Antiostatin A1

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Category Others
Catalog number BBF-00053
CAS
Molecular Weight 324.42
Molecular Formula C20H24N2O2

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Description

Antiostatin A1 is an antioxidant produced by Streptomyces cyaneus 2007-SV1.

Specification

IUPAC Name N-(3-hydroxy-2-methyl-1-pentyl-9H-carbazol-4-yl)acetamide
Canonical SMILES CCCCCC1=C(C(=C(C2=C1NC3=CC=CC=C32)NC(=O)C)O)C
InChI InChI=1S/C20H24N2O2/c1-4-5-6-9-14-12(2)20(24)19(21-13(3)23)17-15-10-7-8-11-16(15)22-18(14)17/h7-8,10-11,22,24H,4-6,9H2,1-3H3,(H,21,23)
InChI Key PWTGEYCIPJPJJO-UHFFFAOYSA-N

Properties

Melting Point 180-183°C(dec.)

Reference Reading

1. First total synthesis of the whole series of the antiostatins A and B
Kerstin E Knott, Stefan Auschill, Anne Jäger, Hans-Joachim Knölker Chem Commun (Camb). 2009 Mar 28;(12):1467-9. doi: 10.1039/b821039j. Epub 2009 Jan 20.
The first synthesis of the whole antiostatin family is described by using an iron-mediated carbazole synthesis, regioselective nitration at C-4 and establishing 5-isobutyl-1-nitrobiuret as a reagent for introduction of the antiostatin B side chain at C-4.
2. First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant
Carole Alayrac, Dieter Schollmeyer, Bernhard Witulski Chem Commun (Camb). 2009 Mar 28;(12):1464-6. doi: 10.1039/b820291e. Epub 2009 Feb 18.
The first total synthesis of the potent antioxidant antiostatin A1 is reported, where its key features rely on a chemo- and regioselective rhodium-catalysed crossed alkyne cyclotrimerisation reaction applying functionalised ynamides and a palladium-catalysed arylamidation reaction.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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