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Further reading
- General experimental procedure for the synthesis of compound 4a-4u Step-1: Preparation of 2-(3-chlorosulfonylphenyl) acetate (1a) To a stirred solution of methyl 2-phenylacetate (40 g, 266 mmol) in DCM (100 mL). RM was cooled to 0 °C and Chloro sulfonic acid (34 g, 293 mmol) was added drop wise followed by stirring at room temperature for 1 h. The reaction was monitored by LCMS and TLC, after completion of reaction, evaporate reaction mixture under reduced pressure and obtained gummy material is washed with excess of hexane and it is crystalized from 20% ethyl acetate: hexane mixture to obtain white solid as 2-(3-chlorosulfonylphenyl)acetate (1a) which is used further for sulfonamide coupling reaction, Yield- (54 g, 81%). Step-2: General experimental procedure for preparation of 2a-2f To a stirred solution of 2-(3-chlorosulfonylphenyl)acetate (1) (1 equiv) in DCM (10 times) was added Pyridine (10 times) the mixture was stirred at rt for 15 min. RM was cooled to 0⁰C and substituted amine (1.5 equiv) was added drop wise followed by stirring at rt for 6 h. The reaction was monitored by TLC and LCMS, after completion of reaction poured reaction mass on cold 2N aqueous HCl and stirred it for 30 min. The precipitation formed in RM. Filtered the obtained solid and washed it with excess of water and cold diethyl ether and cold pentane to obtain all compounds as white solids. For filtrate extracted with DCM twice. The organic layer was washed with brine solution; organic layer was evaporated under reduced pressure to get desired products as white solids. But in most of cases solid compound yields are in 70-80%. Yield- 80-90%. Step-3: General experimental procedure for preparation of 3a-3f To a stirred solution of compound 3 (1 equiv) in THF (10 times) added Ethanol (4 times) and water (2 times), finally added lithium hydroxide (5 equiv) and stirred reaction mixture for 8 h. Progress reaction was monitored by TLC and LCMS. After the completion of reaction, evaporate reaction mixture under reduced pressure to obtained gummy material. Added 10 ml of water in it and extracted it with diethyl ether (10 ml). Collected aqueous layer and adjust its pH to 4 by using 6N aqueous HCl. Precipitation occurs stirred it for 30 min. Filtered the obtained solid and wash it with excess of water, cold diethyl ether (10 mL) and cold pentane (10 mL) to obtain desired compounds as white solids. Yield- 80%-90%. Step-4: General experimental procedure for preparation of 4a-4u The acid (1 equiv.) was dissolved in DCM and treated with EDCI (1.5 equiv), DIPEA (2.5 equiv). Reaction mass stirred for 10 min. then added amine (1.5 equiv) and stirred reaction mixture at room temperature for 8 h. The reaction was monitored by TLC. Added 15 ml of cold water and stirred for 20 min. Then extracted it with 20 ml of DCM .Collected organic layer wash it with 1N aqueous HCl (10 mL) and washed with brine (10 mL). Evaporate the organic layer to obtain compound with 70 to 80% purity of compounds 4a to 4z. Purification done by washing with 5:95% of DCM: hexane. The obtained solid was washed with cold diethyl ether (20 mL) and cold pentane (20 mL) to obtain compounds 4a-4u as white solids (80-90% yield).
- Biological Methods Cell Culture Human cancer cell lines HeLa (cervical), A549 (lungs) andDU-145 (prostate) were grown in DMEM + GlutaMax (Invitrogen, Carlsbad, CA, USA), and MCF-7 (breast) were grown in DMEM-F12 + GlutaMax) medium (Invitrogen), supplemented with 10% heat-inactivated bovine serum (Gibco) and penicillin-streptomycin (Gibco, Gaithersburg, MD, USA) at 37 °C in a humified chamber with 5% CO2 supply Cytotoxicity Assay Cells were seeded (105 cells/well) in 96-well flat-bottom plates (Becton-Dickinson Labware, Franklin Lakes, NJ, USA) a day before treatment and grown overnight. Compounds were dissolved in dimethyl sulfoxide (DMSO; Sigma) and finally prepared as 1.0 mg/mL stocks, respectively in the culture media. The final concentration of DMSO never exceeded 0.1% in the treatment doses. Six different doses of compounds (400, 200, 100, 50, 25 and 10 µM) were further prepared by diluting the stocks in culture media, and cells were treated (in triplicate/dose). 5-fluorouracil was included as standard reference drug (positive control) and untreated culture was considered as negative control. The cultures were further incubated for 48 hrs. At 48 h post-treatment, cell viability test was performed using TACS MTT Cell Proliferation and Viability Assay Kit (TACS) as per manufacturer’s instructions. The optical density (OD) was recorded at 570 nm in a microplate reader (ELx800, BioTek, Winooski, VT, USA) and cell survival fraction was determined. The cell survival fraction was calculated as [(A-B)/A], where A and B are the OD of untreated and of treated cells, respectively. The concentration required for 50% inhibition of cell viability (IC50) was calculated and compared with the reference drug 5-fluorouracil and the results are given in Table 1.