ChemInform Abstract: Synthesis of New [1,3,4]Thiadiazolo[3,2‐a]thieno[2,3‐d]pyrimidinone Derivatives with Antiinflammatory Activity.

Abstract

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Synthesis of Some Thienopyrimidine Derivatives

“…Many thienopyrimidines are found to exhibit a variety of biological activities, including antiinflammatory [1,2], antimicrobial [3] and analgesic [4] properties, inhibition of cancer cell proliferation [5], antagonism of α 1 adrenoceptors [6] and prevention of cartilage destruction in articular diseases [7]. In continuation with our previous work on the title compounds [8,9], we report herein the synthesis of a series of novel thienopyrimidine derivatives.…”

“…Thienylthiourea derivatives 2a-h were prepared by condensation of the amino esters 1a-c with alkyl or aryl isothiocyanates, either by heating at reflux or under microwave irradiation [8,9,13]; the latter method afforded higher yields of the desired products in a shorter time. 4 p -Cl-C 6 H 4 c (CH 2 ) 4 (CH 2 ) 3 CH 3 d (CH 2 ) 2 N(CH 3 )CH 2 C 6 H 5 e (CH 2 ) 2 N(CH 3 )CH 2 p -Cl-C6H4 f (CH 2 ) 2 N(CH 3 )CH 2 (CH 2 ) 3 CH 3 g (CH 2 ) 5 C 6 H 5 h (CH 2 ) 5 p -Cl-C6H4 R 1 R 2 R 3 a (CH 2 ) 4 C 6 H 5 b (CH 2 ) 4 p -Cl-C 6 H 4 c (CH 2 ) 4 (CH 2 ) 3 CH 3 d (CH 2 ) 2 N(CH 3 )CH 2 p -Cl-C 6 H 4 e (CH 2 ) 2 N(CH 3 )CH 2 (CH 2 ) 3 CH 3 f (CH 2 ) 5 C 6 H 5 g (CH 2 ) 5 p -Cl-C 6 H 4 a (CH 2 vi) p -Cl-C 6 H 4 NCS, acetonitrile, reflux, 20h iii) phenylthiourea, EtOH, microwave (MW), 20 sec. vii) R-X, EtOH, reflux, 1-8h iv) KOH, EtOH, reflux, 2-6h Compounds 2a,d were also prepared by condensation of the amino esters 1a,b with phenylthiourea under microwave irradiation.…”

Anti-inflammatory and immunomodulatory effects of RDV-8 [C18H22N2O2S (ethyl 1-butyl-6-methyl-2-phenyl-4-thioxo-1,4-dihydropyrimidine-5-carboxylate)] in a rat model of induced pleurisy and in vitro lymphoproliferation

“…Besides the antineoplastic activity previously described (Shimizu et al 1995), many biological properties were attributed to this class of compounds, such as antiviral (Saladino et al 2002), anti-hypertensive (Salimbeni et al 1995), hypoglycemic (Madhavan et al 2002), anticonvulsive (White et al 2004), anti-histaminic (Temple et al 1979) and anti-inflammatory (Modica et al 2000). In recent researches, pyrimidines derivatives and similar substances containing a carbonyl group in the position of an amino group present in the C 4 heterocyclic ring would further increase the pharmacological potential, besides presenting low toxicity (Anjos et al 2008).…”

Novel Selective 5-HT3 Receptor Ligands: Facile Generation Methods for 2-Amino- and 4-Aminopyrido[4’,3’:4,5]thieno[2,3-d]pyrimidines

“…The precipitated product was filtered off, washed with water, dried, and crystallized from ethanol as pale yellow crystals. Yield 82%, m. p. > 300 • C -IR (KBr):ν = 3380 -3285 (NH 2 -5,6,7,8-tetrahydropyrido[4',3':4,5]thieno [2,3-d] [1,3]thiazine-7-carboxylate (6) A suspension of compound 5 (6.0 g, 13 mmol) in 98% sulfuric acid (60 ml) and few drops of water was stirred at 40 -50 • C for 10 h. The resultant clear solution was slowly poured on ice-water and sodium bicarbonate (300 ml). The precipitate was collected, washed with ethanol and dried to give compound 6.…”