185847-84-1

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate is utilized as a cardiovascular agent for its potential to block calcium channels. This property is instrumental in the treatment of conditions such as hypertension and angina, as it can help regulate blood pressure and alleviate chest pain associated with insufficient blood flow to the heart.
Additionally, due to its dihydropyridine structure, Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate may possess other biological activities that could be beneficial in medicinal chemistry. It may also serve as a building block in the synthesis of other organic compounds, expanding its utility in drug development and organic synthesis processes.
Further research and testing are necessary to fully elucidate the specific properties and potential uses of Benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate, ensuring its safe and effective application in various medical and chemical contexts.

InChI:InChI=1/C13H13NO3/c15-12-6-8-14(9-7-12)13(16)17-10-11-4-2-1-3-5-11/h1-6,8H,7,9-10H2

Upstream product

• 53708-19-3 4-isopropoxypyridine 
• 501-53-1 benzyl chloroformate 
• 620-08-6 4-methoxypyridine 
• 68471-58-9 1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine 
• 66207-23-6 1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine 
• 40064-34-4 piperidine-4,4-diol hydrochloride 
• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 940925-56-4 benzyl 6-bromo-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate 

Downstream Products

• 335266-05-2 (R)-4-oxo-2-phenyl-piperidine-1-carboxylic acid benzyl ester 
• 940925-57-5 benzyl 2-(4-chlorophenyl)-4-oxopiperidine-1-carboxylate 
• 1227150-39-1 Benzyl 2-(3,5-difluorophenyl)-4-oxopiperidine-1-carboxylate 
• 1227150-38-0 benzyl 2-(3-fluorophenyl)-4-oxopiperidine-1-carboxylate 
• 414910-20-6 benzyl 2-(4-fluorophenyl)-4-oxopiperidine-1-carboxylate 
• 849928-35-4 C₂₀H₂₁NO₃ 
• 952183-52-7 Benzyl 2-isopropyl-4-oxopiperidine-1-carboxylate 
• 1228020-85-6 (S)-2-(biphenyl-4-yl)-4-oxo-piperidine-1-carboxylic acid benzyl ester 
• 1379803-09-4 C₁₆H₂₂FNO₅ 

Relevant academic research and scientific papers

Synthesis of Novel Iminosugar Derivatives Based on a 2-Azabi-ccyclo[41.0]heptane Skeleton

Iminosugars are good starting points for the development of different kinds of drugs. Many are polyhydroxylated piperidines that behave as biomimetics of their corresponding pyranoses analogues. In the interaction with carbohydrate processing enzymes, sel

Design and synthesis of benzylidenecyclohexenones as TrxR inhibitors displaying high anticancer activity and inducing ROS, apoptosis, and autophagy

Oxidative therapy, a strategy that specifically increases reactive oxygen species (ROS) levels in tumor cells by disrupting the redox homeostasis has gained increasing interest. The antitumor effects of the natural product piperlongumine (PL) appear to result from its ability to increase intracellular ROS levels via inhibition of antioxidative thioredoxin reductase (TrxR). Twenty-seven benzylidenecyclohexenone-based PL analogues (2a-v and 15a-e) were designed, synthesized and evaluated for their pharmacological properties. Most of the compounds exhibited potent antiproliferative activities against five human cancer cell lines, especially against breast tumor cells. One of the most promising analogueues 2c showed 12-fold higher inhibitory activity against the thioredoxin reductase (TrxR) than PL and surpressed the expression of TrxR1 protein in breast cancer cells and inhibited TrxR enzymatic activity. In addition, 2c increased ROS levels and resulted in marked apoptosis by regulating apoptosis-related proteins expressed in the breast cancer cells. Compound 2c also triggered the formation of autophagosomes and autolysosomes by promoting the expression of LC3-II and Beclin-1 and diminishing the expression of LC3-I and p62 proteins. Finally, 2c displayed low acute toxicity and good inhibitory potency to tumors in mice. Overall, 2c is a promising anti-breast cancer candidate warranting further investigation.

An efficient synthesis of cis-4-hydroxyphosphonic and cis-4-hydroxyphosphinic analogs of pipecolic acid from cyclic enaminones

An expedient synthetic entry to cis-4-hydroxyphosphonic and cis-4-hydroxyphosphinic analogs of cis-4-hydroxypipecolic acid is presented in this paper. The main feature of this methodology is the highly regioselective addition of silyl phosphites or phosph

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

CHEMICAL PROCESS FOR PREPARING PHENYLPIPERIDINYL INDOLE DERIVATIVES

The present invention relates to a method of synthesizing a compound of formula (I) also referred to as 4-((2S,4S)-(4-ethoxy-1-((5-methoxy-7-methyl-1H-indol-4-yl)methyl)piperidin-2-yl))benzoic acid, or a pharmaceutically acceptable salt thereof, and/or intermediates thereof, their use as pharmaceuticals and pharmaceutical compositions and the use of intermediates for preparing a compound of formula (I), or a pharmaceutically acceptable salt thereof.

FXR (farnesol X receptor) agonist

The invention belongs to the technical field of medicine and particularly relates to a compound shown as formula (I) that is shown in the description, and its pharmaceutically acceptable salts, estersor stereoisomers, with R1, R2, R3, M1, M2, Q, L, ring A

Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors

General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.

A consecutive process for C-C and C-N bond formation with high enantio-and diastereo-control: Direct reductive amination of chiral ketones using hydrogenation catalysts

High diastereoselectivity was observed in the Rh-catalysed reductive amination of 3-arylcyclohexanones to form tertiary amines. This was incorporated into a one-pot enantioselective conjugate addition and diastereoselective reductive amination, including an example of assisted tandem catalysis.

Design and synthesis of cenocladamide analogues and their evaluation against breast cancer cell lines

This work describes the total synthesis of the alkaloid cenocladamide and a concise library of nine structural analogues aiming at their evaluation against the breast cancer cell line MDA-MB-231. The most promising compound (3; IC50 = 6.6 μM) was also evaluated in a panel of seven breast cancer cell lines and two non-tumorigenic cell lines. We further conducted an initial investigation on the mechanism of action of analogue 3, which lacks the endocyclic double bond when compared to cenocladamide. The present study presents the discovery of a cenocladamide analogue with interesting cytotoxic activity, which could be useful for further optimization towards new chemotherapeutic agents for breast cancer treatment.

Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP

Allylic oxidation of heteroatom substituted cyclic alkenes by tert-butyl hydroperoxide (70% TBHP in water) using catalytic dirhodium caprolactamate [Rh2(cap)4] forms enone products with a variety of 2-substituted cyclic enamides and 3,4-dihyro-2H-pyrans. These reactions occur under mild reaction conditions, are operationally convenient to execute, and are effective for product formation with as low as 0.25 mol% catalyst loading. With heteroatom stabilization of the intermediate allylic free radical two sites for oxidative product formation are possible, and the selectivity of the oxidative process varies with the heteroatom when R = H. Cyclic enamides produce 4-piperidones in good yields when R = alkyl or aryl, but oxidation of 2H-pyrans also gives alkyl cleavage products. Alternative catalysts for TBHP oxidations show comparable selectivities but give lower product yields.