Mecigestone
Chemical compound
From Wikipedia, the free encyclopedia
Mecigestone, also known as pentarane B, as well as 6α-methyl-16α,17α-cyclohexanoprogesterone, 6α-methylcyclohexano[1',2';16,17]pregn-4-ene-3,20-dione, or 17α-acetyl-6α-methyl-16β,24-cyclo-21-norchol-4-en-3-one, is a steroidal progestin that was developed by the Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences and has been proposed for clinical use as a progestogen but has not been marketed.[1][2][3][4][5] It is the 6α-methylated analogue of pentarane A, which is also known as D'6-pentarane or pregna-D'6-pentarane.[5]
Other namesPentarane B; 6α-Methyl-16α,17α-cyclohexanoprogesterone
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| Other names | Pentarane B; 6α-Methyl-16α,17α-cyclohexanoprogesterone |
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| Formula | C26H38O2 |
| Molar mass | 382.588 g·mol−1 |
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Synthesis
The synthesis has been reported:[6] Patent:[7] Precursor:[8] Micronization technology:[9]
- The Diels-Alder reaction of 16-DPA [979-02-2] (1) with butadiene gives PC99565806 (2). It is important to recognize that for mecigestone the stereochemistry about the E-ring is cis and not trans. The trans isomer is PC99565808.
- Ex 1: Epoxidation of the olefin with ethereal Monoperphthalic acid [2311-91-3] occurs to give (3). A search of the pubchem registry only gave the trans configuration about the E-ring (PC11873237), and not the expected cis stereochemistry.
- The reaction with methyl magnesium iodide occurs with a regioselectivity to the 6 position from the beta face. Saponification of the acetate ester also occurs during the work-up to give (4).
- The Jones oxidation leads to the enone of the finished product. Epimerization of the beta-methyl group also occurred during this step. Thus, completing the synthesis of mecigestone (5).
