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Himbacine
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
Identifiers
CAS number 6879-74-9
ATC code none
PubChem 6436265
Chemical data
Formula C22H35NO2 
Mol. mass 345.27 g/mol
Therapeutic considerations
Pregnancy cat.  ?
Legal status

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 antagonist.[4][5]

References

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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: 3967-3970. doi:10.1016/j.bmcl.2004.05.047. PMID 15225708. 
  4. ^ 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: 3061-3064. doi:10.1021/jm800180e. PMID 18447380. 
  5. ^ "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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