A facile method to transform trans-4-carboxy-3,4-dihydro-3-phenyl-1(2H)- isoquinolones to indeno[1,2-c]isoquinolines

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6496-6498

  Xiao, Xiangshu ^a   Cushman, Mark ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; CONDENSATION; ENZYME INHIBITION; PROTEINS; REACTION KINETICS; TUMORS;

DIASTEREOMERS; SCHIFF BASES; THIONYL CHLORIDE; TOPOISOMERASE I;

KETONES;

4 CARBOXY 3,4 DIHYDRO 3 PHENYL 1(2H) ISOQUINOLONE DERIVATIVE; CHLORIDE; DNA TOPOISOMERASE INHIBITOR; INDENO[1,2 C]ISOQUINOLINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PHTHALIC ANHYDRIDE; QUINOLONE DERIVATIVE; SCHIFF BASE; SELENIUM DERIVATIVE; SELENOXIDE; THIONYL CHLORIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CIS ISOMER; CYCLIZATION; DIASTEREOISOMER; DRUG CLASSIFICATION; DRUG TRANSFORMATION; ELIMINATION REACTION; FRIEDEL CRAFTS REACTION; POLYMERIZATION; TRANS ISOMER;

CYCLIZATION; HYDROGEN; INDENES; ISOQUINOLINES; STEREOISOMERISM; SULFUR OXIDES;

EID: 23044459095     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050831t     Document Type: Article

References (22)

1. Cushman, M.; Cheng, L. J. Org. Chem. 1978, 43, 286-288.
2. Cushman, M.; Cheng, L. J. Org. Chem. 1978, 43, 3781-3783.
3. Kohlhagen, G.; Paull, K.; Cushman, M.; Nagafuji, P.; Pommier, Y. Mol. Pharmacol. 1998, 54, 50-58.
4. Strumberg, D.; Pommier, Y.; Paull, K.; Jayaraman, M.; Nagafuji, P.; Cushman, M. J. Med. Chem. 1999, 42, 446-457.
5. Cushman, M.; Jayaraman, M.; Vroman, J. A.; Fukunaga, A. K.; Fox, B. M.; Kohlhagen, G.; Strumberg, D.; Pommier, Y. J. Med. Chem. 2000, 43, 3688-3698.
6. Jayaraman, M.; Fox, B. M.; Hollingshead, M.; Kohlhagen, G.; Pommier, Y.; Cushman, M. J. Med. Chem. 2002, 45, 242-249.
7. Fox, B. M.; Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Staker, B. L.; Stewart, L.; Cushman, M. J. Med. Chem. 2003, 46, 3275-3282.
8. Nagarajan, M.; Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. J. Med. Chem. 2003, 46, 5712-5724.
9. Antony, S.; Jayaraman, M.; Laco, G.; Kohlhagen, G.; Kohn, K. W.; Cushman, M.; Pommier, Y. Cancer Res. 2003, 63, 7428-7435.
10. Morrell, A.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Bioorg. Med. Chem. Lett. 2004, 14, 3659-3663.
11. Nagarajan, M.; Morrell, A.; Fort, B. C.; Meckley, M. R.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. J. Med. Chem. 2004, 47, 5651-5661.
12. Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Bioorg. Med. Chem. 2004, 12, 5147-5160.
13. Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. J. Org. Chem. 2004, 69, 7495-7501.
14. Xiao, X.; Antony, S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2005, 48, 3231-3238.
15. Xiao, X.; Miao, Z.-H.; Antony, S.; Pommier, Y.; Cushman, M. Bioorg. Med. Chem. Lett. 2005, 15, 2795-2798.
16. Antony, S.; Kohlhagen, G.; Agama, K.; Jayaraman, M.; Cao, S.; Durrani, F. A.; Rustum, Y. M.; Cushman, M.; Pommier, Y. Mol. Pharmacol. 2005, 67, 523-530.
17. Cushman, M.; Gentry, J.; Dekow, F. W. J. Org. Chem. 1977, 42, 1111-1116.
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2004.
19. Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 5813-5815.
20. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper and Row: New York, 1987; pp 318-322.
21. Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. J. Org. Chem. 2005, 70, 350-352.
22. Yadav, J. S.; Reddy, B. V. S.; Raj, K. S.; Prasad, A. R. Tetrahedron 2003, 59, 1805-1809.