Design, Synthesis and Structure‐Activity Relationship Study of Coumarin Benzimidazole Hybrid as Potent Antibacterial and Anticancer Agents

Holiyachi, Megharaja; Shastri, Samundeeswari L.; Chougala, Bahubali M.; Shastri, Lokesh A.; Joshi, Shrinivas D.; Dixit, Sheshagiri R.; Nagarajaiah, H.; Sunagar, Vinay A.

doi:10.1002/slct.201600665

Cited by 28 publications

(18 citation statements)

References 31 publications

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“…The majority of coumarin–benzoimidazole/imidazolium hybrids were devoid of activity or only exhibited weak activity against B. subtilis , B. cereus , S. aureus , Staphylococcus epidermis , P. aeruginosa , K. pneumoniae , and E. coli , [ 63–65 ] whereas hybrids 23a – c (MIC: 1.56 µg/ml) were comparable to ciprofloxacin (MIC: 1.5 µg/ml) and two to >32‐fold more potent than ampicillin, kanamycin, and tetracycline (MIC: 3.15 to >50 µg/ml) against Proteus vulgaris ( P. vulgaris ). [ 63 ]…”

Section: Coumarin–imidazole Hybridsmentioning

confidence: 99%

Coumarin‐containing hybrids and their antibacterial activities

Feng

Zhang

Yang

et al. 2020

Archiv der Pharmazie

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Infections caused by Gram-positive and -negative bacteria are one of the foremost causes of morbidity and mortality globally. Antibiotics are the mainstay of therapy for bacterial infections, but the emergence and wide spread of drug-resistant pathogens have already become a huge issue for public healthcare systems. The coumarin moiety, which is ubiquitous in nature, could bind to the B subunit of DNA gyrase in bacteria and inhibit DNA supercoiling by blocking the ATPase activity; hence, coumarin derivatives possess potential antibacterial activity. Several coumarin-containing hybrids such as coumermycin A1, clorobiocin, and novobiocin have already been used in clinical practice for the treatment of various bacterial infections; thus, it is conceivable that hybridization of the coumarin moiety with other antibacterial pharmacophores may provide opportunities for the development of novel antibiotics. This review outlines the advances in coumarin-containing hybrids with antibacterial potential in the recent 5 years and the structure-activity relationships are also discussed. K E Y W O R D S antibacterial, coumarin, hybrid compounds, structure-activity relationships

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Section: Coumarin–imidazole Hybridsmentioning

confidence: 99%

Coumarin‐containing hybrids and their antibacterial activities

Feng

Zhang

Yang

et al. 2020

Archiv der Pharmazie

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“…Furthermore, compounds that bear benzimidazole ring also show important activity against several viruses such as human cytomegalo virus, HIV and influenza . In recent years, some benzimidazole derivatives have found to have considerable antibacterial activity . The chiral aspects of benzimidazoles derivatives have not attracted much attention due to the numerous articles on benzimidazoles in the category of numerous therapeutic agents in the medical field.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of New Chiral Aminoalcohol and Benzimidazole Hybrids

et al. 2020

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New chiral aminoalcohol‐benzimidazole hybrids have been synthesized from commercially available aminoalcohols [S(+)‐Phenylglycinol, S(−)‐ Phenylalaninol and S(+)‐ Leuicinol] and 2‐(chloromethyl)‐N‐tosyl‐1‐H‐benzimidazole. The synthesized compound were characterized by IR, NMR, and LC‐MS analysis. The antibacterial properties of aminoalcohol‐benzimidazole hybrid molecules 4 a, 4 b, and 4 c were investigated against both gram (+ve) and gram (‐ve) bacterial pathogens by the well‐diffusion method using several standarts. The cell‐based biological experiment was consistent with in silico studies. Furthermore, in silico studies revealed that all synthesized compounds could be suggested as potential drugs for inhibition of both peptide deformylase for bacteria and sterol 14α‐demethylase for yeast.

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“…Combination of two worthwhile heterocyclic scaffolds in one molecule could construct a new bis ‐heterocyclic architecture that may increase its therapeutic potential and biological activity than their individual scaffolds via a synergistic effect . Namely, the bis ‐heterocycle framework containing uracil and benzofuran exhibited a potent anti‐HIV‐1 activity .…”

Section: Introductionmentioning

confidence: 99%

Rhodanine‐Furan Bis‐Heterocyclic Frameworks Synthesis via Green One‐Pot Sequential Six‐Component Reactions: A Synthetic and Computational Study

et al. 2019

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Combinatorial construction of a drug‐like library of novel rhodanine‐furan bis‐heterocyclic scaffolds has been demonstrated through a novel one‐pot sequential six‐component reaction in water under ultrasound irradiation with 100% atom economy. The process is a sequence of tandem Michael reactions followed by domino cycloaddition/zwitterionic adduct formation/Mumm rearrangement/[1+4] cycloaddition processes, involving diverse primary amines, carbon disulfide, maleic anhydride, dialkyl acetylenedicarboxylates and various isocyanides. No catalyst was required, but the use of aqueous two‐phase (on water) conditions was critical. Docking and molecular dynamics calculations performed on human aldose reductase suggest that the bis‐heterocyclic frameworks formed may be useful inhibitors of this enzyme.

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Design, Synthesis and Structure‐Activity Relationship Study of Coumarin Benzimidazole Hybrid as Potent Antibacterial and Anticancer Agents

Cited by 28 publications

References 31 publications

Coumarin‐containing hybrids and their antibacterial activities

Coumarin‐containing hybrids and their antibacterial activities

Synthesis and Antibacterial Activity of New Chiral Aminoalcohol and Benzimidazole Hybrids

Rhodanine‐Furan Bis‐Heterocyclic Frameworks Synthesis via Green One‐Pot Sequential Six‐Component Reactions: A Synthetic and Computational Study

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