63998-62-9

Usage

Uses

Used in Pharmaceutical Research and Development:
4-(4-Chlorophenyl)butan-1-amine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(4-CHLOROPHENYL)BUTAN-1-AMINE is used as a reagent or starting material for the preparation of a wide range of organic compounds. Its amine functionality and 4-chlorophenyl group make it a valuable component in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
4-(4-CHLOROPHENYL)BUTAN-1-AMINE is employed in medicinal chemistry for the design and optimization of drug candidates. Its structural features can be leveraged to create molecules with specific biological activities, contributing to the discovery of new therapeutic agents.
Used in Drug Production:
4-(4-CHLOROPHENYL)BUTAN-1-AMINE is utilized in the industrial production of various drugs and medications. Its presence in the synthesis process can lead to the development of pharmaceuticals with improved efficacy, safety, and pharmacokinetic properties.

Upstream product

• 4521-18-0 4-(4-Chlorophenyl)butyric acid amide 
• 1026465-42-8 2-[4-(4-Chloro-phenyl)-butyl]-isoindole-1,3-dione 
• 13214-66-9 4-phenyl-1-butylamine 
• 104-88-1 4-chlorobenzaldehyde 
• 74591-94-9 N-[4-(p-chlorophenyl)-3-butenyl]phthalimide 
• 3984-34-7 4-(4-chlorophenyl)-4-oxobutanoic acid 
• 54654-08-9 4-(4-chlorophenyl)butanoyl chloride 
• 211692-38-5 N-[4-(benzo[d]1,3-dioxol-5-yl)-3-butenyl]phthalimide 

Downstream Products

• 79945-11-2 C₂₀H₂₇Cl₂N₃O₄S₂ 
• 142757-95-7 3-[2-((1S,2R,3S,4R)-3-{4-[4-(4-Chloro-phenyl)-butylcarbamoyl]-oxazol-2-yl}-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-propionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and evaluation of N-alkyl-S-[3-(piperidin-1-yl)propyl] isothioureas: High affinity and human/rat species-selective histamine H 3 receptor antagonists

S-Alkyl-N-alkylisothiourea compounds containing various cyclic amines were synthesized in the search for novel nonimidazole histamine H3 receptor (H3R) antagonists. Among them, four N-alkyl S-[3-(piperidin-1-yl)propyl]isothioureas 18, 19, 22, and 23 were found to exhibit potent and selective H3R antagonistic activities against in vitro human H3R, but were inactive against in vitro human H 4R. Furthermore, three alkyl homologs 18-20 showed inactivity for histamine release in in vivo rat brain microdialysis, suggesting differences in antagonist affinities between species. In addition, in silico docking studies of N-[4-(4-chlorophenyl)butyl]-S-[3-piperidin-1-yl)propyl]isothiourea 19 and a shorter homolog 17 with human/rat H3Rs revealed that structural differences between the antagonist-docking cavities of rat and human H 3Rs were likely caused by the Ala122/Val122 mutation.

Convenient route to primary (Z)-allyl amines and homologs

A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)-geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C = C double bond in the deprotection with hydrazine was concomitantly observed. Copyright Taylor & Francis Group, LLC.

6-SUBSTITUTED PHENOXYCHROMAN CARBOXYLIC ACID DERIVATIVES

Compounds of Formula (I): in which A1, A2, W, L, G, R7a, R7b, R8, R9 and R10 have the meanings given in the specification, are DP2 receptor modulators useful in the treatment of immunologic diseases.

Aromatic chlorination of ω-phenylalkylamines and ω- phenylalkylamides in carbon tetrachloride and α,α,α- trifluorotoluene

The aromatic halogenation of simple alkylbenzenes with chlorine proceeds smoothly in acetic acid but is much less efficient in less polar solvents. By contrast chlorination of ω-phenylalkylamines, such as 3-phenylpropylamine, occurs readily in either acetic acid, carbon tetrachloride or α,α,α-trifluorotoluene, and in the latter solvents gives high proportions of ortho-chlorinated products. These effects are attributable to the involvement of N-chloroamines as reaction intermediates, with intramolecular delivery of the chlorine electrophile. ω-Phenylalkylamides, such as 3-phenylpropionamide, also easily undergo aromatic chlorination in carbon tetrachloride and α,α,α-trifluorotoluene. These reactions generally show a first-order dependence on the substrate concentration, but not on the amount of chlorine. With carbon tetrachloride, very similar reaction rates are observed with chlorine concentrations ranging from 0.1-1.5 M. In α,α,α-trifluorotoluene, the rates reach a plateau at a chlorine concentration of approximately 0.2 M. These features indicate that the reactions proceed via the formation of intermediates which evidence suggests may be the corresponding O-chloroimidates. Irrespective of the mechanistic details, the reactions are remarkably rapid, being faster than analogous reactions in acetic acid and three to four orders of magnitude more rapid than reactions of simple alkylbenzenes in carbon tetrachloride. Therefore, chlorination of the amines and amides may be accomplished without the need for highly polar solvents, added catalysts or large excesses of chlorine, which are often employed for electrophilic aromatic substitutions. Although the use of carbon tetrachloride is becoming increasingly impractical due to environmental concerns, the trifluorotoluene is a suitable alternative. The Royal Society of Chemistry 2006.

Inhibitors of protein tyrosine phosphatase

The present invention comprises small molecular weight, non-peptidic inhibitors of formulae I-VII of Protein Tyrosine Phosphatase 1 (PTP1) which are useful for the treatment and/or prevention of Non-Insulin Dependent Diabetes Mellitus (NIDDM).

Synthesis and pharmacological characterization of novel 6-fluorochroman derivatives as potential 5-HT(1A) receptor antagonists

A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT(1A) receptor. N-2-[[(6-Fluorochroman-8- yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252- 1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT(1A) receptor, some of which were selective with respect to α1-adrenergic and D2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolinstimulated adenylate cyclase assays in CHO cells expressing the human 5-HT(1A) receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screens and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3- benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT- induced behavioral and electrophysiological responses in rats.

7-oxabicycloheptyl substituted heterocyclic thioamide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease

7-Oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasospastic disease have the structural formula STR1 wherein m is 1, 2 or 3; n is 1, 2, 3 or 4; Z is --(CH2)2 --, --CH=CH-- or STR2 wherein Y is O, a single bond or vinyl, with the proviso that when n is O, if Z is STR3 then Y cannot be O, and when Z is --CH=CH--, n is 1, 2, 3 or 4; and when Y=vinyl, n=0; R is CO2 H, CO2 lower alkyl, CH2 OH, CO2 alkali metal, CONHSOR3, CONHR3a or --CH2 -5-tetrazolyl, X is O, S or NH; and where R1, R2, R3 and R3a are as defined herein.

7-oxabicycloheptyl substituted heterocyclic amide or ester prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease

7-Oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasopastic disease have the structural formula STR1 wherein m is 1, 2 or 3; n is 1, 2, 3 or 4; Z is --(CH2)2 --, --CH=CH-- or STR2 wherein Y is O, a single bond or vinyl, with the proviso that when n is 0, if Z is STR3 then Y cannot be O, and Z is --CH=CH--, n is 1, 2, 3 or 4; and when Y=vinyl, n=0; R is CO2 H, CO2 lower alkyl, CH2 OH, CO2 alkali metal, CONHSOR3, CONHR3a or --CH2 --5-tetrazolyl, X is O, S or NH; and where R1, R2, R3 and R3a are as defined herein.

Imidodisulfamides. I. A novel class of antagonists of slow-reacting substance of anaphylaxis

A series of N',N''-bis(aryl)- and N',N''-(aralkyl)imidodisulfamides was prepared and evaluated as antagonists of slow-reacting substance of anaphylaxis (SRS-A) induced contractions of isolated guinea pig ileum. Some of these compounds, notably N',N''-bis(4-phenylbutyl)- N',N''-bis[2-(4-chlorophenyl)ethyl]-, and N',N''-bis[2-(4-bromophenyl)ethyl]imidodisulfamides (16, 22, and 26), were moderately potent and selective antagonists of SRS-A. The influence of lipophilic (π) and electronic (σ) factors on SRS-A antagonist activity appears to be of considerable importance to the derivation of potent and selective SRS-A antagonists.

Antiallergic imidodisulfamides

Imidodisulfamide derivatives useful in the treatment of allergic conditions are prepared by reaction of an appropriately substituted primary amine and bis(chlorosulfonyl) imide in the presence of a tertiary amine.