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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
214-340-4
MDL number:
Assay:
98%
Form:
solid
InChI key
KNCYXPMJDCCGSJ-UHFFFAOYSA-N
InChI
1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
SMILES string
O=C1CCCC(=O)N1
assay
98%
form
solid
mp
155-157 °C (lit.)
Quality Level
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
Jianhua Ju et al.
Journal of the American Chemical Society, 127(34), 11930-11931 (2005-08-25)
Iso-Migrastatin (10) has been shown to be the main natural product of Streptomyces platensis, which undergoes a facile, H2O-mediated rearrangement into dorrigocin A (2), 13-epi-dorrigocin A (11), dorrigocin B (3), and migrastatin (1). Eight new congeners (12-19) of 10 were
Synthesis of cyclic imides from simple diols.
Jian Zhang et al.
Angewandte Chemie (International ed. in English), 49(36), 6391-6395 (2010-07-28)
Masatoshi Takeiri et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 60(9), 879-888 (2011-06-01)
We have previously synthesized a novel piperidine compound, 3-[(dodecylthiocarbonyl)methyl]glutarimide (DTCM-glutarimide), that inhibits LPS-induced NO production, and in the present research we studied further the anti-inflammatory activity of DTCM-glutarimide in a macrophage cell line and in mice bearing transplanted hearts. Mouse
Chuanjin Tian et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(45), 14305-14313 (2012-10-16)
The significance of the molecular chirality of drugs has been widely recognized due to the thalidomide tragedy. Most of the new drugs reaching the market today are single enantiomers, rather than racemic mixtures. However, many optically pure drugs, including thalidomide
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