NOBEX-AA-007
Chemical Name: 2-Hydroxy-5-[4-[N-(4-hydroxysuccinyl)sulfamoyl]phenylazo]benzoic acid
项目整合开发状态: Preclinical
项目研究机构: Nobex (Originator)
合成路线:The condensation of 4-nitrobenzenesulfonamide (I) with 4-chloro-4-oxobutyric acid methyl ester (II) in refluxing pyridine gives 4-(4-nitrobenzenesulfonamido)-4-oxobutyric acid methyl ester (III),which is reduced with Fe and NH4Cl in methanol/water to yield the corresponding 4-amino derivative (IV).The diazotization of (IV) with NaNO2 and HCl affords the diazonium salt (V),which is condensed with 2-hydroxybenzoic acid (VI) to provide the azo compound (VII).Finally,this compound is hydrolyzed with NaOH to the target succinamic acid derivative.
📌 参考资料/链接：
参考文献标题:5-ASA derivs.having anti-inflammatory and antibiotic activity and methods of treating diseases therewith
文献作者:Ekwuribe,N.N.; Malson,E.; Riggs-Sauthier,J.(Nobex Corp.)
参考来源:US 6458776; WO 0218330
📄 详细内容
合成路线:The condensation of 4-nitrobenzenesulfonamide (I) with 4-chloro-4-oxobutyric acid methyl ester (II) in refluxing pyridine gives 4-(4-nitrobenzenesulfonamido)-4-oxobutyric acid methyl ester (III),which is reduced with Fe and NH4Cl in methanol/water to yield the corresponding 4-amino derivative (IV).The diazotization of (IV) with NaNO2 and HCl affords the diazonium salt (V),which is condensed with 2-hydroxybenzoic acid (VI) to provide the azo compound (VII).Finally,this compound is hydrolyzed with NaOH to the target succinamic acid derivative.
合成路线:The diazotization of 2-(4-aminophenyl)acetic acid (I) by means of NaNO2 and HCl gives the diazonium salt (II),which is then condensed with 2-hydroxybenzoic acid (III) to provide the target azocompound.
参考文献标题:Synthesis and activity of novel 5-aminosalicylic acid (5-ASA)-containing prodrugs for the treatment of inflammatory bowel disease
文献作者:Riggs-Sauthier,J.A.; Malson,E.; Harris,M.; Myung,S.; Liddle,R.; Ekwuribe,N.
参考来源:224th ACS Natl Meet (Aug 18 2002,Boston) 2002,Abst MEDI 305