BE-23372M
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03231 |
| CAS | 145588-13-2 |
| Molecular Weight | 312.27 |
| Molecular Formula | C17H12O6 |
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Description
BE-23372M is a protein tyrosine kinase inhibitor produced by Rhizoctonia solani. It has strong inhibition of epidermal growth factor (EGF) receptor kinase activity.
Specification
| Synonyms | (3E)-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)furan-2(3H)-one |
| IUPAC Name | (3E)-5-(3,4-dihydroxyphenyl)-3-[(3,4-dihydroxyphenyl)methylidene]furan-2-one |
| Canonical SMILES | C1=CC(=C(C=C1C=C2C=C(OC2=O)C3=CC(=C(C=C3)O)O)O)O |
| InChI | InChI=1S/C17H12O6/c18-12-3-1-9(6-14(12)20)5-11-8-16(23-17(11)22)10-2-4-13(19)15(21)7-10/h1-8,18-21H/b11-5+ |
| InChI Key | TZBZGNPXKXHFKI-VZUCSPMQSA-N |
Properties
| Boiling Point | 699.2°C at 760 mmHg |
| Density | 1.616 g/cm3 |
| Solubility | Soluble in DMSO, Methanol, acetone |
Reference Reading
1. Stereoselective synthesis of E-3-(arylmethylidene)-5-(alkyl/aryl)-2(3H)-furanones by sequential hydroacyloxylation-Mizoroki-Heck reactions of iodoalkynes
Gopinathan Muthusamy, Sunil V Pansare Org Biomol Chem. 2018 Oct 31;16(42):7971-7983. doi: 10.1039/c8ob02063a.
A modular, stereoselective synthesis of E-3-(arylidene)-5-(alkyl/aryl)-2(3H)-furanones was developed. The methodology features regioselective addition of β-aryl acrylic acids to iodoacetylenes to furnish the Z-acyloxy iodoalkenes. A stereoselective 5-exo-trig Mizoroki-Heck reaction of the acyloxy iodoalkenes generates the target E-2(3H)-furanones. The approach was applied in a formal synthesis of the naturally occurring kinase inhibitor BE-23372M.
2. BE-23372M, a novel protein tyrosine kinase inhibitor. III. Synthesis
S Tanaka, T Okabe, S Nakajima, E Yoshida, H Morishima J Antibiot (Tokyo). 1994 Mar;47(3):297-300. doi: 10.7164/antibiotics.47.297.
In a preceding paper, the physico-chemical properties and structural elucidation of BE-23372M, a potent novel protein tyrosine kinase inhibitor, were described. In this paper, we report the synthesis of BE-23372M from 3-(3,4-dimethoxybenzoyl)propionic acid and veratraldehyde or 3,4-diacetoxy-benzaldehyde. The structure of BE-23372M was confirmed to be (E)-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)-2(3H)-fur anone.
3. BE-23372M, a novel and specific inhibitor for epidermal growth factor receptor kinase
S Tanaka, T Okabe, S Chieda, K Endo, T Kanoh, A Okura, E Yoshida Jpn J Cancer Res. 1994 Mar;85(3):253-9. doi: 10.1111/j.1349-7006.1994.tb02090.x.
The fungal metabolite BE-23372M is a structurally novel protein kinase inhibitor. Its IC50 for epidermal growth factor (EGF) receptor kinase was 0.03 microM. IC50 values of BE-23372M for other protein tyrosine kinases, erbB-2, p43v-abl, insulin receptor kinase, and p60c-src were 0.42, 1.0, 3.3, and 4.5 microM, respectively, and the IC50 for protein kinase C, a serine/threonine kinase, was 4.1 microM. Cdc2 kinase, casein kinases I and II and cAMP-dependent protein kinase were not inhibited by 20 microM BE-23372M. A kinetic study showed that BE-23372M was competitive with respect to the substrate peptide and to ATP. Autophosphorylation of solubilized EGF receptor kinase was clearly inhibited by 0.1 microM BE-23372M. Autophosphorylation of EGF receptor in A431 cells was also inhibited. These results show that BE-23372M is a potent and specific EGF receptor kinase inhibitor. It should be a valuable tool for EGF receptor kinase research.
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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 ╳
