![]() Packing of the salts is dominated by hydrogen bonding. The conformations are distinctively different for the two independent molecules of the free base, the two independent molecules of the hydrofumarate salt, and the one unique cation of the benzoate salt. The flexible backbone of the bedaquiline structure leads to a landscape of conformations with little commonalities between the bedaquiline entities in the various structures. The conformations of the cations are compared to that of free base bedaquiline and with each other. Both salts feature a 1:1 cation-to-anion ratio, with the fumarate being present as monoanionic hydrofumarate. The much less basic quinoline N atom remains unprotonated. The fumarate and benzoate salts both feature cations monoprotonated at the dimethylamino group. In a first communication, we present the crystal structure of bedaquilinium fumarate and of two new benzoate salts, as well as that of a degradation product of the reaction of bedaquilinium fumarate with sodium ethoxide, 3-benzyl-6-bromo-2-methoxyquinoline, C 17H 14BrNO. ![]() It is marketed in the US as its fumarate salt, and about a dozen other salts of bedaquiline have been described in patent literature, but none have so far been structurally described. Bedaquiline is one of two important new drugs for the treatment of drug-resistant tuberculosis (TB).
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