86539-58-4Relevant academic research and scientific papers
Research on nitro-derivatives of biological interest. XXIX. Hydroxylated 2-nitronaphthofuranes derivatives, synthesis and activity against micro-organisms
Buisson,Lamotte,Demerseman,et al.
, p. 169 - 174 (2007/10/02)
2-Nitro naphtho [2. 1-b] furans hydroxylated at the 7 or 8 position cannot be obtained directly - neither by nitration of the corresponding hydroxy naphtholfurans nor by condensation of bromonitromethane with a naphthalenic aldehyde dihydroxylated at the ortho position of the formyl in an other suitable position on the molecule. The demethylation of 2-nitro 8-methoxy naphtho [2. 1-b]furan by pyridinium chloride only yields a small quantity of 2-nitro 8-hydroxy naphtho [2. 1-b]furan, whereas that of 2-nitro 7-methoxy naphtho [2. 1-b]furan cannot be effectuated without decomposition. The only profitable way to synthesize 7-hydroxy or 8-hydroxy 2-nitro naphtho [2. 1-b]furans consists in releasing them from their acetates which were obtained by action of bromonitromethane on 6-acetoxy or 7-acetoxy 1-formyl 2-hydroxy naphthalenes - the latter formed by an univocal method, i.e., starting from 2-hydroxy 6-methoxy or 7-methoxy naphthalenes. 7-Hydroxy 2-nitro naphtho [2. 1-b]furan is clearly more efficient than its corresponding methylic ether (R 7000) and acetate against bacteria; it is nearly as active against protozoa and oxyures. 8-Hydroxy 2-nitro naphtho [2. 1-b]furan exerts activities fairly similar to that of its methylic ether and acetate.
