Synthesis of 2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide-based azetidinone derivatives as potent antibacterial and antifungal agents

Kumar, Shiv; Kumar, Nitin; Drabu, Sushma; Minhaj, Md. Akram

doi:10.1007/s12039-012-0354-x

J Chem Sci

2013

DOI: 10.1007/s12039-012-0354-x

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Synthesis of 2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide-based azetidinone derivatives as potent antibacterial and antifungal agents

Shiv Kumar¹,

Nitin Kumar²,

Sushma Drabu³

et al.

Abstract: Twelve compounds belonging to series N -[3-chloro-2-oxo-4-(substituted)phenylazetidin-1-yl]-2-(3-methyl-2-oxoquinoxalin-1(2H )-yl)acetamide (5a-l) were synthesized. These compounds were evaluated for their in vitro antibacterial against E. coli, S. aureus, K. pneumoniae, P. aeruginosa and antifungal activity against C. albicans, A. niger and A. flavus by cup-plate method. Structures of all the newly synthesized compounds were confirmed by their spectral data interpretation. Compound 5g having p-dimethylaminoph… Show more

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ChemInform Abstract: Synthesis of 2‐(3‐Methyl‐2‐oxoquinoxalin‐1(2H)‐yl)acetamide‐Based Azetidinone Derivatives as Potent Antibacterial and Antifungal Agents.

Kumar¹,

Kumar²,

Drabu³

et al. 2013

ChemInform

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Synthesis of 2-(3-Methyl-2-oxoquinoxalin-1(2H)-yl)acetamide-Based AzetidinoneDerivatives as Potent Antibacterial and Antifungal Agents. -A variety of new azetidinone derivatives (V) (12 examples) are synthesized and evaluated for their antimicrobial activities. Among them, compound (Vf) is found to be active against all bacterial and fungal strains under investigation. -(KUMAR*, S.; KUMAR, N.; DRABU, S.; MINHAJ, M. A.; J. Chem. Sci. (Bangalore, India) 125 (2013) 1, 129-139, http://dx.doi.org/10.1007/s12039-012-0354-x ; Div. Pharm. Chem., Dep. Pharm., IEC Coll. Eng. Technol., Greater Noida 201 308, India; Eng.) -C. Cyrus 24-161

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ChemInform Abstract: Synthesis of 2‐(3‐Methyl‐2‐oxoquinoxalin‐1(2H)‐yl)acetamide‐Based Azetidinone Derivatives as Potent Antibacterial and Antifungal Agents.

Kumar¹,

Kumar²,

Drabu³

et al. 2013

ChemInform

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Design, Synthesis and Bioactivity Evaluation of Ag(I)‐, Au(I)‐ and Au(III)‐Quinoxaline‐Wingtip N‐Heterocyclic Carbene Complexes Against Antibiotic Resistant Bacterial Pathogens

Sahu,

Mandal,

Biswas

et al. 2024

ChemMedChem

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Intending to homogenize the biological activities of both quinoxaline and imidazole moieties, the proligand, 1‐methyl‐3‐quinoxaline‐imidazolium hexaflurophosphate (1.HPF6), and [Ag(1)2][PF6], (2); [Au(1)2][PF6], (3); and [Au(1)Cl3], (4) NHC complexes were synthesized. All the synthesized compounds were characterized by elemental analysis, NMR, and UV‐Vis spectroscopy. Finally, single crystal X‐ray structures revealed a linear geometry for complex 2 whereas a square planar geometry for complex 4. The formation of complex 3 was confirmed and supported by its MS spectra. The antibacterial activities of all the synthesized complexes were investigated against gram‐positive bacteria and gram‐negative bacteria. The Au(III)‐NHC complex, 4 showed the highest antibacterial activity with extremely low MIC values against both the bacterial strains (0.24 µg.mL‐1). Monitoring of zeta potential supports the higher activity of complex 4 compared to 2 and 3. ROS production by complex 4 has also been measured in vitro in the CT26 cancer cell lines, which is directly responsible for targetting and killing the bacterial pathogens. Cell cytotoxicity assay using 293T cell lines has been performed to investigate the biocompatibility nature of complex 4. Also, an excellent hemocompatibility was assigned to it from its hemolytic studies, which provide valuable insights into the design of novel antibacterial agents.

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Quinoxaline: A Chemical Moiety with Spectrum of Interesting Biological Activities

Sharma

Deep

Marwaha

et al. 2022

MRMC

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: Quinoxaline (C8H6N2), commonly called 1,4-diazanaphthalene, 1,4-benzodiazine, or benzopyrazine, is a very potent nitrogenous heterocyclic moiety consisting of a benzene ring fused with the pyrazine ring. A number of different methods for the synthesis of quinoxaline derivatives have been reported in the literature, but the most effective method, commonly used for the synthesis of quinoxaline analogues involves the condensation of substituted o-phenylenediamines with 1, 2- dicarbonyl compounds in the presence of different catalyst(s). The presence of different types of catalysts and their concentration affects the overall yield of the product. Quinoxaline not only plays an important role as an organic reaction intermediate but also has a wide spectrum of interesting biological activities viz. antibacterial, antifungal, anticancer, anti-inflammatory, antiviral, and antiprotozoal activity, etc. Some commercially available drug molecules containing quinoxaline moiety are echinomycin (as antibacterial, antineoplastic, and nucleic acid inhibitor), triostins (cyclic desipeptide as an antibacterial agent), dioxidine and mequindox (as antibacterial agents), carbadox (controlling swine dysentery), desoxycarbadox (as swine growth promoter) and panadipion (as hepatoprotective agent), etc. A large number of quinoxaline analogues possessing different biological activities and their synthetic procedures have been patented worldwide.

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Synthesis of 2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide-based azetidinone derivatives as potent antibacterial and antifungal agents

Cited by 3 publications

References 32 publications

ChemInform Abstract: Synthesis of 2‐(3‐Methyl‐2‐oxoquinoxalin‐1(2H)‐yl)acetamide‐Based Azetidinone Derivatives as Potent Antibacterial and Antifungal Agents.

ChemInform Abstract: Synthesis of 2‐(3‐Methyl‐2‐oxoquinoxalin‐1(2H)‐yl)acetamide‐Based Azetidinone Derivatives as Potent Antibacterial and Antifungal Agents.

Design, Synthesis and Bioactivity Evaluation of Ag(I)‐, Au(I)‐ and Au(III)‐Quinoxaline‐Wingtip N‐Heterocyclic Carbene Complexes Against Antibiotic Resistant Bacterial Pathogens

Quinoxaline: A Chemical Moiety with Spectrum of Interesting Biological Activities

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