Analogues of Cytostatic, Fused Indazolinones: Synthesis, Conformational Analysis and Cytostatic Activity Against HeLa Cells of Some 1-Substituted Indazolols, 2-Substituted Indazolinones, and Related Compounds
✍ Scribed by Arán, Vicente J. ;Flores, María ;Muñoz, Pilar ;Páez, Juan A. ;Sánchez-Verdú, Prado ;Stud, Manfred
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 1006 KB
- Volume
- 1996
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
A number of indazol‐3‐ol and indazolin‐3‐one derivatives were designed as open‐chain analogues of some previously studied cytostatic tetranuclear indazolinones. The former were prepared by starting with alkylation of the parent indazolinones (11 or its 5‐H analogue). Special mention deserves the method we developed for the direct alkylation of position 2 of indazolinone 11 with benzyl or picolyl halides. The prepared compounds were evaluated as cytostatic agents against HeLa cells, but only 1‐benzylindazolol 5a and 1‐(2‐fluorobenzyl)‐3‐methoxy‐ and 1‐benzyl‐3‐methoxyindazoles 14h, i display significant activity. Additional ^13^C‐NMR studies and conformational analysis using molecular mechanics and quantum‐mechanical semiempirical techniques confirm that the compounds designed as analogues of the model cytostatic indazolinones are not able to mimic effectively the structural features of the latter.