A. Nabiev, and V. U. KhuzhaevA series of new convolvine derivatives based on the alkaloid from Convolvulus subhirsutus and C. pseudocanthabrica were synthesized using alkylhalides and aliphatic and aromatic acid chlorides. Results of biological tests showed that convolvine and its derivatives exhibited pronounced antihypoxic, immunomodulating, and anti-inflammatory activity.The aerial parts of Convolvulus subhirsutus and C. pseudocanthabrica growing in Uzbekistan [1] have previously yielded 10 alkaloids [2-7] that were tropane derivatives, the principal ones being convolvine and convolamine with a content of 45-50% of the total alkaloids. A quantitative determination found that the content of the alkaloid mixture in the aerial part was 0.6%; in the roots, 1.6% of the dry plant weight.The convolvine content in C. subhirsutus and C. pseudocanthabrica reaches 0.3% in the aerial part; 0.7%, in roots. As a result of the availability of convolvine, a series of its derivatives were prepared. Their pharmacological properties were studied in a search for compounds with valuable pharmacological activity. For this, convolvine (1) was reacted with alkyl halides (methyliodide, hexylbromide, amylbromide, nonylbromide, benzylchloride) to produce the corresponding derivatives N-methylconvolvine hydroiodide (2), N-amylconvolvine hydrobromide (3), N-hexylconvolvine hydrobromide (4), N-nonylconvolvine hydrobromide (5), and N-benzylconvolvine (6) according to the scheme:Convolvine was also reacted with aliphatic and aromatic acid chlorides to produce N-benzoylconvolvine (7), N-chloroacetylconvolvine (8), and N-4c-nitrobenzoylconvolvine (9), reduction of 9 produced N-4c-aminobenzoylconvolvine (10), and N-naphthoylconvolvine (11):
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