%0 Journal Article
%T Design, Synthesis, and In Vitro Antimicrobial Evaluation of Fused Pyrano[3,2-e]tetrazolo[1,5-c]pyrimidines and Diazepines
%A Sankari Kanakaraju
%A P. Sagar Vijay Kumar
%A Bethanamudi Prasanna
%A G. V. P. Chandramouli
%J ISRN Organic Chemistry
%D 2013
%R 10.1155/2013/635384
%X A series of novel pyranochromene-containing tetrazoles fused with pyrimidinethiones, pyrimidines, and diazepines 3a–f, 4a–f, and 5a–f were synthesized by condensation of the corresponding tetrazoles 2a–f with carbon disulfide, benzaldehyde, and 4-methoxy phenacyl bromide, respectively. The compound 2a–f was obtained by reaction of pyrano[3,2-c]chromenes 1a–f with sodium azide. The structures of the newly synthesized compounds 2a–f to 5a–f were established on the basis of their elemental analyses, IR, 1H NMR, 13C NMR, and mass spectral data. All of the title compounds were subjected to in vitro antibacterial testing against four pathogenic strains and antifungal screening against two fungi. Preliminary results indicate that some of them exhibited promising activities and that they deserve more consideration as potential antimicrobials. 1. Introduction Pyrano[3,2-c]chromene derivatives are a class of important heterocycles with a wide range of biological properties [1] such as spasmolytic, diuretic, anticoagulant, anticancer, and antianaphylactic activities [2–5]. Tetrazoles represent an important class of heterocyclic compounds with wide ranging applications [6]. The synthesis of novel tetrazole derivatives and the investigation of their chemical and biological behavior has gained more importance in the recent decades for biological and pharmaceutical reasons. They have found use in pharmaceuticals as lipophilic spacers and carboxylic acid surrogates, which improves oral absorption [7]. Their derivatives were reported to possess broad spectrum of biological activity in both medicinal and pharmaceutical areas such as antinociceptive [8], antibacterial [9], antifungal [10], anti-HIV, anticancer, immunosuppressive [11], anti-inflammatory [12] and antiulcer [13], antiproliferative [14], antiallergic [15], and analgesic [16] activities. On the other hand, pyrimidine scaffold was the base of many bioactive molecules such as antitubercular, antimicrobial [17], antiviral [18], antitumor [19, 20], anti-inflammatory, analgesic [21], antioxidant [22], antiproliferative [23], and antileishmanial agents [24]. Consequently, synthetic methodologies for synthesis of novel pyrimidines or pyrimidine fused compounds are of particular interests to organic and medicinal chemists. The diazepine family represents one of the most prominent classes of privileged scaffolds in the field of drugs and pharmaceuticals. These compounds are widely used as anticonvulsant, antianxiety, analgesic, sedative, antidepressive, and hypnotic agents [25–27]. In view of the abovementioned facts,
%U http://www.hindawi.com/journals/isrn.organic.chemistry/2013/635384/