Diaryl Epoxypropanones as Synthons in Synthesis of Some Interesting Potential Anticancer and Antibacterial Heterocyclic Agents

被引:0
|
作者
Kotb, Eman R. [1 ]
Yousif, Nabil M.
Salama, Mowafia A. M.
Ali, Mamdouh M.
Khalaf, Hemat S.
机构
[1] Natl Res Dokki, Photochem Dept, Cairo, Egypt
来源
RESEARCH JOURNAL OF PHARMACEUTICAL BIOLOGICAL AND CHEMICAL SCIENCES | 2015年 / 6卷 / 01期
关键词
Oxiranylmethanone; pyrazoles; triazoles; tetrazoles; anticancer; antimicrobial;
D O I
暂无
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
3-(p-Chlorophenyl)-1-(2'-naphthyl)-2,3-epoxypropanone (2) is an important intermediate for the synthesis of a variety of different heterocyclic compounds with novel cyclic system. Compound 2 reacted with hydrazine hydrate, phenyl hydrazine, hydroxylamine hydrochloride as nitrogen nucleophiles to afford compounds 3-5, and with carbon disulfide and phenylisocyanate as a carbon electrophile to afford compounds 6 and 7. Furthermore, 6-(4-chlorophenyl) -2-hydrazino -4- naphthaline- 2-yl- 1,6- dihydro - pyrimidin-5-one(8) reacted with p-chlorobenzaldehyde to give Schiff base9 which on cyclocondensation with thioglycolic acid affording compound 10. The new compounds 11-13 were synthesizedby the reaction of compound 8 with carbon disulfide, malononitrile and phenyl isothiocyanate. Also compound 8 reacted with aliphatic acid namely: acetic and formic acids and with sodium nitrite to give triazolopyrimidinones14, 15 and tetrazolopyrimidinone16. A novel series of acyclicnucleosides17a, b were synthesized by utilizing compound 8. Most of the tested compounds showed potent cytotoxic activity. However two compounds, 6 and 16, showed cytotoxic activity very close to that of the Doxorubicin as a reference drug against breast carcinoma cell line MCF-7. Also some synthesized compounds were screened for their antimicrobial activity. Among the assayed compounds derivatives 9 and 17a showed the highest antimicrobial activity.
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页码:516 / 528
页数:13
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