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RES-1149-2

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RES-1149-2
Category Bioactive by-products
Catalog number BBF-03364
CAS
Molecular Weight 386.5
Molecular Formula C23H30O5

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

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

RES-1149-2 is an endothelin type B receptor antagonist produced by Aspergillus sp. RE-1149. It selectively inhibits the ET-1 binding to endothelin type B receptor with IC50 value of 20 µmol/L.

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IUPAC Name [(5R,5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1-oxo-3,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] (2E,4E,6E)-octa-2,4,6-trienoate
Canonical SMILES CC=CC=CC=CC(=O)OC1C=C2COC(=O)C2(C3(C1C(CCC3)(C)C)C)O
InChI InChI=1S/C23H30O5/c1-5-6-7-8-9-11-18(24)28-17-14-16-15-27-20(25)23(16,26)22(4)13-10-12-21(2,3)19(17)22/h5-9,11,14,17,19,26H,10,12-13,15H2,1-4H3/b6-5+,8-7+,11-9+/t17-,19+,22+,23+/m1/s1
InChI Key DPTZOOXIEWHODB-XLDMSTKGSA-N
Melting Point 131-134°C
1. RES-1149-1 and -2, novel non-peptidic endothelin type B receptor antagonists produced by Aspergillus sp. II. Structure determination and derivatization
Y Uosaki, M Yoshida, T Ogawa, Y Saitoh J Antibiot (Tokyo). 1996 Jan;49(1):6-12. doi: 10.7164/antibiotics.49.6.
The structures of two novel non-peptidic endothelin type B receptor antagonists, RES-1149-1 and -2 were determined by spectroscopic methods. Several derivatives were synthesized from RES-1149-1 for biological assay.
2. Drimane sesquiterpenoids from the fungus Aspergillus ustus isolated from the marine sponge Suberites domuncula
Hongbing Liu, RuAngelie Edrada-Ebel, Rainer Ebel, Yao Wang, Barbara Schulz, Siegfried Draeger, Werner E G Müller, Victor Wray, Wenhan Lin, Peter Proksch J Nat Prod. 2009 Sep;72(9):1585-8. doi: 10.1021/np900220r.
Seven new drimane sesquiterpenoids (1-3, 6-9), along with the known compounds deoxyuvidin B (4), strobilactone B (5), and RES-1149-2 (10), were obtained from cultures of the fungus Aspergillus ustus, which was isolated from the marine sponge Suberites domuncula. Their structures were established by means of spectroscopic analyses including one- and two-dimensional NMR spectroscopy and high-resolution MS. Compounds 6, 7, and 10 showed cytotoxic activity against a panel of tumor cell lines, including L5178Y, HeLa, and PC12 cells, with 7 being the most active (EC(50) against L5178Y cell line: 0.6 microg/mL).
3. Synthesis and endothelin receptor binding activity of synthetic analogues of RES-1149-2
G A Kraus, X Wang Bioorg Med Chem Lett. 2000 May 1;10(9):895-7. doi: 10.1016/s0960-894x(00)00136-0.
A direct synthesis of analogues 6 and 7 is described. The key transformations are the addition of dibromomethyl lithium to a ketone and the subsequent mild hydrolysis to a hemiacetal.

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