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Louisianin C

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Louisianin C
Category Others
Catalog number BBF-02273
CAS 171784-05-7
Molecular Weight 173.21
Molecular Formula C11H11NO

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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Synonyms 4-allyl-6,7-dihydro-5H-cyclopenta[c]pyridin-5-one; 4-Allyl-6,7-dihydro-[2]pyrindin-5-one; 6,7-dihydro-4-(2-propenyl)-5H-cyclopenta[c]pyridin-5-one; Louisianine C
IUPAC Name 4-prop-2-enyl-6,7-dihydrocyclopenta[c]pyridin-5-one
Canonical SMILES C=CCC1=C2C(=CN=C1)CCC2=O
InChI InChI=1S/C11H11NO/c1-2-3-8-6-12-7-9-4-5-10(13)11(8)9/h2,6-7H,1,3-5H2
InChI Key LTBYIQKSNDZSNC-UHFFFAOYSA-N
Appearance Dark Brown Oily Matter
Solubility Soluble in Methanol
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. Synthesis of louisianin C
John M Beierle, Ekundayo B Osimboni, Costa Metallinos, Yajun Zhao, T Ross Kelly J Org Chem. 2003 Jun 13;68(12):4970-2. doi: 10.1021/jo0341618.
The synthesis of louisianin C (3), a member of a small family of 3,4,5-trisubstituted pyridyl natural products, is achieved in six steps and 11% overall yield starting from commercially available 3,5-dibromopyridine. The key step is a fluoride-induced desilylation-cyclization to afford carbinol 12.
3. 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.

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