title: Synthesis and spectral characterization of new bis(2-(pyrimidin-2-yl)ethoxy)alkanes and their pharmacological activity.
abstract: The pyrimidine nucleus is an important component of nucleic acids (DNA and RNA) and vitamins (B(2)  and folic acid). It is evident from the literature that pyrimidine derivatives possess a wide spectrum of biological activities such as antioxidant, anticancer, antibacterial, and anti-inflammatory activities. On the basis of diverse biological activities, we attempted to synthesize a series of novel bis(2-(pyrimidin-2-yl)ethoxy)alkanes 5a-j in four steps with good yields. 2-Chloropyrimidine (1) was reacted with diethyl malonate in the presence of sodium hydride in dry dimethyl formamide to yield the intermediate diethyl 2-(pyrimidin-2-yl)malonate (2), which on further reaction with sodium chloride and dimethyl sulfoxide yielded ethyl 2-(pyrimidin-2-yl)ethanoate (3). Reduction with sodium borohydride (NaBH(4) ) resulted in the formation of 2-(pyrimidin-2-yl)ethanol (4). This was further reacted with various dibromoalkanes to obtain the title compounds 5a-j. In this current study, we evaluated the antioxidant properties of the title compounds using four in vitro test systems: the 2,2-diphenyl-2-picrylhydrazyl radical-, superoxide radical-, and hydroxyl radical-scavenging assays, and the anti-lipid peroxidation activity test. The title compounds showed promising antioxidant activity when compared to butylated hydroxytoluene. The potency of their antioxidant activity was mainly influenced by the alkyl fragment attached to 2-(pyrimidin-2-yl)ethanol. The ethyl and butyl fragments linked to oxygen led to increased antioxidant activity of the title compounds (i.e., 5b and 5d) in all our in vitro assays.
authors.affiliation: Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh, India.
authors.forename: Vangavaragu Jhansi
authors.initials: VJ
authors.lastname: Rani
authors.forename: Raghavendra
authors.initials: R
authors.lastname: Aminedi
authors.forename: Kishore
authors.initials: K
authors.lastname: Polireddy
authors.forename: Kanala
authors.initials: K
authors.lastname: Jagadeeswarareddy
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002084:Butylated Hydroxytoluene / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical / Q000379:methods; D066298:In Vitro Techniques; D015227:Lipid Peroxidation / Q000187:drug effects; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D044366:Transition Temperature
chemical_list: D000473:Alkanes; D000975:Antioxidants; D011743:Pyrimidines; D002084:Butylated Hydroxytoluene