13250-96-9

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate is used as a reagent for the synthesis of flavoquinolones, which are compounds that may exhibit antibacterial properties. Its role in the synthesis process is crucial for the development of new antibiotics to combat bacterial infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate serves as an intermediate or building block for the creation of more complex molecules with various applications. Its unique structure and functional groups make it a valuable component in the synthesis of a wide range of compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 3348, 1948 DOI: 10.1021/ja01190a038

InChI:InChI=1/C12H12N2O3/c1-3-17-12(16)9-6-13-11-8(10(9)15)5-4-7(2)14-11/h4-6H,3H2,1-2H3,(H,13,14,15)

Upstream product

• 1824-81-3 2-Amino-6-methylpyridine 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 13250-95-8 diethyl 2-{[(6-methyl-2-pyridyl)amino]methylene}propane-1,3-dioate 

Downstream Products

• 33331-57-6 ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate 
• 42025-96-7 7-[trans-2-(5-nitro-furan-2-yl)-vinyl]-4-phenoxy-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 54569-28-7 4-bromo-[1,8]naphthyridine 
• 54569-29-8 1H-[1,8]naphthyridin-4-one 
• 1569-18-2 7-methyl-1,8-naphthyridin-4-ol 
• 91870-10-9 2-diethylaminomethyl-4-(1',8'-naphthyridin-4'-ylamino)phenol 
• 33331-59-8 ethyl 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 13250-97-0 2-methyl-5-hydroxy-1,8-naphthyridine-6-carboxylic acid 
• 389-08-2 nalidixic Acid 

Relevant academic research and scientific papers

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.

Penicillins

New penicillin antibiotics are disclosed which are effective antibacterial agents and which belong to the class of α-(heterocyclic acylamino) penicillins and their salts and esters together with pharmaceutical compositions containing the same and their method of administration. The new compounds are characterized by having an amino substituent on the heterocyclic ring which is linked through an acylamino group to the α-carbon atom of the penicillin side chain. Procedure for preparing the new penicillins is described as well as the antibacterial activity of exemplary compounds against typical microorganisms.