WS75624 B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01657 |
| CAS | |
| Molecular Weight | 380.5 |
| Molecular Formula | C18H24N2O5S |
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Description
WS75624 B is an endothelin converting enzyme (ECE) inhibitor isolated from the fermentation broth of Saccharothrix sp. No. 75624. It also showed other metalloprotease (collagenase and neutral endopeptidase) inhibitory activity with IC50 value of 1 mM/ml.
Specification
| Synonyms | WS-75624 B; WS 75624 B; WS-75624B |
| IUPAC Name | 6-[2-(6-hydroxyheptyl)-1,3-thiazol-4-yl]-4,5-dimethoxypyridine-2-carboxylic acid |
| Canonical SMILES | CC(CCCCCC1=NC(=CS1)C2=C(C(=CC(=N2)C(=O)O)OC)OC)O |
| InChI | InChI=1S/C18H24N2O5S/c1-11(21)7-5-4-6-8-15-19-13(10-26-15)16-17(25-3)14(24-2)9-12(20-16)18(22)23/h9-11,21H,4-8H2,1-3H3,(H,22,23) |
| InChI Key | RGHLFUKUTGFTCO-UHFFFAOYSA-N |
Properties
| Appearance | Solid Powder |
| Melting Point | 139-140°C |
Reference Reading
1. WS75624 A and B, new endothelin converting enzyme inhibitors isolated from Saccharothrix sp. No. 75624. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
Y Tsurumi, H Ueda, K Hayashi, S Takase, M Nishikawa, S Kiyoto, M Okuhara J Antibiot (Tokyo). 1995 Oct;48(10):1066-72. doi: 10.7164/antibiotics.48.1066.
Novel endothelin converting enzyme (ECE) inhibitors, WS75624 A and B, have been isolated from the fermentation broth of Saccharothrix sp. No. 75624. These inhibitors were purified from an acetone extract of whole culture broth followed by HP-20 column chromatography, silica gel column chromatography and HPLC. WS75624 A and B showed highly potent ECE inhibitory activity, and both had IC50 values of 0.03 microgram/ml. WS75624 A and B also showed other metalloprotease (collagenase and neutral endopeptidase) inhibitory activity with IC50 values of 1 microgram/ml. Since large amount of WS75624 B was isolated, we tried in vivo evaluation using WS75624 B. WS75624 B inhibited big endothelin-induced pressor effect when administered to SD rat intravenously with big ET-1.
2. Use of thiazoles in the halogen dance reaction: application to the total synthesis of WS75624 B
Eric L Stangeland, Tarek Sammakia J Org Chem. 2004 Apr 2;69(7):2381-5. doi: 10.1021/jo0351217.
The total synthesis of the pyridine-thiazole-containing natural product WS75624 B (1) is described. This synthesis proceeds via the Stille coupling of appropriately functionalized pyridine and thiazole components, and this paper details our studies on the use of the halogen dance reaction to prepare the desired thiazole. Various halogen dance reactions on thizoles are described, including a novel one-pot multistep reaction in which 2-bromothiazole is treated with LDA in the presence of a silyl chloride at -78 degrees C and quenched with an electrophile to provide the highly functionalized thiazole derivatives 27.
3. WS75624 A and B, new endothelin converting enzyme inhibitors isolated from Saccharothrix sp. No. 75624. II. Structure elucidation of WS75624 A and B
S Yoshimura, Y Tsurumi, S Takase, M Okuhara J Antibiot (Tokyo). 1995 Oct;48(10):1073-5. doi: 10.7164/antibiotics.48.1073.
The structures of WS75624 A and B, novel endothelin converting enzyme inhibitors, were determined to be 1 and 2A, respectively, by a combination of chemical evidence and a series of 2D NMR spectral analyses.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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