Synthesis and antitumor activity of some new xanthotoxin derivatives

European Journal of Medicinal Chemistry

Volumn 44, Issue 7, 2009, Pages 2967-2974

  Abdel Hafez, Omaima M ^a   Amin, Kamellia M ^b   Abdel Latif, Nehad A ^a   Mohamed, Tahia K ^a   Ahmed, Eman Y ^a   Maher, Timothy ^c  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b CAIRO UNIVERSITY   (Egypt)

^c MA Coll of Pharm and Hlth Sci   (United States)

Author keywords

Anhydrides; Antitumor; Schiff's bases; Thiazolidinones; Xanthotoxin

Indexed keywords

1 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL) 3 PHNEYLTHIOUREA; 1 BENZYL 3 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)THIOUREA; 1 ETHYL 3 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)THIOUREA; 2 (4 BROMOPHENYL) 3 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)THIAZOLIDIN 4 ONE; 2 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL AMINO)THIAZOLIDINE 4 ONE; 2 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)BENZO[DE]ISOQUNOLIN 1,3 DIONE; 2 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)PYRROLO[3,4 B]PYRIDIN 5,7 DIONE; 2 FURAN 2 YL 3 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)THIAZOLIDIN 4 ONE; 2,6 BIS (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 SULFONIC ACID) 1,3,5,7 TETRAOXO 3,5,6,7 TETRAHYDRO 1H PYRROLO[3,4 B]ISOINDOL 2 YL AMIDE; 2,6 BIS(9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)PYRROLO[3,4 F]ISOINDOL 1,3,5,7 TETRAONE; 3 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL) 2 (4 METHOXYPHENYL)THIAZOLIDIN 4 ONE; 3 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL) 2 PHENYLTHIAZOLIDIN 4 ONE; 3 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL) 2 THIOXO IMIDAZOLIDINE 4 ONE; 4 (4 BROMOBENZYLIDEAMINO) 9 METHOXY 7H FURO[3,2 G]CHROMEN 7 ONE; 4 (4 METHOXYBENZYLIDENEAMINO) 9 METHOXY 7H FURO[3,2 G]CHROMEN 7 ONE; 4 (4 NITROBENZYLIDENAMINO) 9 METHOXY 7H FURO[3,2 G]CHROMEN 7 ONE; 4 (BENZYLIDENEAMINO) 9 METHOXY 7H FURO[3,2 G]CHROMEN 7 ONE; 4 (FURAN 2 YL METHYLENEAMINO) 9 METHOXY 7H FURO[3,2 G]CHROMEN 7 ONE; 4 (THIOPHEN 2 YL METHYLENEAMINO) 9 METHOXY 7H FURO[3,2 G]CHROMEN 7 ONE; 4 [4 (DIMETHYLAMINO)BENZYLIDENEAMINO] 9 METHOXY 7H FURO[3,2 G]CHROMEN 7 ONE; 6 (9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL)ISOINDOLE 1,3 DIONE; 9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 SULFONIC ACID 4 CHLOROBENZYLIDINE AMIDE; 9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 SULFONIC ACID 4 METHOXYBENZYLIDINE AMIDE; 9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 SULFONIC ACID BENZYLIDINE AMIDE; 9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 SULFONIC ACID FURAN 2 YL METHYLENE AMIDE; 9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 SULFONIC ACID(1,3 DIOXO 1,3 DIHYDRO ISOINDOL 2 YL)AMIDE; 9 METHOXY 7 OXO 7H FURO[3,2 G]CHROMEN 4 YL THIOUREA; METHOXSALEN; METHOXSALEN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; METHOXSALEN;

EID: 67349263680     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.01.006     Document Type: Article

References (29)

1. M. Sakamoto, T. Imaoka, M. Motoyama, Y. Yamomoto, H. Takasu. PCT Int. Appl. WO 94 21, 612 (Cl. C0 7D 215/38) (1994).
2. Chem. Abstr. 123 (1995) 143655m
3. Fahmy I.R., and Abu-Shady H. Q. J. Pharm. Pharmacol. (1947) 281
4. Scott B.R., Pathak M.A., and Mohn G.R. Mutat. Res. 39 (1976) 29
5. Musajo L., Rodighiero G., and Caporale G. Bull. Soc. Chim. Biol. 36 (1954) 1213
6. Vermel E.M., and Tsetlin A.L. Vopr. Onkol. 10 6 (1964) 85
7. Chem. Abstr. 62 (1965) 4497
8. Fujioka T., Furumi K., Fujii H., Okabc H., Mihashi K., Nakano Y., Matsunaga H., Katano M., and Mori M. Chem. Pharm. Bull. 47 1 (1999) 96
9. Popp F.D. J. Org. Chem. 26 (1961) 1566
10. Popp F.D., and Kirsch W. J. Org. Chem. 26 (1961) 3858
11. Modi J.D., Sabins S.S., and Deliwala C.V. J. Med. Chem. 13 (1970) 935
12. Abdel Hamid A.Z., and Facthalla O.A. Egypt J. Pharm. Sci. 34 1-3 (1993) 67
13. Billiman J.H., and Schmidgall R.L. J. Pharm. Sci. 59 8 (1970) 1191
14. Ottana R., Carotti S., Maccari R., Landini I., Chiricosta G., Caciagli B., Vigrita M.G., and Mini E. Biorg. Med. Chem. Lett. 15 (2005) 3930
15. Gududuru V., Hurh E., Dalton J.T., and Miller D.D. J. Med. Chem. 48 7 (2005) 2584
16. Abdel Hafez O.M., Elkrisy E.A., Badria F., and Fathy A.E.M. Arch. Pharm. Res. 26 8 (2003) 686
17. Jiang J.D., Roboz J., Weisz I., Deng L., Ma L., Holland J.F., and Bekesi J.G. Anticancer Drug Des. 13 (1998) 735
18. Miyahara M., Kashiwada Y., Guo X., Chen H.X., Cheng Y.C., and Lee K.H. Heterocycles 39 (1994) 361
19. Katritzky A.R., Oliferenko A., Lomarka A., and Karelson M. Biorg. Med. Chem. Lett. 12 (2002) 3453
20. Wilde R.G., and Bilheimer J.T. Biorg. Med. Chem. Lett. 5 (1995) 173
21. Urban M., Sarek J., Klinot J., Korkinova G., and Hajduch M. J. Nat. Prod. 67 7 (2004) 1100
22. Brozozowski Z., and Saczewski F. J. Med. Chem. 45 (2002) 430
23. Chung E.L. Exp. Lung Res. 27 3 (2001) 319
24. El-Shafei A.K., HassanKh M., and El-Kashef H.S. J. Indian Chem. Soc. LIV (1977) 743
25. Amr A.E., Abdelsalam O.I., Attia A., and Stibor I. Collect. Czech. Chem. Commun. 64 (1999) 288
26. Ragab F.A., and Seif El Nasr M. Bull. Fac. Pharm. Cairo Univ. 30 3 (1992) 209
27. Brokke M.E., and Christensen B.E. J. Org. Chem. 23 (1958) 589
28. El-Tawil B.A.H., El-Beih F.K.A., and Khalil A.M. Pharmazie 36 (1981) 160
29. El-Beih F.K.A., El-Tawil B.A.H., and Khalil A.M. Pol. J. Chem. 59 10-12 (1985) 1247