Synthesis and hypoglycemic activity of N-arylsulfonyl-N′-[7-(1,3,5-triazaadamantyl)]urea

Abstract

As is known [1], substituting 1-adamantyl ring for an alkyl group in the structure of some antidiabetic preparations (chlorpropamide, butamide) leads to an increase in the hypoglycemic activity of the compound. In this connection, it was of interest to replace the alkyl group with 1,3,5-triazaadamantyl ring in the same preparations and study the activity of modified compounds.We used a method analogous to that described in The synthesized compounds appear as crystalline substances of white color, soluble in ethanol and chloroform (compound II, on boiling), and insoluble in ether. The structures of compounds were established on the basis of data of elemental analyses and the IR, U-V, 1H NMR, and mass-spectrometric measurements; the purity of the reaction products was checked by TLC. EXPERIMENTAL CHEMICAL PARTThe IR absorption spectra were measured on an UR-20 spectrophotometer using samples prepared as nujol mulls. The IH NMR spectra were obtained on a Varian T-60 spectrometer (USA) using CDCI3 at the solvent and TMS as the internal standard. The UV spectra were recorded in 96% ethanol with a Specord spectrophotometer. The mass spectra were obtained on an MX-1320 spectrometer. The TLC chromatograms were obtained on Silufol UV-254 plates eluted by a propanol -water (7 : 1) system and developed by a 10% ethanol solution of ninhydrin. The data of elemental analyses of compounds I and II agree with the results of calculations.

Azaadamantanes, a New Promising Scaffold for Medical Chemistry

“… 5,7-Disubstituted 1,3-diazaadamantanes and 1,3,5-triazaadamantane exhibiting anticonvulsant effect and hypoglycemic activity, respectively [ 92 , 93 ]. …”

“…A slight improvement in the hypoglycemic activity (the ability to reduce blood glucose levels) of antidiabetic drugs as a result of the addition of the azaadamantane fragment to biologically active compounds was shown by Agadzhanyan et al [ 93 ]. The substitution of the alkyl group in 4-chloro- N -(propylcarbamoyl)benzenesulfonamide (chlorpropamide; a drug used in the treatment of type 2 diabetes mellitus, diabetic microangiopathy (initial forms), and diabetes insipidus) by 1,3,5-triaazaadamantane ( Fig.…”