RESUMO
A series of new methyl 6-deoxy-6-[N'-alkyl/aryl-N''-(benzothiazol-2-yl)]guanidino-alpha-D-glucopyranosides were obtained from the reaction of an alkyl/aryl amine in the presence of HgCl2 and sugar-thiourea derivatives, followed by the removal of protecting groups. The sugar-thiourea derivatives were obtained from the treatment of 2-aminobenzothiazole derivatives with methyl 2,3,4-tri-O-acetyl-6-deoxy-6-isothiocyanato-alpha-D-glucopyranoside in dry pyridine. Some of the synthesized guanidines displayed anti-influenza activity.
Assuntos
Antivirais/síntese química , Antivirais/farmacologia , Benzotiazóis/química , Glucosídeos/síntese química , Glucosídeos/farmacologia , Guanidina/química , Oxigênio/química , Alquilação , Animais , Antivirais/química , Linhagem Celular , Cristalografia por Raios X , Cães , Glucosídeos/química , Vírus da Influenza B/efeitos dos fármacos , Metilação , Modelos Moleculares , Estrutura Molecular , Tioureia/químicaRESUMO
A novel one-step method of preparing polysubstituted guanidinoglucosides using peracetylated methyl 6-deoxy-6-thioureidoglucosides as starting materials and employing HgO in combination with molecular sieves as an efficient catalyst is reported. The structures of three methyl 2,3,4-tri-O-acetyl-6-[N(2)-(benzothiazol-2-yl)-N(3)-(oxydi-1,2-ethandiyl)]guanidino-6-deoxy-alpha-d-glucopyranosides were unambiguously confirmed by X-ray crystallography. The methodology affords new compounds in good yields and also provides a promising route for the synthesis of carbamate-protected guanidines.
Assuntos
Glucosídeos/síntese química , Guanidina/química , Compostos de Mercúrio/química , Catálise , Cristalografia por Raios X , Glucosídeos/química , Estrutura MolecularRESUMO
A series of new N'-[N-(2,3,4-tri-O-acetyl-ß-d-xylopyranosyl)thiocarbamoyl]-2-[(1-aryl-1H-tetrazol-5-yl)sulfanyl]acetohydrazides 5a-5e were synthesized rapidly in high yields from 2-(1-aryl-1H-tetrazol-5-ylsulfanyl)acetohydrazides 3a-3e and 2,3,4-tri-O-acetyl-ß-d-xylopyranosyl isothiocyanate 4, then 5a-5e were converted to a series of new 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-ß-D-xylopyranosyl)-1,3,4-oxadiazole-2-amines 6a-6e and 5-(1-aryl-1H-tetrazol-5-ylsulfanylmethyl)-N-(2,3,4-tri-O-acetyl-ß-D-xylopyranosyl)-1,3,4-thiadiazole-2-amines 7a-7e, respectively under mercuric acetate/alcohol system or acetic anhydride/phosphoric acid system, then deacetylated in the solution of CH(3)ONa/CH(3)OH. All of the novel compounds were characterized by IR, (1)H NMR, (13)C NMR, MS and elemental analysis. The structures of compounds 2e, 3e, 5a and 5c have been determined by X-ray diffraction analysis. Some of the synthesized compounds displayed PTP1B inhibition and microorganism inhibition.