128372-89-4

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate is used as an intermediate in the synthesis of various pharmaceuticals for its potential as a calcium channel blocker. This property makes it useful in the treatment of cardiovascular diseases such as hypertension and angina.
Used in Agrochemical Industry:
Tert-butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate is also used as an intermediate in the synthesis of agrochemicals, contributing to the development of effective and innovative products in this field.
Used in Medicinal Chemistry:
As a versatile chemical, tert-butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate serves as a building block in the preparation of various organic compounds, playing a significant role in the advancement of medicinal chemistry.
Used in Synthetic Chemistry:
Tert-butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate's versatility extends to synthetic chemistry, where it is utilized in the synthesis of a wide range of organic compounds, showcasing its value in this domain.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 831227-07-7 6-trimethylsilanyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 1215765-59-5 tert-butyl 2-oxo-3-(phenylselanyl)piperidine-1-carboxylate 
• 131667-57-7 tert-butyl 1,2,3,4-tetrahydro-1-pyridinecarboxylate 
• 1372716-04-5 tert-butyl 6-[(diphenoxyphosphoryl)oxy]-3,4-dihydropyridine-1(2H)-carboxylate 
• 1245646-10-9 tert-butyl 4-hydroxy-2-oxopiperidine-1-carboxylate 
• 845267-78-9 tert-butyl 2,4-dioxopiperidine-1-carboxylate 
• 3303-84-2 3-(tert-butyloxycarbonylamino)propionic acid 
• 1415686-28-0 N-(but-3-en-1-yl)prop-2-enamide 
• 358732-56-6 N-(tert-butyloxycarbonyl)-3-(phenylthio)piperidine-2-one 
• 675-20-7 piperidin-2-one 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 6052-73-9 5,6-dihydro-2(1H)-pyridinone 
• 1226623-45-5 tert-butyl 6-oxo-5-[(2E)-3-phenyl-2-propen-1-yl]-3,6-dihydropyridine-1(2H)-carboxylate 
• 1229643-25-7 2,2'-dioxo-5,6,3',4',5',6'-hexahydro-2H,2'H-[3,4]bipyridinyl-1,1'-dicarboxylic acid di-tert-butyl ester 
• 1407488-29-2 (R)-1-(tert-butyloxycarbonyl)-4-(2-methoxyphenyl)-2-piperidone 
• 1407488-30-5 (R)-1-(tert-butyloxycarbonyl)-4-(2-methylphenyl)-2-piperidone 
• 229182-32-5 (R)-5--3-(4-chlorophenyl)pentanoic acid 
• 1407488-19-0 (R)-1-(tert-butyloxycarbonyl)-4-phenyl-2-piperidone 
• 1407488-20-3 (R)-1-(tert-butyloxycarbonyl)-4-(4-methylphenyl)-2-piperidone 
• 1407488-21-4 (R)-1-(tert-butyloxycarbonyl)-4-(4-(tert-butyl)phenyl)-2-piperidone 
• 1407488-22-5 (R)-1-(tert-butyloxycarbonyl)-4-(4-methoxyphenyl)-2-piperidone 
• 1407488-23-6 (R)-1-(tert-butyloxycarbonyl)-4-(4-fluorophenyl)-2-piperidone 
• 229182-29-0 (R)-1-(tert-butyloxycarbonyl)-4-(4-chlorophenyl)-2-piperidinone 
• 1407488-24-7 (R)-1-(tert-butyloxycarbonyl)-4-(4-bromophenyl)-2-piperidone 
• 1407488-25-8 (R)-1-(tert-butyloxycarbonyl)-4-(3-chlorophenyl)-2-piperidone 

Relevant academic research and scientific papers

A facile approach to α,β-unsaturated lactams by ring-closing metathesis

[MediaObject not available: see fulltext.]A facile and efficient strategy for the synthesis of α,β-unsaturated lactams through ring-closing metathesis of easily prepared diene amides is being reported here. Reaction conditions were optimized for metathetic cyclization of diene amides to obtain five- to sevenmembered unsubstituted and β-substituted α,β-unsaturated lactams in good to excellent yield.

Novel pyrrolyllactone and pyrrolyllactam indolinones as potent cyclin-dependent kinase 2 inhibitors

Cyclin-dependent kinases (CDKs) are essential in the control of cell cycle progression. Inhibition of CDKs represents a new approach for pharmacological intervention in the treatment of a variety of proliferative diseases, especially cancer. Based on the crystal structure of CDK2 in complex with an imidazole indolinone compound 1 (SU9516), lead optimization through modeling, synthesis, and SAR studies has led to the discovery of a novel series of pyrrolyllactone and pyrrolyllactam indolinones as potent CDK2 inhibitors.

Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism

We here report the preparation of a new 2,6,8-trisubstituted bicyclic tripeptidomimetic scaffold through TFA-mediated cyclization of a linear precursor containing three side chains. The introduction of a triphenylmethyl-protected thiol into carboxylic aci

Electrochemically driven desaturation of carbonyl compounds

Electrochemical techniques have long been heralded for their innate sustainability as efficient methods to achieve redox reactions. Carbonyl desaturation, as a fundamental organic oxidation, is an oft-employed transformation to unlock adjacent reactivity through the formal removal of two hydrogen atoms. To date, the most reliable methods to achieve this seemingly trivial reaction rely on transition metals (Pd or Cu) or stoichiometric reagents based on I, Br, Se or S. Here we report an operationally simple pathway to access such structures from enol silanes and phosphates using electrons as the primary reagent. This electrochemically driven desaturation exhibits a broad scope across an array of carbonyl derivatives, is easily scalable (1–100 g) and can be predictably implemented into synthetic pathways using experimentally or computationally derived NMR shifts. Systematic comparisons to state-of-the-art techniques reveal that this method can uniquely desaturate a wide array of carbonyl groups. Mechanistic interrogation suggests a radical-based reaction pathway. [Figure not available: see fulltext.]

Design, synthesis, and biological evaluation of a novel indoleamine 2,3-dioxigenase 1 (IDO1) and thioredoxin reductase (TrxR) dual inhibitor

Targeting the Trp-Kyn pathway is an attractive approach for cancer immunotherapy. Thioredoxin reductase (TrxR) enzymes are reactive oxygen species (ROS) modulators that are involved in the tumor cell growth and survival processes. The 4-phenylimidazole scaffold is well-established as useful for indoleamine 2,3-dioxygenase 1 (IDO1) inhibition, while piperlongumine (PL) and its derivatives have been reported to be inhibitors of TrxR. To take advantage of both immunotherapy and TrxR inhibition, we designed a first-generation dual IDO1 and TrxR inhibitor (ZC0101) using the structural combination of 4-phenylimidazole and PL scaffolds. ZC0101 exhibited better dual inhibition against IDO1 and TrxR in vitro and in cell enzyme assays than the uncombined forms of 4-phenylimidazole and PL. It also showed antiproliferative activity in various cancer cell lines, and a selective killing effect between normal and cancer cells. Furthermore, ZC0101 effectively induced apoptosis and ROS accumulation in cancer cells. Knockdown of TrxR1 and IDO1 expression induced cellular enzyme inhibition and ROS accumulation effects during ZC0101 treatment, but only reduced TrxR1 expression was able to improve ZC0101′s antiproliferation effect. This proof-of-concept study provides a novel strategy for cancer treatment. ZC0101 represents a promising lead compound for the development of novel antitumor agents that can also be used as a valuable probe to clarify the relationships and mechanisms of cancer immunotherapy and ROS modulators.

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.

Substituted imidazo[1,2-b]pyridazines as protein kinase inhibitors

The present invention provides protein kinase having one of the following structures (I), (II) or (III): or a stereoisomer, prodrug, tautomer or pharmaceutically acceptable salt thereof, wherein R, R1, R2 and X are as defined herein. Compositions and methods for using the same in the treatment of cancer, autoimmune, inflammatory and other Pim kinase-associated conditions are also disclosed.

CCR2 MODULATORS

Compounds are provided that are modulators of the CCR2 receptor. The compounds have the general formula (I) and are useful in pharmaceutical compositions, methods for the treatment of diseases and disorders involving the pathologic activtation of CCR2 receptors.

Horner-Wadsworth-Emmons approach to piperlongumine analogues with potent anti-cancer activity

Natural products with anti-cancer activity play a vital role in lead and target discovery. We report here the synthesis and biological evaluation of the plant-derived alkaloid, piperlongumine and analogues. Using a Horner-Wadsworth-Emmons coupling approach, a selection of piperlongumine-like compounds were prepared in good overall yield from a novel phosphonoacetamide reagent. A number of the compounds displayed potent anti-cancer activity against colorectal (HCT 116) and ovarian (IGROV-1) carcinoma cell lines, via a mechanism of action which may involve ROS generation. Contrary to previous reports, no selective action in cancer cell (MRC-5) was observed for piperlongumine analogues.

FUSED 9-MEMBERED RING DERIVATIVES HAVING AUTOTAXIN INHIBITORY ACTIVITY

PROBLEM TO BE SOLVED: To provide novel compounds having an autotaxin inhibitory effect. SOLUTION: A compound is represented by a formula in the figure, where each symbol is as defined in the specification. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandI