Synthesis and bioevaluation of some new isoniazid derivatives

Matei, Lilia; Bleoţu, Coralia; Baciu, I; Drăghici, Constantin; Ioniță, Petre; Păun, Andrei; Chifiriuc, Mariana Carmen; Sbarcea, Adriana; Zarafu, Irina

doi:10.1016/j.bmc.2013.06.013

Cited by 20 publications

(12 citation statements)

References 26 publications

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“…Recently, several Medicinal Chemistry groups have reported isoniazid derivatives with potent anti-TB activity; nonetheless, isoniazid keeps on top as one of the best options available for TB treatment even after 64 years of its discovery (Matei et al, 2013;Kumar et al, 2014;Martins et al, 2014;. Indeed, isoniazid plays an important role in the current therapeutic regimen, and several clinical trials have demonstrated its importance in new therapeutic schemes under development (Rangaka et al, 2014;Villarino et al, 2015;Stennis et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Isoniazid: A Review of Characteristics, Properties and Analytical Methods

Fernandes

Salgado

Santos

2017

Critical Reviews in Analytical Chemistry

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Isoniazid is a synthetic antimicrobial and one of the most important first-line drugs used in the treatment of tuberculosis. Since it was introduced in the therapy in 1952, the drug remains at the front line of the antituberculosis treatment mainly due to its potency and high selectivity against Mycobacterium tuberculosis. Pharmaceutical analysis and therapeutic drug monitoring of isoniazid in both, pharmaceuticals and biological samples, plays an important role to comprehend aspects regarding to bioavailability, bioequivalence and therapeutic monitoring during patients following-up. In the last case, validated and simple methods are extremely useful for Public Healthy in order to guarantee the drug efficacy, safety and reduce the tuberculosis resistance. Among the available analytical tools, HPLC-based methods coupled to ultraviolet or mass spectroscopy are the most widely used techniques to quantify isoniazid. Therefore, this review highlights the main analytical methods reported in the literature for determination of isoniazid focusing in HPLC-based methods.

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Section: Introductionmentioning

confidence: 99%

Isoniazid: A Review of Characteristics, Properties and Analytical Methods

Fernandes

Salgado

Santos

2017

Critical Reviews in Analytical Chemistry

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“…Isoniazid (INH) is the most frequently prescribed antibiotic in the treatment of tuberculosis. INH has a greater efficacy and acceptable toxicity and thus belongs to the first-line drugs group for TB treatment, while the second-line ones like kanamycin, amikacin, capreomycin, cycloserine, ethionamide, para-aminosalicylic acid and fluoroquinolones show a lower efficacy or a greater toxicity in TB treatment (Barry, 1997;Vavříková et al 2011;Matei et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

NANOBIOCATALYTIC SYSTEMS BASED ON LIPASE-Fe3O4 AND CONVENTIONAL SYSTEMS FOR ISONIAZID SYNTHESIS: A COMPARATIVE STUDY

Costa

Souza

Fechine

et al. 2016

Braz. J. Chem. Eng.

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-Superparamagnetic nanomaterials have attracted interest in many areas due to the high saturation magnetization and surface area. For enzyme immobilization, these properties favor the enzyme-support contact during the immobilization reaction and easy separation from the reaction mixture by use of low-cost magnetic processes. Iron oxide magnetic nanoparticles (Fe3O4, MNPs), produced by the co-precipitation method, functionalized with 3-aminopropyltriethoxysilane (APTES) and glutaraldehyde (GLU), were evaluated as a solid support for Candida antarctica lipase B (CALB) immobilization. The nanomagnetic derivative (11nm) obtained after CALB immobilization (MNPs/APTES/GLU/CALB) was evaluated as biocatalyst in isoniazide (INH) synthesis using ethyl isonicotinate (INE) and hydrazine hydrate (HID) as substrates, in 1,4-dioxane. The results showed that MNPs/APTES/CALB had a similar performance when compared to a commercial enzyme Novozym 435, showing significant advantages over other biocatalysts, such as Rhizhomucor miehei lipase (RML) and CALB immobilized on non-conventional, low-cost, chitosan-based supports.

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“…A mixture of compound 3 (0.326 g, 1 mmol) and lead acetate (0.321 g, 1 mmol), in acetic acid (30 mL)was refluxed for 2 hr then the mixture was poured onto water and stirred for 15 [ 1 , 2 , 4 ] triazolo [3,4-b] [1,3]thiazin-5-one (5) A mixture of compound 3 (0.326 g, 1 mmol) and sodium ethoxide (0.015 mol in 30 mL ethanol) was heated under reflux for 2 hr. the content of flask was poured onto water to give a yellow powder that collected by filtration and recrystallized from acetic acid to give compound…”

Section: N -( 4 -O X O -6 -P H E N Y L -2 -T H I O X O -3 4dihydropmentioning

confidence: 99%

“…The IR spectrum of compound 7 showed the characteristic broad band of the hydroxyl group at 3394 cm -1 also displayed two different carbonyls at 1683 and 1627cm -1 . The 1 in the 13 C NMR spectrum of compound 7. The reaction of thiosemicarbazide derivative 3 with sodium hypochlorite in the presence of NH 4 OH and NaOH resulted in thiadiazole cyclization affording compound 8 as shown in Scheme 3 via the formation of the non-isolable sulphenyl chloride, amination forming sulphenamide which in turn undergo intramolecular cyclodehydration [21].…”

Section: Chemistrymentioning

confidence: 99%

“…Isoniazid is a manufactured antimicrobial and a standout amongst the most vital first-line drugs utilized as a part of the treatment of tuberculosis (TB). Indeed, even after its discovery more than 60 years ago, the drug stays at the front line of the anti-tuberculosis treatment mainly due to its potency and high selectivity against Mycobacterium tuberculosis [1][2][3][4]. In 2016, the World Health Organization (WHO) announced that there were around 10.4 million new TB cases in worldwide with approximately 1.3 million TB deaths among HIV negative people and 0.374 million deaths among HIV-positive individuals [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

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Heterocyclization of Isoniazid: Synthesis and Antimicrobial Activity of Some new Pyrimidine 1, 3-Thiazole, 1, 2, 4-Thiadiazole, and 1, 2, 4-Triazole, Derivatives Derived from Isoniazid

Farhan

Assy

2018

Egypt. J. Chem.

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T HE REACTION of isonicotinic hydrazide (1) (isoniazid) with cinnamoyl isothiocyanate (2) afforded cinnamoyl thiosemicarbazide derivative 3. Treatment of 3 with lead acetate in acetic acid, sodium ethoxide, sulphuric acid, chloroacetylchloride and sodium hypochlorite and sodium hydroxide gave the corresponding dihydropyrimidine 4, triazolethiazine 5, 1,3,4-thiadiazole 6, 1,3-thiazole 7 and 1,2,4-thiadiazole 8, respectively. The reactivity of isoniazid 1 towards ammonium thiocyanate, cyclohexanone and acetophenone to give 1,2,4-triazole thione 10, hydrazones 9 and 12 was studied. Treatment of hydrazones 9 and 12 with carbon disulfide and aryl isothiocyanates gave 1,3,4-thiadiazolidine 11 and 1,2,4-triazole thione derivatives 13a, b. The antimicrobial activity of these new compounds has been evaluated against 6 microbial strains. Some of the newly synthesized compounds showed moderate activity.

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Synthesis and bioevaluation of some new isoniazid derivatives

Cited by 20 publications

References 26 publications

Isoniazid: A Review of Characteristics, Properties and Analytical Methods

Isoniazid: A Review of Characteristics, Properties and Analytical Methods

NANOBIOCATALYTIC SYSTEMS BASED ON LIPASE-Fe3O4 AND CONVENTIONAL SYSTEMS FOR ISONIAZID SYNTHESIS: A COMPARATIVE STUDY

Heterocyclization of Isoniazid: Synthesis and Antimicrobial Activity of Some new Pyrimidine 1, 3-Thiazole, 1, 2, 4-Thiadiazole, and 1, 2, 4-Triazole, Derivatives Derived from Isoniazid

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