36293-01-3

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 79-04-9 chloroacetyl chloride 
• 593-71-5 Chloroiodomethane 
• 14649-03-7 (S)-phenylethyl isocyanate 
• 14428-98-9 (E)-1-phenyl-N-(1-phenylethylidene)methanamine 

Downstream Products

• 143746-58-1 (4S)-N-((S)-1-phenyleth-1-yl)-4-phenyl-3-azapentanamide 
• 90600-87-6 (E)-3-Methyl-3-phenyl-N-<(S)-1-phenylethyl>glycidamide 
• 90640-02-1 (2R,3R)-3-Methyl-3-phenyl-N-<(S)-1-phenylethyl>glycidamide 
• 90640-01-0 (2S,3S)-3-Methyl-3-phenyl-N-<(S)-1-phenylethyl>glycidamide 
• 188747-38-8 1,4,7,10-tetrakis<(S)-1-(1-phenyl)ethylcarbamoylmethyl>-1,4,7,10-tetraazacyclododecane 
• 308821-51-4 (S,S,S)-1-(2'-methylphenanthridinyl)-4,7,10-tris[1-(1-phenyl)ethylcarbamoylmethyl]-1,4,7,10-tetraazacyclododecane 
• 153645-33-1 N-Phenylethyl hydroxyacetamide 
• 850913-06-3 (S,S,S)-1-(3-methyl-10,11,12,13-tetrahydrodipyrido[3,2-a:2',3'-c]phenazine)-4,7,10-tris[N-(1-phenylethyl)carbamoylmethyl]-1,4,7,10-tetraazacyclododecane 
• 955938-07-5 10-((1-[6-(tert-butyl)-10-oxo-10H-9-oxa-1-azaanthracen-2-yl]-1H-pyrazol-3-yl)methyl)-N⁽¹⁾,N⁽⁴⁾,N⁽⁷⁾-tris[(1S)-1-phenylethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetamide 
• 350681-11-7 N'-[(S)-1'-Phenylethyl]-N-(diphenylmethylene)glycinamide 

Relevant academic research and scientific papers

Synthesis, characterization, and DFT studies of a new chiral ionic liquid from (S)-1-phenylethylamine

A new chiral ionic liquid was synthesized from (S)-1-phenylethylamine and it was studied by IR, Raman, polarimetry, NMR and X-ray crystal diffraction. Its vibrational spectral bands are precisely ascribed to the studied structure with the aid of DFT theor

Rational drug design of benzothiazole-based derivatives as potent signal transducer and activator of transcription 3 (STAT3) signaling pathway inhibitors

The cumulative evidence supports STAT3, a transcriptional mediator of oncogenic signaling, as a therapeutic target in cancer. The development of STAT3 inhibitors remain an active area of research as no inhibitors have yet to be approved for cancer treatment. In a continuing effort to develop more potent STAT3 inhibitors based on our previously identified hit compound 16w, a series of benzothiazole derivatives with unique binding mode in SH2 domain of STAT3 were designed, synthesized and biologically evaluated. Of note, compound B19 demonstrated excellent activity against IL-6/STAT3 signaling pathway with the IC50 value as low as 0.067 μM as determined by a luciferase reporter assay. Moreover, multiple compounds displayed potent antiproliferative activity against MDA-MB-468 and JAK2 mutant HEL cell lines. Further biochemical study using Western blot assay indicated that B19 blocked the phosphorylation of STAT3 at Tyr 705 and Ser 727 and thus suppressed STAT3-mediated gene expression of c-MYC and MCL-1. Simultaneously, it induced cancer cell G2/M phase arrest and apoptosis both in MDA-MB-468 and HEL cell lines. Finally, molecular docking study along with surface plasmon resonance (SPR) and fluorescence polarization (FP) assays disclosed the binding mode of B19 in STAT3 SH2 domain. Taken together, our finding suggests that B19 is a promising therapeutic STAT3 inhibitor for cancer treatment.

Effect of chirality and redox potentials on the cytotoxicity of new ferrocene functionalized chiral tertiary amines

Optically pure enantiomeric pair viz. ferrocene functionalized chiral tertiary amines S,S-(-)-1 and R,R-(+)-2 have been synthesized from ferrocenylmethylamine to probe the influence of chirality and the redox potential on their anti-proliferative activity. Compounds were characterized by microanalysis, HPLC, 1H, 13C NMR, UV-visible, fluorescence, FTIR, thermogravimetric and crystallographic techniques. The single crystal X-ray diffraction (SCXRD) study revealed that the molecules of 1 holding S,S-chirality at benzylic carbons forms a fascinating M-helix while 2 holding R,R-chirality at benzylic carbons forms P-helix by involving intra- and intermolecular H-bonding interactions as verified by Hirshfeld surface analysis. Chirality-related influence was observed on the antiproliferative activity of enantiomeric pair and at the supramolecular level. For instance, enantiomer R,R-(+)-2 is found to be highly active against all the investigated human carcinoma cell lines MCF 7, IMR 32, HepG2, and immortal L132 cell lines. In particular, R,R-(+)-2 exhibited more than 10 folds better antiproliferation (IC 50: 6.35±0.19 μM) than other enantiomer S,S-(-)-1 (IC50: 65.96 ± 0.12 μM) and four folds better activity than highly successful anticancer drug, cisplatin (IC50: 24.3 ± 1.7 μM) against Hep G2 cell line. The electrochemical, DFT calculations and molecular docking study have been performed to justify the experimental outcomes.

Using chiral ionic liquid additives to enhance asymmetric induction in a Diels-Alder reaction

A bis-oxazoline ligand has been complexed using Cu(ii) and Zn(ii) trifluoromethanesulfonate and a range of chiral ionic liquid (CIL) additives based on natural products were used as a co-catalyst for a Diels-Alder reaction. The catalytic performance of th

(S)-N-(1-phenethyl) thioacetamide compound as well as medicinal composition and application thereof

The invention belongs to the field of medicinal chemicals, relates to a STAT3 inhibitor, and in particular to a (S)-N-(1-phenethyl) thioacetamide compound of a structure of formula (I) as shown in the specification, a medicinal composition of the compound as an STAT3 (Signal Transducer and Activator of Transcription 3) signal path inhibitor, and application of the compound in preparing anti-tumor medicines. Results of cell experiment show that the compound targets a Phe-Lys-Thr-Lys-Leu pentapeptide binding region in an STAT3 SH2 structure domain, then inhibits STAT3 protein monomer dimerization and silencing STAT3 signal transduction and functions, has a remarkable anti-tumor effect and good physical and chemical properties, is particularly capable of effectively preventing cell proliferative activity in breast cancer cells with high expression of STAT3 and HEL cells on which JAK2/STAT3 signal paths depend with JAK2 V671F mutation, and moreover is capable of effectively inhibiting phosphorylation of STAT3 in the breast cancer cells with high expression of STAT3 and expression of downstream target genes such as CyclinD1 and Bc1-2.

Homologation of isocyanates with lithium carbenoids: A straightforward access to α-halomethyl- and α,α-dihalomethylamides

Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of α-halo- and α,α-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smoo

Addition of lithium carbenoids to isocyanates: A direct access to synthetically useful N-substituted 2-haloacetamides

The addition of lithium carbenoids to isocyanates provides a versatile access to N-substituted 2-haloacetamides: the reaction tolerates the presence of variously functionalized substituents on the nitrogen atom, including sterically demanding ones and reactive halogens. No erosion of the enantiopurity was observed in the case of optically active isocyanates. One of the substrates prepared has been employed in Charette's type chemoselective addition of a Grignard reagent to access an α-chloroketone.

Asymmetric synthesis of novel (1h-benzo[d]imidazol -2-ylthio)- and (di-n-butylamino-2-ylthio)acetamides

Asymmetric synthesis of novel (1H-benzo[d]imidazol-2-ylthio)- and (di-n-butylamino)acetamides is described. The o-nitrobenzyl oxime ethers were reduced with borane in the presence of oxazaborolidenes derived from norephedrine or diphenylvalinol and diphenylphosphinic amide was reduced with modified sodium tetrahydroborate catalyzed with β-ketoiminato cobalt(II) complex to the corresponding amines with high yields and moderate enantiomeric excess. Reaction of amines with 2-chloroacetyl chloride and next with thiobenzimidazole or n-dibutylamine gave corresponding products with high yields.

Discovery of novel inhibitors of signal transducer and activator of transcription 3 (STAT3) signaling pathway by virtual screening

Inhibition of the signal transducer and activator of transcription 3 (STAT3) signaling pathway has been considered a novel therapeutic strategy to treat human cancers that harbor aberrantly-active STAT3. In this study, nearly 204,000 compounds in Specs database were screened by virtual screening, and samples of top 100 compounds identified as candidate small-molecule inhibitors of STAT3 were evaluated by STAT3-dependent luciferase reporter assay as well as other cell-based assays. A benzothiazole core scaffold containing compound, 9, was identified as an inhibitor of IL-6/STAT3 signaling with an IC50 of 3.567 μM. It is the first time to discover benzothiazole scaffold as a potent STAT3 signaling inhibitor. We further investigated the (structure-activity relationship) SAR of the benzothiazole analogues, and discovered compound 16w as a better small-molecule inhibitor. Both compounds inhibited the phosphorylation of STAT3 and had no obvious effect on upstream JAK2 kinase.

Small molecule as a chiral organocatalyst for asymmetric strecker reaction

A simple and novel chiral amide-based organocatalyst 6 was synthesized from readily available starting materials for the asymmetric Strecker reaction. A variety of N-benzhydryl- and N-tosyl-substituted imines were found to be suitable substrates with i-Pr