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WF-3681

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WF-3681
Category Enzyme inhibitors
Catalog number BBF-01624
CAS 105364-56-5
Molecular Weight 248.23
Molecular Formula C13H12O5

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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

WF-3681 is an aldose reductase inhibitor produced by Chaetomella raphigera Swift No. 3681.

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Synonyms WF 3681
IUPAC Name 3-(4-hydroxy-5-oxo-3-phenyl-2H-furan-2-yl)propanoic acid
Canonical SMILES C1=CC=C(C=C1)C2=C(C(=O)OC2CCC(=O)O)O
InChI InChI=1S/C13H12O5/c14-10(15)7-6-9-11(12(16)13(17)18-9)8-4-2-1-3-5-8/h1-5,9,16H,6-7H2,(H,14,15)
InChI Key PPZVSYXNLXFYAD-UHFFFAOYSA-N
Appearance Crystal
Melting Point 177-179°C
1. Structure of WF-3681, 3-(2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-2-furyl)propionic acid
J I Clark, C R Kissinger, S Turley Acta Crystallogr C . 1988 Mar 15;44 ( Pt 3):512-4. doi: 10.1107/s010827018700845x.
C13H12O5, Mr = 248.24, monoclinic, C2/c, a = 18.757 (8), b = 7.282 (2), c = 17.511 (8) A, beta = 91.20 (3) degrees, V = 2391 (3) A3, Z = 8, Dx = 1.379 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu = 0.859 mm-1, F(000) = 1040, T = 293 K. Final R = 0.054 for 1409 unique observed reflections. The molecule contains two planar regions which differ in orientation by 5.7 degrees. Distances from the carbonyl carbons to the center of the phenyl ring are not in the range found in the crystal structures of other potent aldose reductase inhibitor molecules.
2. Studies on WF-3681, a novel aldose reductase inhibitor. I. Taxonomy, fermentation, isolation and characterization
M Nishikawa, M Okuhara, T Namiki, K Yoshida, Y Tsurumi J Antibiot (Tokyo) . 1987 Oct;40(10):1394-9. doi: 10.7164/antibiotics.40.1394.
WF-3681 was isolated from a cultured filtrate of Chaetomella raphigera as a novel inhibitor of aldose reductase. It was extracted with ethyl acetate and then purified with silica gel chromatography. Its molecular formula was determined to be C13H12O5 by elemental analysis and high resolution electron impact mass spectrometry. IC50 of WF-3681 was 2.5 X 10(-7) M for partially purified aldose reductase of rabbit lens.
3. Studies on WF-3681, a novel aldose reductase inhibitor. II. Structure determination and synthesis
M Hashimoto, I Uchida, T Namiki, M Nishikawa, Y Itoh J Antibiot (Tokyo) . 1987 Oct;40(10):1400-7. doi: 10.7164/antibiotics.40.1400.
The structure of WF-3681, a novel aldose reductase inhibitor produced by Chaetomella raphigera Swift No. 3681, was deduced to be 1 on the basis of its spectroscopic and chemical evidences and confirmed by a total synthesis starting from (E)-5-phenyl-4-pentenol.

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