Synthesis, biochemical and molecular modelling studies of antiproliferative azetidinones causing microtubule disruption and mitotic catastrophe

O’Boyle, Niamh M.; Carr, Miriam; Greene, Lisa M.; Keely, Niall O.; Knox, Andrew J. S.; McCabe, Thomas; Lloyd, David G.; Zisterer, Daniela M.; Meegan, Mary J.

doi:10.1016/j.ejmech.2011.07.039

Cited by 41 publications

(27 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To solve this problem we moved our strategy towards the synthesis of aldimines under solvent free conditions using microwaves. The product formation was observed in short reaction time with excellent yields (80% -87% 3 and CH=N (azomethine) groups in the compound.…”

Section: Resultsmentioning

confidence: 89%

“…The IR spectrum of product showed absorption bands at 1345, 1712 cm -1 attributed to the presence of SO 3 and CHO groups. The 1 H NMR spectrum of this compound showed the presence of a singlet at δ 2.49 and 10.03 ppm attributing to the presence of CH 3 and CHO groups, the appearance of multiple peaks in the region of δ 7.22 -7.93 corresponding to the presence of aromatic ring systems in the molecule. A rapid formation of product, the generation of high purity compound, simple isolation procedure, excellent yield and eco-friendship are the key factors of this method.…”

Section: Resultsmentioning

confidence: 99%

“…C NMR spectroscopic characterization showed absorption at δ 21.672 and 157.124 for CH 3 and CH=N carbons clearly confirms the formation of aldimine product. The formation of product was further confirmed by physical constant and functional group tests.…”

mentioning

confidence: 84%

“…They are mostly prescribed medicines to treat bacterial infections. They were found to possess powerful anti-microbial [1][2], anti-proliferative [3], IFN-gamma [4], cytotoxic [5], anticonvulsant, anti-tubercular [6], cholesterol absorption inhibitor [7], antiinflammatory and anti-degenerative activities [8]. Moreover, the β-Lactams derived from a carbapenem chiron are well known selective inhibitors of human fatty acid amide hydrolase [9].…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Microwave Assisted and Al2O3/K2CO3 Catalyzed Synthesis of Azetidin-2-One Derivatives Containing Aryl Sulfonate Moiety with Anti-Inflammatory and Anti-Microbial Activity

Kendre¹,

Landge²,

Bhusare³

2012

OJMC

View full text Add to dashboard Cite

We report the novel synthesis of azetidin-2-one derivatives containing aryl sulfonate moiety from the reaction of 2-hydroxy benzaldehyde with p-toluene sulfonyl chloride afforded firstly 2-formylphenyl 4-methylbenzene sulfonate (2). The compound (2) on reaction with p-aminobenzoic acid or 2-aminopyridine gave the corresponding aldimines (3). Furthermore, the aldimines are on reaction with chloroacetyl chloride gives corresponding azetidin-2-ones in good to moderate yield. Among the eight synthesized azetidin-2-ones, five selected compounds have been screened for the anti-inflammatory activity, few of them showed good anti-inflammatory activity compared with standard drugs. Antimicrobial activity of all synthesized compounds has been tested and most of the compounds showed good anti-bacterial and anti-fungal activities.

show abstract

Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Microwave Assisted and Al2O3/K2CO3 Catalyzed Synthesis of Azetidin-2-One Derivatives Containing Aryl Sulfonate Moiety with Anti-Inflammatory and Anti-Microbial Activity

Kendre¹,

Landge²,

Bhusare³

2012

OJMC

View full text Add to dashboard Cite

show abstract

“…Modes of cytotoxicity reported include apoptosis (21,44), mitotic catastrophe (45) and autophagy (46,47). Recently we found that CA-432 induced mitotic catastrophe in breast carcinoma cells (48) and autophagy in adenocarcinoma-derived colon cancer cells (47). Mitotic arrest prevents the supply of endothelial cells required for angiogenesis and cytotoxicity leads to the destruction of existing tumour blood vessels, indicating a novel anti-vascular function for the β-lactam CA-4 derivatives.…”

Section: Discussionmentioning

confidence: 99%