Draft:SIR 117
| Submission rejected on 22 May 2025 by Boghog (talk). This topic is not sufficiently notable for inclusion in Wikipedia. Rejected by Boghog 13 days ago. Last edited by Citation bot 12 days ago. |  |
Comment: The only peer reviewed publication that this compound appears in is compound #21 in PMID 4543291 and it is not even the most potent compound disclosed in that publication. Furthermore SIR-117 does not appear to be a neuroleptic tranquilizer, but rather a tricyclic antidepressant. This is not a notable drug. The synthesis of a non-notable drug is even less notable. Boghog (talk) 18:46, 22 May 2025 (UTC)
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| Formula | C22H26ClN |
| Molar mass | 339.91 g·mol−1 |
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SIR 117 is an example of a neuroleptic tranquiliser. The spirocyclic structure is a technological advancement over TCAs such as clomipramine. Chlorination into a molecule is a commonly regarded and well-known method to cause a potentiation in activity. For related compounds see Pramiverine and Chloripramine.
Synthesis
[edit]Synthesis:[1] Patent:[2] Starting Precursor:[3]
Ex 6: The Grignard reaction between 3-chlorodibenzosuberone, PC12264964 (1) and methylal (dimethoxymethane) [109-87-5] then chloromethylether was added. The product of this step is claimed to be called 3-chloro-5-hydroxy-5- methoxymethyldibenzosuberane (2). Boiling with formic acid followed by the addition of 1M sulfuric acid led to 3-chloro-5-formyl-dibenzosuberane (3). Intermolecular ring formation occurred upon treatment with methyl vinyl ketone (MVP), and hexamethylphosphoramide to give 3- chlorodibenzosuberaneSpiro[5.5]cyclohex-6-ene-2-one, PC12524381 (4). Catalytic hydrogenation of the olefin led to 3- chlorodibenzosuberaneSpiro[5.5]cyclohex-2-one (5). Ex 17: A modification of the Leuckart reaction using dimethyl ammonium formate completed the synthesis SIR 117 (6).
References
[edit]- ^ Carnmalm, B.; Jacupovic, E.; Johansson, L.; De Paulis, T.; Ramsby, S.; Stjernstrom, N. E.; Renyi, A. L.; Ross, S. B.; Ogren, S. O. (1974). "Antidepressant agents. 1. Chemistry and pharmacology of amino-substituted spiro[5H-dibenzo[a,d]cycloheptene-5,1'-cycloalkanes]". Journal of Medicinal Chemistry. 17 (1): 65–72. doi:10.1021/jm00247a014.
- ^ Bernt Sigfrid Emanuel Carnmalm, et al., US4053632 (1977 to Astra Lakemedel AB).
- ^ Winthrop, Stanley O.; Davis, M. A.; Myers, G. S.; Gavin, J. G.; Thomas, R.; Barber, R. (1962). "New Psychotropic Agents. Derivatives of Dibenzo[a,d]-1,4-cycloheptadiene". The Journal of Organic Chemistry. 27 (1): 230–240. doi:10.1021/jo01048a057.