Synthesis and characterization of novel trans-3-benzyl/(diphenyl)methyl/naphthyl seleno substituted monocyclic β-lactams: X-ray structure of trans-1-(4′-methoxyphenyl)-3-(diphenyl)methylseleno-4-(4′-methoxyphenyl)azetidin-2-one

Bari, S. S.; Bhalla, Aman; Nagpal, Yogesh; Mehta, S.K.; Bhasin, K. K.

doi:10.1016/j.jorganchem.2010.05.005

Cited by 15 publications

(7 citation statements)

References 38 publications

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“…30,31 The products obtained in good to excellent yields were having cis configuration of hydrogen atoms at C-3/C-4. …”

Section: Methodsmentioning

confidence: 93%

Advances in synthesis of monocyclic beta-lactams

Singh¹,

Sudheesh²

2014

Arkivoc

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Recent years have witnessed significant advancement in cycloaddition and cyclization strategies for the synthesis of monocyclic β-lactams. Cycloadditions include the Staudinger's keteneimine cycloaddtions and related reaction. Cyclization reactions are reported to furnish β-lactams through N 1 -C 2 , N 1 -C 4 and C 3 -C 4 bond formations employing substrates like β-amino esters, β-amino alcohols, β-hydroxamate esters, and α-amino diazocarbonyls, etc. Some other strategies are silyl carbonylation reactions, ring-enlargement of aziridines, cleavage of one ring of a bicyclic β-lactam, and functional group transformations on the β-lactam rings. Recently, some multi-component reactions have also been designed. This article reviews the advances made in synthetic approaches to monocyclic β-lactams during last five years.

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“…30,31 The products obtained in good to excellent yields were having cis configuration of hydrogen atoms at C-3/C-4. …”

Section: Methodsmentioning

confidence: 93%

Advances in synthesis of monocyclic beta-lactams

Singh¹,

Sudheesh²

2014

Arkivoc

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“…After concentration under reduced pressure, the residue was purified by silica-gel chromatography (230-400 mesh) using 30-40% ethyl acetate in petroleum ether. The title compounds (4a-g, 4i-s) were obtained in low to good yields 25 . The 1,3-oxazin-4-one derivatives (4h, 4t) were also obtained under the same reaction conditions in low to moderate yields ranging from 22% to 41%.…”

Section: General Procedures For the Synthesis Of Imines (3a-d)mentioning

confidence: 99%

Monocyclicβ-lactam and unexpected oxazinone formation: synthesis, crystal structure, docking studies and antibacterial evaluation

Aneja

Irfan

Hassan

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Novel monocyclic b-lactam derivatives bearing aryl, phenyl and heterocyclic rings were synthesized as possible antibacterial agents. Cyclization of imines (3h, 3t) with phenylacetic acid in the presence of phosphoryl chloride and triethyl amine did not afford the expected b-lactams. Instead, highly substituted 1,3-oxazin-4-ones (4h, 4t) were isolated as the only product and confirmed by single crystal X-ray analysis of 4t. The results of antibacterial activity showed that compound 4l exhibited considerable antibacterial activity with MIC and MBC values of 62.5 mg/mL against Klebsiella pneumoniae. Cytotoxicity assay on Chinese Hamster Ovary (CHO) cell line revealed non-cytotoxic behavior of compounds 4d, 4h, 4k and 4l up to 200 mg/mL conc. Molecular docking was performed for compound 4l with penicillin binding protein-5 to identify the nature of interactions. The results of both in silico and in vitro evaluation provide the basis for compound 4l to be carried as a potential lead molecule in the drug discovery pipeline against bacterial infections.

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“…In our earlier studies, we have demonstrated the synthesis of selenoalkanoic acids useful as β-lactam precursors [31,32], novel 3-thio/seleno β-lactams and Lewis acid mediated functionalization [33][34][35][36][37][38][39], stereoselective cis-and trans-3-alkoxy-β-lactams [40], spirocyclic β-lactams [35,[41][42], (Z)-and (E)-3-allylidene-β-lactams [43], 3-keto-β-lactams [44] and bicyclic-β-lactams [45]. Recently, hybrid β-lactams I, II, III (Figure 1) with varied heterocyclic moieties have been shown to exhibit antimicrobial, antiprotozoal, anti-inflammatory and analgesic activities [46][47][48].…”

Section: Canadian Chemical Transactionsmentioning

confidence: 99%

Synthesis of Novel Pyrazolylmethylene-Pyrimidine Heterocycles: Potential Synthons for Hybrid Β-Lactams

2015

Can Chem Trans

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Diversely substituted novel pyrazolylmethylene-pyrimidine heterocycles were synthesized via Knoevenagel condensation between substituted formyl pyrazoles and barbituric acids without any base or solid catalyst. All these thirteen novel heterocycles were characterized by FT-IR, NMR spectroscopy ( 1 H, 13 C), 13 C DEPT-135, 1 H- 13C HSQC, elemental analysis and mass spectrometry (in representative case).

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Synthesis and characterization of novel trans-3-benzyl/(diphenyl)methyl/naphthyl seleno substituted monocyclic β-lactams: X-ray structure of trans-1-(4′-methoxyphenyl)-3-(diphenyl)methylseleno-4-(4′-methoxyphenyl)azetidin-2-one

Cited by 15 publications

References 38 publications

Advances in synthesis of monocyclic beta-lactams

Advances in synthesis of monocyclic beta-lactams

Monocyclicβ-lactam and unexpected oxazinone formation: synthesis, crystal structure, docking studies and antibacterial evaluation

Synthesis of Novel Pyrazolylmethylene-Pyrimidine Heterocycles: Potential Synthons for Hybrid Β-Lactams

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