Synthesis and cytotoxic activities of 6-chloro-7-arylamino-5,8- isoquinolinediones

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 8, 1999, Pages 1075-1080

  Ryu, Chung Kyu ^a   Lee, In Kyung ^a   Jung, Sung Hee ^a   Lee, Chong Ock ^b  

^a Ewha Womans University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG STRUCTURE; SYNTHESIS; TUMOR CELL CULTURE;

ANTINEOPLASTIC AGENTS; HUMANS; INHIBITORY CONCENTRATION 50; ISOQUINOLINES; TUMOR CELLS, CULTURED;

EID: 0033583537     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00152-3     Document Type: Article

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12. 8, 138-140°C).
13. +), 229, 227, 201,199, 166.
14. General procedure for synthesis of 6-chloro-7-arylamino-5,8-isoquinolmediones 5a-5l: A mixture of 10 (2.27g, 10mmol) and appropriate arylamine (11mmol) in 95% EtOH (100mL) was refluxed for 4-10h. After the mixture was kept overnight in the refrigerator or was poured into 150mL ice water, the precipitate was collected by filtration. The precipitate was filtered and recrystallized from 95% EtOH or MeOH. And the recrystallized 5a-51 were filtered, washed with cold EtOH and dried (Scheme, Table 1).
15. 2, 17mL/mim as carrier gas, FID).
16. 7 reported that treatment of the compound 10 with aqueous NaOH gave exclusively 6-chloro-7-hydroxy-5,8-isoquinolinedione (11) and suggested a mechanism based on a resonance structure 10a in a positive charge was place at C-7 position. The 10a is the most stable among possible resonance structures, due to the lowest energy of its dipole moment.
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19. 18