Add time:07/28/2019         Source:sciencedirect.com

The kinetics of decomposition of various N-Mannich bases of salicylamide in aqueous solution at 37°C was studied to assess their suitability as pro-drugs for amino compounds. The decomposition, yielding salicylamide, amine and formaldehyde in stoichiometric amounts, showed bell-shaped pH-rate profiles which could be accounted for by assuming spontaneous decomposition of both neutral and protonated Mannich base and unreactivity of the derivatives in the anionic form. For the Mannich bases with the amines piperidine, α-alanine, methylamine and morpholine, the half-lives of decomposition at pH 7.40 and 37°C were 14, 17, 28 and 41 min, respectively, suggesting that salicylamide N-Mannich bases are possible candidates as pro-drugs for compounds containing a primary or secondary amino group. N-Amidomethylation of the amines with salicylamide resulted in a pronounced lowering of their basicity corresponding to 3–4 pKa units which may be of potential utility for the application of N-Mannich bases as pro-drug forms for amines.

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