One pot, simple, and efficient synthesis of (E)- and (Z)-3-allylidene-β-lactams from 3-allyl-3-phenylseleno-β-lactams: analogues of β-lactamase inhibitors

Bhalla, Aman; Bari, S. S.; Vats, Sunil; Bhalla, Jitender; Sharma, Kiran; Narula, Dipika

doi:10.1016/j.tetlet.2016.09.043

Cited by 18 publications

(2 citation statements)

References 22 publications

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“…Till now, our research group has been engaged in the synthesis of selenoalkanoic acids useful as β‐lactam precursors , novel 3‐thio/seleno‐β‐lactams and their Lewis acid mediated functionalization , stereoselective synthesis of cis ‐ and trans ‐3‐alkoxy‐β‐lactams , spirocyclic‐β‐lactams , ( Z )‐ and ( E )‐3‐allylidene‐β‐lactams , 3‐keto‐β‐lactams , bicyclic‐β‐lactams , and 4‐pyrazolyl β‐lactams . Herein, we report the synthesis of novel pyrimidine/pyrazole linked β‐lactams using a facile and efficient methodology.…”

Section: Introductionmentioning

confidence: 99%

Pyrimidine and Pyrazole Linked Azetidin‐2‐ones: Entry to Novel Class of β‐Lactam Heterocycles

Bhalla

Bari

Rathee

et al. 2017

Journal of Heterocyclic Chem

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A novel series of pyrimidine/pyrazole linked β-lactams have been synthesized in excellent yields using a simple and efficient methodology involving conjunction of different heterocyclic substrates. All the new products were characterized on the basis of various spectroscopic techniques viz. FT-IR, 1 H NMR, 13 C NMR, elemental analysis (CHN), 1 H-1 H correlation spectroscopy ( 1 H-1 H COSY) and mass spectrometry (EIMS) in representative cases. Furthermore, theoretical calculations have also been performed on representative compounds and the results were compared with Cefuroxime axetil (a broad spectrum antibacterial agent). The phenomenon of tautomerism was also observed which was confirmed by different NMR experiments (D 2 O exchange study and 1 H-1 H correlation spectroscopy).

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Section: Introductionmentioning

confidence: 99%

Pyrimidine and Pyrazole Linked Azetidin‐2‐ones: Entry to Novel Class of β‐Lactam Heterocycles

Bhalla

Bari

Rathee

et al. 2017

Journal of Heterocyclic Chem

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“…Some functional groups undergo competitive reactions, yielding isomers such as Markovnicov/anti-Markovnicov products of ionic addition on alkenes (Lorusso et al, 2006) and alkynes (Trostyanskaya et al, 2012), Z/E elimination reaction products (Darcsi et al, 2017;Bhalla et al, 2016), nucleophilic oxirane ring opening reaction products (Larin et al, 2014;Marié et al 2007) etc.…”

Section: Introductionmentioning

confidence: 99%

NMR/Binomial Theorem Determination of the Number and the Proportions of Isomers of Poly(identical) Spaced Functional Group Substrate Reactions

Mekni¹

2017

IJC

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Design, Synthesis, DNA Binding, Cytotoxicity, and Molecular Docking Studies of Amonafide‐Linked β‐Lactam

et al. 2019

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This study describes our investigations on the synthesis, molecular modeling, and biological capabilities of a new β‐lactam containing the anticancer agent, amonafide. This is the first time that amonafide has been applied to a β‐lactam synthesis, which involved five steps from naphthalic anhydride. The β‐lactam was structurally characterized by FT‐IR, 1H NMR, 13C NMR, mass spectra, and elemental analysis. UV‐vis and fluorescence spectroscopy studies indicated that the β‐lactam is an effective DNA intercalating agent. Gel electrophoresis confirmed its intercalation into the pBluescript plasmid DNA, causing a considerable decrease in its electrophoretic mobility. The gel electrophoresis pattern in the presence of ethidium bromide, acridine orange, and methyl green also demonstrated that the β‐lactam was stacked tightly between DNA bases via the major groove. Moreover, the MTT assay of the β‐lactam against the HepG2 cancerous cell line showed potential cytotoxic behavior with an IC50 of 65.5 μM and 34.2 μM after 48 and 72 h incubation, respectively. Molecular docking experiments were also in agreement with the experimental data and showed the major groove binding behavior of the β‐lactam.

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One pot, simple, and efficient synthesis of (E)- and (Z)-3-allylidene-β-lactams from 3-allyl-3-phenylseleno-β-lactams: analogues of β-lactamase inhibitors

Cited by 18 publications

References 22 publications

Pyrimidine and Pyrazole Linked Azetidin‐2‐ones: Entry to Novel Class of β‐Lactam Heterocycles

Pyrimidine and Pyrazole Linked Azetidin‐2‐ones: Entry to Novel Class of β‐Lactam Heterocycles

NMR/Binomial Theorem Determination of the Number and the Proportions of Isomers of Poly(identical) Spaced Functional Group Substrate Reactions

Design, Synthesis, DNA Binding, Cytotoxicity, and Molecular Docking Studies of Amonafide‐Linked β‐Lactam

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