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S-15183a

Name: S-15183a
Brand: BOC Sciences
Rating: 5 (1 reviews)

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category	Enzyme inhibitors
Catalog number	BBF-03395
CAS
Molecular Weight	416.5
Molecular Formula	C25H36O5

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

S-15183a is a sphingosine kinase inhibitor produced by Zopfiella inermis SANK 15183. It inhibited sphingosine kinase from rat liver with IC50 value of 2.5 µmol/L. It also inhibited endogenous SPH kinase activity in intact platelets.

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Synonyms	S-15183 a
IUPAC Name	(3-heptyl-7-methyl-6,8-dioxoisochromen-7-yl) octanoate
Canonical SMILES	CCCCCCCC1=CC2=CC(=O)C(C(=O)C2=CO1)(C)OC(=O)CCCCCCC
InChI	InChI=1S/C25H36O5/c1-4-6-8-10-12-14-20-16-19-17-22(26)25(3,24(28)21(19)18-29-20)30-23(27)15-13-11-9-7-5-2/h16-18H,4-15H2,1-3H3
InChI Key	YMXPNDJGGNEMOH-UHFFFAOYSA-N

Appearance

Yellow Oily Matter

1. S-15183a and b, new sphingosine kinase inhibitors, produced by a fungus

K Kono, M Tanaka, Y Ono, T Hosoya, T Ogita, T Kohama J Antibiot (Tokyo). 2001 May;54(5):415-20. doi: 10.7164/antibiotics.54.415.

In the course of our screening for inhibitors of sphingosine kinase, we found two active compounds in a culture broth of a fungus, Zopfiella inermis SANK 15183. The structures of the compounds, named S-15183a and b, were elucidated by a combination of spectroscopic analyses to be new azaphilone-type metabolites. S-15183a and b inhibited sphingosine kinase from rat liver with IC50 values of 2.5 and 1.6 microM, respectively. S-15183a also inhibited endogenous SPH kinase activity in intact platelets.

2. Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization

Jianglong Zhu, Nicholas P Grigoriadis, Jonathan P Lee, John A Porco Jr J Am Chem Soc. 2005 Jul 6;127(26):9342-3. doi: 10.1021/ja052049g.

An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.

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S-15183a

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