19350-66-4

Usage

Uses

Used in Pharmaceutical Research:
2,6-DIMETHYL-1,4-DIHYDRO-PYRIDINE-3,4,5-TRICARBOXYLIC ACID 3,5-DIETHYL ESTER is used as a calcium channel blocker and vasodilator for its ability to regulate calcium flow and improve blood vessel dilation.
Used in Cardiovascular Medicine:
In the field of cardiovascular medicine, 2,6-DIMETHYL-1,4-DIHYDRO-PYRIDINE-3,4,5-TRICARBOXYLIC ACID 3,5-DIETHYL ESTER is used as a therapeutic agent for the treatment of cardiovascular diseases, particularly hypertension and angina, due to its vasodilatory effects that help in reducing blood pressure and improving blood flow to the heart.
Used in Neurological Medicine:
2,6-DIMETHYL-1,4-DIHYDRO-PYRIDINE-3,4,5-TRICARBOXYLIC ACID 3,5-DIETHYL ESTER is of interest for potential therapeutic use in neurological conditions, as it may possess neuroprotective properties that could be beneficial in treating various neurological disorders.

InChI:InChI=1/C14H19NO6/c1-5-20-13(18)9-7(3)15-8(4)10(11(9)12(16)17)14(19)21-6-2/h11,15H,5-6H2,1-4H3,(H,16,17)

Upstream product

• 626-34-6 ethyl aminocrotonate 
• 298-12-4 Glyoxilic acid 
• 626-34-6 ethyl 3-aminobut-2-enoate 

Relevant academic research and scientific papers

Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.

Site-Selective Itaconation of Complex Peptides by Photoredox Catalysis

Site-selective peptide functionalization provides a straightforward and cost-effective access to diversify peptides for biological studies. Among many existing non-invasive peptide conjugations methodologies, photoredox catalysis has emerged as one of the powerful approaches for site-specific manipulation on native peptides. Herein, we report a highly N-termini-specific method to rapidly access itaconated peptides and their derivatives through a combination of transamination and photoredox conditions. This strategy exploits the facile reactivity of peptidyl-dihydropyridine in the complex peptide settings, complementing existing approaches for bioconjugations with excellent selectivity under mild conditions. Distinct from conventional methods, this method utilizes the highly reactive carbamoyl radical derived from a peptidyl-dihydropyridine. In addition, this itaconated peptide can be further functionalized as a Michael acceptor to access the corresponding peptide-protein conjugate.

Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C?O Bond Homolysis

C-aryl glycosyl compounds offer better in vivo stability relative to O- and N-glycoside analogues. C-aryl glycosides are extensively investigated as drug candidates and applied to chemical biology studies. Previously, C-aryl glycosides were derived from lactones, glycals, glycosyl stannanes, and halides, via methods displaying various limitations with respect to the scope, functional-group compatibility, and practicality. Challenges remain in the synthesis of C-aryl nucleosides and 2-deoxysugars from easily accessible carbohydrate precursors. Herein, we report a cross-coupling method to prepare C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from glycosyl esters and bromoarenes. Activation of the carbohydrate substrates leverages dihydropyridine (DHP) as an activating group followed by decarboxylation to generate a glycosyl radical via C?O bond homolysis. This strategy represents a new means to activate alcohols as a cross-coupling partner. The convenient preparation of glycosyl esters and their stability exemplifies the potential of this method in medicinal chemistry.

Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

Carbamoylation of Azomethine Imines via Visible-Light Photoredox Catalysis

A versatile and robust photocatalytic methodology to install the amide functional group into azomethine imine ions is described. This protocol is distinguished by its broad scope and mild reaction conditions, which are well suited for the preparation of s

Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis

1,4-Dicarbonyl compounds are intriguing motifs and versatile precursors in numerous pharmaceutical molecules and bioactive natural compounds. Direct incorporation of two carbonyl groups into a double bond at both ends is straightforward, but also challenging. Represented herein is the first example of 1,2-dicarbonylation of alkenes by photocatalysis. Key to success is that N(n-Bu)4+ not only associates with the alkyl anion to avoid protonation, but also activates the α-keto acid to undergo electrophilic addition. The α-keto acid is employed both for acyl generation and electrophilic addition. By tuning the reductive and electrophilic ability of the acyl precursor, unsymmetric 1,4-dicarbonylation is achieved for the first time. This metal-free, redox-neutral and regioselective 1,2-dicarbonylation of alkenes is executed by a photocatalyst for versatile substrates under extremely mild conditions and shows great potential in biomolecular and drug molecular derivatization.

Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides

Herein, we report a one-electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross-coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive-functional-group-containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron-poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods.

Photoredox-Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4-Dihydropyridine Approach

Functionalization with C1-building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C1-molecule, carbon dioxide, makes alternative carboxylation reactions with CO2-surrogates especially important. We report a photoredox-catalyzed protocol for alkene carbamoylations. Readily accessible 4-carboxamido-Hantzsch esters serve as convenient starting materials that generate carbamoyl radicals upon visible light-mediated single-electron transfer. Addition to various alkenes proceeded with high levels of regio- and chemoselectivity.

Functionalization of Pyridinium Derivatives with 1,4-Dihydropyridines Enabled by Photoinduced Charge Transfer

By exploiting electron donor-acceptor (EDA) complexes between 1,4-dihydropyridines and N-amidopyridinium salts under visible light irradiation, we discovered that photoinduced intermolecular charge transfer induces a single-electron transfer event without requiring a photocatalyst for the facile functionalization of pyridines. The generality of this method is amenable to various types of 1,4-dihydropyridines radical precursors to generate structurally different radicals such as alkyl, acyl, and carbamoyl radicals, ultimately providing facile access to synthetically valuable C4-functionalized pyridines. A broad range of functional groups are well accommodated under mild and metal-free conditions, and the synthetic utility of the present method is showcased by the late-stage functionalization of a variety of biologically relevant pyridine-based compounds, pharmaceuticals, and peptide feedstocks.