Synthesis and antimycobacterial activity of isoniazid derivatives from renewable fatty acids

被引：47

作者：

Rodrigues, Marieli O. ^{[1
]}

Cantos, Jessica B. ^{[2
]}

Montes D'Oca, Caroline R. ^{[3
]}

Soares, Karina L. ^{[1
]}

Coelho, Tatiane S. ^{[2
]}

Piovesan, Luciana A. ^{[1
]}

Russowsky, Dennis ^{[3
]}

da Silva, Pedro A. ^{[2
]}

Montes D'Oca, Marcelo G. ^{[1
]}

机构：

[1] Univ Fed Rio Grande, Lab Kolbe Sintese Organ, Escola Quim & Alimentos, Rio Grande, RS, Brazil

[2] Univ Fed Rio Grande, Lab Micobacteriol, Fac Med, Rio Grande, RS, Brazil

[3] Univ Fed Rio Grande do Sul, Lab Sintese Organ, Inst Quim, Porto Alegre, RS, Brazil

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2013年 / 21卷 / 22期

关键词：

Fatty acids; Mycobacterium tuberculosis; INH-derivatives; Antimycobacterial activity; MYCOBACTERIUM-TUBERCULOSIS; CONSTITUENTS;

D O I：

10.1016/j.bmc.2013.09.034

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

This work describes the synthesis of a series of fatty acid hydrazide derivatives of isoniazid (INH). The compounds were tested against Mycobacterium tuberculosis H37Rv (ATCC 27294) as well as INH-resistant (ATCC 35822 and 1896 HF) and rifampicin-resistant (ATCC 35338) M. tuberculosis strains. The fatty acid derivatives of INH showed high antimycobacterial potency against the studied strains, which is desirable for a pharmaceutical compound, suggesting that the increased lipophilicity of isoniazid plays an important role in its antimycobacterial activity. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：6910 / 6914

页数：5

共 17 条

[1] Regiospecific Synthesis of New Fatty N-Acyl Trihalomethylated Pyrazoline Derivatives from Fatty Acid Methyl Esters (FAMEs) [J].

Beck, Paulo ;

dos Santos, Juliane M. ;

Kuhn, Bruna L. ;

Moreira, Dayse N. ;

Flores, Alex F. C. ;

Martins, Marcos A. P. ;

D'Oca, Marcelo G. M. ;

Piovesan, Luciana A. .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (11) :2122-2127

[2] New N-acylamino acids and derivatives from renewable fatty acids: gelation of hydrocarbons and thermal properties [J].

Duarte, Rodrigo da Costa ;

Ongaratto, Renata ;

Piovesan, Luciana Almeida ;

de Lima, Vania Rodrigues ;

Soldi, Valdir ;

Merlo, Aloir Antonio ;

Montes D'Oca, Marcelo G. .

TETRAHEDRON LETTERS, 2012, 53 (19) :2454-2460

[3] SYNTHETIC TUBERCULOSTATS .8. ACYL DERIVATIVES OF ISONICOTINYL HYDRAZINE [J].

FOX, HH ;

GIBAS, JT .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (10) :1375-1379

[4]

GIANNOLA LI, 1992, PHARMAZIE, V47, P423

[5] Elaiomycins B and C: Alkylhydrazide Antibiotics from Streptomyces sp BK 190 [J].

Helaly, Soleiman E. ;

Pesic, Alexander ;

Fiedler, Hans-Peter ;

Suessmuth, Roderich D. .

ORGANIC LETTERS, 2011, 13 (05) :1052-1055

[6] MULTIDRUG-RESISTANT TUBERCULOSIS AND ITS CONTROL [J].

KOCHI, A ;

VARELDZIS, B ;

STYBLO, K .

RESEARCH IN MICROBIOLOGY, 1993, 144 (02) :104-110

[7] SYNTHESIS OF NEW FATTY ACIDS AMIDES FROM AMINOLYSIS OF FAMES [J].

Lopes, Carolina R. ;

Montes D'Oca, Caroline Da Ros ;

Duarte, Rodrigo da C. ;

Kurz, Marcia H. S. ;

Prime, Ednei G. ;

Clementin, Rosilene M. ;

Villarreyes, Joaquin Ariel M. ;

Montes D'Oca, Marcelo G. .

QUIMICA NOVA, 2010, 33 (06) :1335-1341

[8] New anti-tuberculosis agents amongst known drugs [J].

Lougheed, Kathryn E. A. ;

Taylor, Debra L. ;

Osborne, Simon A. ;

Bryans, Justin S. ;

Buxton, Roger S. .

TUBERCULOSIS, 2009, 89 (05) :364-370

[9] Anti-tuberculosis constituents from the stem bark of Micromelum hirsutum [J].

Ma, CY ;

Case, RJ ;

Wang, YH ;

Zhang, HJ ;

Tan, GT ;

Van Hung, N ;

Cuong, NM ;

Franzblau, SG ;

Soejarto, DD ;

Fong, HHS ;

Pauli, GF .

PLANTA MEDICA, 2005, 71 (03) :261-267

[10] Susceptibility of Mycobacterium tuberculosis to isoniazid and its derivative, 1-isonicotinyl-2-nonanoyl hydrazine:: investigation at cellular level [J].

Mohamad, S ;

Ibrahim, P ;

Sadikun, A .

TUBERCULOSIS, 2004, 84 (1-2) :56-62

← 1 2 →