Pyrrolidinone and pyrrolidine derivatives: Evaluation as inhibitors of InhA and Mycobacterium tuberculosis

Matviiuk, Tetiana; Madacki, Jan; Mori, Giorgia; Orena, Béatrice Silvia; Menendez, Christophe; Kysil, Andrii I.; André-Barrès, Christiane; Rodriguez, Frédéric; Korduláková, Jana; Mallet‐Ladeira, Sonia; Voitenko, Zoia; Pasca, Maria Rosalia; Lherbet, Christian; Baltas, Michel

doi:10.1016/j.ejmech.2016.07.028

Cited by 36 publications

(19 citation statements)

References 44 publications

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“…The modes of actions of selected hydrazones were analyzed by metabolic labeling of M.tb H37Ra strain with 14 C acetate as already described [ 34 ]. Briefly, M.tb H37Ra culture was grown in Middlebrook 7H9 broth (Difco) supplemented with albumin-dextrose-catalase (Difco) and 0.05% Tween 80 (MP Biomedicals) at 37 °C till OD 600 reached 0.24.…”

Section: Methodsmentioning

confidence: 99%

“…Our group is involved both in synthesizing new antitubercular compounds, including cinnamic acid derivatives [ 26 , 27 , 28 , 29 ], triazoles [ 30 , 31 , 32 , 33 ], pyrrolidines [ 34 , 35 , 36 ], semicarbazones and hydrazine/hydrazones [ 37 ], and in searching for new and innovative synthetic reactions. We have recently reported the solvent-free mechanosynthesis of a series of hydrazones [ 38 , 39 ].…”

Section: Introductionmentioning

confidence: 99%

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Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

et al. 2017

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A series of isoniazid derivatives bearing a phenolic or heteroaromatic coupled frame were obtained by mechanochemical means. Their pH stability and their structural (conformer/isomer) analysis were checked. The activity of prepared derivatives against Mycobacterium tuberculosis cell growth was evaluated. Some compounds such as phenolic hydrazine 1a and almost all heteroaromatic ones, especially 2, 5 and 7, are more active than isoniazid, and their activity against some M. tuberculosis MDR clinical isolates was determined. Compounds 1a and 7 present a selectivity index >1400 evaluated on MRC5 human fibroblast cells. The mechanism of action of selected hydrazones was demonstrated to block mycolic acid synthesis due to InhA inhibition inside the mycobacterial cell.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

et al. 2017

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“…colic acids in the form of trehalose monomycolates (TMM) to the periplasmic space or outer membrane of Mtb. The inhibition of the MmpL3 constitutes a cellular target for some promising antitubercular compounds with diverse structure, which undergo clinical developments [4,7,10]. SQ109 is an adamantane derivative, which possesses the active 1,2-ethylenediamine pharmacophore of Eth-ambutol.…”

Section: In Vitro Controlled Release Of Two New Tuberculocidal Adamanmentioning

confidence: 99%

“…In recent years a wide range of factors has led to the resurgence of TB. The causative pathogen Mtb afflicts more frequently patients with weakened immune system and thus, TB is significantly hazardous to those who suffer from the human immune deficiency virus (HIV) [3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

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In vitro Controlled Release of two new Tuberculocidal Adamantane Aminoethers from Solid Pharmaceutical Formulations (II)

et al. 2017

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The aim of the present investigation was to develop matrix tablet formulations for the controlled release of two new tuberculocidal adamantane aminoethers (compounds and ), congeneric to the adamantane derivative which is in final clinical trials, and aminoethers () and (), using carefully selected excipients, such as polyvinylpyrrolidone, sodium alginate and lactose. The tablets were prepared using the direct compression method and dissolution experiments were conducted using the US Pharmacopoeia type II apparatus (paddle method) in gastric and intestinal fluids. The results suggest that both analogues, more lipophilic than and aminoethers () and (), have the requisite release characteristics for oral administration. In conclusion, these formulations merit further assessment by conducting studies, at a later stage.

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Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX₃: Access to Bromine‐Containing Trihalomethylated Pyrrolidines

et al. 2019

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We describe a novel rhodium(I)‐catalyzed cascade radical cyclization of 1,6‐enynes with Br−CX3 (X=Cl,Br). This transformation presents an efficient method for the construction of a variety of bromine‐containing trihalomethylated pyrrolidines in moderate to good yields. A possible radical pathway is proposed based on the relevant literature and control experiments. Moreover, this protocol is also applicable to 1,7‐enyne analogues.

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Pyrrolidinone and pyrrolidine derivatives: Evaluation as inhibitors of InhA and Mycobacterium tuberculosis

Cited by 36 publications

References 44 publications

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

In vitro Controlled Release of two new Tuberculocidal Adamantane Aminoethers from Solid Pharmaceutical Formulations (II)

Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX₃: Access to Bromine‐Containing Trihalomethylated Pyrrolidines

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Pyrrolidinone and pyrrolidine derivatives: Evaluation as inhibitors of InhA and Mycobacterium tuberculosis

Cited by 36 publications

References 44 publications

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

In vitro Controlled Release of two new Tuberculocidal Adamantane Aminoethers from Solid Pharmaceutical Formulations (II)

Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX3: Access to Bromine‐Containing Trihalomethylated Pyrrolidines

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Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX₃: Access to Bromine‐Containing Trihalomethylated Pyrrolidines