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1121-89-7,MFCD00006670
Catalog No.:AA003QP4

1121-89-7 | Glutarimide

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5g
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10g
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25g
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100g
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500g
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003QP4
Chemical Name:
Glutarimide
CAS Number:
1121-89-7
Molecular Formula:
C5H7NO2
Molecular Weight:
113.1146
MDL Number:
MFCD00006670
SMILES:
O=C1CCCC(=O)N1
NSC Number:
58190
Properties
Properties
 
BP:
288°C at 760 mmHg  
Form:
Solid  
MP:
155-157 °C(lit.);  
Refractive Index:
1.4200 (estimate)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
116  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
XLogP3:
-0.7  

Literature

Title: S632A3, a new glutarimide antibiotic, suppresses lipopolysaccharide-induced pro-inflammatory responses via inhibiting the activation of glycogen synthase kinase 3β.

Journal: Experimental cell research 20121210

Title: Enantiomerization mechanism of thalidomide and the role of water and hydroxide ions.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20121105

Title: Synthesis and evaluation of a series of piperidine-2,6-dione-piperazine (piperidine) derivatives as multireceptor atypical antipsychotics.

Journal: Archiv der Pharmazie 20121101

Title: In vitro and in vivo activity of a palladacycle complex on Leishmania (Leishmania) amazonensis.

Journal: PLoS neglected tropical diseases 20120501

Title: Pharmacokinetics, metabolism and excretion of [(14)C]-lenalidomide following oral administration in healthy male subjects.

Journal: Cancer chemotherapy and pharmacology 20120301

Title: Synthesis and biological evaluation of molecular probes based on the 9-methylstreptimidone derivative DTCM-glutarimide.

Journal: Bioorganic & medicinal chemistry letters 20120101

Title: Borreria and Spermacoce species (Rubiaceae): A review of their ethnomedicinal properties, chemical constituents, and biological activities.

Journal: Pharmacognosy reviews 20120101

Title: Positive autoregulation of GDNF levels in the ventral tegmental area mediates long-lasting inhibition of excessive alcohol consumption.

Journal: Translational psychiatry 20111201

Title: Asparagine peptide lyases: a seventh catalytic type of proteolytic enzymes.

Journal: The Journal of biological chemistry 20111104

Title: Evaluation of apoptotic effect of cyclic imide derivatives on murine B16F10 melanoma cells.

Journal: Bioorganic & medicinal chemistry 20111101

Title: Inhibition of macrophage activation and suppression of graft rejection by DTCM-glutarimide, a novel piperidine derived from the antibiotic 9-methylstreptimidone.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20110901

Title: Synthesis of N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide ((-)-julocrotine).

Journal: Journal of natural products 20110624

Title: Development of biomimetic catalytic oxidation methods and non-salt methods using transition metal-based acid and base ambiphilic catalysts.

Journal: Proceedings of the Japan Academy. Series B, Physical and biological sciences 20110511

Title: One-electron reduction of N-chlorinated and N-brominated species is a source of radicals and bromine atom formation.

Journal: Chemical research in toxicology 20110321

Title: Chemical modification of L-glutamine to alpha-amino glutarimide on autoclaving facilitates Agrobacterium infection of host and non-host plants: A new use of a known compound.

Journal: BMC chemical biology 20110101

Title: Synthesis and antiviral activities of synthetic glutarimide derivatives.

Journal: Chemical & pharmaceutical bulletin 20101101

Title: Fractionation and identification of organic nitrogen species from bio-oil produced by fast pyrolysis of sewage sludge.

Journal: Bioresource technology 20101001

Title: Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis.

Journal: Parasitology research 20101001

Title: Multifaceted modes of action for the glutarimide-containing polyketides revealed.

Journal: Chembiochem : a European journal of chemical biology 20100924

Title: Synthesis of cyclic imides from simple diols.

Journal: Angewandte Chemie (International ed. in English) 20100823

Title: Mono- and bidentate imidates of five-coordinate nickel(II) with macrocyclic ligands: spectroscopic and photophysical properties.

Journal: Dalton transactions (Cambridge, England : 2003) 20100628

Title: Glutarimide alkaloids and a terpenoid benzoquinone from Cordia globifera.

Journal: Journal of natural products 20100528

Title: Transpiration response of 'slow-wilting' and commercial soybean (Glycine max (L.) Merr.) genotypes to three aquaporin inhibitors.

Journal: Journal of experimental botany 20100301

Title: Stereoselective aldol reaction of glutarimides using pseudo C(2) symmetry.

Journal: Organic letters 20100115

Title: Chemical-genetic profile analysis of five inhibitory compounds in yeast.

Journal: BMC chemical biology 20100101

Title: Cell-type specific analysis of translating RNAs in developing flowers reveals new levels of control.

Journal: Molecular systems biology 20100101

Title: Sustained spindle-assembly checkpoint response requires de novo transcription and translation of cyclin B1.

Journal: PloS one 20100101

Title: Transforming growth factor-β1 induces matrix metalloproteinase-9 and cell migration in astrocytes: roles of ROS-dependent ERK- and JNK-NF-κB pathways.

Journal: Journal of neuroinflammation 20100101

Title: Induction of cell cycle arrest at G1 and S phases and cAMP-dependent differentiation in C6 glioma by low concentration of cycloheximide.

Journal: BMC cancer 20100101

Title: Synthesis, structures and anti-HBV activities of derivatives of the glutarimide antibiotic cycloheximide.

Journal: The Journal of antibiotics 20091101

Title: iso-Migrastatin, migrastatin, and dorrigocin production in Streptomyces platensis NRRL 18993 is governed by a single biosynthetic machinery featuring an acyltransferase-less type I polyketide synthase.

Journal: The Journal of biological chemistry 20091023

Title: Enantioselective approach to Securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine.

Journal: The Journal of organic chemistry 20090821

Title: Second-generation highly potent and selective inhibitors of the hepatitis C virus NS3 serine protease.

Journal: Journal of medicinal chemistry 20090312

Title: Lactimidomycin, iso-migrastatin and related glutarimide-containing 12-membered macrolides are extremely potent inhibitors of cell migration.

Journal: Journal of the American Chemical Society 20090204

Title: 3-(2,6-Dioxopiperidin-3-yl)-3-aza-bicyclo-[3.2.0]heptane-2,4-dione.

Journal: Acta crystallographica. Section E, Structure reports online 20090201

Title: Evaluation of new migrastatin and dorrigocin congeners unveils cell migration inhibitors with dramatically improved potency.

Journal: Bioorganic & medicinal chemistry letters 20081115

Title: A new series of dendrimers containing two ferrocenyl units and a Fréchet dendron around a triazine nucleus.

Journal: Organic letters 20081016

Title: Calorimetric and computational thermochemical study of 3,3-tetramethyleneglutaric acid, 3,3-tetramethyleneglutaric anhydride, and 3,3-tetramethyleneglutarimide.

Journal: The journal of physical chemistry. A 20081009

Title: Ultrasensitive hot-electron nanobolometers for terahertz astrophysics.

Journal: Nature nanotechnology 20080801

Title: Intercalation of cyclic imides in kaolinite.

Journal: Journal of colloid and interface science 20080715

Title: Solid-phase synthesis of tailed cyclic RGD peptides using glutamic acid: unexpected glutarimide formation.

Journal: Journal of peptide science : an official publication of the European Peptide Society 20080601

Title: Theoretical elucidation of the rhodium-catalyzed [4 + 2] annulation reactions.

Journal: Journal of computational chemistry 20080415

Title: Simple and facile synthesis of tetralone-spiro-glutarimides and spiro-bisglutarimides from Baylis-Hillman acetates.

Journal: Organic & biomolecular chemistry 20080321

Title: Chemical-genetic profile analysis in yeast suggests that a previously uncharacterized open reading frame, YBR261C, affects protein synthesis.

Journal: BMC genomics 20080101

Title: New lactimidomycin congeners shed insight into lactimidomycin biosynthesis in Streptomyces amphibiosporus.

Journal: Organic letters 20071206

Title: Cyclization of the acyl glucuronide metabolite of a neutral endopeptidase inhibitor to an electrophilic glutarimide: synthesis, reactivity, and mechanistic analysis.

Journal: Journal of medicinal chemistry 20071129

Title: The influence of modifications in imide fragment structure on 5-HT(1A) and 5-HT(7) receptor affinity and in vivo pharmacological properties of some new 1-(m-trifluoromethylphenyl)piperazines.

Journal: Bioorganic & medicinal chemistry 20071115

Title: Solubilization of single-walled carbon nanotubes by supramolecular complexes of barbituric acid and triaminopyrimidines.

Journal: Langmuir : the ACS journal of surfaces and colloids 20071023

Title: Investigation of N-hydroxythalidomide in vitro stability and comparison to other N-substituted derivatives.

Journal: Journal of pharmaceutical and biomedical analysis 20071018

Title: Exploring solvent versatility in immobilized cellulose-based chiral stationary phase for the enantioselective liquid chromatographic resolution of racemates.

Journal: Journal of separation science 20070501

Title: Cycloheximide resistance in the Lipomycetaceae revisited.

Journal: Canadian journal of microbiology 20070401

Title: The regulation of cyclin D1 degradation: roles in cancer development and the potential for therapeutic invention.

Journal: Molecular cancer 20070101

Title: A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids.

Journal: Beilstein journal of organic chemistry 20070101

Title: The unified equation for the evaluation of degenerated first-order reactions in dynamic electrophoresis.

Journal: Electrophoresis 20060801

Title: Efficient synthesis of fused bicyclic glutarimides. Its application to (+/-)-alloyohimbane and louisianin D.

Journal: Organic letters 20060706

Title: Chiral separations of piperidine-2,6-dione analogues on Chiralpak IA and Chiralpak IB columns by using HPLC.

Journal: Talanta 20060615

Title: Synthesis and anticonvulsant activities of N-Cbz-alpha-aminoglutarimidooxy carboxylate derivatives.

Journal: Archives of pharmacal research 20060601

Title: A versatile approach for the asymmetric syntheses of (1R,9aR)-epiquinamide and (1R,9aR)-homopumiliotoxin 223G.

Journal: Organic letters 20060330

Title: Synthesis and evaluation of 2,6-piperidinedione derivatives as potentially novel compounds with analgesic and other CNS activities.

Journal: Inflammopharmacology 20060301

Title: Synthesis of naturally derived bioactive compounds of agricultural interest.

Journal: Bioscience, biotechnology, and biochemistry 20060201

Title: Thalidomide attenuates nitric oxide mediated angiogenesis by blocking migration of endothelial cells.

Journal: BMC cell biology 20060101

Title: Isolation, structure determination and biological activity of a new glutarimide antibiotic, S632A3.

Journal: Journal of Asian natural products research 20060101

Title: Detailed studies on the enantioselective synthesis and HPLC enantioseparation of N-protected 3-hydroxyglutarimides.

Journal: Chirality 20051101

Title: EPR, UV-vis, magnetic, spectral studies and electrochemical behaviour of mononuclear transition metal complexes derived from novel hexa-aza-macrotricyclic ligand.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20051101

Title: Iso-migrastatin congeners from Streptomyces platensis and generation of a glutarimide polyketide library featuring the dorrigocin, lactimidomycin, migrastatin, and NK30424 scaffolds.

Journal: Journal of the American Chemical Society 20050831

Title: Identification of 3-(acylamino)azepan-2-ones as stable broad-spectrum chemokine inhibitors resistant to metabolism in vivo.

Journal: Journal of medicinal chemistry 20050210

Title: Three trifluoromethyl-substituted protoporphyrinogen IX oxidase inhibitors.

Journal: Acta crystallographica. Section C, Crystal structure communications 20050201

Title: Three new glutarimide alkaloids from Croton cuneatus.

Journal: Natural product research 20041001

Title: The migrastatin family: discovery of potent cell migration inhibitors by chemical synthesis.

Journal: Journal of the American Chemical Society 20040915

Title: Structure-dependent nonenzymatic deamidation of glutaminyl and asparaginyl pentapeptides.

Journal: The journal of peptide research : official journal of the American Peptide Society 20040501

Title: Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

Journal: The Journal of organic chemistry 20031114

Title: An efficient approach to 3,4-disubstituted pyridin-2-ones. Formal synthesis of mappicine ketone.

Journal: The Journal of organic chemistry 20030711

Title: Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon.

Journal: Organic letters 20030529

Title: Chemical stabilities and biological activities of thalidomide and its N-alkyl analogs.

Journal: Pharmaceutical research 20020801

Title: 5'-OH-thalidomide, a metabolite of thalidomide, inhibits angiogenesis.

Journal: Therapeutic drug monitoring 20020201

Title: Synthesis, spectroscopic characterization, stability assessment and DNA-binding of new 2,6-piperidinedione derivatives.

Journal: Farmaco (Societa chimica italiana : 1989) 20011001

Title: Synthesis and immunological activity of water-soluble thalidomide prodrugs.

Journal: Bioorganic & medicinal chemistry 20010501

Title: Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.

Journal: Biochemical pharmacology 19940817

Title: Synthesis and anticonvulsant activity of 2-benzylglutarimides.

Journal: Journal of medicinal chemistry 19900301

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