Synthesis and antibacterial activity of some novel imidazole-based dicationic quinolinophanes

Rajakumar, Perumal; Raja, Rathinam; Selvam, S. Periyar; Rengasamy, Ramasamy; Subramani, Nagaraj

doi:10.1016/j.bmcl.2009.05.019

Cited by 23 publications

(12 citation statements)

References 28 publications

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“…Most ILs contain heterocyclic derivatives as cations, e.g. 53,54 The current work concentrates on synthesis novel geminal bis-imidazolium and benzimidazolium ILs consist of two substituents symmetric head groups (two identical cations), linked by high rigidity spacer containing benzenesulfonamide moiety in high yield and purity. Drug designs based on high therapeutic properties of the imidazole and benzimidazole are considered as an advantage towards synthesize number of novel clinical agents against various types of diseases.…”

Section: Introductionmentioning

confidence: 99%

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

2015

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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.

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Section: Introductionmentioning

confidence: 99%

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

2015

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“…In the course of identifying new potential targets for bacterial treatment, Rajakumar et al . investigated the synthesis and antibacterial activity of some novel (benz)imidazole‐based dicationic quinolinophanes incorporating catechol and S‐(‐)‐BINOL units (Figure ).…”

Section: Antimicrobial Activities Of (Benz)imidazole‐based Macrocyclesmentioning

confidence: 99%

Medicinal applications of (benz)imidazole‐ and indole‐based macrocycles

Patil

2017

Chem Biol Drug Des

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Macrocyclic chemistry is one of the emerging research areas in the chemical science.Macrocyclic compounds continue to attract significant attention due to their numerous possible applications particularly in the areas like biology, catalysis and industry.This review article summarizes the developments and advances in synthesis and medicinal applications of macrocyclic compounds derived from (benz)imidazoleand indole-based heterocycles. Important medicinal applications of (benz)imidazoleand indole-based macrocycles include antimicrobial and anticancer activities. The representative lead compounds in each series of macromolecules have been discussed. All these initial lead breakthroughs help validate the great potential of (benz) imidazole-and indole-based macrocyclic compounds as a class of effective medicinal agents. S P E C I A L I S S U E A R T I C L E Medicinal applications of (benz)imidazole-and indole-based macrocyclesA macrocycle is a compound that contains a cyclic structure of at least twelve or more atoms. Macrocyclic compounds are natural or synthetic polydentate compounds, containing their donor atoms either incorporated in or less commonly attached to a cyclic backbone. Macrocyclic compounds having heteroatoms are important compounds with broad spectrum of biological activities [1][2][3][4][5][6][7] apart from their potential applications in supramolecular chemistry, catalysis and new materials. [8,9] Over the last few years, macrocyclic chemistry has attracted lot of interest and has become a growing area of research in inorganic and organic chemistry in view of its biological importance. [1][2][3][4] Compared to linear peptide macromolecules, cyclic macromolecules provide improved stability and membrane permeability. These factors were clearly demonstrated in the development of hepatitis C virus (HCV) NS3 protease inhibitor, BILN2061. To optimize multiparameters such as aqueous solubility, microsomal stability and lipophilicity, Zapf et al. used the twelve-membered macrocycles as a promising platform to generate potent Hsp90 inhibitors. Their detailed study revealed that as ring size increased aqueous solubility and microsome stability were decreased whereas lipophilicity increased with increasing ring size.[ [10][11][12][13][14] Within different classes of macrocycles, (benz)imidazoleand indole-based macrocycles have received a great deal attention in drug discovery. These compounds exhibit biological activity as antimicrobial and anticancer agents because of their specific structures. Presently, the syntheses of (benz)imidazole-and indole-based macrocycles have received an increasing attention to synthetic (inorganic and organic) chemists and biologists. Therefore, the newly emerging interest in the antimicrobial and anticancer applications of (benz)imidazole-and indole-based macrocycles led us to examine the few accounts available in the recent literature dealing with this area of research. In this review article, we focus on the synthesis and biological applications such as antimicrobial and a...

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“…The BINOL ring framework is among these bioactive scaffolds that have been considered one of the mainstays in providing novel chemical scaffolds for many drugs. Chiral bicyclic macrocycles, Imidazole based dicationic macrocycles, chiral dendrimers,, Imidazolium salts at 3,3’ substitution on BINOL and [2,1‐ b :1′,2′‐ d ][1,6]dioxacycloalkenes having BINOL as core unit show antibacterial activity. Very few reports are available on 3,3′‐disubstituted chiral ( R )‐BINOL.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Chiral (R)‐BINOL Derivatives under Microwave Irradiation and Evaluation of Their Antibacterial and α‐Glucosidase Inhibitory Activity

Ankireddy¹,

Paidikondala²,

Gundla³

et al. 2019

ChemistrySelect

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Series of new 3,3’‐disubstituted chiral (R)‐BINOL compounds have been synthesized with good yields and short reaction time under microwave‐irradiation. The titled compounds showed great antibacterial activity against gram‐positive and gram‐negative organisms. The results indicated that two compounds (R)‐3,3′‐bis(3,5‐difluorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 a) and (R)‐3,3′‐bis(4‐nitrophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 d) which bearing fluoro and nitro substitution on phenyl group has displayed highest inhibition against pathogens. All the derivatives evaluated in vitro against α‐glucosidase. The results indicates that all the target compounds have significant inhibitory activity and more potent than standard drug Acarbose (IC50 = 586.391 ± 14.017 μM). (R)‐3,3′‐bis(3,5‐dichlorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 b), (R)‐3,3′‐bis(3,5‐difluorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 a), (R)‐3,3′‐bis(4‐nitrophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 d) and (R)‐3,3′‐bis(3,5‐dimethylphenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 f) compounds shows strong inhibitors of α‐glucosidase, with the IC50 values of 25.341 ± 0.009 μM, 29.215 ± 0.017 μM, 30.294 ± 0.012 μM and 32.402 ± 0.041 μM, respectively.

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Synthesis and antibacterial activity of some novel imidazole-based dicationic quinolinophanes

Cited by 23 publications

References 28 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

Medicinal applications of (benz)imidazole‐ and indole‐based macrocycles

Synthesis of New Chiral (R)‐BINOL Derivatives under Microwave Irradiation and Evaluation of Their Antibacterial and α‐Glucosidase Inhibitory Activity

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