178098
Glutarimide
98%
Synonym(s):
2,6-Piperidinedione, NSC 58190
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About This Item
Empirical Formula (Hill Notation):
C5H7NO2
CAS Number:
Molecular Weight:
113.11
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
form
solid
mp
155-157 °C (lit.)
SMILES string
O=C1CCCC(=O)N1
InChI
1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
InChI key
KNCYXPMJDCCGSJ-UHFFFAOYSA-N
General description
A glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities.
Application
Reactant for:
Thionations
Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture
Synthesis of β-adrenoceptor ligands
Enantioselective synthesis of securinega alkaloids
Intramolecular amidocyclopropanation reactions
Synthesis of alpha-fluoro-alpha amino amides
Thionations
Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture
Synthesis of β-adrenoceptor ligands
Enantioselective synthesis of securinega alkaloids
Intramolecular amidocyclopropanation reactions
Synthesis of alpha-fluoro-alpha amino amides
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Jianhua Ju et al.
Journal of the American Chemical Society, 131(4), 1370-1371 (2009-01-10)
Migrastatin (1), iso-migrastatin (5) and lactimidomycin (7) are all glutarimide-containing polyketides known for their unique structures and cytotoxic activities against human cancer cell lines. Migrastatin, a strong inhibitor of tumor cell migration, has been an important lead in the development
Jianhua Ju et al.
Bioorganic & medicinal chemistry letters, 18(22), 5951-5954 (2008-08-08)
Lactimidomycin (LTM, 1), iso-migrastatin (iso-MGS, 2) and migrastatin (MGS, 3) are macrolide antitumor antibiotics differing in macrolide ring size but all bearing a glutarimide side chain. To further develop these natural products and related analogs as drug candidates we have
Jian Wei et al.
Nature nanotechnology, 3(8), 496-500 (2008-08-08)
The submillimetre or terahertz region of the electromagnetic spectrum contains approximately half of the total luminosity of the Universe and 98% of all the photons emitted since the Big Bang. This radiation is strongly absorbed in the Earth's atmosphere, so
Yuan-Ping Ruan et al.
Chirality, 17(9), 595-599 (2005-10-04)
An analytical HPLC method using CHIREX (S)-LEU/(S)-alpha-NEA column was developed for the determination of the enantiomeric excesses of N-protected (S)-3-hydroxyglutarimides. Using this method, detailed studies on the base-promoted ring-expansion reaction of the amidolactones, derived from l-glutamic acid, were undertaken.
Bo Wang et al.
Organic letters, 15(6), 1278-1281 (2013-02-27)
9-Methylstreptimidone is a glutarimide antibiotic showing antiviral, antifungal, and antitumor activities. Genome scanning, bioinformatics analysis, and gene inactivation experiments reveal a gene cluster responsible for the biosynthesis of 9-methylstreptimidone in Streptomyces himastatinicus. The unveiled machinery features both acyltransferase- and thioesterase-less
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