Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India.
Bioorg Med Chem Lett. 2010 Jan 1;20(1):350-3. doi: 10.1016/j.bmcl.2009.10.107. Epub 2009 Oct 29.
The 1,3-dipolar cycloaddition of azomethine ylides derived from substituted isatins and 1,3-thiazolane-4-carboxylic acid to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]-tetrahydro-4(1H)-pyridinones afforded novel spiro-pyrrolothiazoles chemo-, regio- and stereoselectively in quantitative yields. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB) using agar dilution method. Among the synthesized compounds, spiro[5.3'']-5''-nitrooxindole-spiro-[6.3']-1'-methyl-5'-(2,4-di-chlorophenylmethylidene)tetrahydro-4'(1H)-pyridinone-7-(2,4-dichlorophenyl)tetra-hydro-1H-pyrrolo[1,2-c][1,3]thiazole (9k) was found to be the most active with a minimum inhibitory concentration (MIC) of 0.6microM against MTB and MDR-TB.
取代色胺亚胺叶立德和 1,3-噻唑烷-4-羧酸与一系列 1-甲基-3,5-双[(E)-芳基亚甲基]-四氢-4(1H)-吡啶酮的 1,3-偶极环加成反应以定量产率选择性地提供了新型螺吡咯并噻唑。使用琼脂稀释法，这些化合物被筛选用于体外对结核分枝杆菌 H37Rv（MTB）和多药耐药结核分枝杆菌（MDR-TB）的活性。在所合成的化合物中，螺[5.3'']-5''-硝基色酮-螺-[6.3']-1'-甲基-5'-(2,4-二氯苯甲基)四氢-4'(1H)-吡啶酮-7-(2,4-二氯苯基)四氢-1H-吡咯并[1,2-c][1,3]噻唑（9k）表现出最强的活性，对 MTB 和 MDR-TB 的最小抑菌浓度（MIC）为 0.6μM。
