Methyl 3-methoxy-4-[(1-methyl-6-nitro-4-oxoquinolin-2-yl)-methylsulfonyloxymethyl]benzoate | 188244-71-5

• 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 3-methoxy-4-[(1-methyl-6-nitro-4-oxoquinolin-2-yl)-methylsulfonyloxymethyl]benzoate
• CAS: 188244-71-5
• 化学式: C₂₁H₂₀N₂O₉S
• 分子量: 476.464
• InChiKey: XOZOEXMUYRDREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methyl 3-methoxy-4-[(1-methyl-6-nitro-4-oxoquinolin-2-yl)-methylsulfonyloxymethyl]benzoate 在 palladium on activated charcoal N-甲基吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 、 三氟乙酸 为溶剂， 反应 73.0h， 生成 cyclopentyl N-[2-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methyl-4-oxoquinolin-6-yl]carbamate
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new cysLT1 receptor antagonists

  摘要：

  This paper describes the synthesis and pharmacological evaluation of three series of compounds 4a-b, 13a-k and 19, structurally related to the known potent cysLT(1) receptor antagonists RG-12553, ICI-204219 and ONO-1078, respectively. The common structural feature of these new series is the presence of a 4-quinolone nucleus acting as a template for substitution of the aromatic nucleus present in the prototype antagonists. We describe the evolution of these series leading to antagonists with potency at nanomolar concentrations in vitro.

  DOI：

  10.1016/s0223-5234(97)83282-5
• 作为产物：
  描述：

  4-溴甲基-3-甲氧基苯甲酸甲酯 在 manganese(IV) oxide 、 Amberlite carbonate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 19.75h， 生成 Methyl 3-methoxy-4-[(1-methyl-6-nitro-4-oxoquinolin-2-yl)-methylsulfonyloxymethyl]benzoate
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new cysLT1 receptor antagonists

  摘要：

  This paper describes the synthesis and pharmacological evaluation of three series of compounds 4a-b, 13a-k and 19, structurally related to the known potent cysLT(1) receptor antagonists RG-12553, ICI-204219 and ONO-1078, respectively. The common structural feature of these new series is the presence of a 4-quinolone nucleus acting as a template for substitution of the aromatic nucleus present in the prototype antagonists. We describe the evolution of these series leading to antagonists with potency at nanomolar concentrations in vitro.

  DOI：

  10.1016/s0223-5234(97)83282-5

文献信息

• [EN] QUINOLONE SULFONIMIDES HAVING LEUKOTRIENE-ANTAGONISTIC ACTION<br/>[FR] SULFIMIDES DE QUINOLONE AYANT UNE ACTION ANTAGONISTE SUR LES LEUCOTRIENES
  申请人：LABORATORIOS MENARINI S.A.

  公开号：WO1997005114A1

  公开（公告）日：1997-02-13

  (EN) The present invention relates to novel quinolone sulfonimides of formula (I), wherein the substituent containing A is bound at the 5-, 6- or 7-position; the substituent containing COHNSO2 is bound at the 1- or 2-position of the 4-quinolone ring; R1 is bound at the 1- or 2-position of the 4-quinolone ring and is hydrogen, alkyl, -OH, -OCH3, -CH2X, X is -OH, -OCH3 or -COOR8, R8 being hydrogen or alkyl; R2 is hydrogen, fluorine, chlorine, alkyl or -OCH3; R3 is hydrogen, fluorine, chlorine, alkyl or -OCH3; R4 is hydrogen, fluorine, chlorine, or -OCH3; R5 is hydrogen or methyl; R6 is alkyl, cycloalkyl or phenylalkyl; R7 is hydrogen, alkyl, -OCH3 or -CH2X; A is oxygen, methylene or -NR9-; R9 is hydrogen or methyl. Said compounds having a leukotriene-antagonistic activity and they can be used as antiinflammatory and antiallergic agents or in the treatment of cardiovascular diseases.(FR) La présente invention se rapporte à de nouveaux sulfimides de quinolone de formule (I), dans laquelle le substituant contenant A est lié au niveau de la position 5-, 6- ou 7-; le substituant contenant CONHSO2 est lié au niveau de la position 1- ou 2- du cycle de 4-quinolone; R1 est lié au niveau de la position 1- ou 2- du cycle de 4-quinolone et représente hydrogène, alkyle, -OH, -OCH3, -CH2X, X représente -OH, -OCH3 ou -COOR8, R8 représentant hydrogène ou alkyle; R2 représente hydrogène, fluor, chlore, alkyle ou -OCH3; R3 représente hydrogène, fluor, chlore, alkyle ou -OCH3; R4 représente hydrogène, fluor, chlore, alkyle ou -OCH3; R5 représente hydrogène ou méthyle; R6 représente alkyle, cycloalkyle ou phénylalkyle; R7 représente hydrogène, alkyle, -OCH3 ou -CH2X; A représente oxygène, méthylène ou -NR9-; R9 représente hydrogène ou méthyle. Lesdits composés possèdent une activité antagoniste sur les leucotriènes et peuvent être utilisés en tant qu'agents anti-inflammatoires et anti-allergiques ou dans le traitement de maladies cardio-vasculaires.
• Synthesis and pharmacological evaluation of new cysLT1 receptor antagonists
  作者：R Griera、M Armengol、A Reyes、M Alvarez、A Palomer、F Cabré、J Pascual、M.L. Garcia、D Mauleón

  DOI：10.1016/s0223-5234(97)83282-5

  日期：1997.7

  This paper describes the synthesis and pharmacological evaluation of three series of compounds 4a-b, 13a-k and 19, structurally related to the known potent cysLT(1) receptor antagonists RG-12553, ICI-204219 and ONO-1078, respectively. The common structural feature of these new series is the presence of a 4-quinolone nucleus acting as a template for substitution of the aromatic nucleus present in the prototype antagonists. We describe the evolution of these series leading to antagonists with potency at nanomolar concentrations in vitro.