1121-89-7 | Glutarimide

Packsize	Purity	Availability	Price	Discounted Price
5g	98%	in stock	$13.00	$9.00
10g	98%	in stock	$26.00	$18.00
25g	98%	in stock	$30.00	$21.00
100g	98%	in stock	$98.00	$68.00

Description

• Catalog Number: AB74468
• 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

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

Upstream Synthesis Route

Piperidine-2,6-dione, also known as 2,6-piperidinedione, is a versatile organic compound commonly used in chemical synthesis for various applications. This cyclic diketone features a piperidine ring with carbonyl groups at positions 2 and 6, giving it unique reactivity and properties that make it valuable in several synthetic processes.In chemical synthesis, Piperidine-2,6-dione serves as a key building block for the production of various heterocyclic compounds, pharmaceuticals, and agrochemicals. Its bifunctional nature allows it to participate in a range of reactions, including condensation, oxidation, reduction, and cyclization. One of its primary roles is as a precursor in the synthesis of polyheterocyclic compounds, which are crucial in drug discovery and material science.The reactivity of Piperidine-2,6-dione enables chemists to introduce functional groups and create complex molecular structures efficiently. It can undergo different types of transformations to form diverse scaffolds with tailored properties, making it an essential component in the toolkit of synthetic chemists working on the development of new molecules for various applications.

Literature

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

  Experimental cell research 20121210

• Enantiomerization mechanism of thalidomide and the role of water and hydroxide ions.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20121105

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

  Archiv der Pharmazie 20121101

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

  PLoS neglected tropical diseases 20120501

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

  Cancer chemotherapy and pharmacology 20120301

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

  Bioorganic & medicinal chemistry letters 20120101

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

  Pharmacognosy reviews 20120101

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

  Translational psychiatry 20111201

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

  The Journal of biological chemistry 20111104

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

  Bioorganic & medicinal chemistry 20111101

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

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

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

  Journal of natural products 20110624

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

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

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

  Chemical research in toxicology 20110321

• 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.

  BMC chemical biology 20110101

• Synthesis and antiviral activities of synthetic glutarimide derivatives.

  Chemical & pharmaceutical bulletin 20101101

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

  Bioresource technology 20101001

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

  Parasitology research 20101001

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

  Chembiochem : a European journal of chemical biology 20100924

• Synthesis of cyclic imides from simple diols.

  Angewandte Chemie (International ed. in English) 20100823

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

  Dalton transactions (Cambridge, England : 2003) 20100628

• Glutarimide alkaloids and a terpenoid benzoquinone from Cordia globifera.

  Journal of natural products 20100528

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

  Journal of experimental botany 20100301

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

  Organic letters 20100115

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

  BMC chemical biology 20100101

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

  Molecular systems biology 20100101

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

  PloS one 20100101

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

  Journal of neuroinflammation 20100101

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

  BMC cancer 20100101

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

  The Journal of antibiotics 20091101

• 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.

  The Journal of biological chemistry 20091023

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

  The Journal of organic chemistry 20090821

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

  Journal of medicinal chemistry 20090312

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

  Journal of the American Chemical Society 20090204

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

  Acta crystallographica. Section E, Structure reports online 20090201

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

  Bioorganic & medicinal chemistry letters 20081115

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

  Organic letters 20081016

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

  The journal of physical chemistry. A 20081009

• Ultrasensitive hot-electron nanobolometers for terahertz astrophysics.

  Nature nanotechnology 20080801

• Intercalation of cyclic imides in kaolinite.

  Journal of colloid and interface science 20080715

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

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

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

  Journal of computational chemistry 20080415

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

  Organic & biomolecular chemistry 20080321

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

  BMC genomics 20080101

• New lactimidomycin congeners shed insight into lactimidomycin biosynthesis in Streptomyces amphibiosporus.

  Organic letters 20071206

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

  Journal of medicinal chemistry 20071129

• 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.

  Bioorganic & medicinal chemistry 20071115

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

  Langmuir : the ACS journal of surfaces and colloids 20071023

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

  Journal of pharmaceutical and biomedical analysis 20071018

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

  Journal of separation science 20070501

• Cycloheximide resistance in the Lipomycetaceae revisited.

  Canadian journal of microbiology 20070401

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

  Molecular cancer 20070101

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

  Beilstein journal of organic chemistry 20070101

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

  Electrophoresis 20060801

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

  Organic letters 20060706

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

  Talanta 20060615

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

  Archives of pharmacal research 20060601

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

  Organic letters 20060330

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

  Inflammopharmacology 20060301

• Synthesis of naturally derived bioactive compounds of agricultural interest.

  Bioscience, biotechnology, and biochemistry 20060201

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

  BMC cell biology 20060101

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

  Journal of Asian natural products research 20060101

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

  Chirality 20051101

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

  Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20051101

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

  Journal of the American Chemical Society 20050831

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

  Journal of medicinal chemistry 20050210

• Three trifluoromethyl-substituted protoporphyrinogen IX oxidase inhibitors.

  Acta crystallographica. Section C, Crystal structure communications 20050201

• Three new glutarimide alkaloids from Croton cuneatus.

  Natural product research 20041001

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

  Journal of the American Chemical Society 20040915

• Structure-dependent nonenzymatic deamidation of glutaminyl and asparaginyl pentapeptides.

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

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

  The Journal of organic chemistry 20031114

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

  The Journal of organic chemistry 20030711

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

  Organic letters 20030529

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

  Pharmaceutical research 20020801

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

  Therapeutic drug monitoring 20020201

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

  Farmaco (Societa chimica italiana : 1989) 20011001

• Synthesis and immunological activity of water-soluble thalidomide prodrugs.

  Bioorganic & medicinal chemistry 20010501

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

  Biochemical pharmacology 19940817

• Synthesis and anticonvulsant activity of 2-benzylglutarimides.

  Journal of medicinal chemistry 19900301