182074-37-9

Upstream product

• 111687-77-5 (1R,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate 
• 100-52-7 benzaldehyde 
• 73-22-3 L-Tryptophan 

Relevant academic research and scientific papers

Discovery of novel phosphatidylcholine-specific phospholipase C drug-like inhibitors as potential anticancer agents

Phosphatidylcholine–specific phospholipase C (PC-PLC) is a promising target for new anticancer treatment. Herein, we report our work in the discovery of novel drug-like PC-PLC inhibitors. Virtual screening led to the identification of promising hits from

Biological Studies and Target Engagement of the 2- C -Methyl- d -Erythritol 4-Phosphate Cytidylyltransferase (IspD)-Targeting Antimalarial Agent (1 R,3 S)-MMV008138 and Analogs

Malaria continues to be one of the deadliest diseases worldwide, and the emergence of drug resistance parasites is a constant threat. Plasmodium parasites utilize the methylerythritol phosphate (MEP) pathway to synthesize isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are essential for parasite growth. Previously, we and others identified that the Malaria Box compound MMV008138 targets the apicoplast and that parasite growth inhibition by this compound can be reversed by supplementation of IPP. Further work has revealed that MMV008138 targets the enzyme 2-C-methyl-d-erythritol 4-phosphate cytidylyltransferase (IspD) in the MEP pathway, which converts MEP and cytidine triphosphate (CTP) to cytidinediphosphate methylerythritol (CDP-ME) and pyrophosphate. In this work, we sought to gain insight into the structure-activity relationships by probing the ability of MMV008138 analogs to inhibit PfIspD recombinant enzyme. Here, we report PfIspD inhibition data for fosmidomycin (FOS) and 19 previously disclosed analogs and report parasite growth and PfIspD inhibition data for 27 new analogs of MMV008138. In addition, we show that MMV008138 does not target the recently characterized human IspD, reinforcing MMV008138 as a prototype of a new class of species-selective IspD-targeting antimalarial agents.

Convergent synthesis of complex diketopiperazines derived from pipecolic acid scaffolds and parallel screening against GPCR targets

A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "

Microwave accelerated Pictet-Spengler reactions of tryptophan with ketones directed toward the preparation of 1,1-disubstituted indole alkaloids

Using the Pictet-Spengler reactions of tryptophan with aldehydes under acidic conditions at ambient temperature, diastereoisomers of 1,3-disubstituted-1,2,3,4-tetrahydro-β-carbolines could readily be furnished in short time (0.5-4 h) with good to excellent yields (50-98%). Though intrinsically slow in reaction rates, ketone reactions can be accelerated (from days to minutes) using microwaves in open vessels with high isolated yields (67-99%), making those carbolines feasible reaction intermediates for the synthesis of both natural and unnatural indole alkaloids. Preparation of two indole alkaloids, tetrahydro-β-carbolinediketopiperazines and tetrahydro-β-carbolinehydantoins, were briefly discussed. Graphical Abstract

L-tryptophan reacts with naturally occurring and food-occurring phenolic aldehydes to give phenolic tetrahydro-β-carboline alkaloids: Activity as antioxidants and free radical scavengers

The reaction between the essential amino acid L-tryptophan and flavoring or naturally occurring phenyl and phenolic aldehydes was studied, and the alkaloidal reaction products were characterized by NMR and HPLC-MS, Benzaldehyde, vanillin, syringaldehyde, salicylaldehyde, and anisaldehyde condensed with L-tryptophan in aqueous-acidic media affording the corresponding phenolic tetrahydro-β-carboline-3-carboxylic acid as two diastereoisomers, 1S, 3S-cis and 1R, 3S-trans. With the exception of benzaldehyde, the rest of the aldehydes needed heating conditions (70 °C) to significantly form tetrahydro-β-carbolines over time with the cyclization highly favored at low pH. This suggests a likely formation of these compounds under conditions that may occur in foods, food processing, or cooking. The new phenolic tetrahydro-β-carboline alkaloids were assayed, for the first time, for their activity as free radical scavengers and antioxidants and showed good antioxidant properties with Trolox equivalent antioxidant capacity (TEAC) values much higher than those of ascorbic acid and the water soluble vitamin E analogue, Trolox, in the 2,2′-azinobis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) assay.