101488-65-7

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-FLUORO-PHENYL)-PROPYLAMINE is used as a reactant for the synthesis of triazine-based estrogen receptor modulators that display selectivity for estrogen receptor β. These modulators have potential applications in the treatment of various conditions related to estrogen receptor imbalance, such as hormone-dependent cancers and other estrogen-related disorders.
In the synthesis process, 3-(4-FLUORO-PHENYL)-PROPYLAMINE serves as a key component that contributes to the overall structure and activity of the final product. Its unique properties, such as the presence of a fluorine atom and the propylamine group, enable the formation of specific interactions with the target estrogen receptor, leading to the desired selectivity and modulation of its activity. This makes 3-(4-FLUORO-PHENYL)-PROPYLAMINE a valuable compound in the development of novel therapeutic agents for various medical conditions.

InChI:InChI=1/C9H12FN/c10-9-5-3-8(4-6-9)2-1-7-11/h3-6H,1-2,7,11H2

Upstream product

• 642941-68-2 3-(4-(fluoro)phenyl)acrylamide 
• 25468-86-4 3-(4'-fluorophenyl)propanenitrile 
• 352-34-1 4-fluoro-1-iodobenzene 
• 24654-48-6 3-(4-fluorophenyl)acrylonitrile 
• 25468-67-1 3-(4-fluorophenyl)propanamide 
• 1403029-82-2 3-(4-fluorophenyl)propyl carbamic acid methyl ester 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 54930-39-1 3-(4-methylphenyl)propanamine 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 78573-75-8 p-toluenesulfonic acid 3-(4-fluorophenyl)propyl ester 
• 702-15-8 3-(4-fluorophenyl)propan-1-ol 
• 459-57-4 4-fluorobenzaldehyde 
• 136265-10-6 ethyl 4-fluorocinnamate 
• 7116-38-3 ethyl 3-(4-fluorophenyl)propanoate 

Downstream Products

• 465528-50-1 2-{(1-(3-[4-chlorophenyl]propyl)aminocarbonyl)cyclopentylmethyl}-4-methoxybutyric acid tert-butyl ester 
• 931995-48-1 C₁₀H₁₄FNO₂S 
• 852661-50-8 1-(para-fluorophenyl)-3-(acetamido)propane 
• 872214-99-8 tert-butyl 3-(4-fluorophenyl)propylcarbamate 
• 852660-34-5 (1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]amino}-methyl)-cyclohexyl]-carbamic acid benzyl ester 
• 928940-13-0 C₁₆H₁₅FINO 
• 1426152-75-1 C₁₆H₁₅FN₄OS 
• 1418283-50-7 N-[3-(4-fluorophenyl)propyl]-2-(2,4-dichlorophenoxy)propanamide 
• 852661-54-2 (2S,3R)-3-amino-1-{ethyl[3-(4-fluorophenyl)propyl]amino}butan-2-ol 
• 852661-55-3 N-((1R,2S)-3-{ethyl[3-(4-fluorophenyl)propyl]amino}-2-hydroxy-1-methylpropyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852660-32-3 N-((1R,2S)-2-{[[3-(4-fluorophenyl)propyl]amino]methyl}cyclohexyl)-N'-[3-(1-methyl-1H-tetrazol-5-yl)phenyl]urea 
• 852660-36-7 (1R,2S)-2-({tert-butoxycarbonyl-[3-(4-fluorophenyl)-propyl]amino}-methyl)-cyclohexylamine 

Relevant academic research and scientific papers

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists

A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.

Transition-metal-free Intramolecular C-H amination of sulfamate esters and: N -alkylsulfamides

The transition-metal-free intramolecular C-H amination of sulfamate esters using iodine oxidants, tert-butyl hypoiodite (t-BuOI) and N-iodosuccinimide (NIS) is reported. A method using NIS was also successfully applied to the oxidative cyclization of N-alkylsulfamides.

Design and synthesis of sulfonamidophenylethylureas as novel cardiac myosin activator

To optimize the lead urea scaffold 1 and 2 as selective cardiac myosin ATPase activator, a series of urea derivatives have been synthesized to explore its structure activity relationship. Among them N,N-dimethyl-4-(2-(3-(3-phenylpropyl)ureido)ethyl)benzenesulfonamide (13, CMA = 91.6%, FS = 17.62%; EF = 11.55%), N,N-dimethyl-4-(2-(1-methyl-3-(3-phenylpropyl)ureido)ethyl)benzene sulfonamide (40, CMA = 52.3%, FS = 38.96%; EF = 24.19%) and N,N-dimethyl-4-(2-(3-methyl-3-(3-phenylpropyl)ureido)ethyl)benzenesulfonamide (41, CMA = 47.6%, FS = 23.19%; EF = 15.47%) proved to be efficient to activate the cardiac myosin in vitro and in vivo. Further the % change in ventricular cell contractility at 5 μM of 13 (47.9 ± 3.2), 40 (45.5 ± 2.4) and 41 (63.5 ± 2.2) showed positive inotropic effect in isolated rat ventricular myocytes. The potent compounds 13, 40, 41 were highly selective for cardiac myosin over skeletal and smooth muscle myosin, thus proving them these new urea derivatives is a novel scaffold for discovery of cardiac myosin activators for the treatment of systolic heart failure.

Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells

Aldo-keto reductase 1B10 (AKR1B10) is overexpressed in several extraintestinal cancers, particularly in non-small-cell lung cancer, where AKR1B10 is a potential diagnostic marker and therapeutic target. Selective AKR1B10 inhibitors are required because compounds should not inhibit the highly related aldose reductase that is involved in monosaccharide and prostaglandin metabolism. Currently, 7-hydroxy-2-(4-methoxyphenylimino)-2H-chromene-3-carboxylic acid benzylamide (HMPC) is known to be the most potent competitive inhibitor of AKR1B10, but it is nonselective. In this study, derivatives of HMPC were synthesized by removing the 4-methoxyphenylimino moiety and replacing the benzylamide with phenylpropylamide. Among them, 4c and 4e showed higher AKR1B10 inhibitory potency (IC50 4.2 and 3.5 nM, respectively) and selectivity than HMPC. The treatments with the two compounds significantly suppressed not only migration, proliferation, and metastasis of lung cancer A549 cells but also metastatic and invasive potentials of cisplatin-resistant A549 cells.

Activation of electrophilicity of stable Y-delocalized carbamate cations in intramolecular aromatic substitution reaction: Evidence for formation of diprotonated carbamates leading to generation of isocyanates

Although cations with three heteroatoms, such as monoprotonated guanidine and urea, are stabilized by Y-shaped conjugation and such Y-conjugated cations are sufficiently basic to be further protonated (or protosolvated) to dications in strongly acid media, only O-monoprotonated species have been detected in the case of carbamates even in magic acid. We found that the trifluoromethanesulfonic acid-catalyzed cyclization of arylethylcarbamates proceeds to afford dihydroisoquinolones in high yield. In strong acids, methyl carbamates are fully O-monoprotonated, and these monocations do not undergo cyclization even under heating. But, as the acidity of the reaction medium is further increased, the cyclization reaction of methyl phenethylcarbamates starts to proceed as a first-order reaction, with a linear relationship between rate and acidity. The sign and magnitude of the entropy of activation ΔS ? were found to be similar to those of other AAc1 reactions. These results strongly support the idea that further protonation of the O-protonated carbamates is involved in the cyclization, but the concentration of the dications is very low and suggests that the rate-determining step is dissociation of methanol from the diprotonated carbamate to generate protonated isocyanate, which reacts with the aromatic ring. Therefore, O-protonated carbamates are weak bases in sharp contrast to other Y-shaped monocations.

From rigid cyclic templates to conformationally stabilized acyclic scaffolds. Part II: Acyclic replacements for the (3S)-3-benzylpiperidine in a series of potent CCR3 antagonists

Conformational analysis of the 3-benzylpiperidine in CCR3 antagonist clinical candidate 1 (BMS-639623) predicts that the benzylpiperidine may be replaced by acyclic, conformationally stabilized, anti-1,2-disubstituted phenethyl- and phenpropylamines. Ab i

Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder

A series of substituted glutaramides were synthesised using Candoxatrilat 1 as a lead and evaluated for potency against neutral endopeptidase (NEP) as a potential treatment for female sexual arousal disorder (FSAD). In this paper, we describe studies in which we were able to increase NEP activity substantially over the levels reported for previous compounds from this programme by appropriate substitution in both the P1′ and P2′ regions. Optimisation led to the 4-chlorophenpropylamide S-30 which was selected as a candidate for further study.

3-(1-CARBAMOYLCYCLOHEXYL) PROPIONIC ACID DERIVATIVES AS INHIBITORS OF NEUTRAL ENDOPEPTIDASE ENZYME

Compounds of the formula (I) and pharmaceutically acceptable salts, polymorphs, prodrugs and/or solvates thereof wherein R1, X and Y are as described herein, are useful as inhibitors of neutral endopeptidase (NEP).

N-UREIDOALKYL-AMINO COMPOUNDS AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present application describes modulators of chemokine receptors of formula (I), or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.