Design, synthesis and antiproliferative activity evaluation of new 5-azaisoindigo derivatives

Article abstract of DOI:10.3987/COM-14-13036

New 5-azaisoindigo derivatives were synthesized with two key intermediates 5-azaoxindole (7) and substituted indole-2,3-dione (10) in this paper. Intermediate 7 was prepared from 3-methylpyridine (1) through 6 steps containing oxidation reaction and so on. Intermediate 10 was obtained by a convenient Sandmeyer's method. The target compounds 5-azaisoindigo derivatives 11a-f were obtained by condensation of these two intermediates 7 and 10 in acidic condition. All target compounds were evaluated for their antiproliferative activity against seven cell lines by SRB assay. Compounds 11e and 11f showed significant antiproliferative activity against K562 cells (IC₅₀: 8.9 μM and 13.6 μM, respectively).

Full text of DOI:10.3987/COM-14-13036

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1H NMR and C NMR of intermediates and target compounds in
manuscript titled “DESIGN, SYNTHESIS AND ANTIPROLIFERATIVE
ACTIVITY EVALUATION OF NEW 5‐AZAISOINDIGO DERIVATIVES”.
1H NMR of compound 2
1H NMR of compound 3
1

1H NMR of compound 4
1H NMR of compound 5
2

1H NMR of compound 6
1H NMR of compound 7
3

1H NMR of compound 10a
1H NMR of compound 10b
4

1H NMR of compound 10d
1H NMR of compound 10e
5

1H NMR of compound 10f
1H NMR of compound 11a
6

13C NMR of compound 11a
1H NMR of compound 11b
7

13C NMR of compound 11b
1H NMR of compound 11c
8

13C NMR of compound 11c
1H NMR of compound 11d
9

1H NMR of compound 11e
13C NMR of compound 11e
10

1H NMR of compound 11f
13C NMR of compound 11f
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