92589-98-5Relevant academic research and scientific papers
Radioligand and computational insight in structure – Activity relationship of saccharin derivatives being ipsapirone and revospirone analogues
Ku?aga, Damian,Ja?kowska, Jolanta,Sata?a, Grzegorz
, (2021)
Schizophrenia and depression are diseases that significantly impede human functioning in society. Current antidepressant drugs are not fully effective. According to literature data, the effect on D2R or 5-HT1AR can effectively reduce
Microwave-Assisted Solvent-Free Synthesis of Ipsapirone
Ku?aga, Damian,Ja?kowska, Jolanta,Jasiński, Radomir
, p. 1498 - 1504 (2019/05/16)
The currently applied synthetic methods of serotonin receptor ligands belonging to the group of long-chain arylpiperazines, including ipsapirone, require the use of toxic solvents and comprise numerous synthetic steps. Moreover, the reaction yield does not exceed 60% in the majority of cases. These factors lead to an increased energy consumption and negatively impact the environment. This paper describes a more environmentally friendly method of ipsapirone synthesis that we decided to use. Ipsapirone was obtained in two different methods. The first method involved N-alkylation of bromobutyl saccharin with 1-(2-pyrimidyl)piperazine dihydrochloride, while the second was a one-pot method. Neither of these requires the use of toxic and expensive solvents. A shortened synthesis time, not exceeding 10?min due to the use of microwave radiation, is also another advantage of these methods. The yield of the final product, ipsapirone, was 85% and 67% in the first and the second method, respectively. We also attempted to obtain ipsapirone using saccharin and arylpiperazine salt (method III) as starting materials, but to no avail in the tested conditions. As described herein, the green chemistry method for ipsapirone synthesis is rapid, cost-effective, and environment friendly.
