Himbacine
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| Systematic (IUPAC) name | |
| (3aR,4R,4aS,8aR,9aS)- 4-{(E)-[(2R,6S)- 1,6-dimethylpiperidin- 2-yl]vinyl}- 3-methyldecahydronaphtho[2,3-c]furan- 1(3H)-one | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 6879-74-9 |
| ATC code | None |
| PubChem | CID 6436265 |
| ChemSpider | 4940913  |
| ChEMBL | CHEMBL277642 |
| Chemical data | |
| Formula | C22H35NO2 |
| Mol. mass | 345.27 g/mol |
| SMILES | eMolecules & PubChem |
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Himbacine is an alkaloid isolated from the bark of Australian magnolias. Himbacine has been synthesized using a Diels-Alder reaction as a key step.[1] Himbacine's activity as a muscarinic receptor antagonist, with specificity for the Muscarinic acetylcholine receptor M2, made it a promising starting point in Alzheimer's disease research.[2][3] The development of a muscarinic antagonist based on Himbacine failed but an analog is now in clinical trials as a thrombin receptor antagonist.[4][5]
[edit] See also
[edit] References
- ^ Chackalamannil S, Davies RJ, Wang Y, et al. (March 1999). "Total Synthesis of (+)-Himbacine and (+)-Himbeline". J. Org. Chem. 64 (6): 1932–1940. doi:10.1021/jo981983. PMID 11674285.
- ^ Malaska MJ, Fauq AH, Kozikowski AP, Aagaard PJ, McKinney M (1995). "Chemical Modification of Ring C of Himbacine: Discovery of a Pharmacophoric Element for M2-Selectivity". Bioorganic and Medicinal Chemistry Letters 5 (1): 61–66. doi:10.1016/0960-894X(94)00459-S.
- ^ Chackalamannil S, Doller D, McQuade R, Ruperto V (2004). "Himbacine analogs as muscarinic receptor antagonists-effects of tether and heterocyclic variations". Bioorganic and Medicinal Chemistry Letters 14 (15): 3967–3970. doi:10.1016/j.bmcl.2004.05.047. PMID 15225708.
- ^ Chackalamannil S, Wang Y, Greenlee WJ, 'et al. (2008). "Discovery of a Novel, Orally Active Himbacine-Based Thrombin Receptor Antagonist (SCH 530348) with Potent Antiplatelet Activity". J. Med. Chem. 51 (11): 3061–3064. doi:10.1021/jm800180e. PMID 18447380.
- ^ "Blog entry about Himbacine and its history in drug development". http://pipeline.corante.com/archives/2008/05/13/in_which_i_hate_a_wonder_drug.php.
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