|
|||||
|
|
Synthesis and antitubercular evaluation of amidoalkyl dibenzofuranols and 1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazin-3(2H)-ones |
|
| Authors: | Kantevari Srinivas Yempala Thirumal Yogeeswari Perumal Sriram Dharmarajan Sridhar Balasubramanian |
| Institution: | a Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500 007, India b Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500 078, India c Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 607, India |
| Abstract: | A new class of amidoalkyl dibenzofuranols and 1H-benzo2,3]benzofuro4,5-e]1,3]oxazin-3(2H)-ones was synthesized in very good yields through polyphosphoric acid supported on silica (PPA-SiO2) catalyzed one-pot three component condensation of 2-dibenzofuranol; aromatic aldehydes and acetamide or benzamide or urea under solvent free conditions. At 125 °C the reaction led to the formation of amidoalkyl dibenzofuranols 5a-k where as at 160 °C cyclization take place to give oxazin-3(2H)-one analogues 6a-e. Screening all the 16 compounds for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) resulted 1-((4-chlorophenyl)(2-hydroxydibenzob,d]furanyl)methyl)urea 5h; 1-((4-bromophenyl)(2-hydroxydibenzob,d]furanyl)methyl)urea 5i; 1-phenyl-1H-benzo2,3]benzo furo4,5-e]1,3]oxazin-3(2H)-one 6a (MIC 3.13 μg/mL) and 1-(4-chlorophenyl)-1H-benzo2,3]benzofuro4,5-e]1,3]oxazin-3(2H)-one 6b; 1-(4-bromophenyl)-1H-benzo2,3]benzofuro 4,5-e]1,3]oxazin-3(2H)-one 6c (MIC 1.56 μg/mL) as most active antitubercular agents. |
| Keywords: | Oxazin-3(2H)-ones Amidoalkyl dibenzofuranols Dibenzofuran Antimycobacterial activity Mycobacterium tuberculosis |
| 本文献已被 ScienceDirect PubMed 等数据库收录！ | |