Balanol

Structural formula
General
Surname	Balanol
other names	Azepinostatin; 2- [2,6-Dihydroxy-4 - [(3 R , 4 R ) -3 - [(4-hydroxybenzoyl) amino] azepan-4-yl] oxycarbonylbenzoyl] -3-hydroxybenzoic acid;
Molecular formula	C 28 H 26 N 2 O 10
External identifiers / databases
PubChem	5287736
ChemSpider	4450040
DrugBank	DB04098
Wikidata	Q4850048
properties
Molar mass	551.17 g mol −1
Physical state	firmly
Melting point	decomposes above 180 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Balanol is a Azepan - derivative from the Hypocreomycetiden Verticillium balanoides , which in 1993 by Kulanthaivel was isolated. The compound is a potent inhibitor of protein kinase C and is regioisomeric to ophiocordin . Because of its pharmaceutical utility, balanol became a target of combinatorial chemistry .

Structural formula of Ophiocordin

Extraction and presentation

Balanol can be obtained from Boc-GABA-OH . In 2010 a new synthesis from 1,5-pentanediol was presented. This reacts in a Shi epoxidation and a nitrogen substitution to form a correctly configured balanol precursor.

Individual evidence

↑ Entry on Balanol. In: Römpp Online . Georg Thieme Verlag, accessed on March 29, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry in the Fungorum Index
↑ ^a ^b Phannarath Phansavath, Sébastien Duprat de Paule, Virginie Ratovelomanana-Vidal, Jean-Pierre Genêt: An Efficient Formal Synthesis of (-) - balanol by Using Catalyzed Asymmetric Hydrogenation ruthenium . In: European Journal of Organic Chemistry . tape 2000 , no. 23 December 2000, pp. 3903-3907 , doi : 10.1002 / 1099-0690 (200012) 2000: 23% 3C3903 :: aid-ejoc3903% 3E3.0.co; 2-q ( PDF ).
↑ Srinivasarao Yaragorla, Ramaiah Muthyala: Formal total synthesis of (-) - balanol: a potent PKC inhibitor . In: Tetrahedron Letters . tape 51 , no. 3 , January 2010, p. 467-470 , doi : 10.1016 / j.tetlet.2009.10.120 ( PDF ).

[roempp-1] Entry on Balanol. In: Römpp Online . Georg Thieme Verlag, accessed on March 29, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Entry in the Fungorum Index

[phansavath-4] Phannarath Phansavath, Sébastien Duprat de Paule, Virginie Ratovelomanana-Vidal, Jean-Pierre Genêt: An Efficient Formal Synthesis of (-) - balanol by Using Catalyzed Asymmetric Hydrogenation ruthenium . In: European Journal of Organic Chemistry . tape 2000 , no. 23 December 2000, pp. 3903-3907 , doi : 10.1002 / 1099-0690 (200012) 2000: 23% 3C3903 :: aid-ejoc3903% 3E3.0.co; 2-q ( PDF ).

[yaragorla-5] Srinivasarao Yaragorla, Ramaiah Muthyala: Formal total synthesis of (-) - balanol: a potent PKC inhibitor . In: Tetrahedron Letters . tape 51 , no. 3 , January 2010, p. 467-470 , doi : 10.1016 / j.tetlet.2009.10.120 ( PDF ).