2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis

Jallapally, Anvesh; Addla, Dinesh; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas

doi:10.1016/j.bmcl.2014.09.084

Cited by 24 publications

(10 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Minimum inhibitory concentrations MIC (mg/mL) of the studied dicationic ILs were determined, and the results are listed in Table 3. 37,63,64 Therefore, the presence of incorporated benzenesulfonamide moiety adjacent to the imidazolium and benzimidazolium core ILs, successfully promoted the antibacterial activity of the produced geminal dicationic ILs. According to the studies of structure-activity relationship 9 (SAR), the incorporation of two different pharmacophores within the same molecule would enhance the resulting compounds' biological activities.…”

Section: Antibacterial Activitiesmentioning

confidence: 99%

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

2015

View full text Add to dashboard Cite

Based on bis-imidazolium and benzimidazolium, new sets of geminal dicationic ionic liquids containing sulphonamide moiety were successfully synthesized with good yields. Their structures were confirmed by 1 H-NMR, 13 C-NMR, FT-IR, and mass spectroscopy. Selected physicochemical properties of these ILs including; thermal stability by TGA and miscibility in some common organic solvents and water were also determined. Most of the prepared dicationic ILs displayed significant level of antibacterial activities against ten selected bacterial strains of Gram-positive and Gram-negative using micro-broth dilution assay. ͞ calcd. for C 29 H 42 N 5 O 6 S 3+ : 588.2856, found: 588.2919; m/z, [NTF 2 ] ͞ calcd. for C 2 F 6 NO 4 S 2 − : 279.9173, found: 279.9145. N,N-bis[(3-allyl-benzimidazol-1-iumyl)ethyl]-4-methylbenzenesulphonamide-bis(trifluorometh- ylsulphonyl)amide (8a)This compound was prepared analogously to 7d using N, N-bis[(3-allyl-benzimidazol-1-iumyl) ethyl]-4-methylbenzenesulphonamide bromide 6a (0.7 g, 1.0 mmole) and Lithium bis-(trifluoromethanesulphonyl)imide LiNTf 2 (0.72 g, 2.5 mmol) to provide a clear viscous hygroscopic liquid at room temperature in 90% yield (1 g). Ten standard strains of Gram positive and negative bacteria were used to evaluate the antibacterial activities of the synthesized ILs compounds; 5a-f and 6a-f. Based on CLSI guidelines 85 , the activities were assessed in terms of minimum inhibitory concentrations (MICs) using microbroth dilution assays. The MIC's values are given in mg/mL and defined as a lowest concentration that inhibits the bacterial strains growth. Gram positive bacteria included: Streptococcus pyogenes ATCC19615, Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC6051, Rodococcus Ruber ATCC27863, Enterococcus faecalis ATCC 29212, Staphylococcus epidermidis ATCC12228, while Gram negative bacteria included: Escherichia coli ATCC10538, Salmonella typhimurium ATCC14028, Pseudomonas aeruginosa ATCC15442, Acinetobacter calcoaceticus ATCC 23055. These standards strains were obtained from the collection Distilled water was used as negative control to dissolve all the tested ILs in concentrations range of 0.05-0.5 mg/mL, while, commercial antibiotics amoxicillin and kanamycin were used as a positive control in the same range of concentrations. A loopful of bacterial cells from the nutrient agar plates ofThe incorporated benzenesulfonamide moiety and the active side substituents into diimidazolium and benzimidazolium cations enhanced both antibacterial activity and miscibility for the synthesized gimini type ILs.

show abstract

Section: Antibacterial Activitiesmentioning

confidence: 99%

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

2015

View full text Add to dashboard Cite

show abstract

“…The acceptable pharmacokinetics study, including increased half‐life and bioavailability of this compound confirms its potential in preclinical and clinical considerations . Kantevari and co‐workers synthesized and evaluated a series of 2‐butyl‐4‐chloroimidazole‐based substituted piperazine‐thiosemicarbazone derivatives against M. tuberculosis H37Rv and compounds 317 of the series exhibit MIC value of 3.13 μg/mL, similar to that of standard drug ethambutol (MIC = 3.13 μg/mL) …”

Section: Thiosemicarbazonesmentioning

confidence: 82%

“…Shahab and co-workers found that KBF611 (316), a fluoro group containing derivative of thiacetazone exhibit low MIC values of 0.1-0.2 g/mL against M. tuberculosis H37Rv, drug-sensitive and drug-resistant and MDR strains, and high selective index of >300.The acceptable pharmacokinetics study, including increased half-life and bioavailability of this compound confirms its potential in preclinical and clinical considerations 270. Kantevari and co-workers synthesized and evaluated a series of 2-butyl-4-chloroimidazole-based substituted piperazine-thiosemicarbazone derivatives against M. tuberculosis H37Rv and compounds 317 of the series exhibit MIC value of 3.13 g/mL, similar to that of standard drug ethambutol (MIC = 3.13 g/mL) 271. 34 THIOUREA DERIVATIVESThiocarlide (318, THC) was synthesized in 1951, and used for the treatment of TB in the 1960s.…”

mentioning

confidence: 79%

New structural classes of antituberculosis agents

Kumar

Patel

Jain

2017

Medicinal Research Reviews

View full text Add to dashboard Cite

Tuberculosis (TB), one of the deadliest diseases is shattering the health and socioeconomic status of the society. The emergence of multidrug resistant (MDR) and extremely drug resistant (XDR) strains has provided unprecedented lethal character to TB. The development of MDR and XDR strains of TB results in more deaths, longer duration of therapy, and appearance of the disease in the immunocompromised patients. Because of the development of rapid resistance by Mycobacterium tuberculosis, researchers are confronted with serious challenges in combating TB. For instance, the need for potency and specificity in therapeutic agents approaching clinics, and the increasing demand of low toxicity due to long duration of treatment. Recently, it is proposed that such challenges could be addressed by a shift from contemporary or known classes of drugs to new scaffold-containing or entirely new structural classes of drugs that possibly act on the previously unknown targets, resulting in possibly less instances of resistance development. The exploitation of advances made in the biology of TB in the last and present decades have created opportunities to discover a large number of new structural classes that specifically targets TB by molecular mechanism of action(s) unknown earlier. We have earlier reviewed new structural classes of anti-TB agents up to year 2005. This review covers literature reports of the subsequent 10 years on the discovery of new structural classes of synthetic anti-TB agents. Due to the availability of large number of research reports, we have divided new compounds in 38 structural classes, 368 structures, and 307 references.

show abstract

“…Fewer examples are found of complexes with these ligands, and none of those examples showed different coordination. The most interesting feature of those is that the metal coordination gives always a more active compound compared with the free ligands [7–9] . We have found no reports of imidazole TSCN derivatives with palladium as metal nor with different tautomers.…”

Section: Introductionmentioning

confidence: 88%

“…In this work, we have prepared thiosemicarbazones bearing only one imidazole as symmetric as possible to avoid the substituent impact reported in the references [7–9] . In addition, we have used thiosemicarbazones with a phenyl and p ‐tolyl group in the N4 position which gave the corresponding palladium complexes.…”

Section: Introductionmentioning

confidence: 99%

Two Different Thiosemicarbazone Tauto‐Conformers Coordinate to Palladium (II). Stability and Biological Studies of the Final Complexes

et al. 2021

View full text Add to dashboard Cite

Thiosemicarbazone moiety is a valuable scaffold for the synthesis of metallic complexes with anticancer purposes, when bearing N‐heterocyclic the final compounds possess diverse biological activities. Using thiazole as bioisosteres, the resulting thiosemicarbazones can afford synthetic drugs with a variety of pharmacological effects. Trying to elucidate, if metal complexes from α‐N‐heterocyclic thiosemicarbazones can achieve more selectivity versus special tumor lines, we have developed new metal complexes with 1H imidazole‐4‐carboxaldehyde 4 N‐p‐tolyl‐ and 4 N‐phenylthiosemicarbazone (HL1 and HL2 respectively). The solution studies of these ligands showed a tautomeric equilibria in solution and their reaction with Li2PdCl4 proved the stability of both forms affording two mononuclear Pd(II) complexes. Both tautomeric forms are clearly coordinated to palladium center acting as two different bidentate ligands. Palladium complexes’ stability in biological buffers was investigated to stablish the optimal conditions for the evaluation of cytotoxicity, that on the triple negative adenocarcinoma cell line showed IC50 values in the low micromolar range. Complexes were also studied with CT DNA (UV‐Visible spectroscopy and viscosity) and with the pBR322 plasmid supercoiled models, indicating non covalent interaction.

show abstract

2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis

Cited by 24 publications

References 32 publications

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

Bis-imidazolium and benzimidazolium based gemini-type ionic liquids structure: synthesis and antibacterial evaluation

New structural classes of antituberculosis agents

Two Different Thiosemicarbazone Tauto‐Conformers Coordinate to Palladium (II). Stability and Biological Studies of the Final Complexes

Contact Info

Product

Resources

About