52084-10-3

Upstream product

• 24788-07-6 benzyl (S)-(1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 104-94-9 4-methoxy-aniline 
• 79962-07-5 L-thiophenylalanine 
• 696-62-8 para-iodoanisole 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 870533-26-9 (S)-tert-butyl (1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 63-91-2 L-phenylalanine 

Downstream Products

• 1020151-04-5 C₃₁H₃₆N₂O₄ 

Relevant academic research and scientific papers

Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions

The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.

Visible Light-Induced Amide Bond Formation

A metal-, base-, and additive-free amide bond formation reaction was developed under an organic photoredox catalyst. This green approach showed excellent functional selectivity without affecting other functional groups such as alcohols, phenols, ethers, esters, halogens, or heterocycles. This method featured a broad substrate scope, good compatibility with water and air, and high yields (≤95%). The potential utilities were demonstrated by the synthesis of important drug molecules such as paracetamol, melatonin, moclobemide, and acetazolamide.

Bifunctional Naphthoquinone Aromatic Amide-Oxime Derivatives Exert Combined Immunotherapeutic and Antitumor Effects through Simultaneous Targeting of Indoleamine-2,3-dioxygenase and Signal Transducer and Activator of Transcription 3

Indoleamine-2,3-dioxygenase 1 (IDO1) and signal transducer and activator of transcription 3 (STAT3) are important targets in the tumor microenvironment for cancer therapy. In the present study, a set of naphthoquinone aromatic amide-oxime derivatives were designed, which stimulated the immune response via IDO1 inhibition and simultaneously displayed powerful antitumor activity against three selected cancer cell lines through suppressing STAT3 signaling. The representative compound 8u bound effectively to IDO1, with greater inhibitory activity relative to the commercial IDO1 inhibitor 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L) in addition to the efficient suppression of nuclear translocation of STAT3. Consistently, in vivo assays demonstrated a higher antiproliferative activity of compound 8u in both wild-type B16-F10 isograft tumors and an athymic HepG2 xenograft model relative to 1-methyl-l-tryptophan (1-MT) and doxorubicin (DOX). This bifunctional compound with dual immunotherapeutic and anticancer efficacy may represent a new generation of highly efficacious drug candidates for cancer therapy.

Synthesis and biological evaluation of terminal functionalized thiourea-containing dipeptides as antitumor agents

A series of antitumor agents based on terminal functionalized dipeptide derivatives containing the thiourea moiety were synthesized and evaluated for antiproliferative activity using a panel of cancer cell lines, and the effects and mechanism of apoptosis induction were determined. These compounds exhibited significant selectivity to different cancer cell lines with IC50 values at micromolar concentrations. In particular, compound I-11 appeared to be the most potent compound, with an IC50 = 4.85 ± 1.44 μM against the NCI-H460 cell line, at least partly, by the induction of apoptosis. Mechanistically, compound I-11 induced the activation of caspase-12 and CHOP, which triggered apoptotic signalling via the ROS-dependent endoplasmic reticulum pathway and arrested the cell cycle at the S phase. Thus, we concluded that dipeptide derivatives containing the thiourea moiety terminally functionalized by electron-withdrawing substituents may be potential antitumor agents for further investigation.

Cinnamamide compound, and salt, intermediate preparation method and application thereof

The invention discloses a cinnamamide compound as shown in a formula A which is defined in the specification, and a pharmaceutically acceptable salt thereof. The invention also discloses a preparation method, intermediate and application of the cinnamamide compound. The compound is a histone deacetylase inhibitor and is applicable to pharmaceutical compositions with antineoplastic effect.

Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation

A series of dehydroabietic acid (DHAA) dipeptide derivatives containing the sulfonamide moiety were designed, synthesized and evaluated for inhibition of MMPs as well as the effects of in vitro cell migration. These compounds exhibited relatively good inhibition activity against MMPs with IC50 values in low micromolar range. A docking study of the most active compound 8k revealed key interactions between 8k and MMP-3 in which the sulfonamide moiety and the dipeptide group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU. In particular, compound 8k appeared to be the most potent compound against the HepG2 cell line, at least partly, by inhibition of the activity of MMP-3 and apoptosis induction. The treatment of HepG2 cells with compound 8k resulted in inhibition of in vitro cell migration through wound healing assay and G1 phase of cell cycle arrested. In addition, 8k-induced apoptosis was significantly facilitated in HepG2 cells. Thus, we conclude that DHAA dipeptide derivatives containing the sulfonamide moiety may be the potential MMPs inhibitors with the ability to suppress cells migration.

Caproamide derivatives, its preparation method, intermediate and application

The invention discloses a caproamide derivative represented by formula A or a pharmaceutically acceptable salt thereof, wherein R1 is H or halogen; R2 is halogen, or C1-C4 alkyl, C1-C4 alkoxy, or a C3-C7 heterocyclic ring, the number of heteroatom in the heterocyclic ring is 1-3, and the heteroatom is nitrogen and/or oxygen; R0 is benzyl, substituted benzyl or C4 alkyl, and a substituent of substituted benzyl is C1-C3 alkyl. The invention also discloses a preparation method, an intermediate and an application of the caproamide derivative. The caproamide derivative provided by the invention has effective and better antibacterial function, and has higher application value in the medical field.

Synthesis and antitumor activities of novel dipeptide derivatives derived from dehydroabietic acid

A series of dipeptide derivatives from dehydroabietic acid were designed and synthesized as novel antitumor agents. The antitumor activities screening indicated that many compounds showed moderate to high levels of inhibition activities against NCI-H460, HepG2, SK-OV-3, BEL-7404, HeLa and HCT-116 cancer cell lines and that some displayed more potent inhibitory activities than commercial anticancer drug 5-fluorouracil. The mechanism of representative compound 7b was studied by AO/EB staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining, TUNEL assay, DNA ladder assay and flow cytometry, which exhibited that the compound could induce apoptosis in HeLa cells. Further investigation showed that compound 7b induced apoptosis of HeLa cells through a mitochondrial pathway.

Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides

A series of α-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)2 catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process.

Synthesis of rupestonic acid amide derivatives and their in vitro activity against type A3 and B flu virus and herpes simplex I and II

Derivatives of rupestonic acid (5a-e) were synthesized and evaluated preliminarily at the National Center for Drug Screening (PRC) for antiviral activity against type A3 and B flu virus and HSV-I and HSV-II in order to improve the biological ac