The Chemistry of C-Nucleosides and Their Analogs I: C-Nucleosides of Hetero Monocyclic Bases

The construction of a novel series of enantiopure tetrahydrofuranyl 1,2,3-triazolyl C-nucleoside analogues utilizing click reaction of sugar derived tetrahydrofuranyl alkynes with various 'in house' synthesized sugar derived tetrahydrofuranyl azides and an adamantyl azide is described. The biological significance of the synthesized C-nucleosides was highlighted by evaluating them in vitro for anti-bacterial and anti-fungal activity, wherein a number of compounds were found to show excellent anti-bacterial activity and moderate anti-fungal activity.

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of tetrahydrofuranyl 1,2,3-triazolyl C-nucleoside analogues by ‘click’ chemistry and investigation of their biological activity

Reddy¹,

Saquib²,

Mishra³

et al. 2014

“…They differ from parent ribonucleosides only by the absence of the ring structure of the pentosyl residue due to the absence of one or more of the bonds of the pentose moiety to give an open-chain residue. [19][20][21][22][23] They have been reported to have valuable biological activities. [19][20][21][22][23] Sugar hydrazones of theophyllin-7-ylacetic acid were reported by Klosa 24a in 1958 and some of other reported sugar hydrazones have been found to possess antitumor, antibacterial and antiviral activities.…”

Section: Introductionmentioning

confidence: 99%

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

Mosselhi¹,

Abdallah²,

Metwally³

et al. 2010

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.

“…[2][3][4][5][6] Several compounds comprising a 1,3,4-oxadiazole nucleus exhibit various biological activities such as antifungal, 7,8 anti-inflammatory, 9 antibacterial, 10 anticonvulsive, 11 and serotonin antagonist activity. 12 Furthermore, the synthesis 13,14 of C-nucleosides and their acyclic 15,16 analogues received also attention of many investigators due to their documented biological activities. 17 Sugar moieties linked to these structures would enhance their penetration into cells and therefore, contribute to their activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new C-nucleosides by used l-arabinose and d-glucose

El-Farargy¹,

Ghonium²

2008

The reaction of L-arabinose with malonitrile yielded oxazoline 1, which on reaction with thioglycolic acid and acetyl chloride afforded the 4-oxothiazolyl β-L-arabinfurano oxazoline (2) and 1-cyanomethylcarboxamido-2-chloro-β-L-arabinose (3), respectively. The reaction of compound (1) with benzaldehyde led to the formation of oxazoline (4), which was reacted with cyanoacetamide to give compound (5). After treatement of glucose with phenylhydrazine, the compound was reacted with diethylmalonate to give the pyrazole derivative (7). The biological activity of the prepared compounds was investigated.