Louisianin B
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| Category | Others |
| Catalog number | BBF-02272 |
| CAS | |
| Molecular Weight | 191.23 |
| Molecular Formula | C11H13NO2 |
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Description
It is produced by the strain of Str. WK-4028. It has no inhibitory effect on testosterone 5α-reductase, and it has no anti-gram-positive bacteria, gram-negative bacteria, fungi and yeast effects.
Specification
| Synonyms | 6,7-dihydro-4-(2-propenyl)-5H-pyrindine-1,5-diol; 4-Allyl-6,7-dihydro-1,5-dihydroxy-5H-pyrindine |
| IUPAC Name | 4-allyl-6,7-dihydro-5H-cyclopenta[c]pyridine-1,5-diol |
| Canonical SMILES | C=CCC1=CNC(=O)C2=C1C(CC2)O |
| InChI | InChI=1S/C11H13NO2/c1-2-3-7-6-12-11(14)8-4-5-9(13)10(7)8/h2,6,9,13H,1,3-5H2,(H,12,14) |
| InChI Key | NZZUGPBVTIKHMG-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Flake Crystal |
| Melting Point | 168-170°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Louisianins A, B, C and D: non-steroidal growth inhibitors of testosterone-responsive SC 115 cells. I. Taxonomy, fermentation, isolation and biological characteristics
K Komiyama, S Takamatsu, Y P Kim, A Matsumoto, Y Takahashi, M Hayashi, H B Woodruff, S Omura J Antibiot (Tokyo). 1995 Oct;48(10):1086-9. doi: 10.7164/antibiotics.48.1086.
In the course of screening for non-steroidal growth inhibitors of testosterone-responsive Shionogi carcinoma 115 cells, louisianins A, B, C and D, were isolated from fermentation broth of Streptomyces sp. WK-4028. Louisianin A remarkably inhibited the growth of SC 115 cells in the presence of 10(-7) M testosterone at an IC50 value of 0.6 microgram/ml, whereas, no inhibition was observed on the other cell lines. Furthermore, inhibitory activity of testosterone 5 alpha-reductase and antimicrobial activity have not been observed at a concentration of 50 micrograms/ml and 1,000 micrograms/ml, respectively.
2. Louisianins A, B, C and D: non-steroidal growth inhibitors of testosterone-responsive SC 115 cells. II. Physico-chemical properties and structural elucidation
S Takamatsu, Y P Kim, M Hayashi, K Furuhata, H Takayanagi, K Komiyama, H B Woodruff, S Omura J Antibiot (Tokyo). 1995 Oct;48(10):1090-4. doi: 10.7164/antibiotics.48.1090.
New non-steroidal growth inhibitors of testosterone-responsive SC 115 cells, louisianins A (MW: 189; C11H11NO2), B (MW: 191; C11H13NO2), C (MW: 173; C11H11NO) and D (MW: 173; C11H11NO) were isolated from the cultured broth of Streptomyces sp. WK-4028. Their structures were determined on the basis of spectroscopic data. The structure of louisianin A in particular was confirmed by X-ray crystallographic analysis. The four compounds commonly possess a unique pyrindine skeleton in the molecule.
3. Synthesis of the louisianin alkaloid family via a 1,2,4-triazine inverse-electron-demand Diels-Alder approach
Nicola Catozzi, Michael G Edwards, Steven A Raw, Pierre Wasnaire, Richard J K Taylor J Org Chem. 2009 Nov 6;74(21):8343-54. doi: 10.1021/jo901761r.
Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from a conveniently prepared 1,2,4-triazine and via a common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and as the (-)-enantiomer.
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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 ╳
