2014-75-7

Usage

Uses

Used in Perfumery:
Phenyl-2-aminoethyl sulfide is used as a fragrance ingredient for its distinctive sweet, floral, and slightly spicy scent, contributing to the creation of various perfume compositions.
Used in Pharmaceutical Synthesis:
Phenyl-2-aminoethyl sulfide serves as a chemical intermediate in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs and medicinal compounds.
Used in Organic Compound Synthesis:
In the field of organic chemistry, phenyl-2-aminoethyl sulfide is utilized as a building block for the synthesis of other organic compounds, broadening its applications in chemical research and industrial processes.

InChI:InChI=1/C8H11NS/c9-6-7-10-8-4-2-1-3-5-8/h1-5H,6-7,9H2/p+1

Upstream product

• 151-56-4 ethyleneimine 
• 108-98-5 thiophenol 
• 41010-04-2 4-nitro-2-(2-(phenylthio)ethyl)isoindoline-1,3-dione 
• 2173-29-7 N-(2-Phenylmercapto-aethyl)-propionamid 
• 497-25-6 dimethylenecyclourethane 
• 2014-72-4 N-[2-(phenylsulfanyl)ethyl]acetamide 
• 5219-61-4 (phenylthio)acetonitrile 
• 3111-52-2 potassium thiophenolate 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 71-23-8 propan-1-ol 
• 870-24-6 2-chloroethanamine hydrochloride 
• 107-09-5 2-bromoethylamine 
• 16503-79-0 α,α-Difluoro-α-(phenylthio)acetamide 
• 1262850-22-5 C₈H₇F₂NO₂S 

Downstream Products

• 88124-16-7 N-(2-phenylsulfanyl-ethyl)-acetoacetamide 
• 53492-51-6 3-(2-phenylsulfanyl-ethyl)-4-propyl-sydnone 
• 70959-24-9 5-[1-hydroxy-2-(2-phenylthioethylamino)ethyl]-2-methylbenzenesulfonamide 
• 62274-57-1 3-Butylamino-2-phenoxy-5-[(2-phenylsulfanyl-ethylamino)-methyl]-benzenesulfonamide 
• 66859-97-0 (4-fluoro-benzylidene)-(2-phenylsulfanyl-ethyl)-amine 
• 133760-85-7 2-hydroxy-2-phenyl-N-(2-phenylthioethyl)ethylamine 
• 121654-83-9 1-(2-phenylthioethyl)-4-benzyl-2,6-piperazinedione 
• 98325-23-6 2-Ethyl-3-{[(E)-2-phenylsulfanyl-ethylimino]-methyl}-indole-1-carboxylic acid methyl ester 
• 113352-68-4 (E)-1-carbomethoxy-2-methyl-6-methoxy-3-formimidoyl>indole 
• 138803-32-4 1-(6-Chloro-pyridazin-3-yloxy)-3-(2-phenylsulfanyl-ethylamino)-propan-2-ol 
• 82946-36-9 [1-[1-(4-Methoxy-benzenesulfonyl)-2-methyl-1H-indol-3-yl]-meth-(E)-ylidene]-(2-phenylsulfanyl-ethyl)-amine 
• 80664-27-3 (E)-1-<(p-methoxyphenyl)sulfonyl>-2-methyl-3-indole 
• 110696-46-3 6-Chloro-2-[3-(2-phenylsulfanyl-ethylamino)-propyl]-2H-pyridazin-3-one 
• 99657-01-9 (E)-1-carbomethoxy-2-methyl-3-indole 

Relevant academic research and scientific papers

Engineering Catalysts for Selective Ester Hydrogenation

The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.'s Ru-PNP, more commonly known as Ru-MACHO, and Gusev's Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H2 (Waser, M. et al. Org. Proc. Res. Dev. 2018, 22, 862). This work introduces economically competitive Ru-SNP(O)z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C4H9 in ester hydrogenation. It attempts to explain why a maximum turnover is seen to occur starting at 25 mol % base, in contrast to only 10 mol % with ketones as substrates.

SYNTHESIS OF FLUORO HEMIACETALS VIA TRANSITION METAL-CATALYZED FLUORO ESTER AND CARBOXAMIDE HYDROGENATION

This application is directed to use of transition metal-ligand complexes to hydrogenate fluorinated esters and carboxamides into fluorinated hemiacetals. Methods for synthesis of certain ligands are also provided.

En Route Activity of Hydration Water Allied with Uranyl (UO22+) Salts Amid Complexation Reactions with an Organothio-Based (O, N, S) Donor Base

This study provides en route activity of hydration water allied with uranyl salts amid complexation reactions with a donor species L bearing O, N, and S (phenolic, -OH; imine, -HC=N-; and thio-, -S-) donor functionalities. The UO22+/

Synthesis and biological evaluation of heteroalicyclic cyanoguanidines at histamine receptors

Recent studies on histamine receptor (HR) subtypes identified imidazolyl butyl cyanoguanidines, like UR-PI376, as highly potent agonists at the human histamine H4 receptor (hH4R). While imidazole-containing compounds display drawbacks in pharmacokinetics, we studied the possibility of?replacing?the heteroaromatic cycle by nonaromatic six-membered heterocycles (piperidine, morpholine, thiomorpholine, and?N-methylpiperazine) as potential bioisosteres. Beyond that, this approach should give more information about the indispensability of the?aromatic ring as a basic head group. Besides these changes, a variation of the spacer length (C3–C5) connecting the heterocycle and the cyanoguanidine moiety has been made to possibly trigger the selectivity towards the respective HRs. Investigations in radioligand-binding assays exhibited only very weak activity at the hH1R and hH3R, while nearly all compounds were inactive at the hH2R and hH4R. In the case of piperidine-containing compounds, moderate affinities at the hH3R over the single-digit micromolar range were detected.

PROCESS FOR THE PREPARATION OF N-[(3-AMINOOXETAN-3-YL)METHYL]-2-(1,1-DIOXO-3,5-DIHYDRO-1,4-BENZOTHIAZEPIN-4-YL)-6-METHYL-QUINAZOLIN-4-AMINE

The present invention relates to a novel process for the preparation of a compound of the formula (I): and pharmaceutically acceptable acid addition salts thereof, which is useful for prophylaxis and treatment of respiratory syncytial virus (RSV) infection in mammal or human being.

Insights into the Pummerer synthesis of oxazolines

A rapid and simple method to access unnatural 2-substituted 5-thio oxazolines has been developed. This methodology is based on a Pummerer reaction followed by an intramolecular nucleophilic substitution, which changes the paradigm for the normal use of a base in Pummerer chemistry. We also provide a useful two-step method for the synthesis of the starting material and a mechanistic proposal based on experimental observations, which contests the previously proposed reaction pathway. The reaction proved to be general, and different substituents, such as alkyl, aryl, alkenyl and functionalized groups, can be used without a significant decrease in efficiency.

Design, synthesis, and activity evaluation of selective inhibitors of anti-apoptotic Bcl-2 proteins: The effects on the selectivity of the P1 pockets in the active sites

The anti-apoptotic Bcl-2 proteins are attractive targets for anti-cancer drug development, and the discovery of their selective inhibitors has become a research focus. In this Letter, obvious differences in the P1 pocket of the active site between Bcl-2, Bcl-xL, and Mcl-1 proteins were proposed by the structural comparison of these proteins. As a result, the groups in their inhibitors binding to the P1 pockets may have significant effect on the selectivity for these proteins. Based on this hypothesis, five types of derivatives of the lead compound B-1 were designed, and several highly selective inhibitors of Bcl-xL(E-1) or Mcl-1 proteins (G) were found. The selective inhibitors of Mcl-1 protein found in this Letter provide new structural types for the development of novel antitumor agents.

PROCESS FOR THE PREPARATION OF N-[(3-AMINOOXETAN-3-YL)METHYL]-2-(1,1-DIOXO-3,5-DIHYDRO-1,4-BENZOTHIAZEPIN-4-YL)-6-METHYL-QUINAZOLIN-4-AMINE

The present invention relates to a novel process for the preparation of a compound of the formula (I) and pharmaceutically acceptable acid addition salts thereof, which is useful for prophylaxis and treatment of respiratory syncytial virus (RSV) infection in mammal or human being.

Tuning of the copper-thioether bond in tetradentate N3S (thioether) ligands; O-O bond reductive cleavage via a [Cu II2(μ-1,2-peroxo)]2+/[CuIII 2(μ-oxo)2]2+ equilibrium

Current interest in copper/dioxygen reactivity includes the influence of thioether sulfur ligation, as it concerns the formation, structures, and properties of derived copper-dioxygen complexes. Here, we report on the chemistry of {L-CuI}2-(O2) species L = DMMESE, DMMESP, and DMMESDP, which are N 3S(thioether)-based ligands varied in the nature of a substituent on the S atom, along with a related N3O(ether) (EOE) ligand. CuI and CuII complexes have been synthesized and crystallographically characterized. Copper(I) complexes are dimeric in the solid state, [{L-CuI}2](B(C 6F5)4)2, however are shown by diffusion-ordered NMR spectroscopy to be mononuclear in solution. Copper(II) complexes with a general formulation [L-CuII(X)]n+ {X = ClO4-, n = 1, or X = H2O, n = 2} exhibit distorted square pyramidal coordination geometries and progressively weaker axial thioether ligation across the series. Oxygenation (-130 °C) of {( DMMESE)CuI}+ results in the formation of a trans-μ-1,2-peroxodicopper(II) species [{(DMMESE)Cu II}2(μ-1,2-O22-)]2+ (1P). Weakening the Cu-S bond via a change to the thioether donor found in DMMESP leads to the initial formation of [{( DMMESP)CuII}2(μ-1,2-O2 2-)]2+ (2P) that subsequently isomerizes to a bis-μ-oxodicopper(III) complex, [{(DMMESP)CuIII} 2(μ-O2-)2]2+ (2O), with 2P and 2O in equilibrium (Keq = [2 O]/[2P] = 2.6 at -130 °C). Formulations for these Cu/O2 adducts were confirmed by resonance Raman (rR) spectroscopy. This solution mixture is sensitive to the addition of methylsulfonate, which shifts the equilibrium toward the bis-μ-oxo isomer. Further weakening of the Cu-S bond in DMMESDP or substitution with an ether donor in DMMEOE leads to only a bis-μ-oxo species (3O and 4 O, respectively). Reactivity studies indicate that the bis-μ-oxodicopper(III) species (2O, 3O) and not the trans-peroxo isomers (1P and 2P) are responsible for the observed ligand sulfoxidation. Our findings concerning the existence of the 2P/2O equilibrium contrast with previously established ligand-CuI/O2 reactivity and possible implications are discussed.

Design, synthesis, and activity evaluation of broad-spectrum small-molecule inhibitors of anti-apoptotic Bcl-2 family proteins: Characteristics of broad-spectrum protein binding and its effects on anti-tumor activity

On the basis of the comparison of the structure of the Bim BH3: Bcl-x L complex and that of the ABT-737: Bcl-xL complex, a series of class A compounds were designed. These compounds had the basic skeleton of ABT-737 and the h2 residues of Bim BH3. These residues had shown themselves to be relevant to Bim BH3's broad-spectrum binding properties in saturation mutagenesis assays. Unlike ABT-737, which is a selective inhibitor of anti-apoptotic members of the Bcl-2 protein family, the class A compounds showed broad-spectrum binding activity to target proteins similar to those of Bim BH3 peptide. Then class B compounds were synthesized by modifying the structure of the most effective class A compound, A-4. Most of these class B compounds showed better binding affinity to the target proteins than the class A compounds had. They also showed themselves more effective than ABT-737 at inhibiting growth in multiple tumor cell lines known to express Bcl-x L, Bcl-2, and Mcl-1 proteins at high levels. Compounds B-11 and B-12 had the strongest anti-tumor activity of any compounds we produced. This study suggests that it is feasible to design small-molecule inhibitors based on the structure of Bim BH3, which shows broad-spectrum binding to Bcl-xL, Bcl-2, and Mcl-1 proteins. Our results also suggest that the broad-spectrum properties of small-molecule inhibitors binding to target proteins play a critical role in inhibiting the growth of many tumor cells. Finally, our study provides a series of lead compounds that merit further research into anti-cancer therapeutics.