Stereoselective synthesis of <i>trans</i>-3-functionalized-4-pyrazolo[5,1-<i>b</i>]thiazole-3-carboxylate substituted β-lactams: Potential synthons for diverse biologically active agents

Berry, Shiwani; Bari, S. S.; Yadav, Pooja; Garg, Ankita; Khullar, Sadhika; Mandal, Sanjay K.; Bhalla, Aman

doi:10.1080/00397911.2020.1788599

Cited by 15 publications

(4 citation statements)

References 23 publications

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“…Multicomponent cycloaddition reactions have been the most widely employed methods in order to obtain β-lactam derivatives, highlighting the synthesis based on the Staudinger ketene-imine cycloaddition. 2,[28][29][30][31][32][33] This section discusses selected recent examples of metal-free stereoselective cycloaddition syntheses of β-lactams.…”

Section: Metal-free Cycloaddition Reactionsmentioning

confidence: 99%

Stereoselective synthesis of β-lactams: recent examples

Saura‐Sanmartin

Andreu-Ardil

2023

Org. Biomol. Chem.

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Section: Metal-free Cycloaddition Reactionsmentioning

confidence: 99%

Stereoselective synthesis of β-lactams: recent examples

Saura‐Sanmartin

Andreu-Ardil

2023

Org. Biomol. Chem.

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“…[33][34][35] Our previous studies have been dedicated towards the synthesis of aryl/pyrazolyl substituted spirocyclic and pyrazolo[5,1b]thiazole-3-carboxylate/(4-thiophenyl)pyrazolyl/benzimidazolyloxyphenyl conjugated heterocyclic β-lactams. [36][37][38][39] Moreover, the advancement in spirocyclic systems and charismatic contour of thiophene analogs in discovering new pharmaceutically active compounds, encouraged us to design spiro-hybrid heterocyclic building blocks with improved pharmacokinetics and safety profile. By blending various aliphatic and heterocyclic elements, we crafted a focused collection of pioneering spirocyclic-β-lactams poised as potential antimicrobial candidates.…”

Section: Introductionmentioning

confidence: 99%

“…Unsubstituted or multi‐substituted thiophene ring behaves as structural stone in diverse drug derivatives which might be assigned to its consequential pharmacokinetic significance [33–35] . Our previous studies have been dedicated towards the synthesis of aryl/pyrazolyl substituted spirocyclic and pyrazolo[5,1‐ b ]thiazole‐3‐carboxylate/(4‐thiophenyl)pyrazolyl/benzimidazolyloxyphenyl conjugated heterocyclic β‐lactams [36–39] . Moreover, the advancement in spirocyclic systems and charismatic contour of thiophene analogs in discovering new pharmaceutically active compounds, encouraged us to design spiro‐hybrid heterocyclic building blocks with improved pharmacokinetics and safety profile.…”

Section: Introductionmentioning

confidence: 99%

C7‐Halomethylene/methyl‐C3‐thiophenyl‐spirocyclic‐β‐lactams: Synthesis, X‐ray Analysis, Antimicrobial Evaluation, Cytotoxicity Profile and Molecular Docking Interactions

Yadav,

Kumari,

Kaur

et al. 2023

ChemMedChem

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In the realm of healthcare, the continuous evolution of new alternative antimicrobial agents provides hope in addressing the progressively daunting issue of severe multidrug resistance. In our quest to confront drug resistance, we explored the conjugation of thiophene motif with β‐lactams into single matrix to develop a series of spirocyclic‐β‐lactams. For this, stereoselective synthesis of cis‐C3‐alkyloxy‐C4‐thiophenyl substituted monocyclic β‐lactams was achieved which were further subjected to intramolecular sulfenyl‐cyclization to furnish C7‐halomethylene/methyl‐C3‐thiophenyl substituted spirocyclic‐β‐lactams. The synthesized compounds were investigated in vitro for their potential activity against six multidrug‐resistant bacterial strains. The most promising C7‐iodomethylene‐C3‐thiophenyl‐spirocyclic‐β‐lactam 7 a appended with 4′‐methoxyphenyl moiety, exhibited acceptable activity against B. cereus and P. aeruginosa with MIC values of 0.75 and 6.25 μg/mL respectively, surpassing ampicillin and vancomycin. Furthermore, this compound demonstrated antifungal effectiveness against C. tropicalis (1.5 μg/mL). On the basis of substituent type and their respective positions, compounds possessing −OCH3 and −C=CHX (halomethylene) groups exhibited more inhibitory potential than others. Active derivatives tested for their cytotoxicity on normal human hepatic (THLE‐2) cell lines confirmed their non‐toxic nature. Further, molecular docking studies predicted the favourable binding interactions of spirocycles within active sites of target proteins. Moreover, several compounds illustrate satisfactory in silico ADME profile. These outcomes provided bright prospect for development of spirocyclic‐β‐lactams as potential solution to combat evolving multidrug resistance.

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“…Our lab group is also engaged in construction of heterocyclic moities like benzimidazole and thiophenyl‐pyrazolyl, pyrazolo‐thiazol‐3‐carboxylate, oxathiolane‐6‐one embedded β‐lactam analogues with their subsequent synthetic utility [20a–d] . While designing diverse frameworks, we came across the literature work on nitrogen and sulfur based heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Green Synthesis of Functionalized Quinolines of Medicinal Impact (2018‐Present)

Yadav

Bhalla

2022

ChemistrySelect

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The synthetic chemists are awakening to make substantial development in finding safer drugs against the rising communicable and non‐communicable type of diseases. By replacing traditional methods to more sustainable and greener approaches, multicomponent reactions are the rapid and efficient tool for the synthesis of organic molecules of structural diversity and complexity. Heterocyclic chemistry transforms small set of precursors into series of molecules by multicomponent domino reactions. This review covers recent trends of last five years (2018–2022) in construction of potentially drug‐like quinoline derivatives. The methods discussed here are preferable over conventional approaches being inexpensive, consuming lesser reaction time, atom economical, saving energy and manpower while avoiding toxic reagents/materials, chemical wastes and are environmental/occupational benign. The contributions covered here involve metallic, metal free strategies and other catalytic pathways including nanoparticles, ionic liquids and photocatalysis which are operationally safe and reliable.

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Stereoselective synthesis of trans-3-functionalized-4-pyrazolo[5,1-b]thiazole-3-carboxylate substituted β-lactams: Potential synthons for diverse biologically active agents

Cited by 15 publications

References 23 publications

Stereoselective synthesis of β-lactams: recent examples

Stereoselective synthesis of β-lactams: recent examples

C7‐Halomethylene/methyl‐C3‐thiophenyl‐spirocyclic‐β‐lactams: Synthesis, X‐ray Analysis, Antimicrobial Evaluation, Cytotoxicity Profile and Molecular Docking Interactions

Recent Advances in Green Synthesis of Functionalized Quinolines of Medicinal Impact (2018‐Present)

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