Hybocarpone
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-05093 |
| CAS | 245063-71-2 |
| Molecular Weight | 544.46 |
| Molecular Formula | C26H24O13 |
Online Inquiry
Description
Hybocarpone is a cytotoxic naphthomethine derivative derived from Lecanora Hybocarpa Mycobacterium licheniformis culture. It has anti-tumor activity.
Specification
| Synonyms | Dinaphtho[2,3-b:2',3'-d]furan-5,7,12,13-tetrone, 12a,12b-diethyl-5a,6a,12a,12b-tetrahydro-1,3,4,5a,6a,8,9,11-octahydroxy-2,10-dimethyl-, (5aR,6aR,12aR,12bR)-rel-(-)- (9CI); rel-(-)-(5aS,6aS,12aS,12bS)-12a,12b-Diethyl-5a,6a,12a,12b-tetrahydro-1,3,4,5a,6a,8,9,11-octahydroxy-2,10-dimethyldinaphtho[2,3-b:2',3'-d]furan-5,7,12,13-tetrone |
| IUPAC Name | (1S,2S,11S,13S)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-4(9),5,7,15(20),16,18-hexaene-3,10,14,21-tetrone |
| Canonical SMILES | CCC12C(=O)C3=C(C(=C(C(=C3O)C)O)O)C(=O)C1(OC4(C2(C(=O)C5=C(C4=O)C(=C(C(=C5O)C)O)O)CC)O)O |
| InChI | InChI=1S/C26H24O13/c1-5-23-19(33)9-11(17(31)15(29)7(3)13(9)27)21(35)25(23,37)39-26(38)22(36)12-10(20(34)24(23,26)6-2)14(28)8(4)16(30)18(12)32/h27-32,37-38H,5-6H2,1-4H3/t23-,24-,25-,26-/m1/s1 |
| InChI Key | MZNMSRGMWTWFRF-VEYUFSJPSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 942.6±65.0°C (Predicted) |
| Density | 1.811±0.06 g/cm3 (Predicted) |
Reference Reading
1. Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation
Wei Chen, Renyu Guo, Zhen Yang, Jianxian Gong J Org Chem. 2018 Dec 21;83(24):15524-15532. doi: 10.1021/acs.joc.8b02595. Epub 2018 Dec 12.
The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene. Key transformations include a visible-light-promoted benzannulation to construct the key α-naphthol intermediate and a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner. The total synthesis of boryquinone was also achieved in seven steps.
2. Inhibitory activities of lichen-derived compounds against methicillin- and multidrug-resistant Staphylococcus aureus
Tetsuo Kokubun, Winnie Ka Po Shiu, Simon Gibbons Planta Med. 2007 Feb;73(2):176-9. doi: 10.1055/s-2006-957070.
The inhibitory effects of selected phenolic lichen substances were tested against a panel of methicillin- and multidrug-resistant Staphylococcus aureus. Depsidones with long alkyl chains on both of the aromatic rings were consistently active against the strains tested, comparable to or better than the level of clinically used antibacterial drugs. A similar level of activity was also observed for rhizocarpic acid. The previously described cytotoxic pentacyclic compound hybocarpone was by far the most active, exhibiting minimum inhibitory concentrations (MICs) of 4-8 microg/mL (8.13-16.3 microM) against a range of multidrug efflux pump expressing strains of S. aureus.
3. Total synthesis of hybocarpone, a cytotoxic naphthazarin derivative from the lichen Lecanora hybocarpa, and related compounds
Sergey V Dragana, Michael A Pushilin, Valery P Glazunov, Vladimir A Denisenko, Victor Ph Anufriev Nat Prod Commun. 2014 Dec;9(12):1765-8.
The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3-b; 2,3-d]furantetraone structure. It was shown that the first step to tetrahydrofuran features is the bridging hindered S*,S* and R*,S* carbon-carbon bonds of the molecules, setting the relative configurations of the 5aS*,6aS*,12aS*,12bS* and 5aS*,6aR*,12aR*,12bS* diastereomers.
Recommended Products
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
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 ╳
