Synthesis, structure and antimicrobial evaluation of new derivatives of theophylline sugar hydrazones

Abstract

Condensation of 7-ethyl-8-hydrazinotheophylline 1 with aldohexoses 2-4 and aldopentoses 5,6 by heating in an aqueous ethanolic solution and in the presence of a catalytic amount of acetic acid gives the corresponding hitherto unknown aldehydo-sugar (7-ethyl-8-theophyllinyl)hydrazones 7-11. The structures of the sugar hydrazones 7-11 were confirmed by their elemental analyses and spectral (IR, 1 H NMR and FAB-MS) data. Acetylation of the sugar hydrazones 7-11 with acetic anhydride in pyridine at room temperature gave the corresponding poly-O-acetyl derivatives 12-16. Attempted dehydrogenative cyclization of the products 7-11 and 12-16 using various conditions did not afford the corresponding acyclo C-nucleosides (R= sugar or R`= acetylated sugar) 18. On the other hand, the reaction of 7-11 or 12-16 with bromine in acetic acid and sodium acetate afforded 8-bromo-7-ethyltheophylline 17. The structural elucidation of products is reported and also some of the products were screened for their antimicrobial activity.

Synthesis of some novel N5‐sulfonylated and N1‐alkyated pyrazole derivatives and their antimicrobial activity in conjunction with molecular docking study

“…[14] Moreover, 5-amino-1H-pyrazoles considered as a starting material for building pyrazolo-fused ring systems in medicinal field, such as pyrazolopyrimidines, [15][16][17][18] pyrazolopyridines, [19] and pyrazolotriazines. [20,21] Owing to the above mention of the importance of 5-aminopyrazoles and as extension to our work to synthesize heterocyclic ring systems of interest biological activity, [22][23][24][25][26][27][28][29][30][31] we report herein the synthetic route of chemical modification of 5-aminopyrazoles, which can serve as a promising source of bioactive small molecules.…”

Design, Synthesis of New Pyrazoles and Chromenes as ERK‐2 Inhibitors, Apoptosis inducers and Cell cycle interrupters Based on Thiophene‐Chalcone Scaffold

“…[62] In addition, they could act as analgesic [63] and agricultural functions such as herbicidals, [64] molluscicidal, [65] insecticidal, [66] rodenticial activity [67] and they possess other medicinal properties. [68,69] As previously stated, in line with our interest in research program for the development of innovative techniques to the synthesis of molecules with predicted biological activity, [68][69][70][71][72][73][74][75][76][77][78][79] this paper highlights the fact that heterocycles contain thiophene exhibiting remarkable antitumor activity, [80][81][82][83] as thiophene derivatives have a significant anti-breast cancer activity. [84] Moreover, the heterocycle of thiophene is known as "wonder heterocycle" due to its being applicable in medicinal chemistry, and there are many marketed pharmaceutical drugs that contain thiophene nucleus such as tioconazole, etizolam, nocodazole, tenidap tipepidine and tiquizium bromides (Figure 1).…”

Synthesis, Identification and Biological Activity of Some New Chalcone derivatives from 8-Chlorotheophylline

“…In therapy, 8-CTh is used in combination with antihistamines in order to enhance their action against travel sickness and other hearing labyrinth diseases 4 . In this work prepared some derivatives from 8-CTh by chalcone reaction.…”