ABSTRACT
Biscompounds may give better chance of binding with receptors due to increasing the probability of attachment from two sides of the structure with the receptor. On the other hand, the chirality introduces a chance for further adjustment of binding. Materials and methods3,3’-(2-nitropropane-1,3-diyl)bis(4-bromo-1H-indole) has been syn-the sized as a model compound with intentional modications via bromine atoms in order to give rise a possibility of variation in dipole moment around the stable conformer of the structure. Consequently, this may induce the chirality in the compound even without an appar-ent chiral center. NMR and single X-ray crystallography were used to study the chirality of the compound. Subsequently, the generated iso-mers were exposed for docking studies against a group of common serotonin receptors. Results and conclusions. The chirality of the biscompound was confirmed by the analyti-cal tools. Interestingly, its optical isomerism was discriminated by some of the receptors including 5HT3A, 5HT2B-bril, 5HT1F and 5HT1A. The docking scores of the biscompound isomers are not very inferior from those of the positive control; serotonin. Interestingly, some fine modifications such as the reduction of the nitro group in the biscompound generates a candidate compound has even more affinity toward the tested receptors than the positive control, except against 5HT1F.
BMC Proceedings