Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide/sulfonamide derivatives as possible antimicrobial and antitubercular agents

Karuvalam, Ranjith P.; Pakkath, Rajeesh; Haridas, Karickal R.; N, Suchetha Kumari

doi:10.1016/j.ejmech.2013.11.002

Cited by 26 publications

(15 citation statements)

References 27 publications

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“…The established marketed drugs—metronidazole , ketoconazole , and cimetidine for bacterial infections, fungal infections, and gastric ulcers, respectively, also contain imidazole ring. Imidazole derivative finds usage in different capacities such as β‐lactamase inhibitor , 20‐HETE (20‐hydroxy‐5,8,11,14‐eicosatetraenoic acid) synthase inhibitor , carboxypeptidase inhibitor , heme oxygenase inhibitor , anti‐inflammatory , antibacterial and antifungal (antimicrobial) , antiviral , antitubercular , antidiabetic , antianalgesic , anticonvulsant , antioxidant , and anticancer . 1,2,3‐Triazole, an another important N ‐heterocyclic molecule, is endowed with broad spectrum of biological activities like antimicrobial , anti‐human immunodeficiency virus , antiviral , anticonvulsant , antimalarial , and anticancer activities probably because of conjugation with biological targets through hydrogen bond and dipole–dipole interaction.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Antimicrobial Activity and Molecular Docking of Novel 2,4,5‐Trisubstituted‐1H‐Imidazole–Triazole Hybrid Compounds

Chauhan

Verma

Kumar

et al. 2019

Journal of Heterocyclic Chem

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Section: Introductionmentioning

confidence: 99%

Facile Synthesis, Antimicrobial Activity and Molecular Docking of Novel 2,4,5‐Trisubstituted‐1H‐Imidazole–Triazole Hybrid Compounds

Chauhan

Verma

Kumar

et al. 2019

Journal of Heterocyclic Chem

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“…Sulfonamides, being antibacterial, having the prominent mechanism of action including attachment of sulfonamides with the dihydropteroate synthetase (DHPS) enzyme and alteration of bacterial pathways of folic acid synthesis in few eukaryotic cells, but in human beings, this mechanism is not followed [3,4]. The sulfonamides have been recognized due to various reported biological activities such as anticancer [5][6][7][8][9], anti-Alzheimer [10,11], anti-tubercular [12,13], antimicrobial [14][15][16][17], anti-inflammatory [18], carbonic anhydrase inhibitors [19][20][21][22], antidiabetic [11], anticonvulsant [23], and antimalarial [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

“…Due to these facts, there is a prime need to shorten the duration of therapy and ascertain newer antimicrobial agents to avert the emergence of resistance. In continuation of our efforts dedicated toward development of antimicrobials, we have screened compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) reported by Thakral and Singh [27] for antimicrobial potential along with QSAR and computational studies.…”

Section: Introductionmentioning

confidence: 99%

Biological Evaluation, Qsar and Molecular Modeling Studies of 2,4-Dichlorobenzoic Acid Derivatives as Antimicrobial Agents

Thakral

Singh

2019

Asian J Pharm Clin Res

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Objective: The aim of this study was to evaluate 2,4-dichlorobenzoic acid derivatives as antimicrobial agents through in vitro, QSAR and molecular docking studies. Methods: The compounds were subjected to in vitro antimicrobial screening by test tube dilution method and the structural characteristics governing the antimicrobial potential were studied using QSAR methodology. These compounds were also screened for docking simulation to find out binding confirmation of reported compounds with PDB 1aj0 and 5fsa using AutoDock tools and discovery studio. Results: The antimicrobial evaluation data indicated that compounds 13 and 18 were found to be the most effective against all the bacterial strains and Aspergillus niger while compounds 1 and 14 exhibited more antifungal potential against Candida albicans. QSAR studies confirmed the role of molar refractivity and Balaban index (J) as controlling parameters for antimicrobial potential. Molecular modeling study revealed that compounds interact with the active site of PDB by hydrophobic, hydrogen bonding, and Van der Wall interactions. Conclusion: These test compounds were identified as potent candidates for the control of microbial strains tested, and structural relationship with activity may provide valuable information for further design and synthesis of compounds with antimicrobial potential.

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“…Sulfonamides and their derivatives constitute an important class of therapeutic agents that exhibit a broad spectrum of pharmacological profiles, such as anti-bacterial, diuretic, hypoglycaemic, anti-thyroid, anti-viral, anti-inflammatory and anti-parasitic activities among others (Ranjith et al, 2014;Shah et al, 2013;Scozzafava et al, 2013;Greig et al, 2013). In our previous work, we have found that indazoles bearing arylsulfonamide groups showed anti-proliferative activity against human (colon and prostate) and murine (leukaemia) cell lines (Abbassi et al, 2012(Abbassi et al, , 2014Bouissane, et al, 2006).…”

Section: Structure Descriptionmentioning

confidence: 99%

4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate

et al. 2017

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The asymmetric unit of the title compound, 2C 15 H 15 N 3 O 3 SÁH 2 O, comprises two crystallographically independent organic molecules and one water molecule, all in general positions. Each organic molecule comprises an indazolyl system linked through a sulfonamide group to a methoxybenzene ring. The most important difference between the two organic molecules is the dihedral angle between the fused-ring system and the methoxybenzene ring, which is 56.32 (7) in one molecule and 35.35 (8) in the other. In the crystal, the organic and water molecules are connected into supramolecular chains along the c axis through O-HÁ Á ÁN, O-HÁ Á ÁO, N-HÁ Á ÁO and N--HÁ Á ÁN hydrogen bonds; in addition, a -interaction between pyrazolyl rings [inter-centroid separation = 3.7547 (12) Å ] is noted. Structure descriptionSulfonamides and their derivatives constitute an important class of therapeutic agents that exhibit a broad spectrum of pharmacological profiles, such as anti-bacterial, diuretic, hypoglycaemic, anti-thyroid, anti-viral, anti-inflammatory and anti-parasitic activities among others (Ranjith et al., 2014;Shah et al., 2013;Scozzafava et al., 2013;Greig et al., 2013). In our previous work, we have found that indazoles bearing arylsulfonamide groups showed anti-proliferative activity against human (colon and prostate) and murine (leukaemia) cell lines (Abbassi et al., 2012(Abbassi et al., , 2014Bouissane, et al., 2006).The asymmetric unit of the title compound contains two independent organic molecules and one water molecule, as shown in Fig. 1. The fused five-and six-membered rings of each molecule are almost coplanar, with the maximum deviation from the mean plane being 0.020 (2) Å for the C12 atom and 0.022 (2) Å for the C27 atom in the first and data reports second molecules, respectively. The dihedral angles between the indazolyl system and the methoxybenzene ring are 56.32 (7) and 35.35 (8) in the first and second molecules, respectively.In the crystal, the organic molecules are connected through the water molecule by O7-H7AÁ Á ÁN6, O7-H7BÁ Á ÁO2, N1-HN1Á Á ÁO7 and N4-HN4Á Á ÁN3 hydrogen bonds (Table 1), in addition to -interactions between pyrazole rings as shown in Fig. 2. Synthesis and crystallizationA mixture of 1-methyl-7-nitroindazole (1.22 mmol) and anhydrous SnCl 2 (1.1 g, 6.1 mmol) in ethanethiol (25 ml) was heated at 308 K for 4 h. After reduction, the starting material had been consumed and the solution was allowed to cool. The pH of the solution was made slightly basic (pH = 7-8) by addition of 5% aqueous potassium bicarbonate. Extraction with EtOAc followed. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methoxybenzenesulfonyl chloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture had been concentrated in vacuo, the resulting residue was purified by flash chromatography (elution was with EtOAc/hexane 1:9). The title compoun...

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Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide/sulfonamide derivatives as possible antimicrobial and antitubercular agents

Cited by 26 publications

References 27 publications

Facile Synthesis, Antimicrobial Activity and Molecular Docking of Novel 2,4,5‐Trisubstituted‐1H‐Imidazole–Triazole Hybrid Compounds

Facile Synthesis, Antimicrobial Activity and Molecular Docking of Novel 2,4,5‐Trisubstituted‐1H‐Imidazole–Triazole Hybrid Compounds

Biological Evaluation, Qsar and Molecular Modeling Studies of 2,4-Dichlorobenzoic Acid Derivatives as Antimicrobial Agents

4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate

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