3-氯磺酰基-4-甲氧基苯甲酸乙酯 | 262589-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氯磺酰基-4-甲氧基苯甲酸乙酯
• 英文名称: 3-chlorosulfonyl-4-methoxybenzoic acid ethyl ester
• 英文别名: ethyl 3-chlorosulfonyl-4-methoxybenzoate；Ethyl 3-(chlorosulfonyl)-4-methoxybenzoate
• CAS: 262589-79-7
• 化学式: C₁₀H₁₁ClO₅S
• mdl: MFCD10485886
• 分子量: 278.713
• InChiKey: RMXGNRJELOOOAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氯磺酰基-4-甲氧基苯甲酸乙酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 3-mercapto-4-methoxy-benzoic acid ethyl ester
  参考文献：
  名称：

  Imidazole Inhibitors of Cytokine Release:  Probing Substituents in the 2 Position

  摘要：

  Novel 2,4,5-trisubstituted imidazole derivatives were prepared as potential anticytokine agents. Thirty-seven compounds were tested on their ability to inhibit the release of tumor necrosis factor-a (TNF-alpha and interleukin-1beta (IL-beta) from peripheral blood mononuclear cells (PBMC) or human whole blood. SARs (structure activity relationships) for substituents-at the 4 and 5 position of the imidazole core were similar to those described for other inhibitors of cytokine. release and p38 MAP (mitogen-activated protein) kinase. Starting from benzylsulfanyl imidazole 2b (IC50 p(38), 4.0 muM; TNF-alpha, 1.1,muM; IL-1beta, 0.38,muM), the contribution of substituents at the 2 Position to enzyme inhibitory and cellular activity of test compounds was investigated. This strategy led to the identification of compound 2q (IC50 p38, 0.63 muM; TNF-alpha, 0.90 muM; IL-1beta, 0.04,muM), which was 6-10 times more potent than the initial lead 2b with respect to inhibition of p38 and IL-1beta release and equipotently inhibited TNF-alpha release.

  DOI：

  10.1021/jm020873z
• 作为产物：
  描述：

  茴香酸乙酯 在 氯磺酸 作用下， 以 四氯化碳 为溶剂， 生成 3-氯磺酰基-4-甲氧基苯甲酸乙酯
  参考文献：
  名称：

  [DE] 2-THIO-SUBSTITUIERTE IMIDAZOLDERIVATE UND IHRE VERWENDUNG IN DER PHARMAZIE
  [EN] 2-THIO-SUBSTITUTED IMIDAZOLE DERIVATIVES AND THEIR USE IN PHARMACEUTICS
  [FR] DERIVES D'IMIDAZOL 2-THIO-SUBSTITUES ET LEUR UTILISATION DANS LE DOMAINE PHARMACEUTIQUE

  摘要：

  这项发明涉及式(I)的2-硫代取代咪唑衍生物，其中残基R1、R2、R3和m具有描述中所指定的含义。根据本发明的化合物具有免疫调节和/或细胞因子释放抑制作用，因此适用于治疗与免疫系统紊乱相关的疾病。

  公开号：

  WO2004018458A1

文献信息

• 2-arylalkylthio -imidazoles, 2-arylalkenyl -thio -imidazoles and 2-arylalkinyl -thio -imidazoles as anti -inflammatory substances and substances inhibiting the release of cytokine
  申请人：Merckle GmbH

  公开号：US06432988B1

  公开（公告）日：2002-08-13

  The invention relates to 4-heteroaryl-5-phenylimidazole derivatives having 2-arylalkylthio, 2-arylalkenylthio and 2-arylalkynylthio substitution, of the general formula I: in which Ar is a phenyl radical, Het is a hetero aromatic radical, A is an alkylene chain, R1 is an alkylthio, alkylsulfinyl, alkylsulfonyl, sulfonamido or alkylcarbonyl group and R2 is an alkyl, hydroxyl, alkoxy, alkoxycarbonyl, sulfonamido, carboxyl, nitro or aminocarbonyl group or a halogen atom. n can be 1 or 2 and m is 0 to 2. The compounds according to the invention show antiinflammatory activity.

  该发明涉及具有2-芳基烷硫基，2-芳基烯基硫基和2-芳基炔基硫基取代的4-杂环芳基-5-苯基咪唑衍生物，其一般式为I： 其中Ar是苯基基团，Het是杂环芳基基团，A是烷基链，R1是烷硫基，烷砜基，烷砜基，磺胺基或烷基羰基基团，R2是烷基，羟基，烷氧基，烷氧羰基，磺胺基，羧基，硝基或氨基羰基基团或卤原子。n可以是1或2，m为0至2。根据该发明的化合物表现出抗炎活性。
• [DE] 2-THIO-SUBSTITUIERTE IMIDAZOLDERIVATE UND IHRE VERWENDUNG IN DER PHARMAZIE<br/>[EN] 2-THIO-SUBSTITUTED IMIDAZOLE DERIVATIVES AND THEIR USE IN PHARMACEUTICS<br/>[FR] DERIVES D'IMIDAZOL 2-THIO-SUBSTITUES ET LEUR UTILISATION DANS LE DOMAINE PHARMACEUTIQUE
  申请人：MERCKLE GMBH

  公开号：WO2004018458A1

  公开（公告）日：2004-03-04

  Die Erfindung betrifft 2-Thio-substituierte Imidazolderivate der Formel (I) worin die Reste R1, R2, R3 und m die in der Beschreibung angegebene Bedeutung besitzen. Die erfindungsgemässen Verbindungen besitzen eine immunmodulierende und/oder die Cytokinfreisetzung hemmende Wirkung und sind daher geeignet zur Behandlung von Erkrankungen, die mit einer Störung des Immunsystems im Zusammenhang stehen.

  这项发明涉及式(I)的2-硫代取代咪唑衍生物，其中残基R1、R2、R3和m具有描述中所指定的含义。根据本发明的化合物具有免疫调节和/或细胞因子释放抑制作用，因此适用于治疗与免疫系统紊乱相关的疾病。
• US6432988B1
  申请人：——

  公开号：US6432988B1

  公开（公告）日：2002-08-13
• Imidazole Inhibitors of Cytokine Release:  Probing Substituents in the 2 Position
  作者：Stefan A. Laufer、Hans-Günther Striegel、Gerd K. Wagner

  DOI：10.1021/jm020873z

  日期：2002.10.1

  Novel 2,4,5-trisubstituted imidazole derivatives were prepared as potential anticytokine agents. Thirty-seven compounds were tested on their ability to inhibit the release of tumor necrosis factor-a (TNF-alpha and interleukin-1beta (IL-beta) from peripheral blood mononuclear cells (PBMC) or human whole blood. SARs (structure activity relationships) for substituents-at the 4 and 5 position of the imidazole core were similar to those described for other inhibitors of cytokine. release and p38 MAP (mitogen-activated protein) kinase. Starting from benzylsulfanyl imidazole 2b (IC50 p(38), 4.0 muM; TNF-alpha, 1.1,muM; IL-1beta, 0.38,muM), the contribution of substituents at the 2 Position to enzyme inhibitory and cellular activity of test compounds was investigated. This strategy led to the identification of compound 2q (IC50 p38, 0.63 muM; TNF-alpha, 0.90 muM; IL-1beta, 0.04,muM), which was 6-10 times more potent than the initial lead 2b with respect to inhibition of p38 and IL-1beta release and equipotently inhibited TNF-alpha release.