139965-11-0Relevant articles and documents
Microbial oxidation of terfenadine and ebastine into fexofenadine and carebastine
Mazier, Claire,Jaouen, Maryse,Sari, Marie-Agnès,Buisson, Didier
, p. 5423 - 5426 (2004)
Fexofenadine 5 and carebastine 6 were obtained in good yield by optimization of culture conditions of microorganisms. Oxidation of 1 into 9 was observed as described in mammalian metabolism. The oxidation of tert-butyl-phenyl group of title compounds by s
Preparation method of fexofenadine
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, (2021/04/17)
The invention provides a preparation method of fexofenadine, which comprises the following steps: by using bromobenzene as a raw material, carrying out Friedel-Crafts acylation reaction to obtain 4'-bromo-4-chlorophenone ; enabling 4'-bromo-4-chlorobutanone and 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene to subjected to coupling reaction to obtain 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methyl methyl propionate; and sequentially carrying out N-alkylation, carbonyl reduction and alkaline hydrolysis on 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methylpropanoate to obtain fexofenadine. The method has the advantages of cheap and easily available raw materials, easiness in operation, high yield, low cost, no meta-isomer, suitability for industrial production and the like.
A fexofenadine hydrochloride process for synthesizing
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, (2017/02/17)
The invention discloses a synthetic process of fexofenadine hydrochloride. The synthetic process of fexofenadine hydrochloride comprises the following steps of: with alpha, alpha-dimethyl phenylacetic acid as a raw material, carrying out an esterification reaction on alpha, alpha-dimethyl phenylacetic acid and absolute ethyl alcohol under the catalysis of a silica gel loaded phosphotungstic acid (PW12/SiO2) solid acid catalyst to obtain alpha, alpha-dimethyl ethyl phenylacetate; carrying out Friedel-Grafts reaction on alpha, alpha-dimethyl ethyl phenylacetate and 4-chlorobutyryl chloride to obtain alpha, alpha-dimethyl-4-(4-chloro-1-oxo butyl) ethyl phenylacetate; reducing by virtue of sodium borohydride in 95% ethyl alcohol to obtain alpha, alpha-dimethyl-4-(4-chloro-1-hydroxyl butyl) ethyl phenylacetate; and carrying out N-alkylation reaction on alpha, alpha-dimethyl-4-(4-chloro-1-hydroxyl butyl) ethyl phenylacetate and alpha, alpha-dimethyl-4-piperidine methyl alcohol in DMF (dimethyl formamide) for 24 hours at the temperature of 80 DEG C to obtain alpha, alpha-dimethyl-4-[1-hydroxyl-4-[4-(hydroxyl diphenylmethyl)-1-piperidyl]-butyl] ethyl phenylacetate, and then carrying out alkali hydrolysis and salification by virtue of hydrochloric acid, so that fexofenadine hydrochloride is obtained. The synthetic process of fexofenadine hydrochloride is high in yield and low in cost, produces less pollution and is applicable to industrial mass production.
Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus
Perlmutter, Jessamyn I.,Forbes, Lauren T.,Krysan, Damian J.,Ebsworth-Mojica, Katherine,Colquhoun, Jennifer M.,Wang, Jenna L.,Dunman, Paul M.,Flaherty, Daniel P.
, p. 8540 - 8562 (2014/12/11)
Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.
