，CH(NH2)CH2，COCH2或OCH2； R1代表烷基，卤代烷基，烷氧基，卤代烷氧基，卤素或氰基； R2代表氢或卤素； R3代表羧基，羧胺基，烷基氨基甲酰基，羟基，氨基甲酰氧基，2-四唑基或3-甲基-1,2,4-噁二唑-5-基； R4代表烷基，(C1-C4)烷氧基-(C1-C4)烷基，卤代烷基，烯基，芳基烷基，芳基-S(O)m-烷基，杂环芳基烷基，杂环芳基氨基甲酰基烷基，杂环芳基-S(O)m-烷基，CH2—CH═CH-芳基或环烷基-S(O)m-烷基；n为0到3的整数；m为0或2。
• [EN] NEW PIPERIDINE ANTIBIOTICS<br/>[FR] NOUVEAUX ANTIBIOTIQUES DE PIPERIDINE
  申请人：ACTELION PERCUREX AG

  公开号：WO2006038172A1

  公开（公告）日：2006-04-13

  The invention relates to novel, antibacterially active piperidine derivatives of the formula (I) wherein one of U and V represents N, the other represents N or CH; M represents CH2CH2, CH=CH, CH(OH)CH(OH), CH(OH)CH2, CH(NH2)CH2, COCH2 or OCH2; R1 represents alkyl, haloalkyl, alkoxy, haloalkoxy, halogen or cyano; R2 represents hydrogen or halogen; R3 represents carboxy, carboxamido, alkylaminocarbonyl, hydroxy, aminocarbonyloxy, 2-tetrazolyl or 3-methyl-1,2,4-oxadiazol-5-yl; R4 represents alkyl, (C1-C4)alkoxy-(C1-C4)alkyl, haloalkyl, alkenyl, arylalkyl, aryl-S(O)m-­alkyl, heteroarylalkyl, heteroarylaminocarbonylalkyl, heteroaryl-S(O)m-alkyl, CH2-CH=CH­aryl or cycloalkyl-S(O)m-alkyl; n is an integer from 0 to 3; and m is 0o r2.

  这项发明涉及一种新颖的具有抗菌活性的哌啶衍生物，其化学式为（I），其中U和V中的一个代表N，另一个代表N或CH；M代表CH2CH2，CH=CH，CH(OH)CH(OH)，CH(OH)CH2，CH(NH2)CH2，COCH2或OCH2；R1代表烷基，卤代烷基，烷氧基，卤代烷氧基，卤素或氰基；R2代表氢或卤素；R3代表羧基，羧胺基，烷基氨基甲酰基，羟基，氨基甲酰氧基，2-四唑基或3-甲基-1,2,4-噁二唑-5-基；R4代表烷基，（C1-C4）烷氧基-(C1-C4）烷基，卤代烷基，烯烃基，芳基烷基，芳基-S(O)m-烷基，杂环芳基烷基，杂环芳基氨基甲酰基烷基，杂环芳基-S(O)m-烷基，CH2-CH=CH芳基或环烷基-S(O)m-烷基；n为0至3的整数；m为0或2。
• Ethanol or 1,2-Ethanediol Cyclohexyl Antibiotic Derivatives
  申请人：Hubschwerlen Christian

  公开号：US20090005368A1

  公开（公告）日：2009-01-01

  The invention relates to antibiotic ethanol or 1,2-ethanediol cyclohexyl derivatives of formula (I) wherein R1 represents (C 1 -C 4 )alkoxy; one or two of U, V, W and X represents) N and the remaining represent each independently CH or, in the case of V or X, may also represent CR a ; R a represents halogen; R 2 represents H or OH; A represents CH 2 , CO, CH 2 CH═CH or COCH═CH; D represents a phenyl group optionally substituted one or two times by halogen atoms, or D represents a group of the formula (II) in which Q is oxygen or sulphur; and to salts of these derivatives of formula (I).

  本发明涉及公式(I)的抗生素乙醇或1,2-乙二醇环己基衍生物，其中R1代表（C1-C4）烷氧基；U、V、W和X中的一个或两个代表N，其余各自独立地代表CH，或在V或X的情况下，也可以代表CRa；Ra代表卤素；R2代表H或OH；A代表CH2、CO、CH2CH═CH或COCH═CH；D代表苯基，该苯基可以选择地被卤素原子取代一次或两次，或D代表公式（II）中Q为氧或硫的基团；以及公式（I）的这些衍生物的盐。
• Ethanol or 1,2-ethanediol cyclohexyl antibiotic derivatives
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：US07820655B2

  公开（公告）日：2010-10-26

  The invention relates to antibiotic ethanol or 1,2-ethanediol cyclohexyl derivatives of formula (I) wherein R1 represents (C1-C4)alkoxy; one or two of U, V, W and X represents) N and the remaining represent each independently CH or, in the case of V or X, may also represent CRa; Ra represents halogen; R2 represents H or OH; A represents CH2, CO, CH2CH═CH or COCH═CH; D represents a phenyl group optionally substituted one or two times by halogen atoms, or D represents a group of the formula (II) in which Q is oxygen or sulphur; and to salts of these derivatives of formula (I).

  本发明涉及公式（I）的抗生素乙醇或1,2-乙二醇环己基衍生物，其中R1代表（C1-C4）烷氧基; U，V，W和X中的一个或两个代表N，其余各自独立地代表CH，或在V或X的情况下，也可以表示为CRa; Ra代表卤素; R2代表H或OH; A代表CH2，CO，CH2CH═CH或COCH═CH; D代表苯基，该苯基可以选修一次或两次卤素原子，或D代表公式（II）中Q为氧或硫的基团; 以及公式（I）的这些衍生物的盐。