Paper
SYNTHESIS AND SPECTRAL ANALYSIS OF AN ARRAY OF NOVEL 4-(4-MORPHOLINOPHENYL)-6-ARYL-PYRIMIDIN-2-AMINES
Published Dec 1, 2010 ยท J. Thanusu, Kanagarajan, M. Gopalakrishnan
Journal of The Chilean Chemical Society
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Abstract
ABSTRACT An array of newly synthesized novel 4-(4-morpholinophenyl)-6-arylpyrimidin-2-amines (20-28) are synthesized from the respective (E)-1-4-morpholinophenyl)-3-aryl-prop-2-en-1-ones (11-19) by the treatment of guanidine nitrate in refluxing ethanol catalyzed by lithium hydroxide and characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR ( 1 H & 13 C) spectroscopic data. Keywords: 1-(4-morpholinophenyl) ethanone; (E)-1-4-morpholinophenyl)-3-aryl-prop-2-en-1-ones; 4-(4-morpholinophenyl)-6-arylpyrimidin-2-amines; Guanidine nitrate; Synthesis. e-mail: profmgk@yahoo.co.in INTRODUCTION Pyrimidines are the basic nucleus in nucleic acids and have been associ-ated with a number of biological activities. Some notable biological activity of pyrimidine derivatives include adenosine receptor antagonists [1], kinase inhibitors [2], analgesic [3], anti-inflammatory [3], inhibitors of cyclin-De-pendent kinases 1 and 2 [4], calcium channel antagonist [5], antihistaminic [6], antitubercular [7] activities. Substituted aminopyrimidine nuclei are com-mon in marketed drugs such as anti-atherosclerotic aronixil, anti-histaminic thonzylamine, anti-anxielytic buspirone, anti-psoriatic enazadrem, and other medicinally relevant compounds.Morpholine is a simple heterocyclic compound with a great industrial importance. It is used as anticorrosive agent and as chemical intermediate: catalyst, solvent, antioxidant, in the production of various pharmaceuticals and pesticides. 4-Phenyl morpholine derivatives [8] are reported to possess anti-microbial, anti-inflammatory and central nervous system activities. Linezolide (commercially available antimicrobial) also possess a 4-phenyl-morpholine substituent. They are reported to exert a number of important physiological activities such as antidiabetic [9], antiemetic [10], platelet aggregation inhibi-tors, antihyperlipoproteinemics [9], bronchodilators, growth stimulats [11] and antidepressants [12]. These were also used in the treatment of inflammatory diseases, pain, migraine and asthma [13].Recently, we exploited the synthesis of 6-aryl-1,2,4,5-tetrazinane-3-thiones [14], fused indazoles [15], 3,4-dihydropyrimidin-2(1
This study synthesized novel 4-(4-morpholinophenyl)-6-aryl-pyrimidin-2-amines, which show potential as anti-inflammatory, antimicrobial, and central nervous system stimulants.
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