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Relevant academic research and scientific papers

ROSAMINE DERIVATIVES AS AGENTS FOR THE TREATMENT OF CANCER

The present invention relates to a new class of rosamine derivatives, in one embodiment, the compounds have the structure (I) or any pharmaceutically acceptable salt or solvate thereof, wherein: R1 represents aryl, Het1 or C1-6 alkyl, which latter group is optionally substituted by aryl or Het2; R2a and R2b together form C3.8n-alkylene, which alkylene group is optionally substituted by one or more substituents selected from halo, C1-4 alkyl, C(O)OH and C(O)O-C1-4, alkyl.and which alkylene group is optionally interrupted by X1; R3a and R3b together form C3-6 /7-alkylene, which alkylene group is optionally substituted by one or more substituents selected from halo, C1-4 alkyl, C(O)OH and C(O)O-C1-4 alkyl, and which alkylene group is optionally interrupted by X2; X1 and X2 independently represent O, S, or NR4; R4 represents, independently at each occurrence, H, C(O)OR5, C(0)R6a, C(O)N(R6b)R6c or C1-6, alkyl, which latter group is optionally substituted by one or more substituents selected from halo, aryl and Het3 or is substituted by a single C(0)0R1a group; R4a represents H or C1-4 alkyl; R5 represents aryl, Het4 or C1-6 alkyl optionally substituted by one or more substituents selected from halo, aryl and Het5; R5e to R6d independently represent H or R5; each aryl independently represents a C6-10 carbocyclic aromatic group, which group may comprise either one or two rings and may be substituted by one or more substituents selected from halo, CN, C1-6 alkyl (which latter group is optionally substituted by one or more substituents selected from halo, OR7, phenyl, naphthyl and Het6) and OR8; R7 and R8 independently represent H, C1-4 alkyl (optionally substituted by one or more halo groups or by a single phenyl or C(O)OR8a substituent), Het7, phenyl or naphthyl; R8a represents H or C1-4 alkyl; Het1 to Het7 independently represent 5- to 10-membered aromatic, fully saturated or partially unsaturated heterocyclic groups containing one or.more heteroatoms selected from oxygen, nitrogen and/or sulfur, which heterocyclic groups may comprise one or two rings and may be substituted by one or more substituents selected from Halo, CN, C1-6 alkyl (which latter group is optionally substituted by one or more substituents selected from halo, OR9 and phenyl) and OR10; R9 and R10 independently represent H, C1-4 alkyl or phenyl; unless otherwise specified, alkyl groups are optionally substituted by one or more halo atoms; and A' represents a pharmaceutically acceptable anion. Also disclosed are methods for making and using ' compounds as well as pharmaceutical compositions.

Synthesis and spectroscopic properties of rosamines with cyclic amine substituents

(Chemical Equation Presented) There is a close structural similarity between rosamines A and rhodamines B, yet a diversity of structures in the rosamine class and their spectral properties have yet to be explored in depth. This manuscript describes a concise, scalable, solution-phase method to obtain rosamines 1-5 and 12-15, which include some water-soluble derivatives. In one test case (for 15) an illustrative protein conjugate was also formed. Throughout these products were isolated and purified, and the syntheses were found to be scalable. Further, the rosamines with these cyclic amine substituents display solvent-dependent fluorescence intensities, and high quantum yields in chlorinated hydrocarbons. In some cases the nature of the cyclic amine substituent was shown to modulate the fluorescence of the parent molecules in pH-dependent ways. The ring size of those amine substituents also correlated with some of their spectroscopic properties. Several water-soluble rosamines were prepared from some of the addition products 1-5, and one of these, 15, was efficiently conjugated to avidin via an amide linkage. The spectroscopic properties of 15 and 15-avidin in aqueous media were very similar.