Gollapudi Ravi Kumar1,2, Chandra Rao Dasireddy3,4, Ravi Varala5, Vijay Kotra6, Hari Babu Bollikolla1. 1. Department of Chemistry, Acharya Nagarjuna University, Guntur, Andhra Pradesh India. 2. Department of Chemistry, Government Degree College, Husnabad, Telangana India. 3. CSIR-Indian Institute of Chemical Technology (IICT), Hydearabad, Telangana India. 4. Retention Chromatography & Chemicals Pvt. Ltd., Secunderabad, Telangana India. 5. Scrips Pharma, Hyderabad, Telangana India. 6. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Quest International University Perak, Ipoh, Negeri Perak Malaysia.
Abstract
A series of nine methyl sulphones ( 3a -3 i ) starting from the aldehydes ( 1a-1i ) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols ( 2a-2i ) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF 3 .Et 2 O in acetic acid medium at room temperature for about 2-3 h. The reaction conditions are simple, yields are high (85%-95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1 H, 13 C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.
A series of nine methyl sulphones ( 3a -3 i ) starting from the n class="Chemical">aldehydes ( 1a-1i ) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols ( 2a-2i ) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF 3 .Et 2 O in acetic acid medium at room temperature for about 2-3 h. The reaction conditions are simple, yields are high (85%-95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1 H, 13 C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.
Authors: Miles W Johnson; Scott W Bagley; Neal P Mankad; Robert G Bergman; Vincent Mascitti; F Dean Toste Journal: Angew Chem Int Ed Engl Date: 2014-03-20 Impact factor: 15.336