Alkoxymethyl Substituents Research Articles

New Salts of N-Substituted Piracetam

Methyl (2-oxo-1-pyrrolidinyl)acetate reacts with (aminomethyl)pyridines with the elimination of methanol to form (2-oxo-1-pyrrolidinyl)(N-pyridinylmethyl)acetamide, which, quaternized smoothly by ROCH2Cl, gives the new salts of N-substituted piracetam. Both steps occur in high yields. The obtained pyridinium chlorides showed antielectrostatic properties, which depend on a carbon chain in alkoxymethyl substituent and bactericidal and fungicidal activity.

Porphyrins. 38. Reaction of Porphyrins Containing Hydroxy(alkoxy)ethyl or Alkoxymethyl Substituents with Nucleophiles in the Presence of Zinc Acetate. A Novel, Promising Method for the Modification of Porphyrins on the Periphery of the Macrocycle

Porphyrins which contain 1-hydroxy(alkoxy)ethyl or alkoxymethyl substituents on the periphery of the macrocycle (i.e. formally able to yield “benzyl type” carbocations) react with nucleophiles (4-tert-butylphenol or the β-diketones acetylacetone, benzoylacetone, dibenzoylmethane, or 4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione) in the presence of excess zinc acetate. They give high yields of the corresponding addition products, which are the zinc complexes of porphyrins with a 1-(4-tert-butylphenoxy)ethyl substituent or with substituents containing β-diketone residues.

Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K+ channels: synthesis and photoreactivity.

A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1. 3.

Ortho-Hydroxybenzylation and Alkoxymethylation of 5-Phenyltetrazole

Abstract A simple method for introducing the 2-hydroxybenzyl or alkoxymethyl substituents into the tetrazole ring with the use of, respectively, N-(2-hydroxybenzyl)- or N-(alkoxymethyl) succinimide has been developed.