171001-99-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-(Boc-aMino)-2-phenylethyl 4-Methylbenzenesulfonate is used as a key intermediate in the synthesis of various pharmaceuticals. Its role is crucial in the development of new drugs, as it provides a stable and protected amine group that can be further modified or incorporated into more complex molecular structures.
Used in Agrochemical Production:
In the agrochemical industry, (S)-2-(Boc-aMino)-2-phenylethyl 4-Methylbenzenesulfonate is employed as a building block for the creation of novel compounds with potential applications in pest control, crop protection, and other agricultural areas. Its unique structure allows for the design of targeted and effective agrochemicals.

Upstream product

• 117049-14-6 tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate 
• 98-59-9 p-toluenesulfonyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 20989-17-7 (2S)-2-phenylglycinol 
• 59410-82-1 (S)-α-phenylglycine ethyl ester hydrochloride 

Downstream Products

• 172823-12-0 (R)-3-(N-tert-butoxycarbonylamine)-3-phenylpropanenitrile 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 171002-01-0 (S)-N-t-Boc-2-amino-2-phenyl-1-thiophenylethane 
• 171002-02-1 ((S)-2-tert-Butylsulfanyl-1-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 171002-00-9 (S)-tert-butyl (2-(methylthio)-1-phenylethyl)carbamate 
• 1240474-61-6 4-((S)-2-dimethylamino-1-phenyl-ethylamino)-quinazoline-8-carboxamide 
• 1240476-05-4 4-((S)-2-cyclopropylamino-1-phenyl-ethylamino)-quinazoline-8-carboxamide 
• 1160983-80-1 (S)-2-azido-1-phenyl-ethylamine hydrochloride 
• 1239019-97-6 (S)-tert-butyl (2-(diphenylphosphino)-1-phenylethyl)carbamate 

Relevant academic research and scientific papers

Construction and activity evaluation of novel benzodioxane derivatives as dual-target antifungal inhibitors

Ergosterol exert the important function in maintaining the fluidity and osmotic pressure of fungal cells, and its key biosynthesis enzymes (Squalene epoxidase, SE; 14 α-demethylase, CYP51) displayed the obvious synergistic effects. Therefore, we expected to discover the novel antifungal compounds with dual-target (SE/CYP51) inhibitory activity. In the progress, we screened the different kinds of potent fragments based on the dual-target (CYP51, SE) features, and the method of fragment-based drug discovery (FBDD) was used to guide the construction of three different series of benzodioxane compounds. Subsequently, their chemical structures were synthesized and evaluated. These compounds displayed the obvious biological activity against the pathogenic fungal strains. Notably, target compounds 10a-2 and 22a-2 possessed the excellent broad-spectrum anti-fungal activity (MIC50, 0.125–2.0 μg/mL) and the activity against drug-resistant strains (MIC50, 0.5–2.0 μg/mL). Preliminary mechanism studies have confirmed that these compounds effectively inhibited the dual-target (SE/CYP51) activity, they could cause fungal rupture and death by blocking the bio-synthetic pathway of ergosterol. Further experiments discovered that compounds 10a-2 and 22a-2 also maintained a certain of anti-fungal effect in vivo. In summary, this study not only provided the new dual-target drug design strategy and method, but also discover the potential antifungal compounds.

Identification of Clinical Candidate M2698, a Dual p70S6K and Akt Inhibitor, for Treatment of PAM Pathway-Altered Cancers

Herein, we report the discovery of a novel class of quinazoline carboxamides as dual p70S6k/Akt inhibitors for the treatment of tumors driven by alterations to the PI3K/Akt/mTOR (PAM) pathway. Through the screening of in-house proprietary kinase library, 4-benzylamino-quinazoline-8-carboxylic acid amide 1 stood out, with sub-micromolar p70S6k biochemical activity, as the starting point for a structurally enabled p70S6K/Akt dual inhibitor program that led to the discovery of M2698, a dual p70S6k/Akt inhibitor. M2698 is kinase selective, possesses favorable physical, chemical, and DMPK profiles, is orally available and well tolerated, and displayed tumor control in multiple in vivo studies of PAM pathway-driven tumors.

Synthesis and selective recognition toward zinc ion of chiral poly(imine-triazole)

A novel AB type of clickable monomer, (S)-2-[(2-azido-1-phenylethylimino) methyl]-5-propargyloxyphenol (AMPP) was designed and polymerized to yield a class of main-chain chiral poly(imine-triazole)s through the metal-free click reaction. With the thermally induced polymerization, the desired polytriazoles can be easily prepared in high yields by a stepwise heating-up process and have the number-average molecular masses ranging from 5.1 × 103 to 58.1 × 103 (polydispersity indices = 1.38-1.68). The polymers were characterized by Fourier Transform Infrared spectroscopy (FTIR), 1H Nuclear Magnetic Resonance (NMR), and gel permeation chromatography, and their optical properties were studied by fluorescence and circular dichroism (CD) spectroscopies. As a chemosensor, these polymers exhibited a selective "turn-on" fluorescence enhancement response toward Zn2+ ion over other cations such as Na+, K +, Mg2+, Ca2+, Ag+, Pb2+, Cd2+, Hg2+, Mn2+, and Ni2+ in dimethyl sulfoxide. However, the Zn2+-induced fluorescence signal was subject to serious interference by Al3+, Cu2+, Cr 3+, and Fe3+ ions. Interestingly, the chiral polymer showed distinctive changes in the CD spectra on complexation with Zn 2+, which allowed for the discrimination of this ion in the presence of other species tested including those interfering ions observed in the fluorescent detection.

Synthesis of iron P-N-P' and P-NH-P asymmetric hydrogenation catalysts

Complexes of the type mer,trans-[Fe(P-N-P)(CO)2Br]BF4 are known to be precatalysts for the asymmetric direct hydrogenation of ketones and imines. Employing related ligand scaffolds, we successfully generated and tested the series of three new precatalysts [Fe(PCy2CH2CH-NCH(R)CH2PPh2)(CO)2Br]BF4 with chirality derived from (S)-amino alcohols with phenyl, benzyl, and isopropyl substituents (R), yielding fairly active and selective systems. For the reduction of acetophenone to (S)-1-phenylethanol turnover frequencies up to 920 h-1 and up to 74% enantiomeric excess at 50 °C and 5-25 atm of H2 were obtained. We found, however, that placing these large groups R next to nitrogen was found to be deleterious to catalytic activity. Extending the scope of the ligand structure, we then developed a series of six P-N-P and five P-NH-P systems starting with o-diphenylphosphinobenzaldehyde and the phosphine-amines PPh2CHR1CHR2NH2 (R1 = H, Ph, CH2Ph, iPr with R2 = H or R1 = Me, Ph with R2 = Ph) as well as their corresponding [Fe(P-N-P)(NCMe)3][BF4]2 and [Fe(P-NH-P)(NCMe)3][BF4]2 complexes, which were not catalytically active. Finally, we made the new achiral iron complex mer,cis-Fe(PPh2(o-C6H4)CHNCH2CH2PPh2)(CO)Br2, which was active for the direct hydrogenation of acetophenone, achieving turnover frequencies of 800 h-1 at 50°C and 25 atm of H2.

BICYCLIC AZAHETEROCYCLIC CARBOXAMIDES AS INHIBITORS OF THE KINASE P70S6K

The invention provides novel bicyclic azaheterocyciic carboxamide compounds according to Formula (I), their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

5-Lipoxygenase-activating protein inhibitors. Part 2: 3-{5-((S)-1-Acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid (AM679)-A potent FLAP inhibitor

A series of potent 5-lipoxygenase-activating protein (FLAP) inhibitors are herein described. SAR studies focused on the discovery of novel alicyclic moieties appended to an indole core to optimize potency, physical properties and off-target activities. Subsequent SAR on the N-benzyl substituent of the indole led to the discovery of compound 39 (AM679) which showed potent inhibition of leukotrienes in human blood and in a rodent bronchoalvelolar lavage (BAL) challenge model.

Syntheis of new chiral 5,6,7,8-tetrahydrotetrazolo[1,5-a]pyrazines from α-amino acid derivatives following "click" chemistry

An efficient and practical synthesis of new chiral fused tetrazoles have been synthesized following [3+2] cycloaddition reaction starting from α-amino acid derivatives.

Selenium promoted synthesis of enantiopure pyrrolidines starting from chiral aminoalcohols

Starting from commercially available enantiomerically pure aminoalcohols and using simple conversions promoted by organoselenium reagents, several enantiomerically pure substituted pyrrolidines were prepared. After double protections (R)- or (S)-2-phenylg

Preparation of an advanced phenylglycine-derived intermediate en route to the southern hemisphere tetraene of viridenomycin

A high-yielding synthesis of a phenylglycine derived (E,Z)-dienylboronate en route to the C16-C23 tetraene of the polyene macrolide viridenomycin is described. Crucial to this synthesis was the development of conditions enabling ready access to synthetically useful amino acid derivatives that should be widely applicable to other amino acids. These conditions confer advantages of increased yield and reliability over many of the existing literature alternatives, and also circumvent several of the problems encountered when dealing with such derivatives. The synthesis features a highly selective Heck coupling between an N-protected (Z)-alkenyl iodide and a hexylene glycol derived vinylboronate ester.

Synthesis of the kappa-agonist CJ-15,161 via a palladium-catalyzed cross-coupling reaction.

Syntheses of CJ-15,161 (1) involving intermolecular N-arylation of an appropriately functionalized diamine, obtained from the precursor alpha-amino acids or, more conveniently, from the corresponding 1,2-amino alcohols via 1,2,3-oxathiazolidine-2,2-dioxide 22, are reported.