title: A First Microwave-Assisted Synthesis of a New Class of Purine and Guanine Thioglycoside Analogs.
abstract: A first microwave-assisted synthesis of a new class of novel purine thioglycoside analogs from readily available starting materials has been described. The key step of this protocol is the formation of sodium pyrazolo[1,5-a]pyrimidine-7-thiolate and 7-mercaptopyrazolo[1,5-a]pyrimidine derivatives via condensation of 5-amino-1H-pyrazoles with sodium 2,2-dicyanoethene-1,1-bis(thiolate) salts or 2-(dimercaptomethylene)malononitrile, respectively, under microwave irradiation, followed by coupling with halo sugars to give the corresponding purine thioglycoside analogs. The obtained purines and purines thioglycosides derivatives were evaluated in vitro against lung (A549), colon (HCT116), liver (HEPG2), and prostate (PC3) cancer cell lines. Some of these compounds (5b, 5d, 5f, and 9a-d) exhibited little potency toward the four cell lines. On the other hand, compound 5a elicited higher cytotoxicity on both prostate (PC3) and colon (HCT116), respectively, while it was found moderate on lung (A549), and inactive on liver (HEPG2). Moreover, compound 5c was found moderate with LC50 values 52.0-88.9 μM for almost all the cell lines.
authors.affiliation: a Chemistry Department, Faculty of Science , Helwan University , Helwan , Cairo , Egypt.
authors.forename: Galal
authors.initials: G
authors.lastname: Elgemeie
authors.affiliation: b Green Chemistry Department , National Research Centre , Dokki , Giza , Egypt.
authors.forename: Mamdouh
authors.initials: M
authors.lastname: Abu-Zaied
authors.affiliation: a Chemistry Department, Faculty of Science , Helwan University , Helwan , Cairo , Egypt.
authors.forename: Ali
authors.initials: A
authors.lastname: Hebishy
authors.affiliation: a Chemistry Department, Faculty of Science , Helwan University , Helwan , Cairo , Egypt.|c Chemistry Department, Faculty of Science , Taibah University , Saudi Arabia.
authors.forename: Nermen
authors.initials: N
authors.lastname: Abbas
authors.affiliation: a Chemistry Department, Faculty of Science , Helwan University , Helwan , Cairo , Egypt.
authors.forename: Mai
authors.initials: M
authors.lastname: Hamed
mesh_terms: D000072283:A549 Cells; D000970:Antineoplastic Agents / Q000494:pharmacology; D004317:Doxorubicin / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006147:Guanine / Q000737:chemistry*; D045325:HCT116 Cells; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008872:Microwaves; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D011684:Purine Nucleosides; D013865:Thioglycosides; D006147:Guanine; D004317:Doxorubicin
keywords: Microwave synthesis; antimetabolites; ketene dithiolate salts; nucleoside analogs; purine thioglycoside analogs; thioglycosides