Abstract
Pyrimidine derivative 3 was afforded through the reaction of compound (1) with 5-ureidohydantion (2). Product 3 underwent a cyclization to produce fused pyrimidine derivative 7, although the latter product 7 was synthesized through one step via the reaction of compound (1) with 5-ureidohydantion (2) using another catalyst. Compound 3 was oriented to react with cyclic ketones 8a,b in the presence of elemental sulfur, salicylaldehyde (10), aryldiazonium chlorides 12a,b and ω-bromo-4-methoxy- acetophenone (14), which afforded, fused thiophene derivatives 9a,b, coumarin derivative 11, arylhdrazono derivatives 13a,b and 4-methoxyphenyl butenyl derivative 15, respectively. The latter product 15 was reacted with either potassium cyanide (16a) or potassium thiocyanide (16b) to form cyano and thiocyano derivatives 17a,b, respectively. Compound 17a underwent further cyclization to afford pyridopyrimidine derivative 19. Compound 15 was reacted with either hydrazine (20a) or phenylhydrazine (20b) to produce hydrazo derivatives 21a,b and these products were cyclize to produce pyrrole derivatives 23a,b. Finally, 5-ureidohydantion (2) was reacted with compounds 24a,b,c to afford pyrimidine derivatives 25a,b,c. The structures of the synthesized compounds were confirmed using IR, 1 H NMR, 13C NMR and mass spectrometry techniques. Compounds 11 and 19 have promising as analgesic and antipyretic activities.
Highlights
A series of studies was introduced to discover that hydantoin derivatives, important heterocyclic compounds, act as antioxidant agents (Gus’kov et al, 2004)
Compound 3 was oriented to react with cyclic ketones 8a,b in the presence of elemental sulfur, salicylaldehyde (10), aryldiazonium chlorides 12a,b and ω-bromo-4-methoxy- acetophenone (14), which afforded, fused thiophene derivatives 9a,b, coumarin derivative 11, arylhdrazono derivatives 13a,b and 4-methoxyphenyl butenyl derivative 15, respectively
The goals of this work were to study the possibility of using compounds 2 and 3 in heterocyclic synthesis to produce the pyridopyrimidine derivative 7; thiophene derivatives 9a,b; coumarin derivative 11; pyrimidine derivatives 13,15,17a,b,21a,b; pyridine derivative 19; pyrazole derivatives 23a,b and iminopyrimidine derivatives 25a,b,c, as well as biologically evaluate these compounds for analgesic, antipyretic and anti-inflammatory activities
Summary
A series of studies was introduced to discover that hydantoin derivatives, important heterocyclic compounds, act as antioxidant agents (Gus’kov et al, 2004). Imidazolidine-2,4 dione derivatives are specific biologically active compounds and act as antiproliferative agents (Reddy et al, 2010), hypoglycemic, aldose reductase inhibitor agents (Iqbal et al, 2015) and Bcl-2 inhibitors (Wang et al, 2015). Pyridopyrimidine derivatives have a wide variety of biological properties, including antileishmanial (Agarwal et al, 2005) and antitubercular activities (Horvati et al, 2015; Rajesh et al, 2011). Fused thiophene derivatives have antitumor activity (Dallemagne et al., 2003) and pyrimidine derivatives containing the coumarin moiety have analgesic and anti-pyretic effects (Keri et al, 2010). In this article we aimed to improve and discover the analgesic, antipyretic and anti-inflammatory activities of synthesized compounds
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