208592-60-3Relevant articles and documents
An investigation into the cytotoxicity and mode of action of some novel N-alkyl-substituted isatins
Vine, Kara L.,Locke, Julie M.,Ranson, Marie,Pyne, Stephen G.,Bremner, John B.
, p. 5109 - 5117 (2007)
A range of substituted N-alkylisatins were synthesized and their cytotoxicity evaluated against several cancer cell lines in vitro. SAR studies indicated that the introduction of an aromatic ring with a one or three carbon atom linker at N1 enhanced the activity from that of the allyl, 2′-methoxyethyl, and 3′-methylbutyl N-substituted isatins. Furthermore, electron-withdrawing groups substituted at the meta or para position of the ring were favored over the ortho orientation. Of the 24 compounds screened, nine displayed sub-micromolar IC50 values and in general demonstrated greater selectivity toward leukemia and lymphoma cell lines over any of the carcinoma cell lines tested. 5,7-Dibromo-N-(p-methylbenzyl) isatin (6) was the most active compound, inhibiting the metabolic activity of both U937 and Jurkat cancer cell lines at 0.49 μM. Various N-alkylisatins were also found to dramatically alter lymphocyte morphology, destabilize microtubules, inhibit tubulin polymerization, induce G2/M cell cycle arrest, and activate the effector caspase-3 and -7.
A convenient methodology for the N-alkylation of isatin compounds
Garden, Simon J.,Torres, Jose C.,Da Silva, Leonardo E.,Pinto, Angelo C.
, p. 1679 - 1689 (2007/10/03)
A simple, high yielding, methodology for the N-alkylation of substituted isatin derivatives using calcium hydride in DMF is detailed.
