新产品编号:459289

合成路线:Removal of acetyl group of acetazolamide (I) by refluxing with concentrated HCl affords 5-amino-1,3,4-thiadiazole-2-sulfonamide (II),which is then coupled to Boc-protected beta-alanine (III) by means of EDC and Et3N in acetonitrile to yield the protected derivative (IV).Finally,(IV) is treated with TFA in CH2Cl2 for Boc removal to provide the target compound.Alternatively,conversion of (II) into the desired compound can be achieved by first condensation of (II) with 3-phthalimidopropionyl chloride (V) in pyridine to give the N-phthalimido derivative (VI),which is then subjected to hydrazinolysis and finally treated with TFA.

参考文献标题:Carbonic anhydrase inhibitors.Synthesis of topically effective intraocular pressure lowering agents derived from 5-(omega-aminoalkylcarboxamido)-1,3,4-thiadiazole-2-sulfonamide
文献作者:Barboiu,M.; Supuran,C.T.; Menabuoni,L.; Scozzafava,A.; Mincione,F.; Briganti,F.; Mincione,G.
参考来源:J Enzym Inhib 1999,15(1),23


合成路线:Removal of acetyl group of acetazolamide (I) by refluxing with concentrated HCl affords 5-amino-1,3,4-thiadiazole-2-sulfonamide (II),which is then coupled to Boc-protected beta-alanine (III) by means of EDC and Et3N in acetonitrile to yield the protected derivative (IV).Finally,(IV) is treated with TFA in CH2Cl2 for Boc removal to provide the target compound.Alternatively,conversion of (II) into the desired compound can be achieved by first condensation of (II) with 3-phthalimidopropionyl chloride (V) in pyridine to give the N-phthalimido derivative (VI),which is then subjected to hydrazinolysis and finally treated with TFA.

参考文献标题:Carbonic anhydrase inhibitors: Synthesis of water-soluble,topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: Is the tail more important than the ring?
文献作者:Borras,J.; Scozzafava,A.; Menabuoni,L.; Mincione,F.; Briganti,F.; Mincione,G.; Supuran,C.T.
参考来源:Bioorg Med Chem 1999,7(11),2397


合成路线:Removal of acetyl group of acetazolamide (I) by refluxing with concentrated HCl affords 5-amino-1,3,4-thiadiazole-2-sulfonamide (II),which is then coupled to Boc-protected beta-alanine (III) by means of EDC and Et3N in acetonitrile to yield the protected derivative (IV).Finally,(IV) is treated with TFA in CH2Cl2 for Boc removal to provide the target compound.Alternatively,conversion of (II) into the desired compound can be achieved by first condensation of (II) with 3-phthalimidopropionyl chloride (V) in pyridine to give the N-phthalimido derivative (VI),which is then subjected to hydrazinolysis and finally treated with TFA.

参考文献标题:Carbonic anhydrase inhibitors: Synthesis of membrane impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes
文献作者:Scozzafava,A.; Briganti,F.; Ilies,M.A.; Supuran,C.T.
参考来源:J Med Chem 2000,43(2),292


合成路线:Removal of acetyl group of acetazolamide (I) by refluxing with concentrated HCl affords 5-amino-1,3,4-thiadiazole-2-sulfonamide (II),which is then coupled to Boc-protected beta-alanine (III) by means of EDC and Et3N in acetonitrile to yield the protected derivative (IV).Finally,(IV) is treated with TFA in CH2Cl2 for Boc removal to provide the target compound.Alternatively,conversion of (II) into the desired compound can be achieved by first condensation of (II) with 3-phthalimidopropionyl chloride (V) in pyridine to give the N-phthalimido derivative (VI),which is then subjected to hydrazinolysis and finally treated with TFA.

参考文献标题:Carbonic anhydrase inhibitors - Part 78.Synthesis of water-soluble sulfonamides incorporating beta-alanyl moieties,possessing long lasting-intraocular pressure lowering properties via the topical route
文献作者:Supuran,C.T.; Briganti,F.; Menabuoni,L.; Mincione,G.; Mincione,F.; Scozzafava,A.
参考来源:Eur J Med Chem 2000,35(3),309


合成路线:Removal of acetyl group of acetazolamide (I) by refluxing with concentrated HCl affords 5-amino-1,3,4-thiadiazole-2-sulfonamide (II),which is then coupled to Boc-protected beta-alanine (III) by means of EDC and Et3N in acetonitrile to yield the protected derivative (IV).Finally,(IV) is treated with TFA in CH2Cl2 for Boc removal to provide the target compound.Alternatively,conversion of (II) into the desired compound can be achieved by first condensation of (II) with 3-phthalimidopropionyl chloride (V) in pyridine to give the N-phthalimido derivative (VI),which is then subjected to hydrazinolysis and finally treated with TFA.

参考文献标题:Carbonic anhydrase inhibitors.Synthesis of water-soluble,topically effective intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties.Is the tail more important than the ring?
文献作者:Scozzafava,A.; Menabuoni,L.; Mincione,F.; Briganti,F.; Mincione,G.; Supuran,C.T.
参考来源:J Med Chem 2000,42(14),2641


合成路线:Removal of acetyl group of acetazolamide (I) by refluxing with concentrated HCl affords 5-amino-1,3,4-thiadiazole-2-sulfonamide (II),which is then coupled to Boc-protected beta-alanine (III) by means of EDC and Et3N in acetonitrile to yield the protected derivative (IV).Finally,(IV) is treated with TFA in CH2Cl2 for Boc removal to provide the target compound.Alternatively,conversion of (II) into the desired compound can be achieved by first condensation of (II) with 3-phthalimidopropionyl chloride (V) in pyridine to give the N-phthalimido derivative (VI),which is then subjected to hydrazinolysis and finally treated with TFA.
参考文献标题:Complexes with biologically active ligands.Part 8.Synthesis and carbonic anhydrase inhibitory activity of 5-benzoylamido- and 5-(3-nitrobenzoylamido)-1,3,4-thiadiazole-2-sulfonamide and their metal complexes
文献作者:Jitianu,A.; Ilies,M.A.; Scozzafava,A.; Supuran,C.T.
参考来源:Main Group Met Chem 1997,20147-153