13250-95-8

Usage

Uses

Used in Pharmaceutical Synthesis:
Diethyl [[(6-methyl-2-pyridyl)amino]methylene]malonate is used as a key reagent for the preparation of substituted quinoline carboxyguanidines. These compounds have been found to possess antidiabetic properties, making them an important class of drugs for the treatment of diabetes mellitus. The compound's unique structure allows for the efficient synthesis of these bioactive molecules, contributing to the development of novel and effective treatments for diabetes.
Used in the Preparation of Antidiabetic Agents:
In the pharmaceutical industry, diethyl [[(6-methyl-2-pyridyl)amino]methylene]malonate is used as a starting material for the synthesis of quinoline carboxyguanidines. These agents have demonstrated potential in managing blood glucose levels and improving insulin sensitivity, which are crucial factors in the treatment of diabetes. The compound's role in the synthesis of these antidiabetic agents highlights its importance in the development of new therapeutic options for patients suffering from this chronic condition.

InChI:InChI=1/C14H18N2O4/c1-4-19-13(17)11(14(18)20-5-2)9-15-12-8-6-7-10(3)16-12/h6-9H,4-5H2,1-3H3,(H,15,16)

Upstream product

• 80287-53-2 5-Amino-2-methylpyridine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 1824-81-3 2-Amino-6-methylpyridine 

Downstream Products

• 13317-11-8 1,4-Dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid 
• 49655-73-4 7-methyl[1,8]naphthyridin-4(1H)-one 
• 23443-11-0 6-methyl-4H-pyrido<1,2-a>pyrimidin-4-one 
• 16867-53-1 3-Ethoxycarbonyl-6-methyl-4-oxo-4H-pyrido<1,2-a>pyrimidine 
• 35482-56-5 ethyl 7-methyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 1569-18-2 7-methyl-1,8-naphthyridin-4-ol 
• 1772-45-8 5-chloro-2-methyl-1,8-naphthyridine 
• 1076222-50-8 (7-methyl-[1,8]naphthyridin-4-yl)-(5-methyl-2-phenylsulfanylphenyl)-amine hydrochloride 
• 867012-52-0 C₂₄H₂₇F₆N₃O₂ 
• 867011-71-0 C₂₆H₂₉F₆N₃O₃ 
• 1028260-73-2 4-Chloro-7-methyl-[1,8]naphthyridine-3-carboxylic acid dimethylamide 
• 33331-59-8 ethyl 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 389-08-2 nalidixic Acid 
• 13250-96-9 ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate 

Relevant academic research and scientific papers

Limitations of the Jacobs-Gould reaction using microwave irradiation

Upon investigating the green synthesis of some antimicrobial quinolone compounds, some atypical ring-closing patterns were observed during the synthesis of various intermediates using the Jacobs-Gould reaction.

On the Regioselectivity of the Gould–Jacobs Reaction: Gas-Phase Versus Solution-Phase Thermolysis

A detailed investigation of the regioselectivity in the thermal cyclization of (pyridyl)aminomethylenemalonates both in the gas- and solution phase is presented. Flash vacuum pyrolysis (FVP) as a gas-phase thermolysis technique is used to study the Gould–Jacobs reaction at temperatures between 450–650 °C, while different solution-phase heating techniques (reflux, microwave, and continuous flow) were employed at 260–350 °C. Depending on the position of the substituent in the pyridine moiety and the applied thermolysis technique, the regioselectivity of the cyclization can be controlled either in favor of the kinetic (pyridopyrimidinone) or the thermodynamic (naphthyridinone) product. Under FVP conditions, 6-substituted pyridopyrimidinones were obtained in high regioselectivity, which was not demonstrated before under standard Gould–Jacobs reaction conditions. DFT calculations have been additionally performed to provide further insights into the mechanistic pathways of this specific Gould–Jacobs reaction.

Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor

Fused pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents along with the high conversions of these reactions allowed for facile workup and isolation. The methods reported herein are highly amenable for fast and efficient heterocycle synthesis as well as compound scale-ups.

Design, synthesis and structure-activity-relationship of 1,5-tetrahydronaphthyridines as CETP inhibitors

This Letter describes the discovery and SAR optimization of 1,5-tetrahydronaphthyridines, a new class of potent CETP inhibitors. The effort led to the identification of 21b and 21d with in vitro human plasma CETP inhibitory activity in the nanomolar range (IC50 = 23 and 22 nM, respectively). Both 21b and 21d exhibited robust HDL-c increase in hCETP/hApoA1 dual heterozygous mice model.

ANTI-VIRAL COMPOUNDS

Compounds effective in inhibiting replication of Hepatitis C virus ( HCV ) or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, coformulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

SUBSTITUTED QUINOLONES AND METHODS OF USE

Substituted quinolone compounds and compositions are provided along with methods for the use of those compounds in the treatment of diseases and disorders such as cancer.

Synthesis of selected novel covalently linked flavoquinolones

The synthesis of novel covalently linked flavoquinolones via amide bond is described using mixed anhydride method and their spectroscopic studies have been done by UV/Vis and 1H NMR spectroscopic data. Georg Thieme Verlag Stuttgart.

Preparation and use of ortho-sulfonamido bicyclic heteroaryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors

This invention provides, low molecular weight, non-peptide inhibitors of matrix metalloproteinases and TNF-α converting enzyme (TACE, tumor necrosis factor-α converting enzyme) of formula: B wherein B is T, U, W, and X are each, independently, carbon or nitrogen, provided that when T or U is carbon, either may be optionally substituted with R1; Y is carbon, nitrogen, oxygen or sulfur, provided that at least one of T, U, W, X, and Y is not carbon, and further provided that no more than 2 of T, U, W, and X are nitrogen; is a phenyl ring or is a heteroaryl ring of ring 5-6 atoms which may contain 0-2 heteratoms selected from nitrogen, oxygen, and sulfur, in addition to any heteroatoms defined by W or X; wherein the phenyl or heteroaryl ring may be optionally mono-, di-, or tri- substituted with R1; Z is a phenyl, naphthyl, heteroaryl, or heteroaryl fused to phenyl, wherein the heteroaryl moiety contains of 5-6 ring atoms and 1-3 heteroatoms selected from nitrogen, oxygen, or sulfur; wherein the phenyl, naphthyl, heteroaryl, or phenyl fused heteroaryl moieties may be optionally mono-, di-, or tri- substituted with R1; R1 is hydrogen, halogen, alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cyclocalkyl of 3-6 carbon atoms, —(CH2)nZ, —OR2, —CN, —COR2, perfluoroalkyl of 1-4 carbon atoms, —CONR2R3, —S(O)xR2 —OPO(OR2)OR3, —PO(OR2)R3, —OC(O)NR2R3, —COOR2, —CONR2R3, —SO3H, —NR2R3, —NR2COR3, —NR2COOR3, —SO2NR2R3, —NO2, —N(R2)SO2R3, —NR2CONR2R3, —NR2C(═NR 3)NR2R3, —SO2NHCOR4, —CONHSO2R4, -tetrazol-5-yl, —SO2NHCN, —SO2NHCONR2R3 or Z; V is a saturated or partially unsaturated heterocycloalkyl ring of 5-7 ring atoms having 1-3 heteroatoms selected from N, O, or S, which may be optionally mono-, or di-substituted with R2; R2 and R3 are each, independently, hydrogen, alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cycloalkyl of 3-6 carbon atoms; perfluoroalkyl of 1-4 carbon atoms, Z or V; R4 is alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cycloalkyl of 3-6 carbon atoms; perfluoroalkyl of 1-4 carbon atoms, Z or V; R5 is hydrogen, alkyl of 1-8 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, Z, or V; n=1-6; x=0-2 or a pharmaceutically acceptable salt thereof.

Ortho-sulfonamido bicyclic hydroxamic acids as matrix metalloproteinase and TACE inhibitors

This invention provides, low molecular weight, non-peptide inhibitors of matrix metalloproteinases and TNF-α converting enzyme (TACE, tumor necrosis factor-α converting enzyme) of formula: B wherein B is P and Q are provided that when P is Q is and vice versa; or a pharmaceutically acceptable salt thereof.

Synthesis and evaluation of quinoline carboxyguanidines as antidiabetic agents

The synthesis and in vivo activities of a series of substituted quinoline carboxyguanidines as a possible novel class of antidiabetic agents is described. (C) 2000 Elsevier Science Ltd. All rights reserved.