Synthesis of certain new thieno[2,3-d] pyrimidines as potential antitumor and radioprotective agents

Arzneimittel-Forschung/Drug Research

Volumn 56, Issue 7, 2006, Pages 553-560

  Ghorab, Mostafa M ^a   Ragab, Fatma A ^b   Noaman, Eman ^a   Heiba, Helmy I ^a   Galal, Marwa ^a  

^a NATIONAL CENTER FOR RADIATION RESEARCH AND TECHNOLOGY   (Egypt)

^b CAIRO UNIVERSITY   (Egypt)

Author keywords

Antitumor agents; Radioprotective agents; Thieno 2,3 d pyrimidines, synthesis

Indexed keywords

1,4 BIS[5,6 DIMETHYL 4 OXO 2 THIOXO 2,3 DIHYDRO THIENO(2,3 D)PYRIMIDIN 3 YL]BENZENE; 2 (3 BUTYL THIOUREIDO) 4,5 DIMETHYL THIOPENE 3 CARBOXYLIC ACID ETHYL ESTER; 2 (HYDROXY ETHOXYTHIOCARBONYLAMINO) 4,5 DIMETHYL THIOPENE 3 CARBOXYLIC ACID ETHYL ESTER; 2 ETHOXYTHIOCARBONYLAMINO 4,5 DIMETHYL THIOPENE 3 CARBOXYLIC ACID ETHYL ESTER; 2 [3 (2 AMINO PHENYL)THIOUREIDO] 4,5 DIMETHYL THIOPENE 3 CARBOXYLIC ACID ETHYL ESTER; 2 [3 (2 HYDROXY PHENYL)THIOUREIDO] 4,5 DIMETHYL THIOPENE 3 CARBOXYLIC ACID ESTER; 3 (2 HYDROXY ETHYL) 2 THIOXO 2,3,5,6,7,8 HEXAHYDRO 1H BENZO(4,5)THIENO(2,3 D)PYRIMIDIN 4 ONE; 3 (2 HYDROXY ETHYL) 5,6 DIMETHYL 2 THIOXO 2,3 DIHYDRO 1H THIENO(2,3 D)PYRIMIDIN 4 ONE; 3 (3 HYDROXY PROPYL) 2 THIOXO 2,3,5,6,7,8 HEXAHYDRO 1H BENZO(4,5)THIENO(2,3 D)PYRIMIDIN 4 ONE; 3 (3 HYDROXY PROPYL) 5,6 DIMETHYL 2 THIOXO 2,3 DIHYDRO 1H THIENO(2,3 D)PYRIMIDIN 4 ONE; 4,5 DIMETHYL 2 (3 PHENYL THIOUREIDO) THIOPENE 3 CARBOXYLIC ACID ETHYL ESTER; ANTINEOPLASTIC AGENT; RADIOPROTECTIVE AGENT; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLUTATHIONE; MALONALDEHYDE; PYRIMIDINE DERIVATIVE; SUPEROXIDE DISMUTASE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; INFRARED SPECTROMETRY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; ANIMAL; BLOOD; CANCER TRANSPLANTATION; DRUG EFFECT; EHRLICH ASCITES TUMOR; GAMMA RADIATION; LIPID PEROXIDATION; METABOLISM; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CARCINOMA, EHRLICH TUMOR; FEMALE; GAMMA RAYS; GLUTATHIONE; INDICATORS AND REAGENTS; LIPID PEROXIDATION; MALONDIALDEHYDE; MICE; NEOPLASM TRANSPLANTATION; PYRIMIDINES; RADIATION-PROTECTIVE AGENTS; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDE DISMUTASE;

EID: 33746929925     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296751     Document Type: Article

References (38)

1. Ghorab, M. M., A new thienopyrimidine and thienopyrodine derivatives as potential biological avtivity and effect of gamma irradiation on some of these compounds, Egypt. J. Rad. Sci. Appl. 8, 179 (1995)
2. Ghorab, M. M., Abdel-Hamid, S. G., Synthesis and effect of gamma radiation on some sulfur containing 3-substituted-4-oxo-2,4,5,6,7,8- hexahydrobenzo[b]thieno[2,3-b]pyrimidines of biological interest, Phosphorous, Sulphur and Silicon 106, 9 (1995)
3. Heiba, H. I., Ghorab, M. M., Amin, N. E. et al., Activity of some new sulfur compounds bearing tetrahydrobenzo[b]thieno[2,3-d]pyrimidine moiety on non-irradiated and irradiated Bacillus cereus, Egypt, J. Biotechnol. 4, 46 (1998)
4. Ghorab, M. M., New biologically active N-(tetrahydrobenzothienopyrimidin- 4-yl)-amino acids, thiourethane, sulfonamides and related compounds, Phosphorous, Sulfur and Silicon 165, 221 (2000)
5. Ghorab, M. M., El-Batal, A. I., Synthesis of some new thiazole derivatives. Antifungal activity and ultrastructure changes of some micotoxins producing fungi, Boll. Chim. Farm. 141, 110 (2002)
6. El-Gaby, M. S. A., Abdel-Hamid, S. G., Ghorab, M. M. et al., Synthesis and anticancer activity in vitro of some new pyrimidines, Acta Pharm. 49, 149 (1999)
7. Ghorab, M. M., Hassan, A. Y., Nassar, O. M., Synthesis of novel heterocyclic compounds for antitumor and radioprotective activities, Phosphorous, Sulfur and Silicon 134/135, 447 (1998)
8. Ghorab, M. M., Nassar, O. M., Hassan, A. Y., Synthesis of some sulfur containing tetrahydro-benzo[b]thieno (pyridines, quinolines, oxazines and pyrimidines) as possible radioprotective and antineoplastic agents, Phosphorous, Sulfur and Silicon 134/135, 57 (1998)
9. Ghorab, M. M., Abdel-Hamid, S. G., Abo-Zeid, M. M., Synthesis of some new thiadiazole, selena, trizole and cyanopyridine derivatives with assay for their antitumor activities, Phosphorous, Sulfur and Silicon 122, 7 (1996)
10. Heiba, H. I., Ghorab, M. M., El-Gawish, M. A., Biological and chemical screening of some amino acid thienopyrimidinone derivatives for potential radioprotective character, Phosphorous, Sulphur and Silicon 131, 197 (1997)
11. Hassan, A. Y., Ghorab, M. M., Nassar, O. M., Synthesis and antiradiation activity of some sulfur containing thiophene derivatives, Phosphorous, Sulfur and Silicon 134/135, 77 (1998)
12. Ghorab, M. M., Nassar, O. M., Heiba, H. I. et al., Synthesis of some phthalazinone derivatives: Biological studies and radioprotective activity, Acta Pharm. 48, 101 (1998)
13. Abdel-Hamid, S. G., Ghorab, M. M., El-Hifnawi, H. N., Effect of novel biologically active oxadiazino-, oxadiazolo- and oxathiadiazolo-quinazolinones on non-irradiated and radioresistant Staphylococcus aureus, Acta Pharm. 48, 249 (1998)
14. Heiba, H. I., Ghorab, M. M., Amin, N. E. et al., Synthesis of (5,6,7,8-tetrahydro-benzo[b]thieno[2,3-d]pyrimidin-4-yl)-N-(4-aryl-3-chloro-2- oxo-azetidin-1-yl)-thioacetamides and biochemical screening for radioprotective character, Egypt. J. Biotechnol. 4, 16 (1998)
15. Ghorab, M. M., Abdel-Gawad, S. M., El-Gaby, M. S. A., Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents, Farmaco 55, 249 (2000)
16. Abdel-Gawad, S. A., El-Gaby, M. S. A., Ghorab, M. M., Synthesis and antifungal activity of novel pyrano[2′,3′':4,5]-thiazolo[2,3-b] quinazolines, pyrido[2′,3′:4,5]thiazolo[2,3-b]quinazolines and pyrazolo[2′,3′:4,5]thiazolo[2,3-b]quinazolines, Farmaco 55, 287 (2000)
17. Ghorab, M. M., Abdel-Hamid, S. G., Farrag, H. A., Synthesis of novel quinolones, pyranoquinolines, furoquinolines, thienoquinolines and their effect on the ultrastructure of some pathogenic microorganisms, Acta Pol. Pharm. 58, 175 (2001)
18. Ghorab, M. M., Abdel-Hamid, S. G., El-Gaby, M. S. A. et al., Synthesis and effect of some [12,4]triazolo[4,3-a]quinazolin-5(4H)ones and related compounds on Ehrlich ascites carcinoma cells, Acta Pharm. 49, 1 (1999)
19. Ghorab, M. M., Abdel-Hamid, S. G., El-Sayed, S. M., Novel quinazolone derivatives as antitumor agents, Phosphorous, Sulfur and Silicon 142, 57 (1998)
20. Nassar, O. M., Hassan, A. Y., Heiba, H. I. et al., Synthesis and reactions of some mercapto-heterocyclic compounds and their radioprotection, Al-Azhar Bull. Sci. 8, 435 (1997)
21. 1A receptor. Synthesis and structure affinity relationships, Eur. J. Med. Chem. 35, 677 (2000)
22. Ellis, G. P., The chemistry of heterocyclic compounds, Vol. 47; Taylor, E. C., Synthesis of fused heterocycles, p. 226; John Wiley and Sons, New York (1987)
23. El-Merzabani, M. M., El-Aaser, A. A., Attia, M. A. et al., Screening system for Egyptian plants with potential antitumor activity, Planta Medica. 36, 150 (1979)
24. Osman, A. M., Sayed Ahmed, M. M., Khayyal, M. T. et al., Hyperthermic potentiation of cisplatin on solid Ehrlich carcinoma, Tumori 79, 268 (1993)
25. Yoshioka, T., Kawada, K., Shmada, T. et al., Lipid peroxidation in maternal and cord blood and protective mechanism against activated oxygen toxicity in the blood. Am. J. Obstet. Gynecol. 135, 372 (1979)
26. Beutler, E., Duron, O., Kelly, D. M., Improved method of the determination of blood glutathione, J. Lab. Clin. Med. 61, 882 (1963)
27. Minami, M., Yoshikawa, H., A simplified assay method of superoxide dismutase, Clin. Chem. Acta 92, 337 (1979)
28. Snedecor, G. W., Cochron, W. G., Statistical methods, 8th ed., Louis State University Press, Ames, Lowa (1989)
29. Gewald, K., Schinke, E., Bottcher, H., Heterocyclen aus CH-aciden Nitrilen, VIII. 2-Amino-thiophene aus methylenaktiven Nitrilen, Carbonylverbindungen und Schwefel, Chem. Ber. 99, 94 (1965)
30. Kienzle, F. von, Kaiser, A., Minder, R. E., 15. Die Synthese von 2,3,4,5-1H-Tetrahydroimidazo[2,1-b]chinazolin-2,5-dionen und analogen 2,3,4,5-1H-Tetrahydroimidazo[1,2-a]thieno[2,3-d](bzw.)[3,2-d]-pyrimidin-2, 5-dionen, Helv. Chem. Acta 66, 148 (1983)
31. Brusick, D. J., Cytogenetic assays, aberrations and SCE techniques in carcinogenesis and mutagenesis testing, pp. 265-276, Human Press, Clifton, New Jersey (1984)
32. Modica, M., Santagati, M., Santagati, A., Synthesis of new thienotriazolopyrimidine and thienopyrimidotetrazine derivatives from bifunctional intermediates, J. Heterocycl. Chem. 38, 973 (2001)
33. Sohal, R. S, Weindruch, R., Oxidative stress, caloric restriction and aging, Science 273, 59 (1996)
34. Beckman, K. B, Ames, B. N, The free radical theory of aging matures, Physiol. Rev. 78, 547 (1998)
35. Bonnetfont, D., Rousselot, J., Irradiation of cell membranes, J. Chim. Phys. Physicochim. Biol. 191, 968 (1994)
36. Tenchova, V, Acute gamma irradiation effect on lipid peroxidation and antioxidant activity in rat hemopoietic organs and plasma, Rentgenologiya-I- Radiologiya 33, 49 (1994)
37. Navarro, J., Obrador, E., Carretero, J. et al., Changes in glutathione status and the antioxidant system in blood and in cancer cells associated with tumor growth in vivo, Free Radical Biol. Med. 26, 410 (1999)
38. Sahu, S. K., Oberley, L. W, Stevens, R. H. et al., Superoxide dismutase activity of Ehrlich ascites tumor cells, J. Natl. Cancer Inst. 58, 1125 (1977)