88229-16-7

Usage

Uses

Used in Pharmaceutical Industry:
N-Cyclopropyl 4-fluorobenzamide is used as a potential ligand for cannabinoid receptors in the endocannabinoid system for its potential therapeutic effects. Its interaction with these receptors may contribute to the modulation of various physiological processes and could be beneficial in the treatment of a range of medical conditions.
Used in Drug Development:
N-Cyclopropyl 4-fluorobenzamide is used as a potential drug candidate for further research and development. Its unique structure and properties make it a valuable compound for exploring new therapeutic approaches and potentially developing novel medications to address unmet medical needs.
Used in Research Applications:
N-Cyclopropyl 4-fluorobenzamide is used as a research tool in the study of the endocannabinoid system and its role in various physiological and pathological processes. Its use in research settings aids in understanding the mechanisms of action and potential therapeutic applications of compounds interacting with cannabinoid receptors.

Upstream product

• 456-22-4 4-Fluorobenzoic acid 
• 765-30-0 Cyclopropylamine 
• 403-43-0 4-fluorobenzoyl chloride 

Downstream Products

• 1246084-21-8 N-cyclopropyl-4-(4-((2,8-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)benzamide 
• 1246083-28-2 N-cyclopropyl-4-(4-((8-methoxy-2-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)piperazin-1-yl)benzamide 
• 1018529-73-1 N-cyclopropyl-4-(piperazin-1-yl)benzamide 
• 70001-45-5 4-fluoro-N-isopropylbenzamide 
• 1192139-71-1 N-(cyclopropyl)-4-fluorobenzimidoyl chloride 

Relevant academic research and scientific papers

Diamine Synthesis via the Nitrogen-Directed Azidation of σ- And π-C-C Bonds

Diamines are essential building blocks for the synthesis of agrochemicals, drugs, and organic materials, yet their synthesis remains challenging, as both nitrogens need to be differentiated and diverse substitution patterns (1,2, 1,3, or 1,4) are required. We report herein a new strategy giving access to 1,2, 1,3, and 1,4 amido azides as orthogonally protected diamines based on the nitrogen-directed diazidation of alkenes, cyclopropanes, and cyclobutanes. Commercially available copper thiophene-2-carboxylate (CuTc, 2 mol %) as catalyst promoted the diazidation of both πand σ C-C bonds within 10 min in the presence of readily available oxidants and trimethylsilyl azide. Selective substitution of the formed α-amino azide by carbon nucleophiles (electron-rich aromatic, malonate, organosilicon, organoboron, organozinc, and organomagnesium compounds) was then achieved in a one-pot fashion, leading to the formation of 1,2-, 1,3-, and 1,4-diamines with the amino groups protected orthogonally as an amide/carbamate and an azide.

Oxidative Fluorination of Cyclopropylamides through Organic Photoredox Catalysis

We report an oxidative ring-opening strategy to transform cyclopropylamides and cyclobutylamides into fluorinated imines. The imines can be isolated in their more stable hemiaminal form, with the fluorine atom installed selectively at the γ or δ position. Both inexpensive benzophenone with UVA light or organic and inorganic dyes with blue light could be used as photoredox catalysts to promote this process. Various fluorinated amines were then obtained by nucleophilic attack on the hemiaminals in one pot, giving access to a broad range of useful building blocks for medicinal chemistry.

Synthesis of thiochromans via [3+3] annulation of aminocyclopropanes with thiophenols

We report the one-pot synthesis of 4-amino thiochromans using simple aminocyclopropanes and thiophenols through a formal [3+3] annulation reaction. This reaction proceeds under mild conditions with good functional group tolerance. The thiochroman core was

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates

We report an oxidative ring-opening strategy to transform acyl, sulfonyl or carbamate protected aminocyclopropanes into 1,3-dielectrophilic carbon intermediates bearing a halide atom (Br, I) and a N,O-acetal. Replacing the alkoxy group of the N,O-acetal can be achieved under acidic conditions through an elimination–addition pathway, while substitution of the halides by nucleophiles can be done under basic conditions through a SN2 pathway, generating a wide range of 1,3-difunctionalized propylamines. A proof of concept for asymmetric induction was realized using a chiral phosphoric acid (CPA) as catalyst, highlighting the potential of the method in enantioselective synthesis of important building blocks.

N-(R-cyclopropyl)fluorobenzimidoyl phosphonates

Reaction of N-(R-cyclopropyl)benzimidoyl chloride with triethyl phosphite has yielded the corresponding N-(R-cyclopropyl)-substituted benzimidoyl phosphonates existing predominantly in the E-configuration [E: Z ≈ (8-10): 1] at room temperature. 19/s

Discovery of novel benzo[b][1,4]oxazin-3(4H)-ones as poly(ADP-ribose) polymerase inhibitors

Structure based drug design of a series of novel 1,4-benzoxazin-3-one derived PARP-1 inhibitors are described. The synthesis, enzymatic & cellular activities and pharmacodynamic effects are described. Optimized analogs demonstrated inhibition of poly-ADP-ribosylation in SW620 tumor bearing nude mice through 24 h following a single dose.

POTENTIAL CENTRAL NERVOUS SYSTEM ACTIVE AGENTS. 3. SYNTHESIS OF SOME SUBSTITUTED BENZAMIDES AND PHENYLACETAMIDES.

The preparation and special properties (IR, **1H NMR) are given for 45 benzamides and 10 phenylacetamides substituted on nitrogen with allyl, benzhydryl, benzyl, or cyclopropyl groups, and variously substituted on the acyl part with halo, methoxyl, methyl, or nitro groups. The benzamide derivatives were synthesized by the Schotten-Baumann method, and the phenylacetamide derivatives were prepared by heating the appropriate N-benzhydrylammonium salt in o-xylene. Thirty-one of the compounds are new.