56814-11-0

Basic information

• Product Name: 2-AMINO-N-CYCLOHEXYLBENZAMIDE
• Synonyms: AKOS BBB/033;2-AMINO-N-CYCLOHEXYLBENZAMIDE;benzamide, 2-amino-N-cyclohexyl-;2-(Cyclohexylcarbamoyl)aniline, [(2-Aminobenzoyl)amino]cyclohexane;A2345/0099023;ARONIS006299;Maybridge1_003298;Oprea1_673490
• CAS NO: 56814-11-0
• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.29
• Mol File: 56814-11-0.mol

Chemical Properties

• Melting Point: 153-156°C
• Boiling Point: 421.5 °C at 760 mmHg
• Flash Point: 208.7 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 2.59E-07mmHg at 25°C
• Refractive Index: 1.575
• PKA: 14.31±0.20(Predicted)
• CAS DataBase Reference: 2-AMINO-N-CYCLOHEXYLBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-N-CYCLOHEXYLBENZAMIDE(56814-11-0)
• EPA Substance Registry System: 2-AMINO-N-CYCLOHEXYLBENZAMIDE(56814-11-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 56814-11-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-Amino-N-cyclohexylbenzamide is used as an intermediate in pharmaceutical research for its potential role in drug development. Its unique chemical structure allows for the synthesis of various compounds with therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Amino-N-cyclohexylbenzamide serves as a valuable intermediate, enabling the creation of a wide range of organic compounds with diverse properties and uses.
Used in Antitumor Applications:
2-Amino-N-cyclohexylbenzamide is studied for its potential as an antitumor agent. Its biological activity suggests that it may have the ability to inhibit tumor growth and progression, making it a candidate for further research and development in cancer treatment.
Used in Enzyme Inhibition:
2-AMINO-N-CYCLOHEXYLBENZAMIDE has also been investigated for its potential to inhibit certain enzymes. This property could be harnessed in the development of drugs targeting specific enzymatic pathways involved in various diseases.
Further research is necessary to fully understand and exploit the potential applications of 2-Amino-N-cyclohexylbenzamide, as its current uses and studies are still in the exploratory phase.

InChI:InChI=1/C13H18N2O/c14-12-9-5-4-8-11(12)13(16)15-10-6-2-1-3-7-10/h4-5,8-10H,1-3,6-7,14H2,(H,15,16)

Upstream product

• 118-48-9 isatoic anhydride 
• 108-91-8 cyclohexylamine 
• 91-56-5 indole-2,3-dione 
• 271-58-9 anthranil 
• 21563-73-5 2-aminobenzoyl chloride 
• 118-92-3 anthranilic acid 
• 28144-70-9 anthranilic acid amide 
• 491-36-1 4-Hydroxyquinazoline 
• 60007-51-4 3-(2-oxo-2-phenylethyl)quinazolin-4(3H)-one 

Downstream Products

• 950-31-2 1H-spiro(cyclohexane-1,2-quinazolin)-4(3H)-one 
• 5943-92-0 3-cyclohexyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 80283-42-7 3-Cyclohexyl-2-(4-methoxy-phenyl)-2-thioxo-2,3-dihydro-1H-2λ⁵-benzo[1,3,2]diazaphosphinine-4-thione 
• 14663-51-5 3-cyclohexylquinazolin-4(3H)-one 
• 348612-65-7 N-cyclohexyl-2-(methylamino)benzamide 
• 1308660-41-4 6-cyclohexyl-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione 
• 1542097-99-3 3-cyclohexyl-2-(5-ethylthiophen-2-yl)-2,3-dihydroquinazolin-4(1H)-one 

Relevant articles and documents

Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one

Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.

N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones

N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.

Synthesis of new di- And triamides as potential organocatalysts for asymmetric aldol reaction in water

New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0 °C in the presence of benzoic acid as co-catalyst. (S)-me

Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.

Thermo-Promoted Reactions of Anthranils with Carboxylic Acids, Amines, Phenols, and Malononitrile under Catalyst-Free Conditions

A convenient and atom-economical procedure for the thermo-promoted reactions of anthranil with different substrates was developed. The catalyst-free process affords various useful building blocks with good to moderate yields. This chemistry enables several step- and cost-effective approaches for biologically interesting molecules and provides an efficient platform for the investigation of untapped reactions at high temperature.

NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

An efficient transformation of 2-aminobenzamides to 1,2,3-benzotriazin-4(3H)-ones in the presence of sodium nitrite (NaNO2) and Iodine (I2) is described. The reaction is proposed to proceed via formation of nitrosyl halide that induces nitrosylation of the amino group of 2-aminobenzamide leading to diazotization followed by intramolecular cyclization.

De novo synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazolin-4(1H)-one compounds

A new versatile and efficient strategy for the synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazoline-4(1H)-one compounds has been developed by one-pot multicomponent reaction with isatoic anhydride, amines followed by in situ-generated Vilsmeier reagent. The reaction has also been studied with different amines and solvents.

Ionic liquid supported on magnetic nanoparticles as a novel reusable nanocatalyst for the efficient synthesis of tetracyclic quinazoline compounds

A magnetic ionic liquid supported on γ-Fe2O3 nanocatalyst was synthesized successfully and characterized by Fourier transform infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, differential scanning calorimetry, X-ray diffraction and scanning electron microscopy. The resulting nano-Fe3O4-supported, ionic liquid was an efficient catalyst for preparation of a series of tetracyclic quinazoline compounds by three components reaction of a mixture of isatoic anhydride and amine with ninhydrin in PEG and the desired products were obtained in good to excellent yields. High efficiency, waste-free, mild reaction conditions, effortless magnetic recovery and reusability up to four continuous cycles are the noteworthy features of the currently employed heterogeneous catalytic system.

The therapeutic compound, use and related method (by machine translation)

PROBLEM TO BE SOLVED: To provide a pharmaceutical composition containing a compound or its salt which prevents or treats a central nervous system disease in which integration dysfunction syndrome and agnosia are enumerated as exemplary disorders.SOLUTION: The pharmaceutical composition includes the compound or its salt represented by chemical formula (A) which modulates striatal-enriched protein tyrosine phosphatase (STEP).

Novel β-carboline-quinazolinone hybrid as an inhibitor of Leishmania donovani trypanothione reductase: Synthesis, molecular docking and bioevaluation

Trypanothione reductase (TR) is a vital enzyme in the trypanothione based redox metabolism of trypanosomatid parasites. It is one of the few chemically validated targets for Leishmania. Herein, we report the synthesis of novel β-carboline-quinazolinone hybrids that are able to inhibit Leishmania donovani TR (LdTR) and subsequently inhibit cell growth. A molecular modeling approach based on docking studies and subsequent binding free energy estimation was performed in the active site of LdTR to understand their possible binding sites. With the enzymatic assay on LdTR with compounds, we were able to identify six hit compounds (8j-8o) that were all found to be the competitive inhibitors of TR with Ki in the range of 0.8-9.2 μM. The whole-cell screening assay highlighted the analogues 8k, 8l and 8n as the most active compounds with IC50 of 4.4, 6.0 and 4.3 μM, respectively, along with an adequate selectivity index (SI) of >91, 36 and 24, respectively. This journal is