Synthesis of New 5-Substituted Hydantoins and Symmetrical Twin-Drug Type Hydantoin Derivatives

Abstract

In connection with our studies on hydantoin derivatives, a conventional regioselective chemical transformation of 5-methylene hydantoins 4a-c to 5-aminomethyl-substituted hydantoins 5-10 or to 5-amino-5-methyl-disubstituted hydantoins 11-14 is described. Synthesis of bivalent twin-drug type hydantoin derivatives 19-24 and the binding property of a bivalent symmetrical hydantoin derivative 24b to sulfated glycosaminoglycans are also described.

Synthesis and Antiviral Activities of Some 2,4,6-Trisubstituted 1,3,5-Triazines

“…From this aspect of molecular symmetry, we have already reported a few examples of such types of new symmetrical molecules for the purpose of finding new biological active compounds. [7][8][9] We have recently reported some molecular modifications of 2,4,6-trichloro-1,3,5-triazine (TCTAZ) to C 3 -, or C Ssymmetrical trisubstituted TAZ molecules and the results of biological evaluation of synthesized symmetrical 2,4,6-trisubstituted TAZ derivatives. 7) Among previously targeted TAZ derivatives, some alkoxy-amino-substituted derivatives showed significant anti-herpes simplex virus type 1 (HSV-1) activities.…”

Synthesis and Antiviral Evaluation of Some <i>C</i>₃-Symmetrical Trialkoxy-Substituted 1,3,5-Triazines and Their Molecular Geometry

“…In connection with our synthetic works on such symmetrical molecules, we have already designed and synthesized a few new symmetrical molecules and evaluated their bioactivities in order to find new types of bioactive compounds. [8][9][10][11][12][13][14][15][16][17] In connection with the above projects, we have recently reported some molecular modifications of 2,4,6-trichloro-1,3,5-triazine (TCT AZ) (1) to symmetrical 2,4,6-trisubstituted 1,3,5-triazine (TAZ) molecules and the results of biological evaluation of synthesized symmetrical 2,4,6-trisubstituted TAZ derivatives. 8,9) Among previously targeted trisubstituted TAZ derivatives, we found that a C 3 -symmetrical TAZ derivative with three isopropoxy groups on a TAZ template such as compound 4e showed a high level of anti-herpes simplex virus (HSV)-1 activity and low cytotoxity, and it therefore seemed to be a potential lead in the search for preferred anti-HSV-1 activity with a good selectivity index (SI).…”

Synthesis and Biological Evaluation of 1,3,8-Triazaspiro[4.5]decane-2,4-dione Derivatives as Myelostimulators

“…IR spectra were recorded on Nicolet «5700 FT-IR» spectrometer in a thin film. 13 C and 1 H NMR spectra of synthesized compounds were recorded at Varian's «Mercury-300» spectrometer using CDCl 3 as a solvent. The shooting temperature is 25 ∘ C, unless otherwise specified.…”

“…Also some hydantoin derivatives, like barbiturates, have a soporific effect [10]. Some of the hydantoin derivatives possess anticancer and other types of activities [11][12][13].…”