Himbacin

Himbacin
IUPAC ime
	(3aR,4R,4aS,8aR,9aS)- 4(E)-[(2R,6S)- 1,6-dimethylpiperidin- 2-yl]vinyl 3-methyldecahydronaphtho[2,3-c]furan- 1(3H)-one
Identifikatori
CAS broj	6879-74-9
ATC kod	none
PubChem	CID 6436265
ChemSpider	4940913
Hemijski podaci
Formula	C22H35NO2
Molarna masa	345.27 g/mol
	SMILES O=C3O[C@H]([C@@H]4[C@H](/C=C/[C@@H]1N(C)[C@@H](C)CCC1)[C@@H]2[C@H](CCCC2)C[C@H]34)C; ;
	InChI InChI=1S/C22H35NO2/c1-14-7-6-9-17(23(14)3)11-12-19-18-10-5-4-8-16(18)13-20-21(19)15(2)25-22(20)24/h11-12,14-21H,4-10,13H2,1-3H3/b12-11+/t14-,15-,16+,17+,18-,19+,20-,21+/m0/s1 ; Key:FMPNFDSPHNUFOS-LPJDIUFZSA-N ;

Himbacin je alkaloid koji je izolovan iz kore Australijskih magnolija. Himbacin je bio sintetisan koristeći Diels-Alderovu reakciju kao ključni korak.^[1] Aktivnost himbacina kao antagonista muskarinskog receptora, sa specifičnošću za muskarinski acetilholinski receptor M2, mu je dala status obećavajuće početne tačke u istraživanjima Alchajmerove bolesti.^[2]^[3]

Razvoj muskarinskih antagonista zasnovanih na himbacinu je bio neuspešan, ali je jedno analogno jedinjenje u kliničkim ispitivanjima kao antagonist trombinskog receptora.^[4]^[5]

Literatura

^ Chackalamannil S; Davies RJ; Wang Y; et al. (1999). „Total Synthesis of (+)-Himbacine and (+)-Himbeline”. J. Org. Chem. 64 (6): 1932—1940. PMID 11674285. doi:10.1021/jo981983.
^ 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. PMID 15225708. doi:10.1016/j.bmcl.2004.05.047.
^ 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. PMID 18447380. doi:10.1021/jm800180e.
^ „Blog entry about Himbacine and its history in drug development”. Архивирано из оригинала 19. 01. 2011. г.

Spoljašnje veze

[pmid11674285-1] Chackalamannil S; Davies RJ; Wang Y; et al. (1999). „Total Synthesis of (+)-Himbacine and (+)-Himbeline”. J. Org. Chem. 64 (6): 1932—1940. PMID 11674285. doi:10.1021/jo981983.

[Malaska_et_al-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. doi:10.1016/0960-894X(94)00459-S.

[pmid15225708-3] 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 (15): 3967—3970. PMID 15225708. doi:10.1016/j.bmcl.2004.05.047.

[pmid18447380-4] 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 (11): 3061—3064. PMID 18447380. doi:10.1021/jm800180e.

[urlIn_Which_I_Hate_A_Wonder_Drug._In_the_Pipeline:-5] „Blog entry about Himbacine and its history in drug development”. Архивирано из оригинала 19. 01. 2011. г.

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