Six novel thiosemicarbazones containing sugar and thiosemicarbazide moieties were synthesized by a five-step procedure using D-galactose and D-xylose as the starting materials and the corresponding glycosyl isothiocya...Six novel thiosemicarbazones containing sugar and thiosemicarbazide moieties were synthesized by a five-step procedure using D-galactose and D-xylose as the starting materials and the corresponding glycosyl isothiocyanates as the intermediates. The target compounds were characterized by IR, ^1H NMR, and elemental analysis. The coupliug constants between H1 and H2 in the sugar rings, all fail within the range of J = 9. 2-10.0 Hz, confirming the β-configuration of the compounds.展开更多
The practical synthesis of pseudonucleosides incorporating thiourea derivative by coupling of monosaccharides （D-glucose and D-galactose） per-O-acetylated glycosyl isothiocyanates and different heterocyclic hydrazid...The practical synthesis of pseudonucleosides incorporating thiourea derivative by coupling of monosaccharides （D-glucose and D-galactose） per-O-acetylated glycosyl isothiocyanates and different heterocyclic hydrazide derivatives is reported. The method involves the preparation ofper-O-acetylated glycosyl isothiocyanates from per-O-acetylated sugars （two-step synthesis）, which couple with heterocyclic hydrazides from amines to give thiourea-linked pseudonucleosides. All newly synthesized pseudo-nucleosides were assayed against human lung cancer-cell lines （PG） and human liver cancer-cell lines （BEL-7402） in vitro. The 6,6-dimethyl-benzothiophen-3-carbo-hydrazide-4-one pseudonucleosides showed moderate inhibition against these two cancer-cell lines with ECs0 from 22.8 to 76.4 mM and from 54.9 to 82.4 mM, respectively. And the other compounds did not demonstrate any significant cytotoxicity even at concentrations up to 200 mM.展开更多
基金supported by the National Natural Science Foundation of China(Grant No.20462006)Xinjiang Key Laboratory of Plant Resources & Natural Products Chemistry
基金Supported by the Program for New Century Excellent Talents in University(No. NCET-04-04649)the National Natural Sci-ence Foundation of China(No 20475030)the Start-up Fund for Doctoral Scientific Research of Qingdao University of Science andTechnology.
文摘Six novel thiosemicarbazones containing sugar and thiosemicarbazide moieties were synthesized by a five-step procedure using D-galactose and D-xylose as the starting materials and the corresponding glycosyl isothiocyanates as the intermediates. The target compounds were characterized by IR, ^1H NMR, and elemental analysis. The coupliug constants between H1 and H2 in the sugar rings, all fail within the range of J = 9. 2-10.0 Hz, confirming the β-configuration of the compounds.
文摘The practical synthesis of pseudonucleosides incorporating thiourea derivative by coupling of monosaccharides （D-glucose and D-galactose） per-O-acetylated glycosyl isothiocyanates and different heterocyclic hydrazide derivatives is reported. The method involves the preparation ofper-O-acetylated glycosyl isothiocyanates from per-O-acetylated sugars （two-step synthesis）, which couple with heterocyclic hydrazides from amines to give thiourea-linked pseudonucleosides. All newly synthesized pseudo-nucleosides were assayed against human lung cancer-cell lines （PG） and human liver cancer-cell lines （BEL-7402） in vitro. The 6,6-dimethyl-benzothiophen-3-carbo-hydrazide-4-one pseudonucleosides showed moderate inhibition against these two cancer-cell lines with ECs0 from 22.8 to 76.4 mM and from 54.9 to 82.4 mM, respectively. And the other compounds did not demonstrate any significant cytotoxicity even at concentrations up to 200 mM.
