Eco-friendly synthesis and potent antifungal activity of 2-substituted coumaran-3-ones

Solanki, P. R.; Shekhawat, Prachi B.

doi:10.13057/nusbiosci/n040302

Cited by 2 publications

(1 citation statement)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…33,41 The present route for the synthesis of 2,5dihydro-1,2-oxaphosphole-2-oxide core is highly adaptable with simple reaction procedures and hence eliminates the use of expensive precursors (Figure 1). As phospha-coumaranones (phospha-γ-lactones) are analogues of coumaranones (coumaran derivatives) by structure and as coumaranones are potential antiplasmodial, 42 antifungal, 43 anti-neoplasia, 44 and anticancer 45 agents, we have designed the synthesis of their phosphorus analogues bearing a cyclic phosphonic acid group (hydroxy group located on the phosphoryl group), which easily facilitates ring opening operations in vivo metabolic processes (hydrolysis) and hence acts as potential prodrugs. 46 This has motivated us to investigate the anti-pancreatic cancer activity and to identify the mechanistic aspects of cell cycle inhibition.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Anti-Pancreatic Cancer Activity Studies of Novel 3-Amino-2-hydroxybenzofused 2-Phospha-γ-lactones

et al. 2021

View full text Add to dashboard Cite

A series of 3-amino-2-hydroxybenzofused 2-phosphalactones ( 4a–l ) has been synthesized from the Kabachnik–Fields reaction via a facile route from a one-pot three-component reaction of diphenylphosphite with various 2-hydroxybenzaldehyes and heterocyclic amines in a new way of expansion. The in vitro anti-cell proliferation studies by MTT assay have revealed them as potential Panc-1, Miapaca-2, and BxPC-3 pancreatic cell growth inhibitors, and the same is supported by molecular docking, QSAR, and ADMET studies. The MTT assay of their SAHA derivatives against the same cell lines evidenced them as potential HDAC inhibitors and identified 4a , 4b , and 4k substituted with 1,3-thiazol, 1,3,4-thiadiazol, and 5-sulfanyl-1,3,4-thiadiazol moieties on phenyl and diethylamino phenyl rings as potential ones. Additionally, the flow cytometric analyses of 4a , 4b , and 4k against BxPC-3 cells revealed compound 4k as a lead compound that arrests the S phase cell cycle growth at low micromolar concentrations. The ADMET properties have ascertained their inherent pharmacokinetic potentiality, and the wholesome results prompted us to report it as the first study on anti-pancreatic cancer activity of cyclic α-aminophosphonates. Ultimately, this study serves as a good contribution to update the existing knowledge on the anticancer organophosphorus heterocyclic compounds and elevates the scope for generation of new anticancer drugs. Further, the studies like QSAR, drug properties, toxicity risks, and bioactivity scores predicted for them have ascertained the synthesized compounds as newer and potential drug candidates. Hence, this study had augmented the array of α-aminophosphonates by adding a new collection of 3-amino-2-hydroxybenzofused 2-phosphalactones, a class of cyclic α-aminophosphonates, to it, which proved them as potential anti-pancreatic cancer agents.

show abstract