Synthesis of some novel pyrimidine, thiophene, coumarin, pyridine and pyrrole derivatives and their biological evaluation as analgesic, antipyretic and anti-inflammatory agents

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, 13 C NMR and mass spectrometry techniques. Compounds 11 and 19 have promising as analgesic and antipyretic activities.

RMD86, a thiophene derivative, promotes antinociceptive and antipyretic activities in mice

“…For this, the yeast-induced pyrexia model was used, and RMD86 presented antipyretic activity at 30-120 min. This result is in accordance with another study performed by El-Sharkawy & AlBratty (2018) [55], where thiophene derivatives demonstrated antinociceptive and antipyretic activities lasting up to 4 h.…”

Structural and theoretical studies of 4-chloro-2-methyl-6-oxo-3,6-dideuteropyrimidin-1-ium chloride (d 6)

“…Pyrimidines represent one of the most active classes of compounds, possessing a wide spectrum of biological activities such as significant in vitro activity against unrelated DNA and RNA viruses including polio herpes viruses, and diuretic, antitumor, anti-HIV, and cardiovascular (Kappe, 1993) activity. In addition to this, various analogs of pyrimidines have been found to possess antibacterial (Sharma et al, 2004;Prakash et al, 2004;Botta et al, 1992;Cieplik et al, 2015), antifungal (Agarwal et al, 2000;Oliver et al, 2016), antileishmanial (Ram et al, 1992;Alptuzun et al, 2013), anti-inflammatory (Amir et al, 2007;Sondhi et al, 2008), analgesic (Vega et al, 1990; Gupta et al, 2011), anti- hypertensive (Hannah & Stevens, 2003;Rana et al, 2004;Alam et al, 2010), antipyretic (Smith & Kan, 1964;El-Sharkawy et al, 2018), antiviral (Balzarini & McGuigan, 2002;Nasr & Gineinah, 2002), antidiabetic (Lee et al, 2005;Reddy et al, 2019), antiallergic (Juby et al, 1979;Gupta et al, 1995), anticonvulsant (Gupta et al, 1994;Shaquiquzzaman et al, 2012), antioxidant (Krivonogov, et al, 2001;Abu-Hashem et al, 2010, antihistaminic (Prasad & Rahaman, 2008;Rahaman et al, 2009), herbicidal (Nezu et al, 1996;Li et al, 2018), and anticancer activities (Abu-Hashem et al, 2010Xie et al, 2009;Kaldrikyan et al, 2000;Mohamed et al, 2...…”

Promising Lead Compounds in the Development of Potential Clinical Drug Candidate for Drug-Resistant Tuberculosis

“…Coumarins act as intermediate in the synthesis of chromenes, coumarones, furocoumarins, and 2-acylresorcinols [57]. Coumarin and most of its derivatives possess a wide range of therapeutic effects such as antimicrobial [58][59][60][61][62][63], antioxidant [64][65][66], antidepressant [67][68][69], anti-inflammatory [70][71][72][73][74], antitumor [75][76][77][78][79], antinociceptive [80][81][82], antiasthmatic [83][84][85], anti-Alzheimer [85][86][87][88], antipyretic [89,90], and antihyperlipidemic [91][92][93][94] activities. A substantial effort has been made in past few decades to explore coumarin-based entities as antitubercular drug, which is agile against clinically approved therapeutic targets reflecting terrific therapeutic outcomes.…”