Rapid microwave-enhanced synthesis of C5-alkynyl pyranonucleosides as novel cytotoxic antitumor agents

Dimopoulou, Athina; Manta, Stella; Kiritsis, Christos; Gkaragkouni, Dimitra-Niki; Papasotiriou, Ioannis; Balzarini, Jan; Komiotis, Dimitri

doi:10.1016/j.bmcl.2012.12.092

Cited by 15 publications

(10 citation statements)

References 17 publications

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“…[14][15][16][17][18][19][20][21][22][23][24] In our previous investigations, we demonstrated that base-modified pyranonucleosides rank among the most potent glycogen phosphorylase (GP) [25,26] and thymidylate synthase (TS) [27] inhibitors, and were endowed with a pronounced cytostatic and antiviral action. [28] As a continuation of this research and based on the pharmacological properties of thiopurine analogues, we now report the synthesis and biology of new thiopurine pyranonucleosides via glycosylation of mercaptopurine and thioguanine pyranonucleosides bearing D-glucose, D-galactose, D-xylose, D-mannose, and D-lyxose as sugar moiety.…”

Section: Introductionmentioning

confidence: 98%

Synthesis of Novel Thiopurine Pyranonucleosides: Evaluation of Their Bioactivity

Dimopoulou

Manta

Parmenopoulou

et al. 2015

Nucleosides, Nucleotides and Nucleic Acids

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We report the synthesis of novel thiopurine pyranonucleosides. Direct coupling of silylated 6-mercaptopurine and 6-thioguanine with the appropriate pyranoses 1a-e via Vorbrüggen nucleosidation, gave the N-9 linked mercaptopurine 2a-e and thioguanine 4a-e nucleosides, while their N-7 substituted congeners 10a-e and 7a-e, were obtained through condensation of the same acetates with 6-chloro and 2-amino-6-chloropurines, followed by subsequent thionation. Nucleosides 3a-e, 5a-e, 8a-e, and 11a-e were evaluated for their cytostatic activity in three different tumor cell proliferative assays.

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Section: Introductionmentioning

confidence: 98%

Synthesis of Novel Thiopurine Pyranonucleosides: Evaluation of Their Bioactivity

Dimopoulou

Manta

Parmenopoulou

et al. 2015

Nucleosides, Nucleotides and Nucleic Acids

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“…anticonvulsant activity, 3-(2-chloro-3-[trifluoromethylfuran]phenyl)-1-(5-methyfuran-2-yl) prop-2-en-1-one and 3-(3,4,5-trifluorophenyl)-1-(5methyfuran-2-yl)prop-2-en-1-one for their microbial activities were reported using microwave irradiation and in all cases, high yields were obtained (Kulathooran and Dhamodaran, 2015;Shakil et al, 2013;Dimopoulou et al, 2013;Pastore et al, 2013). This study was designed to compare the efficiency of conventional method of synthesizing 2hydroxychalcone derivatives with solvent-free grinding technique and microwave-assisted method.…”

Section: Amole Lk; Bello Ia; Oyewale Aomentioning

confidence: 99%

Synthesis, characterization and biological evaluation of three derivatives of 2-hydroxychalcones

Amole¹,

Bello²,

Oyewale³

2019

Journal of Applied Sciences and Environmental Management

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In an attempt to compare the efficiency of classical method of synthesizing 2-hydroxychalcones with mechanical and microwave-assisted methods, three derivatives of 2-hydroxychalcone, (E)-3-(4'-methyphenyl)-1-(2hydroxyphenyl)prop-2-en-1-one, (E)-3-(4'-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one and (E)-3-(2'chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one; were synthesized by a modified Claisen-Schmidt condensation of appropriate acetophenones with various substituted aromatic aldehydes and successfully characterized using spectroscopic analysis. Microwave-assisted and mechanical methods were found to be more efficient in terms of eco-friendly reaction conditions, simple reaction procedure, short reaction time and excellent yields of the product where the reactions took not more than 3 mins to complete under microwave irradiation and not more than 30 mins to complete using mechanical grinding, while it took up to 6 hrs for some reactions to complete under classical method (heating). The synthesized compounds were evaluated for their antimicrobial activity against S. aureus, S. pyogenes, S. feacalis, C. albicans and C. krusei by the agar diffusion method. The compounds exhibited varying degrees of inhibition against the tested pathogens with (E)-3-(2'-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one, that has the 2'-chlorophenyl moiety as the Bring displaying moderate inhibition against the tested pathogens [MIC = 50 µg/ml] with the exception of S. feacalis.

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“…In view of the above observations and as a continuation of our long-term interest in glucopyranosyl analogues as antitumor/antiviral agents and potent enzyme inhibitors (Parmenopoulou et al, 2014;Dimopoulou et al, 2013;Manta et al, 2012;Kantsadi et al, 2012), it was envisaged that compounds bearing a glucopyranosyl moiety linked with various aralkyl and aralkenyl groups (Somsák et al, 2008a, b) via the pharmacophore linkers NHCO and NHCONHCO would be endowed with pronounced antitumor activity. We hereby report the facile synthesis and biological properties of novel acetylated as well as fully deprotected N-acyl-b-D-glucopyranosylamines (3a-f, 4af) and ureas (6a-f, 7a-f), respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel N-acyl-β-d-glucopyranosylamines and ureas as potential lead cytostatic agents

et al. 2016

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Novel classes of acetylated and fully deprotected N-acyl-b-D-glucopyranosylamines and ureas have been synthesized and biologically evaluated. Acylation of the per-O-acetylated b-D-glucopyranosylurea (5), easily prepared via its corresponding phosphinimine derivative, by zinc chloride catalyzed reaction of the corresponding acyl chlorides RCOCl (a-f) gave the protected N-acyl-b-Dglucopyranosylureas (6a-f), in acceptable-to-moderate yields. Subsequent deacetylation of analogues 6a-f under Zemplén conditions afforded the fully deprotected derivatives 7a,b,d,e,f, while the desired urea 7c was formed after treatment of 6c with dibutyltin oxide. All protected and unprotected compounds were examined for their cytotoxic activity in different L1210, CEM and HeLa tumor cell lines and were also evaluated against a broad panel of DMA and RNA viruses. Derivative 7c exhibited cytostatic activity against the three evaluated tumor cell lines (IC 50 9-24 lL) and might be the basis for the synthesis of structure-related derivatives with improved cytostatic potential. Only analogue 6f weakly but significantly inhibited the replication of parainfluenza-3 virus, Sindbis virus and Coxsackie virus B4 in cell cultures at concentrations of 45-58 lM.

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Rapid microwave-enhanced synthesis of C5-alkynyl pyranonucleosides as novel cytotoxic antitumor agents

Cited by 15 publications

References 17 publications

Synthesis of Novel Thiopurine Pyranonucleosides: Evaluation of Their Bioactivity

Synthesis of Novel Thiopurine Pyranonucleosides: Evaluation of Their Bioactivity

Synthesis, characterization and biological evaluation of three derivatives of 2-hydroxychalcones

Synthesis of novel N-acyl-β-d-glucopyranosylamines and ureas as potential lead cytostatic agents

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