Design, synthesis, and biological evaluation of indole-modified tamoxifen relatives as potent anticancer agents.

Modulation of existing drugs is an attractive strategy to achieve improved activity in cancer therapy by lowering their effective dose. Preparation of relatives has been suggested and explored to improve the therapeutic effect of anticancer agents. In the current study, we attempted to modulate tamoxifen (TMX) by replacing the -phenyl ring in its backbone with an indole or oxindole.

Solvent-controlled regioselective C(5)-H/N(1)-H bond alkylations of indolines and C(6)-H bond alkylations of 1,2,3,4-tetrahydroquinolines with -quinone methides.

Solvent-promoted and -controlled regioselective bond alkylation reactions of -quinone methides (-QMs) with -H free-indoline and 1,2,3,4-tetrahydroquinoline (THQ) under metal-free conditions have been developed. In the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the solvent, 1,6-addition alkylation reactions of -QMs with NH-free indolines and THQs efficiently gave C5-alkylated indolines and C6-alkylated THQs. Using catalytic amounts of HFIP in DCM, the reaction of indolines and -QMs resulted in the alkylation of indolines at the N1-position.

The impact of metal coordination on the assembly of bis(indolyl)methane-naphthalene-diimide amphiphiles.

The self-assembly and coordination of amphiphiles comprised of naphthalenediimide (NDI) and bis(indolyl)methane (BIM) chromophores were investigated as a function of pH and metal. As observed by TEM, SEM and AFM imaging, the self-assembly of NDI-BIM 1 produced irregular nanostructures at neutral pH in CH3CN-H2O (1 : 1); whereas, well-defined nanotubes were observed at pH 2. Conversely, Fmoc-protected, NDI-BIM 2 formed nanotubes at neutral pH and nonspecific aggregates at pH 2.