15936-09-1

Usage

Uses

Used in Pharmaceutical Research:
1,8-NAPHTHYRIDIN-2(8H)-ONE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds due to its reactive carbonyl group and aromatic ring.
Used in Chemical Research:
1,8-NAPHTHYRIDIN-2(8H)-ONE is used as a research compound for studying the properties and reactivity of naphthyridine-based structures, which can lead to the development of new chemical entities and materials.
Used in Drug Development:
1,8-NAPHTHYRIDIN-2(8H)-ONE is used as a starting material for the design and synthesis of new drug candidates, particularly in the field of medicinal chemistry, where its heterocyclic structure may contribute to novel biological activities and therapeutic applications.
Used in Material Science:
1,8-NAPHTHYRIDIN-2(8H)-ONE is used as a building block for the development of new materials with potential applications in various industries, such as electronics, coatings, and advanced materials, due to its unique chemical structure and reactivity.

InChI:InChI=1/C8H6N2O/c11-7-4-3-6-2-1-5-9-8(6)10-7/h1-5H,(H,9,10,11)

Upstream product

• 15936-10-4 2-chloro-1,8-naphthyridine 
• 6298-19-7 2-chloro-3-aminopyridine 
• 15992-83-3 [1,8]naphthyridin-2-ylamine 
• 104830-06-0 3-iodo-2-aminopyridine 
• 292638-85-8 acrylic acid methyl ester 
• 78607-36-0 2-chloro-3-iodopyridine 
• 104830-08-2 ethyl 2-chloro-3-pyridineacrylate 
• 104830-07-1 ethyl 2-amino-3-pyridineacrylate 
• 127446-37-1 2-<(2,2-Dimethyl-1-oxopropyl)amino>-β-hydroxy-3-pyridinepropanoic Acid, 1,1-Dimethylethyl Ester 
• 125902-24-1 2-(Trichloromethyl)-1,8-naphthyridine 
• 141-86-6 2.6-diaminopyridine 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 1452560-14-3 (E)-methyl 3-(2-aminopyridin-3-yl)acrylate 
• 7521-41-7 2-Aminonicotinaldehyde 

Downstream Products

• 15936-10-4 2-chloro-1,8-naphthyridine 
• 110681-64-6 [Rh₃(C₈H₅N₂O)2(CO)4(P(C₆H₅)3)2]⁽¹⁺⁾*ClO₄^(1-)=[Rh₃(C₈H₅N₂O)2(CO)4(P(C₆H₅)3)2]ClO₄ 
• 40000-79-1 3,4-dihydro-1H-[1,8]naphthyridin-2-one 
• 960590-82-3 binaphthyridylamine 
• 61323-17-9 2-bromo-1,8-naphthyridine 

Relevant academic research and scientific papers

Nonhelical heterometallic [Mo2M(npo)4(NCS)2] string complexes (M = Fe, Co, Ni) with high single-molecule conductance

Using the planar 1,8-naphthyridin-2(1H)-one (Hnpo) ligand, novel nonhelical HMSCs [Mo2M(npo)4(NCS)2] (M = Fe, Co, Ni) were synthesised and they exhibited high single-molecule conductance.

Conformational change in the association of a heterocyclic urea derivative forming two intramolecular hydrogen bonds in polar solvent

The association of a model, heterocyclic compound capable of forming two intramolecular hydrogen bonds was studied with the use of various anionic and neutral species in highly polar solvents, but also, for some of them, in chloroform. The hydrogen bonding of anions was tuned through the substituents present in their structures. This approach was used in distinguishing which part of the bisurea heterocyclic derivative is preferred during complex formation. Neutral counterparts capable of forming three or five hydrogen bonds were also used. Moreover, triple association was probed, suggesting the formation of a complex only in chloroform. DFT computations were helpful in the interpretation of the experimental data related to complicated equilibria. These are based on the energy of rotation about single bonds, energy of interaction and QTAIM-based energies of hydrogen bonds.

BIARYLTRIAZOLE INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR

The present disclosure describes biaryl triazole compounds, as well as their compositions and methods of use. The compounds inhibit the activity of macrophage migration inhibitory factor and are useful for the treatment of diseases, e.g., inflammatory dis

Design, synthesis, and protein crystallography of biaryltriazoles as potent tautomerase inhibitors of macrophage migration inhibitory factor

Optimization is reported for biaryltriazoles as inhibitors of the tautomerase activity of human macrophage migration inhibitory factor (MIF), a proinflammatory cytokine associated with numerous inflammatory diseases and cancer. A combined approach was taken featuring organic synthesis, enzymatic assaying, crystallography, and modeling including free-energy perturbation (FEP) calculations. X-ray crystal structures for 3a and 3b bound to MIF are reported and provided a basis for the modeling efforts. The accommodation of the inhibitors in the binding site is striking with multiple hydrogen bonds and aryl-aryl interactions. Additional modeling encouraged pursuit of 5-phenoxyquinolinyl analogues, which led to the very potent compound 3s. Activity was further enhanced by addition of a fluorine atom adjacent to the phenolic hydroxyl group as in 3w, 3z, 3aa, and 3bb to strengthen a key hydrogen bond. It is also shown that physical properties of the compounds can be modulated by variation of solvent-exposed substituents. Several of the compounds are likely the most potent known MIF tautomerase inhibitors; the most active ones are more than 1000-fold more active than the well-studied (R)-ISO-1 and more than 200-fold more active than the chromen-4-one Orita-13.

HETEROBICYCLIC COMPOUNDS

Heterobicyclic compounds of Formula (I): or a pharmaceutically-acceptable salt, tautomer, or stereoisomer thereof, as defined in the specification, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, Huntington's Disease, and the like.

CYCLIC COMPOUNDS CONTAINING ZINC BINDING GROUPS AS MATRIX METALLOPROTEINASE INHIBITORS

This invention provides compounds defined by Formula I Z-L-R1-Q-D-(V1)m-R2 I or a pharmaceutically acceptable salt thereof, wherein Z, L, R1, Q, D, V1, m, and R2 are as defined in the specification. The invention also provides pharmaceutical compositions comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, as defined in the specification, together with a pharmaceutically acceptable carrier, diluent, or excipient. The invention also provides methods of inhibiting an MMP-13 enzyme in an animal, comprising administering to the animal a compound of Formula I, or a pharmaceutically acceptable salt thereof. The invention also provides methods of treating a disease mediated by an MMP-13 enzyme in a patient, comprising administering to the patient a compound of Formula I, or a pharmaceutically acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides methods of treating diseases such as heart disease, multiple sclerosis, osteo- and rheumatoid arthritis, arthritis other than osteo- or rheumatoid arthritis, cardiac insufficiency, inflammatory bowel disease, heart failure, age-related macular degeneration, chronic obstructive pulmonary disease, asthma, periodontal diseases, psoriasis, atherosclerosis, and osteoporosis in a patient, comprising administering to the patient a compound of Formula I, or a pharmaceutically acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides combinations, comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, together with another pharmaceutically active component as described in the specification.

Methylamination of some 3,6-dinitro-1,8-naphthyridines with liquid methylamine - potassium permanganate

3,6-Dinitro-1,8-naphthyridine and its 2-substituted derivatives are dehydro-methylaminated with the solution of potassium permanganate in liquid methylamine (LMA-PP) to the corresponding mono- or mono- and bis(methylamino)-3,6-dinitro-1,8-naphthyridines. In the case of 2-chloro- and 2-methoxy-3,6-dinitro-1,8-naphthyridine the replacement of chloro and methoxy substituents by the NHCH3 group occurs as well. Quantum-chemical calculations indicate the reactions to be controlled by the interaction of the frontal molecular orbitals (FMO) of the reagents. Moreover the heats of formation of intermediary methylamino-σ-adducts and transition states are calculated for the reaction studied. The calculations show satisfactory agreement between calculated and observed results. A convenient synthesis of some 2-substituted-3,6-dinitro-1,8-naphthyridines is reported.

A General Approach to the Synthesis of 1,6-, 1,7-, and 1,8-Naphthyridines

A new three-step procedure for pyridine annulation is described and illustrated with efficient syntheses of various 1,6-, 1,7-, and 1,8-naphthyridin-2-ones as well as 6-chloroquinolin-2-one.The regiospecific ortho metalation and subsequent formylation of

Functionalization of 2-Methyl- and 2,7-Dimethyl-1,8-naphthyridine

A new synthesis of 2,7-dimethyl-1,8-naphthyridine (dmnap) from 2-methyl-1,8-naphthyridine (mnap) upon treatment with 3 equiv of methyllithium is described.Oxidation of dmnap with 8 equiv of N-chlorosuccinimide gave (98percent) 2,7-bis(trichloromethyl)-1,8-naphthyridine (2), while oxidation with 4 equiv gave (97percent) 2,7-bis(dichloromethyl)-1,8-naphthyridine (1).Hydrolysis of 2 phosphoric acid followed by esterification gave the corresponding diester 3 in 80percent overall yield.Reduction of 3 with NaBH(OMe)3 afforded (55percent) diol 4.Similar functionalization of mnap afforded 2-(trichloromethyl)-1,8-naphthyridine (6) in 85-94percent yield along with 6-chloro-2-(trichloromethyl)-1,8-naphthyridine (7).Methanolysis of 6 gave (78percent) 2-(methoxycarbonyl)-1,8-naphthyridine (8), which upon reduction with NaBH(OMe)3 afforded (59percent) the alcohol 9.Treatment of 6 with KOH caused a displacement of the trichloromethyl moiety, generating 1,8-naphthyridin-2-one (10) as the sole product.Similarly, 2 gave 7-(trichloromethyl)-1,8-naphthyridin-2-one (11) under mild conditions or 7-(ethoxycarbonyl)-1,8-naphthyridin-2-one (12) when refluxed.

Condensed Heteroaromatic Ring Systems. IV. Synthesis of Naphthyridine Derivatives by Cyclization of Aminopyridineacrylic Esters

The reaction of aminohalopyridines with ethyl acrylate in the presence of palladium(II)acetate and triarylphosphine gave ethyl aminopyridineacrylates.The cyclization of the resulting acrylates under basic conditions gave naphthyridinones having a carbostyril-type moiety.Keywords- intramolecular cyclization; palladium catalyst; ethyl acrylate; naphthyridinone; pyridineacrylic ester