Synthesis, antitumor and antioxidant evaluation of some new thiazole and thiophene derivatives incorporated coumarin moiety

被引:71
作者
Gouda, Moustafa A. [1 ]
Berghot, Moged A. [1 ]
Baz, Eman A. [1 ]
Hamama, Wafaa S. [1 ]
机构
[1] Mansoura Univ, Fac Sci, Dept Chem, Mansoura 35516, Egypt
关键词
Coumarin; Synthesis; Antitumor; Antioxidant activities; ANTIMICROBIAL ACTIVITY;
D O I
10.1007/s00044-011-9610-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
3-Acetylcoumarin (1) was utilized as a key intermediate for the synthesis of 2-aminothiazole derivative 3 via bromination of 1 followed by treatment of the formed acetylbromide 2 with thiourea or via Bignailli reaction of 1. Treatment of 3 with 2 afforded the bis-coumarin 4, whereas, cyanoacetylation of 3 followed by treatment of the formed cyanoacetamide 6 with salicyaldehyde give the bis-coumarin 7. Reaction of 6 with phenyl isothiocyanate in DMF/KOH produced the potassium salt 8, which cyclized with chloroacetyl chloride to give the thiazolidinone 9. Acidification of 8 with HCl afforded the thiocarbamoyl 10, which condensed with 2 in DMF to give the mercapto derivative 12, whereas in DMF/TEA gave the thiophene derivative 13. The thiophenes 15a-c were achieved via treatment of the thiocarbamoyls 14a-c with 2 in DMF/TEA, whereas, in DMF gave the corresponding thiazoles 16a-c. Treatment of the components 17a, b with carbon disulfide in DMF/KOH followed by addition of 2 afforded the dithioacetals 19a, b. Cyclization of 19b under alkaline condition gave the desired thiophene 20. Representative compounds of the synthesized products were evaluated as antitumor and antioxidant agents. 3-Acetylcoumarin (1) was utilized as a key intermediate for the synthesis of different coumarin derivatives. Newly synthesized compounds were elucidated by analytical and spectral data. Representative compounds of the synthesized products were evaluated as antitumor and antioxidant agents.
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收藏
页码:1062 / 1070
页数:9
相关论文
共 30 条
[1]   Synthesis of some new pyrimido[2′,1′:2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents [J].
Abu-Hashem, A. A. ;
Gouda, M. A. ;
Badria, F. A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (05) :1976-1981
[2]   No effect of the novel antidiabetic agent nateglinide on the pharmacokinetics and anticoagulant properties of warfarin in healthy volunteers [J].
Anderson, DM ;
Shelley, S ;
Crick, N ;
Buraglio, M .
JOURNAL OF CLINICAL PHARMACOLOGY, 2002, 42 (12) :1358-1365
[3]   REACTION OF PHENYLISOTHIOCYANATE WITH ALPHA-HETARYL NITRILES AND KETONES [J].
AUGUSTIN, M ;
DOLLING, W .
JOURNAL FUR PRAKTISCHE CHEMIE, 1982, 324 (02) :322-328
[4]  
Dawod K.M., 1998, J. Chem. Res. Synopses, V4, P208
[5]   ALPHA-OXO KETENE DITHIOACETALS AND RELATED-COMPOUNDS - VERSATILE 3-CARBON SYNTHONS [J].
DIETER, RK .
TETRAHEDRON, 1986, 42 (12) :3029-3096
[6]  
El-Desoky S. I., 2002, SULFUR LETT, V25, P199, DOI DOI 10.1080/02786110214496
[7]  
FORBIS RM, 1970, J AM CHEM SOC, V92, P6995
[8]   Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries [J].
Gorobets, NY ;
Yousefi, BH ;
Belaj, F ;
Kappe, CO .
TETRAHEDRON, 2004, 60 (39) :8633-8644
[9]   Synthesis and Antimicrobial of Certain New Thiazolidinone, Thiazoline, and Thiophene Derivatives [J].
Gouda, M. A. ;
Berghot, M. A. ;
Shoeib, A. I. ;
Khalil, A. M. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (07) :1455-1462
[10]   Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety [J].
Gouda, M. A. ;
Berghot, M. A. ;
El-Ghani, Ghada E. Abd ;
Khalil, A. M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (04) :1338-1345