RES-1149-2
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| Category | Bioactive by-products |
| Catalog number | BBF-03364 |
| CAS | |
| Molecular Weight | 386.5 |
| Molecular Formula | C23H30O5 |
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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.
Specification
| 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 |
Properties
| Melting Point | 131-134°C |
Reference Reading
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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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
