Cyclic imides are privileged pharmacophores and important building blocks for the synthesis drugs, agrochemicals, advanced materials and polymers. A number of valuable natural products contain an imid fragment in their structure, in particular, Migrastatin, lamprolobin, julocrotine, cladoniamide A. Phthalimide contains the imide structure -CO-N (R) -CO-, which is one of the factors of the biological activity of this compound and indicates its pharmaceutical utility. It is known that some derivatives of phthalimide exhibit anticancer, antimicrobial, antioxidant, anti-inflammatory, anticonvulsant, CNS depressant, antitumor, antiproliferative and antipyretic activity.
Of interest in this aspect of research can be the combination in one structure phthalimide and thiosulfonate fragments.
In view of this, in the presented work an alternative way of synthesis of promising S-esters of 4-phthalimidomethylbenzenethiosulfonic acid was developed. The starting material for obtaining the above thiosulfoesters was 4-phthalimidomethylbenzensulfochloride. The recovery of sulfochloride by sodium sulfite in alkaline medium has been investigated. The 4-phthalimidomethylbenzensulfinic acid was obtained and converted into potassium salt of 4-phthalimidomethylbenzenethiosulfonic acid by interaction with sulfur in an aqueous solution of potassium hydroxide. Synthesized potassium salt was alkylated with different alkylation reagents and target esters of 4-phthalimidomethylbenzenthiosulfoacid were obtained.
The structure and properties of synthesized compounds are confirmed by 1Н NМR and IR spectral data and also data of element analysis.
In order to optimize experimental biological researches and finding promising new drug substances we carried out prediction of biological activity of synthesized esters of 4-phthalimidomethylbenzenethiosulfonic acid for structural formula in the online version of the computer program PASS (Prediction of Activity Spectra for Substances). Perspective directions of experimental biological researches of synthesized thiosulfoesters have been found out on the basis of information of virtual pharmacological screening.
Using the freely available on-line service GUSAR, in silico determination of acute rat toxicity of esters of 4-phthalimidomethylbenzenethiosulfonic acid have been carried out with four type of administration of substancet.
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