Synthesis of mono-, bis-spiro- and dispiro-β-lactams and evaluation of their antimalarial activities

Jarrahpour, Aliasghar; Ebrahimi, Edris; Clercq, Erik De; Sinou, Véronique; Latour, Christine; Bouktab, Lamia Djouhri; Brunel, Jean Michel

doi:10.1016/j.tet.2011.09.041

Cited by 54 publications

(34 citation statements)

References 70 publications

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“…The organic phase was washed with brine, dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product was then purified by recrystallization with ethanol to afford the desired compounds in good to excellent yields 24 .…”

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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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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“…Over recent years, there has been a surge of attention towards synthesizing spirocyclic β-lactams in view of their inimitable biological properties such as antiviral [6], antibacterial [7], antimalarial (A,B) [8], antidiabetic [9], acyl-CoA cholesterol O-acyl transferase (ACAT) inhibitors (C) [10,11], β-turn mimetics [12] and β-lactamase inhibitors (D) [13]. The spiro-β-lactam (E) serves as a precursor for the synthesis of glutamine synthetase inhibitor [14] (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

Narula¹,

Bari²,

Banik³

et al. 2017

Asian J. Chem.

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A mild and efficient synthetic approach for the synthesis of novel 4-halomethyl-1,3-oxaselenolane substituted spirocyclic β-lactams via intraselenyl cyclization of cis-3-allyloxy-3-benzylselenoazetidin-2-one mediated by halogens (I2, Br2) is described. The mechanism involves step-wise electrophilic addition-dealkylation sequence generating spiroseleno-β-lactams stereospecifically. The novel synthesized β-lactams have been characterized by spectroscopic techniques viz. NMR ( 1 H, 13 C, 77 Se), FT-IR and elemental analysis. The cis configuration of the nucleophilic substituent at C-3 was assigned with respect to C4-H. Intraselenyl cyclization is a novel approach in the chemistry of β-lactam research.

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“…A monocyclic azetidin‐2‐one ezetimibe is now in clinical use as cholesterol absorption inhibitor . Apart from these three main biological activities, studies are also in progress to synthesize new β‐lactams and explore their anticancer activity, hypoglycemic activity, antileishmanial activity, antiplasmodial activity , and so forth.…”

Section: Introductionmentioning

confidence: 99%

“…The Staudinger's ketene–imine cycloaddition is one of the most common cycloaddition reactions that is used for the synthesis of β‐lactams . This method, which involves generation of ketenes from acid chlorides in the presence of a tertiary base or directly from carboxylic acid employing an acid activator and a tertiary bases, has been used recently by several groups for the synthesis of diverse types of azetidin‐2‐ones . Our group has been using thermal decomposition of 2‐diazo‐1,2‐diarylethanones to generate diarylketenes in situ as a clean and convenient method requiring no base or any special reaction condition .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial, and Brine Shrimps Lethality Assays of 3,3‐Diaryl‐4‐(1‐methyl‐1H‐indol‐3‐yl)azetidin‐2‐ones

Singh

Al-Kahraman

Mpadi

et al. 2014

Journal of Heterocyclic Chem

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The paper describes the synthesis, characterization data, and biological activity (antibacterial, antifungal, and brine shrimps lethality) of new azetidin‐2‐ones. The compounds have been synthesized by the reaction of diarylketenes, generated in situ from thermal decomposition of the 2‐diazo‐1,2‐diarylethanones, with N‐(1‐methyl‐1H‐indol‐3‐yl)methyleneamines. The compounds have been characterized by elemental analysis and spectral (IR, 1H and 13C NMR, and MS) data. The paper also reports the results of antibacterial, antifungal, and brine shrimps lethality assays of these compounds. Some of the compounds exhibited significant biological activity.

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Synthesis of mono-, bis-spiro- and dispiro-β-lactams and evaluation of their antimalarial activities

Cited by 54 publications

References 70 publications

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

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

Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

Synthesis, Antimicrobial, and Brine Shrimps Lethality Assays of 3,3‐Diaryl‐4‐(1‐methyl‐1H‐indol‐3‐yl)azetidin‐2‐ones

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