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

Medicinal Chemistry Research

Volumn 21, Issue 7, 2012, Pages 1062-1070

  Gouda, Moustafa A ^a   Berghot, Moged A ^a   Baz, Eman A ^a   Hamama, Wafaa S ^a  

^a Mansoura University   (Egypt)

Author keywords

Antioxidant activities; Antitumor; Coumarin; Synthesis

Indexed keywords

2 AMINOTHIAZOLE DERIVATIVE; 2 CYANO N ( 4 ( 2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL)ACETAMIDE; 2 IMINO N ( 4 ( 2 OXO 2H CHROMEN 3 YL)THIAZOL 2 YL) 2H CHROMEN 3 CARBOXAMIDE; 3 ACETYLCOUMARIN; ACETAL DERIVATIVE; ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE; ACETYLBROMIDE; ALKALINE EARTH METAL; ASCORBIC ACID; BIS COUMARIN; BROMINE DERIVATIVE; CARBON DISULFIDE; CHLORIDE; CHLOROACETYL CHLORIDE; CHROMENE DERIVATIVE; COUMARIN; COUMARIN DERIVATIVE; CYANOACETAMIDE; DITHIOACETAL; FLUOROURACIL; PHENYL ISOTHIOCYANATE; POTASSIUM HYDROXIDE; POTASSIUM SALT; THIAZOLE DERIVATIVE; THIAZOLIDINE DERIVATIVE; THIOPHENE; THIOPHENE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACETYLATION; ACIDIFICATION; ALKALINITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BIGNAILLI REACTION; BROMINATION; CELL VIABILITY; CHEMICAL COMPOSITION; CHEMICAL REACTION; CONTROLLED STUDY; CYANOACETYLATION; CYCLIZATION; CYCLOADDITION; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; TUMOR CELL;

EID: 84861860917     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9610-8     Document Type: Article

References (30)

1. Abu-Hashem AA, Gouda MA, Badria FA (2010) Synthesis of some new pyrimido[2′,1′:2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents. Eur J Med Chem 45:1976-1981. doi:10.1016/j.ejmech.2010.01.042
2. Anderson DM, Shelley S, Crick N, Buraglio M (2002) No effect of the novel antidiabetic agent nateglinide on the pharmacokinetics and anticoagulant properties of warfarin in healthy volunteers. J Clin Pharmacol 42: 1358-1365. http://jcp.sagepub.com/content/42/12/1358.full.pdf?html
3. Augustin M, Doelling W (1982) Reaction of phenylisothiocyanate with α-hetaryl nitriles and ketones. J Prakt Chem 324:322-328
4. Dawood KM, Kandeel ZE, Farag AM (1998) J Chem Res Synop 4:208-209
5. Dieter RK (1986) a-Oxo ketene dithioacetals and related compounds: versatile three-carbon synthons. Tetrahedron 42:3029-3096. doi: 10.1016/S0040-4020(01)87376-2
6. El-Desoky SI, Etman HA, Bondock SB, Fadda AA, Metwally MA (2002) Utility of isothiocyanates in heterocyclic synthesis. Sulfur Lett 25:199-205. doi:10.1080/02786110214496
7. Gorobets NY, Yousefi BH, Belaj F, Kappe CO (2004) Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries. Tetrahedron 60:8633-8644. doi:10.1016/j.tet.2004.05.100
8. Gouda MA, Berghot MA, Abd El-Ghani GE, Khalil AM (2010) Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety. Eur J Med Chem 45:1338-1345. doi:10.1016/j.ejmech.2009.12.020
9. Gürsoy A, Karali N (2003) Synthesis, characterization and primary antituberculosis activity evaluation of 4-(3-coumarinyl)-3-benzyl- 4-thiazolin-2-one Benzylidenehydrazones. Turk J Chem 27:545-552. http://mistug.tubitak.gov.tr/bdyim/toc.php?dergi=kim&yilsayi=2003/5
10. Habib NS, Khali MA (1984) Synthesis and antimicrobial activity of novel quinazolone derivatives. J Pharm Sci 73:982-985. doi: 10.1002/jps.2600730731
11. Hauser CR, Reynolds GA (1948) Reactions of β-keto esters with aromatic amines: syntheses of 2- and 4-hydroxyquinoline derivatives. J Am Chem Soc 70:2402-2404. doi:10.1021/ja01187a025
12. Junjappa H, Ila H, Asokan CV (1990) α-Oxoketene-S,S-, N,S- and N,N-acetals: versatile intermediates in organic synthesis. Tetrahedron 46:5423-5506. doi:10.1016/S0040-4020(01)87748-6
13. 3 thymidine. Medicina et Pharmacologia 13:124-130. doi:10.1159/000135602
14. Khalil AM, Berghot MA, Gouda MA (2009a) Synthesis and antibacterial activity of some new thiazole and thiophene derivatives. Eur J Med Chem 44:4434-4440. doi:10.1016/j.ejmech.2009.06.002
15. Khalil AM, Berghot MA, Gouda MA (2009b) Synthesis and antibacterial activity of some new heterocycles incorporating phthalazine. Eur J Med Chem 44:4448-4454. doi:10.1016/j.ejmech.2009.06.003
16. Khalil AM, Berghot MA, Gouda MA, Abd El-Ghani GE (2010a) Synthesis and antimicrobial evaluation of some new thiophene derivatives. Synthetic Commun 40:1658-1669. doi:10.1080/00397910903161652
17. Khalil AM, Berghot MA, Gouda MA, Shoeib AI (2010b) Synthesis and antimicrobial of certain new thiazolidinone, thiazoline, and thiophene derivatives. Phosphorus Sulfur Silicon 185:1455-1462. doi: 10.1080/ 10426500903074858
18. Koelsch CF (1950) Bromination of 3-Acetocoumarin. J Am Chem Soc 72(7):2993-2995. doi:10.1021/ja01163a053
19. Lafitte D, Lamour V, Tsvetkov PO, Makarov AA, Klich M, Deprez P, Moras D, Briand C, Gilli R (2002) DNA gyrase interaction with coumarin-based inhibitors: the role of the hydroxybenzoate isopentenyl moiety and the 5′-methyl group of the noviose. Biochemistry Biochem 41: 7217-7223. http://www.ncbi.nlm. nih.gov/pubmed/12044152
20. Lissi EA, Modak B, Torres R, Escobar J, Urzua A (1999) Total antioxidant potential of resinous exudates from Heliotropium species, and a comparison of the ABTS and DPPH methods. Free Rad Res 30:471-477
21. Mitscher LA (2002) Principles of medicinal chemistry. In: Foye WO, Lemke TL, Williams DA 5th edn. Williams and Wilkins, Baltimore, pp 819-864
22. Mukerjee AK, Ashare R (1991) Isothiocyanates in the chemistry of heterocycles. Chem Rev 91(1):1-24. doi:10.1021/cr00001a001
23. Nofal ZM, Fahmy HH, Mohamed HS (2002) Synthesis and antimicrobial activity of new substituted anilinobenzimidazoles. Arch Pharmacal Res 25(3):250-257. doi:10.1007/BF02976622
24. Rinehart KL Jr, Forbis RM (1970) Nybomycin. IV. Total synthesis of deoxynybomycin. J Am Chem Soc 92(23):6995-6996. doi: 10.1021/ja00726a061
25. Russo F, Romeo G, Santagati NA, Caruso A, Cutuli V, Amore D (1994) Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties. Eur J Med Chem 29:569-578. doi:10.1016/0223-5234(94)90149-X
26. Siddiqui N, Arshad MF, Khan SA (2009) Synthesis of some new coumarin incorporated thiazolyl semicarbazones as anticonvulsants. Acta Pol Pharm 66(2):161-167
27. Stone WB, Okoniewski JC, Stedelin JR (1999) Poisoning of wildlife with anticoagulant rodenticides in New York. J Wildl Dis 35: 187-193. http://www.jwildlifedis.org/cgi/reprint/35/2/187
28. Tassies D, Freire C, Pijoan J, Maragall S, Monteagudo J, Ordinas A, Reverter JC (2002) Pharmacogenetics of acenocoumarol: cytochromeP450CYP2C9 polymorphisms influence dose requirements and stability of anticoagulation. Haematologica 87: 1185-1191. http://www.haematologica.org/cgi/reprint/87/11/1185
29. Weber US, Steffen B, Siegers C (1998) Antitumor activities of coumarin, 7-hydroxy-coumarin and its glucuronide in several human tumor cell lines. Res Commun Mol Pathol Pharmacol 99:193-206
30. Weick J, Thorn RS (2002) Effects of acute sublethal exposure to coumaphos or diazinon on acquisition and discrimination of odor stimuli in the honey bee (Hymenoptera: Apidae). J Econ Entomol 95:227-236. doi:10.1603/0022-0493-95.2.227