?-BHC (I), one of eight isomers of 1,2,3,4,5,6-hexachlorocyclohexane(BHC, HCH) shows a potent insecticidal activity and is known to be an antagonist of GABA on GABA-gated Cl- channel(GABA receptor). ?-BHC analogs replaced its one Cl atom with OCH3, namely 1-OCH3 and 3-OCH3 show similar level of insecticidal activities against the housefly and German cockroach as ?-BHC. Surprisingly their demethylated OH-analogs have equipotent activities on GABA receptor as GABA antagonist. The OCH3 and OH substituents are interesting groups in terms of bioisosterism with Cl atom. Various OCH3 and OHanalogs of ?-BHC were synthesized stereoselectively and also stereospecifically retaining the similar configuration of Cl atoms on the cyclohexane ring as ?-BHC.The results of the in vitro activity evaluation of these analogs using [3H]EBOB binding and membrane potential assays will be discussed in the light of the structure-activity relationships of the ?-BHC analogs.

Synthesis of OCH<sub>3</sub>-, OH-substituted ?-BHC analogs, and their inhibitory activities on the GABA-gated Cl<sup>-</sup> channel

248th National Meeting (2014)

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Synthesis of OCH3-, OH-substituted ?-BHC analogs, and their inhibitory activities on the GABA-gated Cl- channel

Synthesis of OCH₃-, OH-substituted ?-BHC analogs, and their inhibitory activities on the GABA-gated Cl^- channel