CRYSTAL STRUCTURES OF DUAL DOPAMINE D2 AND SEROTONIN 5-HT1A ACTIVE ARYLPIPERIDINYL-2(1H)-3,4-DIHYDROQUINOLINONES
N. Ullah, M. Altaf, M. Mansha, A. O. Ba-Salem
Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia
Keywords: arylpiperidinyl-2(1H)-3,4-dihydroquinolinones, 5-HT receptor, D receptor, schizophrenia, adoprazine
Abstract
8-(1-((5-Cyclopentenylpyridin-3-yl)methyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (1) and 8-(1-(3-cyclopentenylbenzyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (2) are synthesized and obtained in the crystalline state for X-ray diffraction studies. In the asymmetric unit of compound 1, there are two independent molecules (A and B) having similar conformations. In the crystals of compounds 1 and 2, individual molecules are linked by pairs of N-H⋯O hydrogen bonds forming A-A and B-B inversion dimers with (8) ring motifs. The dimers are stabilized by N-O hydrogen bonds and are linked via C-H⋯O short contact interactions, forming a three-dimensional and two-dimensional networks in 1 and 2 respectively. The network in 2 is further stabilized by a number of C-H⋯p interactions. Compounds 1 and 2 have a dual dopamine D2 and serotonin 5-HT1A receptor profile.
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