Reaction of 2-imino-2H-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties
Ali, TE; Assiri, MA; Metwally El-Shaaer, Hafez; Hassan, MM; Fouda, AM; Hassanin, NM;
Abstract
Novel chromenyl α-aminophosphonic acid 4 and dialkyl chromenyl phosphonate 6 have been obtained. In addition, some novel types of chromene fused with phosphorus heterocycles such as chromeno[4,3-c][1,2]azaphospholes 5 and 7, chromeno[2,3-d][1,3,2]diazaphosphinine 8 and 1,2-oxaphosphinino[3,4-c]pyridine 10 have been synthesized. The methodology depended on treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus esters. The synthesized compounds were evaluated for antioxidant and cytotoxic activities. Among the synthesized compounds, compound 5 exhibited the most antioxidant activity with IC50 = 2.8 μg/mL in comparison with ascorbic acid as standard antioxidant. Also, compound 5 had significant cytotoxic effects against four cancer cell lines. Its IC50 values ranged between 4.96 and 7.44 μg/mL in comparison to doxorubicin (IC50 = 0.426–0.493 μg/mL).
Other data
Title | Reaction of 2-imino-2H-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties | Authors | Ali, TE; Assiri, MA; Metwally El-Shaaer, Hafez ; Hassan, MM; Fouda, AM; Hassanin, NM | Keywords | 1;Antioxidant;BIOLOGICAL-ACTIVITY;2-azaphosphole;chromene;cytotoxicity;3;2-diazaphosphinine;2-oxaphosphinino;phosphonate;phosphorus esters;ETHYL 2-AMINO-6-(3,5-DIMETHOXYPHENYL)-4-(2-ETHOXY-2-OXOETHYL)-4H-CHROMENE-3-CARBOXYLAT CXL017 | Issue Date | 2019 | Publisher | TAYLOR & FRANCIS INC | Journal | Synthetic Communications | ISSN | 0039-7911 | DOI | 10.1080/00397911.2019.1652323 | Scopus ID | 2-s2.0-85071044437 | Web of science ID | WOS:000481653900001 |
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