&lt;strong&gt;Reaction of 2-hydroxy-N&lt;sup&gt;`&lt;/sup&gt;-[(4-oxo-4&lt;em&gt;H&lt;/em&gt;-chromen-3-yl)methylidene]benzohydrazide with some phosphorus reagents: Synthesis and evaluation of anticancer activities of some novel &amp;alpha;-hydrazinophosphonic acid, 1,4,5,2-oxadiazaphosphinines and 1,3,2-benzoxaza-phosphinines bearing a chromone ring.&lt;/strong&gt;

Tarik Ali

doi:10.3390/ecsoc-20-b020

Abstract

Some novel 1,4,5,2-oxadiazaphosphinines, 1,3,2-benzoxazaphosphinines and α-hydrazino-phosphonic acid bearing a chromone ring have been obtained from reaction of 2-hydroxy-N`-[(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide (2) with some phosphorus reagents such as phosphonic acid and its diesters, phosphorus sulfides and phosphorus halides in dry dioxane. The compounds were evaluated for their anticancer activities and on the expression of VEGF inhibition. Among the synthesized compounds, compounds 3 and 7 exhibited high effect against breast cancer cells MCF-7 in comparison with the standard drug and on the expression of VEGF inhibition.

Highlights

Chromone compounds are oxygen-containing heterocyclic compounds with a benzo-annulated γ-pyrone ring
Since it was hypothesized that the inhibition of angiogenesis could be an effective strategy for cancer therapy [12] several regulators of angiogenesis, such as vascular endothelial growth factor (VEGF), platelet-derived growth factor (PDGF), basic fibroblast growth factor (BFGF), and angiopoietin, have been identified [13,14,15,16]
VEGF signaling pathway that acts through the VEGF receptor 2 (VEGFR-2) has been shown to play a key role in the regulation of tumor angiogenesis, in which the binding of VEGF to VEGFR-2 leads to receptor dimerization, which is followed by the autophosphorylation of tyrosine residues in the intracellular kinase domain, resulting in potent mitogenic and chemotactic effects on endothelial cells [17]

Summary

Introduction

Chromone compounds are oxygen-containing heterocyclic compounds with a benzo-annulated γ-pyrone ring They are a group of naturally and synthetic compounds which have received attention in the literature, mainly due to their biological properties [1,2]. These biological activities are antioxidant, antimicrobial, anticonvulsant and antihypertensive [3,4,5,6]. The synthesized compounds were examined for their anticancer properties against human breast MCF-7, liver HepG2, colon HCT116 and prostate PC3 cancer cell lines that may act through angiogenesis inhibition

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OPX H NS

Biological evaluation Anticancer activity of the synthesized compounds