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صفحه اصلی
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بیست و نهمین کنفرانس شیمی آلی ایران
The green Synthesis of papaverine one of opium alkaloids in water
نویسندگان :
AliHossein Amini ( دانشگاه مازندران ) , Yaghoub Sarrafi ( دانشگاه مازندران ) , Khosrow Jadidi ( دانشگاه شهید بهشتی ) , Masoumehossadat Hosseini ( دانشگاه شهید بهشتی ) , Valid Taheri ( دانشگاه شهید بهشتی ) , Rana Amini ( دانشگاه زنجان )
کلید واژه ها :
opium،isoquinoline،papaverine،chemical synthesis
چکیده مقاله :
Opium mixture serves as a vital source of alkaloids, including significant medicinal compounds used in the pharmaceutical industry. One such compound is papaverine (6), a benzylisoquinolinic alkaloid found in opium mixture, possessing distinct medicinal properties. This artcle addresses the limitations associated with extracting substances from natural compounds by focusing on the synthesis of papaverine in four comprehensive steps. The synthetic route employs 2-(4,3-dimethoxyphenyl) acetic acid (1), which undergoes transformation to yield methyl 2-(4,3-dimethoxyphenyl) acetate (2). Through the binding of compound (2) with commercially available 2-(4,3-dimethoxyphenyl) ethane amine (3), amide (4) is obtained. Subsequently, ring closure of compound (4) is efficiently achieved using polyphosphoric acid (PPA) in refluxing toluene, leading to the formation of 1-(4,3-dimethoxy-benzyl)-7,6-dimethoxy-4,3-dihydroisoquinoline (5). The next crucial step involves the hydrogenation of compound (5) with Pd/C in a water-solvent medium, successfully yielding the desired product, papaverine (6), with an impressive efficiency of 58.7%. Characterization of the formed products is carried out using FTIR, 1H NMR, 13C NMR, and Mass spectrometry techniques, confirming their chemical identities. By developing a synthetic approach to produce papaverine, this study offers valuable insights into the efficient synthesis of this important medicinal compound, potentially paving the way for its widespread application in the pharmaceutical industry.
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