Determination of Lipophilicity of Allyl Thiosemicarbazide, N¹-Thiocarbamylamidrazone Derivatives, and their Cyclic Products by RP-HPLC, RP-TLC, and Theoretical Methods: Effects of Selected Compounds on the CNS of Mice

Abstract

The allyl thiosemicarbazide, N¹-thiocarbamylamidrazone derivatives, and the products of their cyclization: the 1,2,4-triazole, 1,3,4-thiadiazole, 1,2,4-triazole[3,4-b]1,3-thiazine, 1,2,4-triazole[3,2-b]1,3-thiazine, 1,3,4-thiadiazole[3,2-a]pyrimidine, 5,6-dihydrothiazolo[2,3-c][1,2,4]triazole, and benzoic acid derivatives have been analyzed by RP-HPLC and RP-TLC methods using the methanol-water mixtures as the mobile phase and the octadecyl stationary phase. The lipophilicity was expressed as the chromatographically derived descriptors: mean of k (mk), mean of logk (mlogk), logk_W, S, and ϕ₀, scores of k, logk, and R_M corresponding to the first principal component. Additionally, the authors propose to introduce a descriptor (logk_m) corresponding to the residual specific interactions. Chromatographic parameters of lipophilicity were compared with the partition coefficient (logP) calculated by various softwares (milogP, clogP, AlogPs, AClogP, AlogP, MlogP, KOWWIN, XlogP2, XlogP3). The matrices were created with logk_W or R_MW and logP and they have been the subject of PCA analysis. The effects of the selected compounds on the central nervous system (CNS) of mice were studied.

Keywords:

• chromatography
• lipophilicity
• N¹-thiocarbamylamidrazone
• PCA
• thiosemicarbazide