Drug Designing: Open Access
Open Access

Synthesis, characterization, antimicrobial and antioxidant activities of a (18)-annulene derivative incorporating three thienocoumarin fragments

9^th Annual Congress on Drug Design & Drug Formulation

October 19-20, 2017 Seoul, South Korea

Emmanuel Sopbue Fondjo, Kamal sorel Djeukoua Dimo, Joseph Tsemeugne, Jean-de-Dieu Tamokou, Jules Roger Kuiate, Kouamo Sylvian, Ngouanet Doriane, Chouna Jean Roudolphe, Nkeng-Efouet Alango Pepin, Teponno Remy Bertrand, Ngongang Djintchui Arnaud and Sondengam Beibam Lucas

University of Dschang, Cameroon
Technical University Munich, Germany
University of Yaounde I, Cameroon

Posters & Accepted Abstracts: Drug Des

Abstract :

To face the issue of global drug resistance, one of the solutions suggested by WHO is the search of new actives molecules, at low cost and that are easily accessible in order to discourage counter factors, who are partly responsible of the emergence of resistances. In this perspective, we investigate the possibilities of preparing new potentially bioactive diazo-compounds from fused 2-aminothiopene substrates such as compound (2). In this work, we used the third version of the Gewald reaction to synthesize 3-amino-4H-thieno [3, 4-c][1]benzopyran-4-one (2). This compound was diazotized with sodium nitrite in concentrated sulfuric acid at 0-5 �?ºC. The in situ formed 4-oxo-4H-thieno[3,4-c]chromene-3-diazonium sulfate (3) in the coupling reactions involving the parent 2-aminothiophene (2) and various phenolic and aryl aminesâ�?�? couplers, readily undergoes homocyclotrimerization at low temperature to afford in fairly good yield the first ever reported 18 member ring heteroaromatic holigomer (4). Compound 4 was fully characterized by its IR, 1H-NMR, 13C-NMR and HRMS spectral data. The HMBC and HSQC techniques were used to ascertain the structural assignments. A comparative study on the antimicrobial and antioxidant activities of compounds 1, 2 and 4 was carried out to assess the SAR due to the transformations (from 1 to 4 via 2) on the tested compounds. It was found that compounds 2 and 4 were respectively the most active compounds against bacteria (MIC=64-256 �?¼g/ml) and yeasts (MIC=32-128 �?¼g/ml). Compound 4 also showed high radical-scavenging activities and ferric reducing power when compared with vitamin C and BHT used as reference antioxidants.