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Methimazole-disulfide as an Anti-Thyroid Drug Metabolite Catalyzed the Highly Regioselective Conversion of Epoxides to Halohydrins with Elemental Halogens
| Content Provider | Semantic Scholar |
|---|---|
| Author | Eshghi, Hossein Tayyari, Sayyed Faramarz Rezvani-Amin, Z. Roohi, Hossein |
| Copyright Year | 2008 |
| Abstract | The regioselective ring opening of epoxides using elemental iodine and bromine in the presence of methimazole (MMI, a anti-thyroid drug) and its metabolite methimazole-disulfide as new catalysts are studied. MMI easily converted in vitro to MMI-disulfide without any double activation presented in vivo. FT-Raman and UV spectroscopies are used to study the interaction of iodine with these catalysts. The results indicate that both catalysts are efficient in polyiodide formation, but MMI-disulfide can catalyze this reaction in higher yield and regioselectivity. The complex [(MMI-disulfide)I] + .I3 − is considered to be formed initially which could be bulkier by addition of excess of iodine in the course of the reaction. These bulky nucleophiles have a fundamental role in the high regioselectivity by attacking the less sterically hindered epoxide carbon. In this study we suggest that MMI is readily converted to MMI-disulfide by interaction with iodine or activated iodine in thyroid gland, and this process is responsible for high anti-thyroid activity of MMI. |
| Starting Page | 51 |
| Ending Page | 56 |
| Page Count | 6 |
| File Format | PDF HTM / HTML |
| DOI | 10.5012/bkcs.2008.29.1.051 |
| Volume Number | 29 |
| Alternate Webpage(s) | http://pdf.easechem.com/pdf/32/b216351d-8b74-469e-a4e4-f39c7d58eb8d.pdf |
| Alternate Webpage(s) | https://doi.org/10.5012/bkcs.2008.29.1.051 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
