19311-72-9

Upstream product

• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 108-31-6 maleic anhydride 
• 51-67-2 tyrosamine 

Downstream Products

• 904315-33-9 C₃₁H₃₂N₂O₆ 

Relevant academic research and scientific papers

Synthesis of jacaranone-derived nitrogenous cyclohexadienones and their antiproliferative and antiprotozoal activities

The cytotoxic and antiprotozoal activities of the phytoquinoide, jacaranone, and related compounds have been an ongoing topic in recent drug discovery. Starting from the natural product-derived cyclohexadienone scaffold, a series of nitrogen-containing derivatives were synthesized and subsequently evaluated for their antiproliferative and antiprotozoal activity. Anticancer potency was analyzed using different types of cancer cell lines: MDA-MB-231 breast cancer, CCRF-CEM leukemia, HCT-116 colon cancer, U251 glioblastoma, and, in addition, non-tumorigenic MRC-5 lung fibroblasts. Antiproliferative activities at micromolar concentrations could be shown. Antiprotozoal activity was assessed against Plasmodium falciparum NF54 and Trypanosoma brucei rhodesiense STIB900. For all compounds, selectivity indices (SI) were calculated based on assessed cytotoxicity towards L6 cells. In addition, the structure-activity-relationships and physicochemical parameters of these compounds are discussed.

A Photochemical Ligation System Enabling Solid-Phase Chemiluminescence Read-Out

The peroxyoxalate chemiluminescence (PO-CL) reaction is among the most powerful and versatile techniques for the detection of hydrogen peroxide (H2O2) and has been employed in various biological and chemical applications over the past 50 years. However, its two-component nature (peroxyoxalate and fluorophore) limits its use. This contribution introduces an innovative and versatile photochemical platform technology for the synthesis of inherently fluorescent PO probes by exploiting the nitrile imine-mediated tetrazole-ene cycloaddition (NITEC) reaction. In the presence of hydrogen peroxide, the pioneered “2-in-1” molecule emits either yellow or blue light, depending on tetrazole (Tz) structure. Even in the absence of base, the emitted light remains visible and H2O2 could be detected in the nanomolar range. Critically, the PO-Tz can be readily incorporated into polymeric materials. As a first application of this promising material, a tailor-made PO-Tz is grafted on poly(divinylbenzene) (PDVB) particles to enable solid-phase chemiluminescence on microspheres.

Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions

DNA-encoded chemical libraries are increasingly being employed for the identification of binding molecules to protein targets of pharmaceutical relevance. Here, we describe the synthesis and characterization of a DNA-encoded chemical library, consisting of 4000 compounds generated by Diels-Alder cycloaddition reactions. The compounds were encoded with unique DNA fragments which were generated through a stepwise assembly process and serve as amplifiable bar codes for the identification and relative quantification of library members.

Thebaine adducts with maleimides. Synthesis and transformations

Diels-Alder reaction of thebaine with maleimides is structurally specific and yields [7,8,3′,4′]-succinimido-endo-ethenotetrahydrothebaines containing N′-alkyl, cycloalkyl, aralkyl or aryl substituents. N′-[1(S)-hydroxymethyl-2-methylpropyl]-succinimido-6,14-endo- ethenotetrahydrothebaine formed in reaction of S-valinol with (7α,8α)-anhydrido-6,14-endo-ethenotetrahydrothebaine. The reduction of the adducts by LiAlH4 afforded N′-substituted 7,8-pyrrolidino-endo-ethenotetrahydrothebaines. The reduction of fused succinimides by NaBH4 resulted in the corresponding 2′α-hydroxylactam derivatives. O-Demethylation of the tetrahydrothebaine pyrrolidine derivatives effected by BBr3 afforded compounds of the tetrahydrooripavine series. The O-demethylation of tetrahydrothebaine succinimide derivatives gave rise to the corresponding 6-demethyl-endo-ethenotetrahydrooripavines. Alkylation conditions were found for N′-(4-hydroxyphenethyl)-substituted tetrahydrothebaine succinimide derivatives. 2005 Pleiades Publishing, Inc.