Synthesis And Properties Study Of Heterocycles Linked To Carbohydrate Residues

ABSTRACT This thesis consists of seven chapters. The first chapter is the review, which discusses the research background and the advances of the synthesis and properties study of heterocycles linked to carbohydrate residues. In chapter 2 By the nucleophilic substitution reaction of 6-O-tosyl-1,2:3,4-di-O- isopropylidene-a-D-galactopyranose with some substituted I ,2,4-triazole-3-thiols or 1,2.3 ,4-tetrazole-5-thio is, nine 6-S-(substituted triazoiy or tetrazolyl)- 1 ,2:3,4-di-O- isopropylidene-a-D-galactopyranoses were prepared in high yields. Their structu- res and configurations were established and analyzed by elemental analyse, IR, NMR,MS spectra data and conformational calculations. And the biological activities were tested. In chapter 3 Acetylation of N?(aldopyranosylainino) guanidines gave rise to N? per(O-acetylglycopyranosylamino)-N?N2,N3-triacetylguanidines in good yields. The acvlaminoguanidines prepared have been cyclized under mild conditions in NaOMe solution to afford 3-aniino-N?glycopyranosyl-5-methyl- IH- I ,2,4-triazoles.The structures of these pyranosyl nucleosides were discussed using 慔 and ?CNMR spectroscope and MS spectrometry and the cyclization mechanism was discussed. The biological activities were tested. In chapter 4 The cyano branched carbohydrates were obtained stereoselectively by nucleophilic addition of sodium cyanide to the I ,2:4,5-di-O-isopropyliene -f3-D- ervthro-2,3-hexodiulo-2,6-pyranose on application of phase transition catalysis met- hod. Then it reacted with sodium azide and the product acylated to afford the 1,3,4 - oxadiazole derivatives. The cyciization mechanism was discussed. The absolute configuration of the key intermediate of the acetylated cyano branched carbohydrate s were established by x-ray crystallographic analysis. All the new compounds were identified by IR, NMR, and elemental analyse. Some compounds were established by H-H COSY and DEPT. The biological activities of antitumor were tested. In chapter 5 1 ,2:4,5-di-O-isopropyliene -3-C-cyano-f3-D-ribo-hex-2-ulo pyranose reacted with NH,OH gave rise to the key intermediate3-C-aniidoxime derivative, then it reacted with acylation reagents to afford the 1 ,2,4-oxadiazole derivatives. The V cyclization mechanism was studied. The absolute configuration of compound 11 was established by x-ray crystallographic analysis. All the new compounds were identified by IR, NMR, MS and elemental analyse. Some compounds were establis- hed by H-H COSY and DEPT. The biological activities of antitunior were tested. In chapter 6 Reaction of l,2:4,5-di-O-isopropyliene -f3-D-erythro-2,3-hexodiulo- 2,6-pyranose 1 with aromatichydrazine afforded the aromatichydrazole 2a-f. Trea- tment of 2 with boiling acetic anhydride afforded crystalline products 7a-f stereoselectively. The structures were confirmed by the IR, NMR, MS and elemental analyse. The absolute configuration of compound 7a was established by x-ray crystallographic analysis. The cyclization mechanism was studied. The biological activities of 7a-f were tested. Among them, the compounds 7d, 7f were presented the obvious antitumor activities. These two ne抳 compounds have been applied for a national paten of china. In chapter 7 Treated with thiosemicarbazide, o-aminophenol to the ketosugar derivative 2 gave in good yields the corresponding spiro-derivatives 6,8. The new compounds...