NDLI: Carbodiimides – key mediators in the synthesis of novel cytotoxic and analgesic/antiinflammatory motifs based on α-amino-, enaminophosphonates, and azaphosphones

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Carbodiimides – key mediators in the synthesis of novel cytotoxic and analgesic/antiinflammatory motifs based on α-amino-, enaminophosphonates, and azaphosphones

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Carbodiimides – key mediators in the synthesis of novel cytotoxic and analgesic/antiinflammatory motifs based on α-amino-, enaminophosphonates, and azaphosphones

Content Provider	Royal Society of Chemistry (RSC)
Author	Barghash, Reham F. Bekheit, Mohamed S. Abdou, Wafaa M.
Copyright Year	2013
Abstract	Based on the prediction results (PASS program), a new series of α-aminophosphonate derivatives and azaphosphones was synthesized and evaluated as antitumor agents against breast-, cervical-, liver, and colon cancer diseases. The analgesic/antiinflammatory properties of the new phosphorylated pyrazoles were also investigated. The study demonstrated an efficient site selective method for making condensation products of phosphonate derivatives in high yields from carbodiimides and different types of HE reagents (74–78%) as well as dialkyl phosphites (54–65%) and hexaalkyltriamidophosphites (80–85%). Their antitumor properties against four carcinoma cell lines representing human-liver (HEPG2), -colon (HCT116), -breast (MCF7), and -cervix (HeLa) were investigated. The results showed that at least two out of the five tested phosphonates exhibited remarkable antitumor activity (IC50: 4.15–6.95 μM mL−1) when compared to the standard drugs (IC50: 5.7–9.3 μM mL−1). Nevertheless, four phosphonate products showed an analgesic capacity >80%, when compared to aspirin (73%) at the same dose of 100 mg kg−1. Furthermore, QSAR results indicated that the fused azaphosphones, thiazolopyrimidine- and pyridine-α-aminophosphonate derivatives (6 of 11 tested compounds), possess inflammatory inhibitory potency (99–117%) when compared to the standard drug (100%) after 360 min.
Starting Page	1528
Ending Page	1540
Page Count	13
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	3
Issue Number	5
Journal	RSC Advances
DOI	10.1039/c2ra22769j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Aspirin Carcinoma MCF-7 Colorectal cancer HeLa Liver cancer Analgesic IC50 Quantitative structure\u2013activity relationship Anti-inflammatory Phosphonate Cervical cancer Cancer NCI-60
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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Carbodiimides – key mediators in the synthesis of novel cytotoxic and analgesic/antiinflammatory motifs based on α-amino-, enaminophosphonates, and azaphosphones