Louisianin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02271 |
| CAS | 171784-03-5 |
| Molecular Weight | 189.21 |
| Molecular Formula | C11H11NO2 |
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Description
It is produced by the strain of Str. WK-4028. In the presence of 10-7 mol/L testosterone, it can significantly inhibit the growth of SC115 cells (IC50 is 0.6 μg/mL). 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 | Louisianine A; 4-allyl-6,7-dihydro-1H-cyclopenta[c]pyridine-1,5(2H)-dione |
| IUPAC Name | 4-prop-2-enyl-6,7-dihydro-2H-cyclopenta[c]pyridine-1,5-dione |
| Canonical SMILES | C=CCC1=CNC(=O)C2=C1C(=O)CC2 |
| InChI | InChI=1S/C11H11NO2/c1-2-3-7-6-12-11(14)8-4-5-9(13)10(7)8/h2,6H,1,3-5H2,(H,12,14) |
| InChI Key | WHKQLFRGMDYOMK-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Melting Point | 189-191°C |
| Solubility | Soluble in Methanol, Acetonitrile |
Reference Reading
1. 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.
2. Synthesis of 2-pyridones by cycloreversion of [2.2.2]- bicycloalkene diketopiperazines
Kaila A Margrey, Amy D Hazzard, Jonathan R Scheerer Org Lett. 2014 Feb 7;16(3):904-7. doi: 10.1021/ol403632t. Epub 2014 Jan 29.
A general strategy for the conversion of [2.2.2]-diazabicyclic alkene structures to 2-pyridone aromatic heterocyclic products is reported. The reaction sequence starts from 2,5-diketopiperazine (DKP) derivatives, is compatible with both aromatic and aliphatic aldehyde components, and can intercept either intra- or intermolecular cycloaddition manifolds. Priming of one aza-bridging function in the intermediate [2.2.2]-DKP scaffold permits cycloreversion (microwave heating) and selective extrusion of cyanate derivatives leading to the formation of 2-pyridone structures. Progress toward the synthesis of louisianin A and B, antiproliferative 2-pyridone natural products, is also disclosed.
3. First total synthesis of louisianin A
Ching-Yao Chang, Hui-Ming Liu, Tahsin J Chow J Org Chem. 2006 Aug 4;71(16):6302-4. doi: 10.1021/jo060935j.
The first total synthesis of louisianin A, 4-allyl-6,7-dihydro-1-hydroxycyclopenta[c]pyridin-5-one, is achieved from 2-chloro-4-cyanopyridine 5 via seven steps in an overall 24% yield. The key step is a cyclization-decarboxylation sequence toward the formation of a cyclopentenone ring.
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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 ╳
