Abstract
The antihypertensive drug Cilnidipine (1) is photolabile under UV-A light. Irradiation of a chloroform solution of Cilnidipine under aerobic and anaerobic conditions produces a common photoproduct which was isolated as 2-methoxyethyl-3-phenyl-2-propenyl pyridine dihydro-2,6-dimethyl-4-(3-nitrophenyl) pyridine-3,5-dicarboxylate (2). The formation of products was explained by photochemical aromatization of Cilnidipine.
Highlights
The last few years have witnessed a growing interest of the scientific community in photoinitiated reactions of drugs [1]
Pure Cilnidipine was obtained from Sigma Aldrich (India); IR spectra were recorded as KBr discs on a Perkin Elmer model spectrum RXI. 1H-NMR and 13CNMR spectra were recorded on a Bruker Avance-DRX-300 Spectrometer using TMS as internal standard and CD3OD as solvent
At the end of reaction the formation of a number of products was indicated on TLC and the photoproduct was isolated by eluting with chloroform and petrol (60 : 40, v/v) on silica column. Under both aerobic and anaerobic conditions 2 is obtained as major photoproduct and identified as 2-methoxyethyl-3-phenyl-2propenyl pyridine dihydro-2,6-dimethyl-4-(3-nitrophenyl) pyridine-3,5-dicarboxylate (2) from the following spectral properties
Summary
The last few years have witnessed a growing interest of the scientific community in photoinitiated reactions of drugs [1]. Pure Cilnidipine was obtained from Sigma Aldrich (India); IR spectra were recorded as KBr discs on a Perkin Elmer model spectrum RXI. Cilnidipine (265 mg) was dissolved in 400 mL chloroform and irradiated at room temperature for 1 hr in a Rayonet photochemical reactor (The Southern New England Ultraviolet Co. Model RPR208 equipped with four RUL-300 nm fluorescence lamps) for the complete conversion of the reactants.
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