Synthesis of n-aminoglycosides derived from alkaloid cytisine, their biological activity and crystal structure of N-(β-D-galactopyranosyl)cytisine

Abstract

Optimal conditions were found for the synthesis of a number of new N-aminoglycosides of the alkaloid cytisine, using commercially available monosaccharides, namely, D-glucose, D-galactose, D-xylose, and L-arabinose. X-ray structural analysis indicated an absolute -anomeric configuration of N-(-D-galactopyranosyl)cytisine in the crystalline state. The comparative cytotoxicity of cytisine and some of its N-aminoglycosides was determined.

Maillard Reaction Products with Anti-Tobacco Mosaic Virus Activities Generated in Processed Thermopsis lanceolata R. Br. Seed Extract

“…Interestingly, compounds 1 – 4 possessed three undescribed dimerization patterns containing cytisine, while compounds 5 and 6 represented the first example of addition products of cytisine and 5,6-dihydroxy-4-hexanolide (Figure ). In addition, compound 7 was identified as N -(β- d -glucopyranosyl)­cytisine . Further biological studies showed that some compounds exhibited strong anti-tobacco mosaic virus (TMV) activities.…”

Synthesis of Some New Heterocycles Derived from Ethyl 7‐Amino‐3‐(3‐methyl‐5‐oxo‐1‐phenyl‐2‐pyrazolin‐4‐yl)‐5‐aryl‐5H‐thiazolo[3,2‐a]pyrimidine‐6‐carboxylate of Biological Importance

“…The formation of a new fused heterocyclic ring is an important task for heterocyclic chemistry from various points of view. The reactions of thiazolo[3,2‐ a ]pyrimidines have attracted the attention of many chemists and used them in the synthesis of different heterocycles [1–15] possessing biological [10–14] and medicinal activities [15]. These observations in continuation with our general interest in these compounds led us to examine the chemistry of pyrazolinyl thiazolopyrimidine carboxylate to be used as starting material for the synthesis of novel thiazolopyrimidines and thiazolopyrimidopyrimidines bearing pyrazolone moiety, which have biological activities.…”

Synthesis and biological activity of 3,4-dihydropyrimidin-2-thione aminomethylene derivatives based on the alkaloid cytisine

“…Among these, compounds with types of biological activity that are uncharacteristic of cytisine itself are constantly being discovered. Until now many cytisine derivatives with various heterocylic groups such as coumarin [2,3]; 1,2,3-triazole [4]; 1,2,4-thiadiazole [5]; 1,3-thiazoline [6]; 2,5-dimercapto-1,3,4-thiadiazole [7]; barbituric acid [8]; pyridine [9]; 1,4-dihydropyridine [10]; and phenothiazine [11] were prepared.The Mannich reaction, which is widely used in organic chemistry to synthesize a variety of practically important compounds, is a convenient method for preparing new N-derivatives of cytisine in addition to the broadly used nucleophilic substitution and addition reactions of cytisine [2][3][4][5][6][7][9][10][11].The starting synthons for preparing new N-heterocyclic cytisine derivatives were 3,4-dihydropyrimidin-(1H)-2-thione derivatives, which were obtained via three-component condensation using a Biginelli reaction. The number of publications on the chemistry of 4-aryl-3,4-dihydropyrimidin-2-ones and 4-aryl-3,4-dihydropyrimidin-2-thiones has recently increased significantly in the scientific literature.…”

“…The Mannich reaction, which is widely used in organic chemistry to synthesize a variety of practically important compounds, is a convenient method for preparing new N-derivatives of cytisine in addition to the broadly used nucleophilic substitution and addition reactions of cytisine [2][3][4][5][6][7][9][10][11].…”

“…Among these, compounds with types of biological activity that are uncharacteristic of cytisine itself are constantly being discovered. Until now many cytisine derivatives with various heterocylic groups such as coumarin [2,3]; 1,2,3-triazole [4]; 1,2,4-thiadiazole [5]; 1,3-thiazoline [6]; 2,5-dimercapto-1,3,4-thiadiazole [7]; barbituric acid [8]; pyridine [9]; 1,4-dihydropyridine [10]; and phenothiazine [11] were prepared.…”