Draft:Perithiaden
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Comment: The synthesis section of this article is very difficult to understand as it is written right now. Please fix its prose to make it more understandable to laypeople (or at least, those only with basic knowledge of biomolecules). Also, the majority of citations are devoted to the Synthesis section. More citations should be about its biological activity. You don't need to put CAS numbers after compounds, either. Pygos (talk) 03:49, 5 December 2024 (UTC)
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| Chemical and physical data | |
| Formula | C20H21NS |
| Molar mass | 307.46 g·mol−1 |
| 3D model (JSmol) | |
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Perithiaden is from the Dibenzothiepin family of agents.
It is useful as sedative-neuroleptic, muscle-relaxant and sleep-promoting agent.[1]
This compound is very similar in structure to both Dothiepin (Dosulepin) as well as the related six membered ring system that called pimethixene (Mepithiathene) [314-03-4]. The relative rigidity of the piperidine ring as well as the olefinic bridge that can covalently bind to the receptor would both be expected to affect the activity. The SAR is also related to Pipethiadene.
Synthesis
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The Grignard reaction between Dibenzo[b,e]thiepin-11(6H)-one, PC73741 (1) and 4-Chloro-1-Methylpiperidine [5570-77-4] (2) gives the corresponding carbinol and hence PC14175795 (3). Acid catalyzed dehydration to the olefin completed the synthesis of Perthiaden (4). If desired, urethane formation and hydrolysis gives the secondary amine but is an additional step.
References
[edit]- ^ Metysova J, Metys J, Votava Z (December 1963). "[Pharmacological Properties of 6,11-Dihydrodibenz(b,e)thiepin Derivatives. 1]". Arzneimittel-Forschung (in German). 13: 1039–43. PMID 14208672.
- ^ Anton Ebnother, et al. US4072756 (1978 to Sandoz KK).
- ^ Masafumi Minomura, et al. EP0530016 (1993 to Ajinomoto Co Inc).
- ^ Yasuo Ito, et al. EP0451772 (1991 to Hokuriku Pharmaceutical Co Ltd).