Himbacin
Himbacin je alkaloid koji je izolovan iz kore Australijskih magnolija. Himbacin je bio sintetisan koristeći Diels-Alderovu reakciju kao ključni korak.[4] Aktivnost himbacina kao antagonista muskarinskog receptora, sa specifičnošću za muskarinski acetilholinski receptor M2, mu je dala status obećavajuće početne tačke u istraživanjima Alchajmerove bolesti.[5][6]
(IUPAC) ime | |||
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(3aR,4R,4aS,8aR,9aS)- 4(E)-[(2R,6S)- 1,6-dimethylpiperidin- 2-yl]vinyl 3-methyldecahydronaphtho[2,3-c]furan- 1(3H)-one | |||
Klinički podaci | |||
Identifikatori | |||
CAS broj | 6879-74-9 | ||
ATC kod | nije dodeljen | ||
PubChem[1][2] | 6436265 | ||
ChemSpider[3] | 4940913 | ||
Hemijski podaci | |||
Formula | C22H35NO2 | ||
Mol. masa | 345.27 g/mol | ||
SMILES | eMolekuli & PubHem | ||
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Farmakoinformacioni podaci | |||
Trudnoća | ? | ||
Pravni status |
Razvoj muskarinskih antagonista zasnovanih na himbacinu je bio neuspešan, ali je jedno analogno jedinjenje u kliničkim ispitivanjima kao antagonist trombinskog receptora.[7][8]
Literatura uredi
- ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.
- ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
- ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.
- ↑ 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”. Arhivirano iz originala na datum 2011-01-19.