54398-84-4

Usage

Uses

Used in Pharmaceutical Industry:
3-amino-5-methylcyclohex-2-en-1-one is used as a starting material for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of diverse chemical entities with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-amino-5-methylcyclohex-2-en-1-one is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and structural features enable the production of effective compounds for agricultural applications.
Used in Fine Chemicals Synthesis:
3-amino-5-methylcyclohex-2-en-1-one is employed as a building block in the preparation of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, flavors, and specialty chemicals. Its versatility in organic synthesis facilitates the creation of high-value products.
Used in Material Science:
3-amino-5-methylcyclohex-2-en-1-one has potential applications in material science, where it may be used in the development of new materials with unique properties. Its structural attributes could contribute to the design of innovative materials for various applications.
Used as a Reagent in Chemical Reactions:
In the field of chemistry, 3-amino-5-methylcyclohex-2-en-1-one serves as a reagent in various chemical reactions, facilitating the synthesis of complex molecules and compounds. Its reactivity and functional groups make it a valuable component in chemical processes.
Used in Medicinal Chemistry Research:
3-amino-5-methylcyclohex-2-en-1-one is a subject of research in medicinal chemistry, where it is explored for its potential use in the synthesis of complex molecules with therapeutic applications. Its unique structure and reactivity make it a promising candidate for the development of novel pharmaceutical agents.

InChI:InChI=1/C7H11NO/c1-5-2-6(8)4-7(9)3-5/h4-5H,2-3,8H2,1H3

Upstream product

• 4341-24-6 5-methylcyclohexan-1,3-dione 
• 70150-66-2 5-methyl-3-hydroxycyclohex-2-enone 

Downstream Products

• 82419-81-6 diethyl N-(3-keto-5-methyl-1-cyclohexen-1-yl)aminomethylenemalonate 
• 698981-92-9 2,7-dimethyl-5,6,7,8-tetrahydroquinoline-5-one 
• 1377150-72-5 5-methyl-N-(5-methyl-3-oxocyclohex-1enyl)isoxazole-3-carboxamide 

Relevant academic research and scientific papers

6 Hz active anticonvulsant fluorinated n-benzamide enaminones and their inhibitory neuronal activity

A small library of novel fluorinated N-benzamide enaminones were synthesized and evaluated in a battery of acute preclinical seizure models. Three compounds (GSA 62, TTA 35, and WWB 67) were found to have good anticonvulsant activity in the 6-Hz ‘psychomotor’ 44-mA rodent model. The focus of this study was to elucidate the active analogs’ mode of action on seizure-related molecular targets. Electrophysiology studies were employed to evaluate the compounds’ ability to inhibit neuronal activity in central olfactory neurons, mitral cells, and sensory-like ND7/23 cells, which express an assortment of voltage and ligand-gated ion channels. We did not find any significant effects of the three compounds on action potential generation in mitral cells. The treatment of ND7/23 cells with 50 μM of GSA 62, TTA 35, and WWB 67 generated a significant reduction in the amplitude of whole-cell sodium currents. Similar treatment of ND7/23 cells with these compounds had no effect on T-type calcium currents, indicating that fluorinated N-benzamide enaminone analogs may have a selective effect on voltage-gated sodium channels, but not calcium channels.

Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions

A highly efficient protocol for copper-catalyzed thio-alkynylation of enaminone-based thiocyanates with terminal alkynes under mild conditions has been developed. This scalable amino group-directed thio-alkynylation proceeds in the open air with a broad substrate scope and an excellent yield. The demonstrated synthetic transformation creates the opportunity for a wide variety of sulfur-containing useful materials. Gram-scale synthesis and further synthetic transformations of alkynyl sulfides highlight the potential utility of the method.

N-phenyl and N-benzyl enaminones and methods for using same

The present disclosure provides compounds, compositions, and methods for use of the compounds. The compounds are N-phenyl or N-benzyl enaminones. The compositions can be pharmaceutical compositions. For example, the compounds/compositions are used in treating seizure disorders. The methods entail administering a composition comprising one or more of the compounds to a subject in need thereof. Articles of manufacture comprising one or more of the compounds/compositions are also provided.

Discovery and optimization of novel benzothiophene-3-carboxamides as highly potent inhibitors of Aurora kinases A and B

Aurora kinases as regulators of cell division have become promising therapeutic targets recently. Here we report novel, low molecular weight benzothiophene-3-carboxamide derivatives designed and optimized for inhibiting Aurora kinases. The most effective compound 36 inhibits Aurora kinases in vitro in the nanomolar range and diminishes HCT 116 cell viability blocking cytokinesis and inducing apoptosis. According to western blot analysis, the lead molecule inhibits Aurora kinases equipotently to VX-680 (Tozasertib) and similarly synergizes with other targeted drugs.

BENZO[B]THIOPHENE DERIVATIVES AND THEIR USE FOR THE INHIBITION OF FIBROBLAST GROWTH FACTOR RECEPTOR KINASES (FGFRS) FOR THE USE OF NEO- AND HYPERPLASIA THERAPIES

The present invention relates to benzo[b]thiophene derivatives of general formula (I) and pharmaceutically acceptable salts, solvates, hydrates, stereoisomeric and polymorphic forms thereof wherein R1 is selected from the group of hydrogen; hydroxyl; substituted or unsubstituted heterocyclyl; optionally substituted amino; X, Y and Z are selected independently from the followings: CH (methine), nitrogen; R2, R3, R4 and R5 may stand for e.g. hydrogen, halogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxy and amino. The invention also relates to the use of them as of medication, as well as pharmaceutical compositions containing at least one of them as pharmaceutically active agent(s) together with pharmaceutically acceptable carrier, excipient and/or diluent, especially for the inhibition Fibroblast Growth Factor Receptor kinases (FGFR's), e.g. for the treatment of cancer.

Cyclization of cyanoethylated ketones as a route to 6-substituted indole derivatives

δ-Cyanoketones are quickly cyclized with KOtBu to 3-aminocyclohex-2-enone derivatives, which in turn will give substituted indoles when treated with oxalyl chloride. Thus, 3-amino-6,6-dimethylcyclohex-2-enone gave 3-chloro-6,6-dimethyl-2,5,6,7-tetrahydroindole-2,5-dione, whose structure was corroborated by X-ray crystallography, whereas the corresponding molecule without the blocking gem-dimethyl groups, 3-aminocyclohex-2-enone, gave via hydrogen shifts 6-chloro-3-hydroxyoxindole.

Synthetic access to poly-substituted 11H-pyrido[3,2-a]carbazoles, A dna-intercalating ellipticine related structure, and their antiproliferative activity

The facile procedure for the synthesis of the 11H-pyrido[3,2-a]carbazole structure involving the Fischer indole cyclization on tetrahydroquinolinones, available from enaminones and methyl 2-formyl-3-oxopropanoate, followed by the aromatization of the resulting 5,6-dihydro derivatives is described. This method allows for the introduction of substituents at C2, C6, and C8 to the scaffold by choice of the starting materials. In the biological testing, introduction of the phenyl group at C6 is significantly effective to improve the antiproliferative activity.

Enaminones 12. An explanation of anticonvulsant activity and toxicity per Linus Pauling's clathrate hypothesis

The x-ray crystal structure of 3-((5-methylisoxazol-3-yl)amino)-5- methylcyclohex-2-enone (12b) and 3-((5-methylisoxazolyl-3-yl)amino)-5,5- dimethylcyclohex-2-enone (12c) were determined and correlated to their anticonvulsant activity in mice and rats. A hypothesis for the toxicity of the analogs are advanced. In addition, a series of 5-methyl-N-(3-oxocyclohex-1-enyl) -isoxazole-3-carboxamides were synthesized and evaluated for anticonvulsant activity. These compounds were compared to the activity of the corresponding amino and aminomethyl enaminones. Additional investigation involved the synthesis and evaluation of a trifluoromethyl analog of the active isoxazole tert-butyl 4-(5-methisoxazol-3-yl-amino)-6-methyl-2-oxo-cyclohex-3-ene carboxylate (4f).

Substituted tetralins, chromans and related compounds in the treatment of asthma

PCT No. PCT/US87/02734 Sec. 371 Date Apr. 11, 1990 Sec. 102(e) Date Apr. 11, 1990 PCT Filed Oct. 19, 1987Substituted tetralins, chromans and related compounds which, by inhibiting 5-lipoxygenase enzyme and/or blocking leukotriene receptors, are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals; pharmaceutical compositions comprising said compounds; a method of treatment with said compounds; and intermediates useful in the synthesis of said compounds.

Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants

A comparison of enaminones from various unsubstituted and p-substituted benzamides to the analogous benzylamines has been undertaken with the aim of elucidating the essential structural parameters necessary for anticonvulsant activity. Initial studies on methyl 4-N-(benzylamino)-6-methyl-2-oxocyclohex- 3-en-1-oate, 3a, 3-N-(benzylamino)cyclohex-2-en-1-one, 3p, and 5,5-dimethyl- 3-N-(benzylamino)-cyclohex-2-en-1-one, 3r indicated that benzylamines possessed significant anti-maximal electroshock seizure (MES) activity. Evaluation of the analogous benzamides revealed significant differences in anticonvulsant activity, these differences were most probably related to the differences in their three-dimensional structures. (C) 1999 Elsevier Science Ltd.