Quantum-Chemical Study of the Relationships between Electronic Structure and the Affinity of Benzisothiazolylpiperazine Derivatives for the Dopamine Hd2l and Hd3 Receptors

Abstract Schizophrenia is a mental illness that induces a cognitive deficit, affects a large part of the world’s population, and in particular Africa where it is ignored. To treat this disease, the antipsychotic derivatives of benzisothiazolylpiperazine (N-(trans-4-(2-(4-(benzo [d] isothiazol-3-yl) piperazin-1-yl) ethyl)cyclohexyl) amides) are employed because of their inhibitory powerfor the dopamine HD2L and HD3 receptors. The present study aims to establish relationships between the electronic structure and the antipsychotic activity of benzisothiazolylpiperazine derivatives and to generate a 2D pharmacophore for predicting the antipsychotic activity of these derivatives. The KPG technique was employed. The electronic structure of all the molecules was calculated at the DFT/B3LYP/6-31G (d,p) level of theory. We obtained two statistically significant equations for predicting the inhibition constant. The process seems to be charge and orbital controlled for receptor HD2L and orbital controlled for HD3. The two prediction equations obtained can be useful for proposing new derivatives with antipsychotic activity having an affinity with the dopamine HD2L and HD3 receptors. The two pharmacophores derived from these prediction models would be very useful for proposing new molecules with potent antipsychotic activity.

Keywords Schizophrenia, QSAR, hD2L receptor, hD3 receptor, KPG method, DFT.

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Updated: January 20, 2024 — 8:08 am