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Development of water-soluble 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents.

Abstract：

:In this work, four series of tertiary amine-containing derivatives of 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents were prepared, and their in vitro antimycobacterial effects were evaluated. We found that the studied compounds showed lipophilicity-dependent antimycobacterial activity. The N-benzylpiperazine derivatives, which had the highest lipophilicity among all of the series, showed the highest in vitro antimycobacterial activities against Mycobacterium tuberculosis CNCTC My 331/88 (H37Rv), comparable to those of the first-line drugs isoniazid and rifampicin. The presence of two tertiary amines in these N-benzylpiperazine derivatives enabled us to prepare water-soluble dihydrochloride salts, overcoming the serious drawback of previously described 3,5-dinitrophenyl tetrazole and oxadiazole lead compounds. The water-soluble 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents described in this work are good candidates for further in vitro and in vivo pharmacokinetic and pharmacodynamic studies.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Roh J,Karabanovich G,Vlčková H,Carazo A,Němeček J,Sychra P,Valášková L,Pavliš O,Stolaříková J,Klimešová V,Vávrová K,Pávek P,Hrabálek A

doi

10.1016/j.bmc.2017.08.010

subject

Has Abstract

pub_date

2017-10-15 00:00:00

pages

5468-5476

issue

20

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(17)31113-6

journal_volume

25

pub_type

杂志文章

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