New steroidal anti-inflammatory antedrugs: 21-thioalkylether derivatives of methyl 16-prednisolone carboxylates was written by Khan, M. Omar F.;Park, Kwan K.;Glynn, Sharye N.;Lee, Henry J.. And the article was included in Medicinal Chemistry in 2007.Quality Control of Sodium 2-methyl-2-propanethiolate This article mentions the following:
Antedrug approach of the corticosteroids has been described as a fundamentally sound approach for the development of safer anti-inflammatory steroids devoid of systemic side effects. In our continued efforts under the antedrug paradigm, we have recently extended this effort to synthesize the 21-thioalkyl ether derivatives of Me 16-prednisolonecarboxylates. The 21-mesylate of the methyl-16-prednisolonecarboxylates and 9-fluoro-17-dehydro Me 16-prednisolonecarboxylate were reacted with Na-thioalkoxides to furnish the desired thioalkyl ethers in 60-75% yields. These newly synthesized thioalkyl ether steroid series were tested for their in vitro metabolism and corticosteroid receptor binding affinity. They were metabolized in predictable manner to inactive 16-carboxylic acids. All the newly synthesized antedrugs showed lowered glucocorticoid receptor binding affinity than prednisolone indicating that the replacement of the 21-OH function with thioalkyl ether of the 16-prednisolone carboxylate esters decreases their receptor binding affinity. In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Quality Control of Sodium 2-methyl-2-propanethiolate).
Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Quality Control of Sodium 2-methyl-2-propanethiolate
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts