57189-90-9

Usage

Uses

Used in Pharmaceutical Industry:
(4-Amino-phenyl)-cyclopropylmethanone is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its cyclopropyl and ketone functional groups contribute to the development of novel drugs with unique mechanisms of action and therapeutic benefits.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (4-Amino-phenyl)-cyclopropylmethanone serves as a valuable research tool for studying the structure-activity relationships of drug molecules. Its unique reactivity and properties allow scientists to explore new chemical space and identify potential drug candidates with improved pharmacokinetic and pharmacodynamic profiles.
Used in Drug Design and Development:
(4-Amino-phenyl)-cyclopropylmethanone is employed as a building block in the design and development of new pharmaceuticals. Its cyclopropyl ring and functional groups can be modified to create diverse chemical entities with potential therapeutic applications, enhancing the discovery of innovative treatments for various diseases and conditions.

Upstream product

• 56924-11-9 1-(4-acetylaminophenyl)-4-chloro-1-butanone 
• 3481-02-5 cyclopropyl phenyl ketone 
• 108-86-1 bromobenzene 
• 772-31-6 cyclopropyl(4-fluorophenyl)methanone 
• 540-37-4 p-aminoiodobenzene 
• 4023-34-1 cyclopropanecarboxylic acid chloride 
• 6952-89-2 (4-bromophenyl)(cyclopropyl)methanone 
• 103-84-4 Acetanilid 
• 93639-12-4 cyclopropyl(4-nitrophenyl)methanone 

Downstream Products

• 93639-12-4 cyclopropyl(4-nitrophenyl)methanone 
• 166337-94-6 (4-Cyclopropanecarbonyl-phenyl)-carbamic acid benzyl ester 
• 166337-20-8 {4-[Cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydro-2H-cycloocta[b]pyran-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester 
• 166337-21-9 3-[(4-Aminophenyl)cyclopropylmethyl]-5,6,7,8,9,10-hexahydro-4-hydroxy-2H-cycloocta[b]pyran-2-one 
• 166337-95-7 [4-(Cyclopropyl-hydroxy-methyl)-phenyl]-carbamic acid benzyl ester 
• 93639-13-5 4-chloro-4'-nitrobutyrophenone 
• 85562-17-0 8-<4-(4-nitrophenyl)-4-oxobutyl>-1-phenyl-1,3,8-triazaspiro<4.5>decan-4-one 
• 150717-69-4 4-(4-chlorophenyl)-1-<4-(4-nitrophenyl)-4-oxobutyl>-4-piperidinol 
• 749-02-0 spiperone 
• 52-86-8 haloperidol 

Relevant academic research and scientific papers

Silver-catalyzed intermolecular amination of fluoroarenes

A novel highly selective Ag-catalyzed intermolecular amination of fluoroarenes has been developed. This transformation starts from readily available 4-carbonyl fluorobenzene and NaN3 or other nitrogen-source, via amination followed by C-F bond cleavage, thus affording the desired 4-carbonyl arylamine products under mild conditions. The reaction is accelerated using a small amount of water. This pathway is distinct from a previously reported radical amination reaction.

Direct preparation of new organozinc reagents, aminophenylzinc iodides, and their applications

New organozinc reagents, 4-aminophenyl zinc iodide (A) and 3-aminophenyl zinc iodide (B), have been generated easily and effectively by the direct insertion of active zinc to iodoanilines which possess acidic protons. The subsequent coupling reactions of the organozincs with various acid chlorides turned out to be an efficient tool for the preparation of aminophenyl ketones.

SULFONAMIDE DERIVATIVE AND MEDICINAL USE THEREOF

Provided are sulfonamide derivatives of a specific chemical structure in which a sulfonamide group having, as a substituent, a phenyl group or a heterocyclic group having a hetero atom(s) as a constituent element(s) is present at its terminal, and pharmaceutically acceptable salts thereof. These compounds are novel compounds having excellent α4 integrin-inhibitory action.

Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides

A number of structural analogues of the known toxicant para- aminopropiophenone (PAPP) have been prepared and evaluated for their capacity to induce methemoglobinemia - with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed for alkyl analogues of PAPP (aminophenones 1-20; compound 6 metHb% = 74.1 ± 2). Besides lipophilicity, this structural sub-class suggested there were certain structural requirements for activity, with both branched (10-16) and cyclic (17-20) alkyl analogues exhibiting inferior in vitro metHb induction. Of the four candidates (compounds 4, 6, 13 and 23) evaluated in vivo, 4 exhibited the greatest toxicity. In parallel, aminophenone bioisosteres, including oximes 30-32, sulfoxide 33, sulfone 34 and sulfonamides 35-36, were found to be inferior metHb inducers to lead ketone 4. Closer examination of Hammett substituent constants suggests that a particular combination of the field and resonance parameters may be significant with respect to the redox mechanisms behind PAPPs metHb toxicity.

Structure-based design of nonpeptidic HIV protease inhibitors: The sulfonamide-substituted cyelooctylpyranones

Recently, cyclooctylpyranone derivatives with m-carboxamide substituents (e.g. 2c) were identified as potent, nonpeptidic HIV protease inhibitors, but these compounds lacked significant antiviral activity in cell culture. Substitution of a sulfonamide group at the meta position, however, produces compounds with excellent HIV protease binding affinity and antiviral activity. Guided by an iterative structure-based drug design process, we have prepared and evaluated a number of these derivatives, which are readily available via a seven-step synthesis. A few of the most potent compounds were further evaluated for such characteristics as pharmacokinetics and toxicity in rats and dogs. From this work, the p-cyanophenyl sulfonamide derivative 35k emerged as a promising inhibitor, was selected for further development, and entered phase I clinical trials.

Rapid and efficient synthesis of high-purity fluorine-18 labeled haloperidol and spiperone via the nitro precursor in combination with a new HPLC separation method

We have completed a convenient synthesis of fluorine-18 labeled butyrophenone neuroleptics from their nitro precursors. Thus, we have developed an efficient single-columm HPLC system using a C18-bonded vinyl alcohol copolymer gel (octadecyl polymer, ODP) column and strongly alkaline solvent systems for purifying of the 18F-labeled butyrophenone neuroleptics obtained by a single-stp 18F-for-nitro exchange reaction. The method has been applied to the synthesis of two typical butyrophenone neuroleptics ([18F]haloperidol and [18F]spiperone) with high purity in high yield. With information concerning the optimized conditions for the 18F-for-nitro exchange reaction, the synthetic method would be useful for synthesizing various 18F-labeled compounds.