5176-32-9

Usage

Uses

Used in Chemical Synthesis:
3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one is used as a key intermediate in the synthesis of various organic compounds. Its unique molecular structure allows for versatile chemical reactions, enabling the production of a wide range of compounds with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one is used as a building block for the development of novel drugs. Its specific reactivity and functional groups make it a valuable component in the design and synthesis of new pharmaceutical compounds with potential therapeutic effects.
Used in Material Science:
3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one is utilized in material science for the development of advanced materials with unique properties. Its incorporation into polymers, for example, can result in materials with enhanced stability, conductivity, or other desirable characteristics.
Used in Analytical Chemistry:
In analytical chemistry, 3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one can be employed as a reagent or a reference compound in various analytical techniques. Its distinct chemical properties make it suitable for use in assays, chromatography, or spectroscopy to analyze and characterize other compounds.
Used in Research and Development:
3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one serves as a valuable research compound in scientific studies. Its unique structure and properties make it an interesting subject for investigations into new chemical reactions, mechanisms, or potential applications in various fields.

InChI:InChI=1/C10H11N3O/c1-8-3-5-9(6-4-8)13-10(14)7-12(2)11-13/h3-7H,1-2H3/p+1

Upstream product

• 5176-28-3 N-(tert-butoxycarbonyl)-1,4-dihydro-1,4-iminonaphthalene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1072-85-1 o-fluorobromobenzene 
• 118-92-3 anthranilic acid 
• 5176-27-2 N-tert-butyloxycarbonyl-pyrrole 

Downstream Products

• 5176-30-7 1,2,3,4-tetrahydro-1,4-epiminonaphthalene 
• 55257-99-3 N-methyl-1,2,3,4-tetrahydro-1,4-iminonaphthalene 
• 5176-31-8 1,2,3,4-tetrahydro-1,4-iminonaphthalene hydrochloride 
• 942491-77-2 2,2,2-trifluoro-1-(1,2,3,4-tetrahydro-1,4-epiminonaphth-9-yl)ethanone 

Relevant academic research and scientific papers

COMPOUNDS AND COMPOSITIONS FOR TREATING CNS DISORDERS

The present disclosure provides compounds and pharmaceutical compositions thereof. Methods of making and using the compounds are also provided. The compounds can be used for the treatment, prevention, diagnosis and/or management of various CNS disorders.

RESORCINOL DERIVATIVE AS HSP90 INHIBITOR

The present invention relates to a compound represented by formula (I) of a resorcinol derivative as an HSP90 inhibitor or pharmaceutically accepted salts thereof. The compound in the present invention has the activity of inhibiting heat shock protein HSP90. Therefore, the compound in the present invention is used to treat proliferative diseases such as cancer and neurodegenerative diseases. The present invention further provides the compounds and preparation methods for pharmaceutical compositions comprising the compounds, a method for treating diseases, and pharmaceutical compositions comprising the compounds.

7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines

Nitrosamines are potent carcinogens and toxicants in the rat and potential genotoxins in humans. They are metabolically activated by hydroxylation at an α-carbon atom with respect to the nitrosoamino group, catalyzed by cytochrome P450. However, there has been little systematic investigation of the structure-mutagenic activity relationship of N-nitrosamines. Herein, we evaluated the mutagenicity of a series of 7-azabicyclo[2.2.1]heptane N-nitrosamines and related monocyclic nitrosamines by using the Ames assay. Our results show that the N-nitrosamine functionality embedded in the bicyclic 7-azabicylo[2.2.1]heptane structure lacks mutagenicity, that is, it is inert to α-hydroxylation, which is the trigger of mutagenic events. Further, the calculated α-C-H bond dissociation energies of the bicyclic nitrosamines are larger in magnitude than those of the corresponding monocyclic nitrosamines and N-nitrosodimethylamine by as much as 20-30 kcal/mol. These results are consistent with lower α-C-H bond reactivity of the bicyclic nitrosamines. Thus, the 7-azabicyclo[2.2.1]heptane structural motif may be useful for the design of nongenotoxic nitrosamine compounds with potential biological/medicinal applications.

Transnitrosation of thiols from aliphatic N-nitrosamines: S-nitrosation and indirect generation of nitric oxide

S-Nitrosothiols and heme nitrosyl species are nitric oxide (NO)-derived metabolites that provide an endogenous reservoir of NO and also play roles in protein S-nitrosation, that is, transnitrosation of thiols (or thiolates) in proteins, thereby regulating protein functions and signal transduction pathways. Intriguingly, endogenous N-nitrosamines are present in similar abundance to S-nitrosothiols, and though they are thought to play similar physiological roles to S-nitrosothiols, their transnitrosation reactivities and their contribution to biological events are little understood. Herein we report aliphatic N-nitroso derivatives of 7-azabicyclo[2.2.1]heptanes, which do not act as NO donors themselves, but can transnitrosate thiols. On the basis of the calculated activation energies of transnitrosation and the aorta smooth-muscle relaxation activities of these N-nitrosamines, we present a possible scenario of S-transnitrosation from aliphatic N-nitrosamines, leading to indirect generation of NO. Copyright

An Evaluation of Amide Group Planarity in 7-Azabicyclo[2.2.1]heptane Amides. Low Amide Bond Rotation Barrier in Solution

Here we show that amides of bicyclic 7-azabicyclo[2.2.1]heptane are intrinsically nitrogen-pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo[2.2.1]heptane, exhibited nitrogen-pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo[2.2.1]heptanes in solution. The observed reduction of the rotational barriers of the bicyclic amides, as compared with those of the monocyclic pyrrolidine amides, is consistent with a nitrogen-pyramidal structure of 7-azabicyclo[2.2.1]heptane amides in solution. A good correlation was found between the magnitudes of the rotational barrier of N-benzoyl-7-azabicyclo[2.2.1]heptanes bearing para-substituents on the benzoyl group and the Hammett's σp+ constants, and this is consistent with the similarity of the solution structures. Calculations with the density functional theory reproduced the nitrogen-pyramidal structures of these bicyclic amides as energy minima. The calculated magnitudes of electron delocalization from the nitrogen nonbonding nN orbital to the carbonyl π* orbital of the amide group evaluated by application of the bond model theory correlated well with the rotational barriers of a variety of amides, including amides of 7-azabicyclo[2.2.1]heptane. The nonplanarity of the amide nitrogen of 7-azabicyclo[2.2.1]heptanes would be derived from nitrogen-pyramidalization due to the CNC angle strain and twisting of the amide bond due to the allylic strain.

Development of two processes for the synthesis of bridged azabicyclic systems: Intermolecular radical addition-homoallylic rearrangements leading to 2-azanorborn-5-enes and neophyl-type radical rearrangements to 2-azabenzonorbornanes

Radical thiol additions to 7-azanorbornadienes give 7-thio-substituted 2-azanorbornenes and Barton deoxygenations of 7-azabenzonorbornanols give 2-azabenzonorbornanes. The processes both involve novel nitrogen-directed radical rearrangements. The kinetics and mechanisms of the reactions are also discussed.

2-azabenzonorbornanes from 7-azabenzonorbornanols by a nitrogen-directed neophyl-type radical rearrangement

(equation presented) Barton deoxygenation of 7-azabenzonorbornanols leads to a synthetically useful neophyl-like rearrangement to give 2-azabenzonorbornane derivatives in 64-90% yields.