A Facile and Stereoselective Synthesis of 3‐Phenylsulfinyl‐β‐lactams Using Selectfluor

Pandey, Suvidha; Thakur, Anup; Reshma,; Bari, S. S.; Thapar, Renu

doi:10.1002/slct.201904114

Cited by 3 publications

(3 citation statements)

References 45 publications

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“…Our previous studies have proved the use of 3-phenylthio-β-lactams as an important synthons for C-3 functionalization reactions, thereby resulting in synthesis of a variety of novel β-lactams [24][25][26][27][28]. In continuation of such studies, we became interested in finding out the method to increase the utility of these compounds.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, characterization, and antibacterial activity studies of β‐lactam capped silver nanoparticles

Thakur,

Pandey,

Mittal

et al. 2024

Journal of Heterocyclic Chem

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A highly efficient, novel, two‐phase liquid method using phase transfer catalyst is reported to prepare β‐lactam‐conjugated silver nanoparticles as an approach to improve antibacterial activity of β‐lactams. In the method assisted by cetyltrimethylammonium bromide, NaBH4 reduced AgNO3 producing silver NPs that are coated with β‐lactams. The studies conducted provide a generalized method applicable to all types of β‐lactam substrates for capping on silver NPs. The NPs have been characterized by UV–Visible, Fourier transform infrared spectroscopy, x‐ray diffraction, transmission electron microscopy, and dynamic light scattering methods.

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Section: Resultsmentioning

confidence: 99%

“…These were characterized by spectral analysis. The stereochemistry of synthesized β‐lactams has been assigned on the basis of C‐3‐H and C‐4‐H coupling constant ( J = 2.36 Hz) [24]. The spectral peaks for the representative compound 3a showed a sharp band at 1764 cm −1 for the carbonyl group in the IR spectrum.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, and antibacterial activity studies of β‐lactam capped silver nanoparticles

Thakur,

Pandey,

Mittal

et al. 2024

Journal of Heterocyclic Chem

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“…However, 2-azetidinones are also directly accessible from imines and carboxylic acids via mixed anhydrides [65], using activating agents such as methoxymethylene-N,N-dimethyliminium salt, [66], the Vilsmeier reagent, the Mukaiyama reagent and triphosgene [67]. 3-Chloro-3-thioaryl-β-lactams, obtained by the chlorination of 3-thioaryl-β-lactams with sulfuryl chloride, are reported as suitable substrates for Lewis acid catalysed nucleophilic substitution reactions [68]. In the present work, the Staudinger reaction of the imines 9a-9k and 9m-9s with chloroacetyl chloride in the presence of triethylamine (Scheme 2) afforded the β-lactam products 10a-m and 10o as racemic mixtures in yields of 3-57%.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Antiproliferative Evaluation of 3-Chloroazetidin-2-ones with Antimitotic Activity: Heterocyclic Bridged Analogues of Combretastatin A-4

et al. 2021

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Antimitotic drugs that target tubulin are among the most widely used chemotherapeutic agents; however, the development of multidrug resistance has limited their clinical activity. We report the synthesis and biological properties of a series of novel 3-chloro-β-lactams and 3,3-dichloro-β-lactams (2-azetidinones) that are structurally related to the tubulin polymerisation inhibitor and vascular targeting agent, Combretastatin A-4. These compounds were evaluated as potential tubulin polymerisation inhibitors and for their antiproliferative effects in breast cancer cells. A number of the compounds showed potent activity in MCF-7 breast cancer cells, e.g., compound 10n (3-chloro-4-(3-hydroxy-4-methoxy-phenyl)-1-(3,4,5-trimethoxyphenyl)azetidin-2-one) and compound 11n (3,3-dichloro-4-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-azetidin-2-one), with IC50 values of 17 and 31 nM, respectively, and displayed comparable cellular effects to those of Combretastatin A-4. Compound 10n demonstrated minimal cytotoxicity against non-tumorigenic HEK-293T cells and inhibited the in vitro polymerisation of tubulin with significant G2/M phase cell cycle arrest. Immunofluorescence staining of MCF-7 cells confirmed that β-lactam 10n caused a mitotic catastrophe by targeting tubulin. In addition, compound 10n promoted apoptosis by regulating the expression of pro-apoptotic protein BAX and anti-apoptotic proteins Bcl-2 and Mcl-1. Molecular docking was used to explore the potential molecular interactions between novel 3-chloro-β-lactams and the amino acid residues of the colchicine binding active site cavity of β-tubulin. Collectively, these results suggest that 3-chloro-2-azetidinones, such as compound 10n, could be promising lead compounds for further clinical anti-cancer drug development.

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Synthesis of Novel β-Lactams via Substitution Reactions of Thiolaryl Substituted β-Lactam Precursors

Thakur,

Pandey,

Thapar

2023

Organic Preparations and Procedures International

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A Facile and Stereoselective Synthesis of 3‐Phenylsulfinyl‐β‐lactams Using Selectfluor

Cited by 3 publications

References 45 publications

Synthesis, characterization, and antibacterial activity studies of β‐lactam capped silver nanoparticles

Synthesis, characterization, and antibacterial activity studies of β‐lactam capped silver nanoparticles

Synthesis and Antiproliferative Evaluation of 3-Chloroazetidin-2-ones with Antimitotic Activity: Heterocyclic Bridged Analogues of Combretastatin A-4

Synthesis of Novel β-Lactams via Substitution Reactions of Thiolaryl Substituted β-Lactam Precursors

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