Basidalin
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| Category | Antibiotics |
| Catalog number | BBF-00269 |
| CAS | |
| Molecular Weight | 139.11 |
| Molecular Formula | C6H5NO3 |
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Description
Basidalin is produced by the strain of Leucoagaricus naucina NZ157. It has the ability of anti-gram-positive bacteria, negative bacteria and inhibition of mouse leukemia L-1210 cell.
Specification
| Synonyms | (Z)-4-Amino-5-(formylmethylene)-2(5H)-furanone; (Z)-(3-Amino-5-oxo-2(5H)-furanylidene)acetaldehyde; Acetaldehyde, (3-amino-5-oxo-2(5H)-furanylidene)- |
| IUPAC Name | (2E)-2-(3-amino-5-oxofuran-2-ylidene)acetaldehyde |
| Canonical SMILES | C1=C(C(=CC=O)OC1=O)N |
| InChI | InChI=1S/C6H5NO3/c7-4-3-6(9)10-5(4)1-2-8/h1-3H,7H2/b5-1+ |
| InChI Key | FFJHVCSTCUPZJW-ORCRQEGFSA-N |
Properties
| Antibiotic Activity Spectrum | gram-positive bacteria; gram-negative bacteria; neoplastics (Tumor) |
| Melting Point | 142-149 °C |
Reference Reading
1. Synthesis and medicinal chemistry of tetronamides: Promising agrochemicals and antitumoral compounds
Júnio G Silva, Amanda S de Miranda, Fyaz M D Ismail, Luiz C A Barbosa Bioorg Med Chem. 2022 Aug 1;67:116815. doi: 10.1016/j.bmc.2022.116815. Epub 2022 May 13.
Butenolides and tetronic acids occupy a prominent position in synthetic chemistry due to their ubiquitous distribution in nature. This has stimulated investigations firstly in the synthesis of such systems and, laterly, the interest has turned to the understanding of the quantum structure of such systems, allowing a deeper understanding of the mechanism and reactivity of this cyclic scaffold. In contrast, tetronamides, which consist of compounds bearing a 4-aminofuran-2(5H)-one backbone, are relatively rare in nature and synthetic routes to such compounds are poorly explored. This review highlights both the importance of the tetronamide scaffold in medicinal chemistry and the most relevant recondite synthetic strategies for obtaining compounds of this class.
2. 7-Chloro-4,6-dimethoxy-1(3H)-isobenzofuranone and basidalin: antibiotic secondary metabolites from Leucoagaricus carneifolia Gillet (basidiomycetes) [corrected]
T Huff, H G Kuball, T Anke Z Naturforsch C J Biosci. 1994 Jul-Aug;49(7-8):407-10. doi: 10.1515/znc-1994-7-803.
Two antibiotic metabolites were isolated from cultures of Leucoagaricus carneifolia. Their structures were elucidated by spectroscopic methods. The first compound, 7-chloro-4,6-dimethoxy-1(3H)-isobenzofuranone [corrected] (1) had to our knowledge not been described from natural sources whereas the second, basidalin (2), is a known metabolite of L. naucina (H. Iinuma et al., 1983). 1 exhibits antibiotic activities with minimal inhibitory concentrations of 20 micrograms/ml against Botrytis cinerea, the most sensitive microorganism.
3. Total Synthesis of the Antitumor Antibiotic Basidalin
Jaime A M Acosta, Ramesh Muddala, Luiz C A Barbosa, John Boukouvalas J Org Chem. 2016 Aug 5;81(15):6883-6. doi: 10.1021/acs.joc.6b01255. Epub 2016 Jul 7.
The first synthesis of the tetronamide antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-γ-ylidene-β-bromobutenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal.
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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 ╳
