【药物名称】
化学结构式(Chemical Structure):
参考文献No.548642
标题:Carbonic anhydrase inhibitors: Synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route
作者:Scozzafava, A.; Briganti, F.; Mincione, G.; Menabuoni, L.; Mincione, F.; Supuran, C.T.
来源:J Med Chem 1999,42(18),3690
合成路线图解说明:

The condensation of 5-amino-1,3,4-thiadiazol-2-sulfonamide (I) with the protected guanidinoacetic acid (II) by means of EDC in acetonitrile gives the corresponding amide (III), which is then deprotected with HCl in hot dioxane.

合成路线图解说明:

The condensation of 5-amino-1,3,4-thiadiazol-2-sulfonamide (I) with the protected guanidinodipeptide (II) by means of EDC in acetonitrile gives the corresponding amide (III), which is then deprotected with HCl in hot dioxane.

合成路线图解说明:

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No.561675
标题:Carbonic anhydrase inhibitors. Synthesis of topically effective intraocular pressure lowering agents derived from 5-(omega-aminoalkylcarboxamido)-1,3,4-thiadiazole-2-sulfonamide
作者:Barboiu, M.; Supuran, C.T.; Menabuoni, L.; Scozzafava, A.; Mincione, F.; Briganti, F.; Mincione, G.
来源:J Enzym Inhib 1999,15(1),23
合成路线图解说明:

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No.561786
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?
作者:Borras, J.; Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C.T.
来源:Bioorg Med Chem 1999,7(11),2397
合成路线图解说明:

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No.563832
标题:Carbonic anhydrase inhibitors: Synthesis of membrane impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes
作者:Scozzafava, A.; Briganti, F.; Ilies, M.A.; Supuran, C.T.
来源:J Med Chem 2000,43(2),292
合成路线图解说明:

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No.574809
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
作者:Supuran, C.T.; Briganti, F.; Menabuoni, L.; Mincione, G.; Mincione, F.; Scozzafava, A.
来源:Eur J Med Chem 2000,35(3),309
合成路线图解说明:

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No.578646
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?
作者:Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C.T.
来源:J Med Chem 2000,42(14),2641
合成路线图解说明:

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No.803901
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
作者:Jitianu, A.; Ilies, M.A.; Scozzafava, A.; Supuran, C.T.
来源:Main Group Met Chem 1997,20147-153
合成路线图解说明:

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.

Drug Information Express,Drug R&D,Chemical Database,Patent Search.
Copyright © 2006-2024 Drug Future. All rights reserved.Contact Us