methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate | 333782-30-2

• 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: methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate
• 英文别名: (3R,4R)-methyl 4-(3-(6-methoxyquinolin-4-yl)-3-oxopropyl)piperidine-3-carboxylate；methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)-3-oxopropyl]piperidine-3-carboxylate
• CAS: 333782-30-2
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: SGFHXWJMYMNURF-DYVFJYSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate 在 sodium tetrahydroborate 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4R)-methyl 4-(3-hydroxy-3-(6-methoxyquinolin-4-yl)propyl)-1-(2-(thiophen-2-ylthio)ethyl)-piperidine-3-carboxylate
  参考文献：
  名称：

  Selenophene-Containing Inhibitors of Type IIA Bacterial Topoisomerases

  摘要：

  We investigated compounds related to the previously reported anti-staphyloccocal agent AVE6971 in an effort to attenuate inhibition of hERG potassium channel current that has been noted for this and related antibacterial drug classes. While most modifications of the original thiophene group compromised antibacterial activity, one selenophene analogue displayed (i) improved activity against the primary target enzyme DNA gyrase, (ii) similar activities against a panel of MRSA clinical isolates, and (iii) reduced hERG channel inhibition.

  DOI：

  10.1021/jm2002124
• 作为产物：
  描述：

  (3R,4R)-1-tert-butyl 3-methyl 4-(3-(6-methoxyquinolin-4-yl)-3-oxopropyl)piperidine-1,3-dicarboxylate 在 磷酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate
  参考文献：
  名称：

  磷酸水溶液作为氨基丁酸叔丁酯，酯和醚脱保护的温和试剂

  摘要：

  磷酸水溶液（85重量％）是用于脱保护的有效，环境友好的试剂叔丁基氨基甲酸酯，叔丁基酯，和叔-丁基醚。反应条件温和，在其他酸敏感基团（包括氨基甲酸CBZ，氮杂环丁烷，苄基和甲基酯，TBDMS和甲基苯基醚）存在下，具有良好的选择性。反应的温和性在克拉霉素衍生物4的合成中得到了进一步证明，其中叔酸在环状氨基甲酸酯，内酯，缩酮，乙酸酯和可差向异构的甲基酮官能团存在下，除去丁酯。该反应保留了底物的立体化学完整性。反应产率高，后处理方便。

  DOI：

  10.1021/jo061377b

文献信息

• SUBSTITUTED HETEROCYCLIC DERIVATIVES AND THEIR PHARMACEUTICAL USE AND COMPOSITIONS
  申请人：BRICKNER Steven Jospeh

  公开号：US20080280879A1

  公开（公告）日：2008-11-13

  Compounds of the general Formula I, wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , Y 1 , n, m, p and q are defined as above, their preparation and their use as antimicrobial agents.

  通式I的化合物，其中X1、X2、X3、X4、X5、X6、X7、R1、R2、R4、R5、R6、R7、R8、R9、R10、Y1、n、m、p和q如上所定义，它们的制备以及它们作为抗微生物药剂的用途。
• Quinolylpropylpiperidine derivatives, their preparation and the compositions which comprise them
  申请人：Aventis Pharma S.A.

  公开号：US06403610B1

  公开（公告）日：2002-06-11

  Quinolylpropylpiperidine derivatives of formula (I) which are particularly advantageous antimicrobial agents, their compositions, and their use.

  配方（I）的喹诺啉丙基哌啶衍生物，特别有优势的抗微生物药剂，其组成成分和用途。
• Quinolylpropylpiperidine derivatives, intermediates and compositions containing them, and preparation therefor
  申请人：——

  公开号：US20040087619A1

  公开（公告）日：2004-05-06

  Quinolylpropylpiperidine derivatives of general formula (I) in which R 1 is hydrogen or fluorine, R 2 is carboxyl, carboxymethyl or hydroxymethyl, R 3 is alkyl substituted either with phenylthio optionally substituted with halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, carboxyl, alkyloxycarbonyl, cyano or amino, or with cycloalkylthio (3 to 7 members) optionally substituted with halogen or trifluoromethyl, or with heteroarylthio (5 to 6 members and 1 to 4 heteroatoms chosen from N, O and S), optionally substituted with halogen, hydroxyl, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, carboxyl, alkyloxycarbonyl, cyano or amino or R 3 is propargyl substituted by phenyl or heteroaryl as defined above and R 4 is alkyl, alkenyl-CH 2 — or alkynyl-CH 2 —, cycloalkyl or cycloalkylalkyl, in their various isomeric forms, separate or as mixtures, and also their salts, their preparation process and intermediates and the compositions containing them. These novel derivatives are potent antibacterial agents. 1

  通式为（I）的喹诺啉基丙基哌嗪衍生物，其中R1为氢或氟，R2为羧基、羧甲基或羟甲基，R3为烷基，其上取代基为苯硫基，可选取代基为卤素、羟基、烷基、烷氧基、三氟甲基、三氟甲氧基、羧基、烷氧羰基、氰基或氨基，或为环烷基硫基（3至7个成员），可选取代基为卤素或三氟甲基，或为杂环芳基硫基（5至6个成员，1至4个杂原子选自N、O和S），可选取代基为卤素、羟基、烷基、烷氧基、三氟甲基、三氟甲氧基、羧基、烷氧羰基、氰基或氨基，或R3为乙炔基，其上取代基为上述定义的苯基或杂环芳基，且R4为烷基、烯基-CH2-或炔基-CH2-、环烷基或环烷基烷基，在其各种异构体形式中，单独或混合存在，以及它们的盐、制备过程和中间体以及含它们的组合物。这些新颖的衍生物是有效的抗菌剂。
• Quinolylpropylpiperidine derivatives, preparation process and intermediates, and compositions including them
  申请人：Aventis Pharma S.A.

  公开号：US20040058919A1

  公开（公告）日：2004-03-25

  Quinolylpropylpiperidine derivatives of general formula (I) in which: R 1 is NH 2 , alkylamino, dialkylamino, hydroxyamino, alkyl(alkyloxy)amino or alkyloxyamino, R 2 is a carboxyl, carboxymethyl or hydroxymethyl radical, R 3 is alkyl (1 to 6C) substituted by phenylthio which can itself carry 1 to 3 substituents selected from halogen, OH, alkyl, alkyloxy, CF 3 , OCF 3 , COOH, alkyloxycarbonyl, CN and NH 2 , by cycloalkylthio (3 to 7 members) or by heteroarylthio (5 to 6 members) comprising 1 to 4 heteroatoms selected from N, S and O and optionally itself substituted [by halogen, OH, alkyl, alkyloxy, CF 3 , OCF 3 , ═O, COOH, alkyloxycarbonyl, CN or NH 2 ] or R 3 is propargyl substituted by phenyl which can itself carry 1 to 3 substituents selected from halogen, OH, alkyl, alkyloxy, CF 3 , OCF 3 , COOH, alkyloxycarbonyl, CN and NH 2 or substituted by cycloalkyl comprising 3 to 7 members or substituted by 5- to 6-membered heteroaryl comprising 1 to 4 heteroatoms chosen from N, O or S and optionally itself substituted by halogen, OH, alkyl, alkyloxy, CF 3 , OCF 3 , ═O, COOH, alkyloxycarbonyl, CN or NH 2 , and R 4 is alkyl (1 to 6C), alkenyl-CH 2 —, alkynyl-CH 2 — (3 to 7C), cycloalkyl or (cycloalkyl)alkyl, in their diastereoisomeric forms or their mixtures, and their pharmaceutically acceptable salts. These novel derivatives are particularly advantageous antimicrobial agents. 1

  通式（I）的喹诺啉基丙基哌啶衍生物，其中：R1为NH2，烷基氨基，二烷基氨基，羟基氨基，烷基（烷氧基）氨基或烷氧基氨基；R2为羧基，羧甲基或羟甲基基团；R3为烷基（1至6C），其上取代苯硫基，该苯硫基本身可以携带1至3个取代基，所选取代基为卤素，OH，烷基，烷氧基，CF3，OCF3，COOH，烷氧羰基，CN和NH2，或为环烷基硫基（3至7个成员）或杂环芳基硫基（5至6个成员），其中包括1至4个异原子，所选异原子为N，S和O，且该环烷基硫基或杂环芳基硫基本身可以被卤素，OH，烷基，烷氧基，CF3，OCF3，═O，COOH，烷氧羰基，CN或NH2取代；或R3为丙炔基，其上取代苯基，该苯基本身可以携带1至3个取代基，所选取代基为卤素，OH，烷基，烷氧基，CF3，OCF3，COOH，烷氧羰基，CN和NH2，或为取代的环烷基（3至7个成员）或取代的5至6成员杂环芳基，其中包括1至4个异原子，所选异原子为N，O或S，且该取代的环烷基或取代的杂环芳基本身可以被卤素，OH，烷基，烷氧基，CF3，OCF3，═O，COOH，烷氧羰基，CN或NH2取代；R4为烷基（1至6C），烯基-CH2-，炔基-CH2-（3至7C），环烷基或（环烷基）烷基，以其对映异构体形式或其混合物形式及其药学上可接受的盐。这些新的衍生物是特别有优势的抗微生物剂。
• Substituted Heterocyclic Derivatives and Their Pharmaceutical Use and Compositions
  申请人：Brickner Steven Joseph

  公开号：US20110092480A1

  公开（公告）日：2011-04-21

  Compounds of the general Formula I, wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , Y 1 , n, m, p and q are defined as above, their preparation and their use as antimicrobial agents.

  通式I的化合物，其中X1、X2、X3、X4、X5、X6、X7、R1、R2、R4、R5、R6、R7、R8、R9、R10、Y1、n、m、p和q的定义如上所述，它们的制备及其作为抗微生物剂的用途。