Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agents

Abstract

Synthesis of pyranopyrazolo N-glycoside and pyrazolopyranopyrimidine C-glycoside derivatives as promising antitumor and antimicrobial agentsAs a part of systematic investigation of the synthesis and biological activities of pyrazole analogues linked to various heterocyclic systems, a new series of pyrazolo-N-glycoside derivatives, pyrazolopyranopyrimidine and C-glycoside of pyrazolopyranotriazolo-pyrimidine derivatives was synthesized through the reaction of the key intermediateStructures of the newly synthesized compounds were elucidated by elemental microanalysis and spectroscopic methods. The compounds were subjected to in vitro antitumor evaluation using the MTT assay. N-(b-D-ribofuranosyl)-and N-(b-D-xylofuranosyl)-6{[(1E)-4-chlorophenyl)-methylene]amino}4-(4-fl orophenyl)-3-methyl-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile (6a,b) were the most active compounds against three human cancer cell lines. Also, most of the newly synthesized compounds exhibited high activity towards Gram-negative and Gram-positive bacteria. Compound 6a exhibited excellent activity towards bacteria compared to ofl oxacine as the reference drug.

One-Pot Microwave Synthesis of Pyrimido[4,5-b]quinoline and its C- and S-Glycosides with Anti-Inflammatory and Anticancer Activities

“…[29] In this study the synthetic pathways depicted in Schemes 1 and 2 outlines the chemistry of the present study. Thus, pyrimido- [4,5-b]quinoline as the starting materials 3a,b are easily prepared following the well established procedure reported in the literature.…”

Synthesis and antibacterial activity evaluation of N (7) position-modified balofloxacins

“…Modifiying groups were selected based upon the drug metabolism pathways in the human body, such as glycosylation, acetylation, and amino acidification (Ma et al, 2018). Sugar-substituted fluoroquinolones were reported previously and were not particularly potent (Hafez and El-Gazzar, 2015). Here, alkyl, aromatic, acetyl groups, partial amino acid moieties, and heterocyclic substituents such as triazole, which were used in antibacterial agents, were respectively introduced into balofloxacin.…”

One Pot Synthesis of Pyranopyrazole Using Sodium Lactate as an Efficient Catalyst

“…Pyranopyrazolescaffolds are reported for various biological activities such as analgesic, anti-inflammatory, 1 antibacterial, 2 anti-microbial, 3 andantitumor activity. 4 Many methods are reported for the synthesis of pyranopyrazoles involving the use of three or four component condensation using CeCl3, 5 InCl3, 6 La(NO3)3, 7 ionic liquids such as [(CH2)4SO3HMIM][HSO4], 8 [H-NMP][MeSO3], 9 cetyltrimethylammonium chloride, 10 amino acids such as glycine, 11 L-tyrosine, 12 nano-particles such as CuI, 13 Fe3O4, 14 Fe3O4@SiO2, 15 1,3,5-triazine-2,4,6triamine modified nano rice husk silica, 16 MgO, 17 ZnO, 18,19 and vitamin B1 on silica coated ferrite (Fe2O3@SiO2) nanoparticles. 20 Some heterogeneous catalysts like cerium (IV) carboxymethylcellulose, 21 acidic montmorillonite K-10 clay 22 are also documented for the one pot synthesis of pyranopyrazoles.…”