Heterocyclic Building Blocks-Naphthyridine

Protective effect of vinpocetine against neurotoxicity of manganese in adult male rats was written by Nadeem, Rania I.;Ahmed, Hebatalla I.;El-Sayeh, Bahia M.. And the article was included in Naunyn-Schmiedeberg’s Archives of Pharmacology in 2018.Synthetic Route of C22H26N2O2 This article mentions the following:

Vinpocetine, a synthetic derivative of the alkaloid vincamine, is used to improve the cognitive function in cerebrovascular diseases. The present work was designed to explore the potential neuroprotective mechanisms exerted by vinpocetine in the Mn-induced neurotoxicity in rats. Rats were allocated into four groups. First group was given saline. The other three groups were given MnCl₂; two of them were treated with either L-dopa, the gold standard antiparkinsonian drug, or vinpocetine. Rats receiving MnCl₂ exhibited lengthened catalepsy duration in the grid and bar tests, motor impairment in the open-field test and short-term memory deficit in the Y-maze test. Addnl., histol. examination revealed structural alterations and degeneration in different brain regions. Besides, striatal monoamines and mitochondrial complex I contents were declined, apoptotic biomarker caspase-3 expression and acetylcholinesterase activity were elevated. Moreover, oxidative stress and inflammation were detected in the striata. L-dopa or vinpocetine exerted protective effects against MnCl₂-induced neurotoxicity. It could be hypothesized that modulation of monoamines, upregulation of mitochondrial complex I, antioxidant, antiinflammatory, and antiapoptotic activities are significant mechanisms underlying the neuroprotective effect of vinpocetine in the Mn-induced neurotoxicity model in rats. In the experiment, the researchers used many compounds, for example, (41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate (cas: 42971-09-5Synthetic Route of C22H26N2O2).

(41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate (cas: 42971-09-5) belongs to naphthyridine derivatives. Functionalized naphthyridines and their benzo/heterofused analogs are present in numerous marine products and reported to possess wide-ranging activities such as antiproliferative, antiaggressive, and HIV-1 integrase inhibition in addition to their use as anti-HCV agents. Imidazonaphthyridines have been prepared through a ‘one-pot’ three-component ‘domino’ reaction between the keto-ester, acrolein, and ethylenediamine in presence of 4 Å molecular sieves. The corresponding thiazolonaphthyridine is obtained from a similar reaction using 2-aminoethanethiol and Dowex basic anion-exchange resin.Synthetic Route of C22H26N2O2

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Some properties of semiempirical Hamiltonians was written by Koutecky, Jaroslav. And the article was included in Journal of Chemical Physics in 1967.Application of 253-50-9 This article mentions the following:

The Hamiltonian used in semiempirical Pariser-Parr-Pople (P.P.P)-type treatments is put in a form such that (a) the parameters on which correlation effects depend become obvious and (b) the part of the Hamiltonian responsible for deviations from pairing properties of conjugated heterocycles with alternant topology is isolated. A set of approx. rules based on this analysis is derived. The rules concerning the extent of correlation effects are compared for some conjugated hydrocarbons with computations by full configuration interaction in the π-electron approximation Generalizations are derived of known conditions under which heterocyclic systems are paired. The character of the two first excited states of heteroanalogs and heteroderivs. of alternant hydrocarbons is discussed, and rules determining deviations from the behavior of parent alternant hydrocarbons are formulated. This makes it possible to predict the polarizations of the first two transitions in these compounds in the P.P.P. approximation with limited configuration interaction. The predictions are compared with some results of calculations on azines and amines. In the experiment, the researchers used many compounds, for example, 2,6-Naphthyridine (cas: 253-50-9Application of 253-50-9).

2,6-Naphthyridine (cas: 253-50-9) belongs to naphthyridine derivatives. Six naphthyridine isomers are white solids with a surprisingly wide span of melting points: 1,6-Naphthyridine’s is the lowest at <40 ºC; 2,6-naphthyridine’s is the highest at 114–115 ºC. Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones.Application of 253-50-9

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Activating Transcription Factor 6 Mediates Inflammatory Signals in Intestinal Epithelial Cells Upon Endoplasmic Reticulum Stress was written by Stengel, Stephanie T.;Fazio, Antonella;Lipinski, Simone;Jahn, Martin T.;Aden, Konrad;Ito, Go;Wottawa, Felix;Kuiper, Jan W. P.;Coleman, Olivia I.;Tran, Florian;Bordoni, Dora;Bernardes, Joana P.;Jentzsch, Marlene;Luzius, Anne;Bierwirth, Sandra;Messner, Berith;Henning, Anna;Welz, Lina;Kakavand, Nassim;Falk-Paulsen, Maren;Imm, Simon;Hinrichsen, Finn;Zilbauer, Matthias;Schreiber, Stefan;Kaser, Arthur;Blumberg, Richard;Haller, Dirk;Rosenstiel, Philip. And the article was included in Gastroenterology in 2020.Product Details of 1009820-21-6 This article mentions the following:

Excess and unresolved endoplasmic reticulum (ER) stress in intestinal epithelial cells (IECs) promotes intestinal inflammation. Activating transcription factor 6 (ATF6) is one of the signaling mediators of ER stress. We studied the pathways that regulate ATF6 and its role for inflammation in IECs. We performed an RNA interference screen, using 23,349 unique small interfering RNAs targeting 7783 genes and a luciferase reporter controlled by an ATF6-dependent ERSE (ER stress-response element) promoter, to identify proteins that activate or inhibit the ATF6 signaling pathway in HEK293 cells. To validate the screening results, intestinal epithelial cell lines (Caco-2 cells) were transfected with small interfering RNAs or with a plasmid overexpressing a constitutively active form of ATF6. Caco-2 cells with a CRISPR-mediated disruption of autophagy related 16 like 1 gene (ATG16L1) were used to study the effect of ATF6 on ER stress in autophagy-deficient cells. We also studied intestinal organoids derived from mice that overexpress constitutively active ATF6, from mice with deletion of the autophagy related 16 like 1 or X-Box binding protein 1 gene in IECs (Atg16l1ΔIEC or Xbp1ΔIEC, which both develop spontaneous ileitis), from patients with Crohn’s disease (CD) and healthy individuals (controls). Cells and organoids were incubated with tunicamycin to induce ER stress and/or chem. inhibitors of newly identified activator proteins of ATF6 signaling, and analyzed by real-time polymerase chain reaction and immunoblots. Atg16l1ΔIEC and control (Atg16l1fl/fl) mice were given i.p. injections of tunicamycin and were treated with chem. inhibitors of ATF6 activating proteins. We identified and validated 15 suppressors and 7 activators of the ATF6 signaling pathway; activators included the regulatory subunit of casein kinase 2 (CSNK2B) and acyl-CoA synthetase long chain family member 1 (ACSL1). Knockdown or chem. inhibition of CSNK2B and ACSL1 in Caco-2 cells reduced activity of the ATF6-dependent ERSE reporter gene, diminished transcription of the ATF6 target genes HSP90B1 and HSPA5 and reduced NF-κB reporter gene activation on tunicamycin stimulation. Atg16l1ΔIEC and or Xbp1ΔIEC organoids showed increased expression of ATF6 and its target genes. Inhibitors of ACSL1 or CSNK2B prevented activation of ATF6 and reduced CXCL1 and tumor necrosis factor (TNF) expression in these organoids on induction of ER stress with tunicamycin. Injection of mice with inhibitors of ACSL1 or CSNK2B significantly reduced tunicamycin-mediated intestinal inflammation and IEC death and expression of CXCL1 and TNF in Atg16l1ΔIEC mice. Purified ileal IECs from patients with CD had higher levels of ATF6, CSNK2B, and HSPA5 mRNAs than controls; early-passage organoids from patients with active CD show increased levels of activated ATF6 protein, incubation of these organoids with inhibitors of ACSL1 or CSNK2B reduced transcription of ATF6 target genes, including TNF. Ileal IECs from patients with CD have higher levels of activated ATF6, which is regulated by CSNK2B and HSPA5. ATF6 increases expression of TNF and other inflammatory cytokines in response to ER stress in these cells and in organoids from Atg16l1ΔIEC and Xbp1ΔIEC mice. Strategies to inhibit the ATF6 signaling pathway might be developed for treatment of inflammatory bowel diseases. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6Product Details of 1009820-21-6).

5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6) belongs to naphthyridine derivatives. The naphthyridines have 10 delocalized π-electrons located in five molecular orbitals, each of which is distorted by the presence of the nitrogen atoms causing an electron drift in that direction. Halogen atoms attached to the naphthyridine moiety can be easily replaced by other nucleophiles such as alkoxides and amines.Product Details of 1009820-21-6

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

CK2 inhibition with silmitasertib promotes methuosis-like cell death associated to catastrophic massive vacuolization of colorectal cancer cells was written by Silva-Pavez, Eduardo;Villar, Paulina;Trigo, Cesar;Caamano, Esteban;Niechi, Ignacio;Perez, Pablo;Munoz, Juan P.;Aguayo, Francisco;Burzio, Veronica A.;Varas-Godoy, Manuel;Castro, Ariel F.;Colombo, Maria I.;Tapia, Julio C.. And the article was included in Cell Death & Disease in 2019.Safety of 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid This article mentions the following:

Protein kinase CK2 is a highly conserved and constitutively active Ser/Thr-kinase that phosphorylates a large number of substrates, resulting in increased cell proliferation and survival. A known target of CK2 is Akt, a player in the PI3K/Akt/mTORC1 signaling pathway, which is aberrantly activated in 32% of colorectal cancer (CRC) patients. On the other hand, mTORC1 plays an important role in the regulation of protein synthesis, cell growth, and autophagy. Some studies suggest that CK2 regulates mTORC1 in several cancers. The most recently developed CK2 inhibitor, silmitasertib (formerly CX-4945), has been tested in phase I/II trials for cholangiocarcinoma and multiple myeloma. This drug has been shown to induce autophagy and enhance apoptosis in pancreatic cancer cells and to promote apoptosis in non-small cell lung cancer cells. Nevertheless, it has not been tested in studies for CRC patients. We show in this work that inhibition of CK2 with silmitasertib decreases in vitro tumorigenesis of CRC cells in response to G2/M arrest, which correlates with mTORC1 inhibition and formation of large cytoplasmic vacuoles. Notably, mol. markers indicate that these vacuoles derive from massive macropinocytosis. Altogether, these findings suggest that an aberrantly elevated expression/activity of CK2 may play a key role in CRC, promoting cell viability and proliferation in untreated cells, however, its inhibition with silmitasertib promotes methuosis-like cell death associated to massive catastrophic vacuolization, accounting for decreased tumorigenicity at later times. These characteristics of silmitasertib support a potential therapeutic use in CRC patients and probably other CK2-dependent cancers. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6Safety of 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid).

5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6) belongs to naphthyridine derivatives. Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. Imidazonaphthyridines have been prepared through a ‘one-pot’ three-component ‘domino’ reaction between the keto-ester, acrolein, and ethylenediamine in presence of 4 Å molecular sieves. The corresponding thiazolonaphthyridine is obtained from a similar reaction using 2-aminoethanethiol and Dowex basic anion-exchange resin.Safety of 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

ALSUntangled 57: Vinpocetine was written by Bedlack, Richard;Armon, Carmel;Barkhaus, Paul;Barnes, Benjamin;Bereman, Michael;Bertorini, Tulio;Carter, Greg;Chen, Amy;Crayle, Jesse;Cudkowicz, Merit;Jackson, Carlayne;Kiernan, Matthew;Levitsky, Gleb;McDermott, Christopher;Pattee, Gary;Pioro, Erik;Salmon, Kristiana;Staats, Kim;Stephens, James;Wicks, Paul. And the article was included in Amyotrophic Lateral Sclerosis and Frontotemporal Degeneration in 2021.Recommanded Product: (41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate This article mentions the following:

Vinpocetine (chem. name 14-ethoxycarbonyl- (3a,16a-ethyl)-14,15-eburnamine) is a product derived from an alkaloid substance in the periwinkle plant Vinca minor (2). In many countries it is classified as a prescription drug and is used for the treatment of acute stroke and cognitive impairment(3). Systematic reviews have failed to confirm any benefits for patients with these conditions (4,5). In the Unites States, it is classified as a nutritional supplement (3). At least one website claims that Vinpocetine might be “beneficial for ALS” (6). A published case series demonstrated that Vinpocetine was associated with reduced cramping in PALS and suggested further study, including determining whether it could slow ALS progression (7). This review examines Vinpocetine′s potential role in slowing ALS progression. In the experiment, the researchers used many compounds, for example, (41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate (cas: 42971-09-5Recommanded Product: (41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate).

(41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate (cas: 42971-09-5) belongs to naphthyridine derivatives. The naphthyridines have 10 delocalized π-electrons located in five molecular orbitals, each of which is distorted by the presence of the nitrogen atoms causing an electron drift in that direction. Very few metal complexes of naphthyridines other than 1,8-naphthyridine have been described.Recommanded Product: (41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Development of a Microencapsulated Medicinal Form of Vinpocetine for Administration by Inhalation was written by Penkina, Yu. A.;Pavlovskaya, O. P.;Avramenko, G. V.. And the article was included in Pharmaceutical Chemistry Journal in 2017.Electric Literature of C22H26N2O2 This article mentions the following:

A method for the microencapsulation of vinpocetine by solvent evaporation in polylactide (PLA) shells with different mol. weights using a mixture of polyvinyl alc. (PVA) and dioctylsulfosuccinate sodium (Aerosol OT, AOT) at a mass ratio of 1:1 as stabilizer was developed. Microencapsulation efficiency was found to increase when PLA with higher mol. weight was used, though the process was essentially independent of the quantity used. Microcapsule dispersity was evaluated. The best samples were obtained using PLA with a mol. weight of 30,500 Da and a vinpocetine:PLA mass ratio of 1:10. In the experiment, the researchers used many compounds, for example, (41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate (cas: 42971-09-5Electric Literature of C22H26N2O2).

(41S,13aS)-Ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate (cas: 42971-09-5) belongs to naphthyridine derivatives. The naphthyridines have 10 delocalized π-electrons located in five molecular orbitals, each of which is distorted by the presence of the nitrogen atoms causing an electron drift in that direction. Very few metal complexes of naphthyridines other than 1,8-naphthyridine have been described.Electric Literature of C22H26N2O2

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Olefin Oxygenation by Water on an Iridium Center was written by Ghatak, Tapas;Sarkar, Mithun;Dinda, Shrabani;Dutta, Indranil;Rahaman, S. M. Wahidur;Bera, Jitendra K.. And the article was included in Journal of the American Chemical Society in 2015.Recommanded Product: 1772625-41-8 This article mentions the following:

Oxygenation of 1,5-cyclooctadiene (COD) is achieved on an Ir center using H₂O as a reagent. A H-bonding interaction with an unbound N atom of the naphthyridine-based ligand architecture promotes nucleophilic attack of H₂O to the metal-bound COD. Irida-oxetane and oxo-irida-allyl compounds are isolated, products which are normally accessed from reactions with H₂O₂ or O₂. DFT studies support a ligand-assisted H₂O activation mechanism. In the experiment, the researchers used many compounds, for example, (S)-4-Benzyl-2-(1,8-naphthyridin-2-yl)-4,5-dihydrooxazole (cas: 1772625-41-8Recommanded Product: 1772625-41-8).

(S)-4-Benzyl-2-(1,8-naphthyridin-2-yl)-4,5-dihydrooxazole (cas: 1772625-41-8) belongs to naphthyridine derivatives. Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. Transition metal complexes of 1,5-naphthyridine (1,5-napy) seems to form one-dimensional coordination polymers with the ligand acting as bidentate in a “stepped” bridging fashion.Recommanded Product: 1772625-41-8

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Non-catalytic allostery in α-TAT1 by a phospho-switch drives dynamic microtubule acetylation was written by Roy, Abhijit Deb;Gross, Evan G.;Pillai, Gayatri S.;Seetharaman, Shailaja;Etienne-Manneville, Sandrine;Inoue, Takanari. And the article was included in Journal of Cell Biology in 2022.Recommanded Product: 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid This article mentions the following:

Spatiotemporally dynamic microtubule acetylation underlies diverse physiol. and pathol. events. Despite its ubiquity, the mol. mechanisms that regulate the sole microtubule acetylating agent, α-tubulin-N-acetyltransferase1 (α-TAT1), remain obscure. Here, we report that dynamic intracellular localization of α-TAT1 along with its catalytic activity determines efficiency of microtubule acetylation. Specifically, we newly identified a conserved signal motif in the intrinsically disordered C-terminus of α-TAT1, consisting of three competing regulatory elements-nuclear export, nuclear import, and cytosolic retention. Their balance is tuned via phosphorylation by CDK1, PKA, and CK2, and dephosphorylation by PP2A. While the unphosphorylated form binds to importins and resides both in cytosol and nucleus, the phosphorylated form binds to specific 14-3-3 adapters and accumulates in the cytosol for maximal substrate access. Unlike other mols. with a similar phospho-regulated signal motif, α-TAT1 uniquely uses the nucleus as a hideout. This allosteric spatial regulation of α-TAT1 function may help uncover a spatiotemporal code of microtubule acetylation in normal and aberrant cell behavior. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6Recommanded Product: 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid).

5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6) belongs to naphthyridine derivatives. Functionalized naphthyridines and their benzo/heterofused analogs are present in numerous marine products and reported to possess wide-ranging activities such as antiproliferative, antiaggressive, and HIV-1 integrase inhibition in addition to their use as anti-HCV agents. Halogen atoms attached to the naphthyridine moiety can be easily replaced by other nucleophiles such as alkoxides and amines.Recommanded Product: 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Advances in the chemistry of naphthyridines was written by Litvinov, V. P.. And the article was included in Advances in Heterocyclic Chemistry in 2006.Computed Properties of C8H6N2 This article mentions the following:

A review in which an anal. is made of the synthesis and properties of 6 isomeric heterocyclic systems containing 2 fused pyridine rings with different mutual arrangements of N atoms, naphthyridines (pyridopyridines, diazanaphthalenes). In the experiment, the researchers used many compounds, for example, 2,6-Naphthyridine (cas: 253-50-9Computed Properties of C8H6N2).

2,6-Naphthyridine (cas: 253-50-9) belongs to naphthyridine derivatives. Six naphthyridine isomers exist, based on the positions of the nitrogen atoms; they can be in the 1,5, 1,6, 1,7, 1,8, 2,6, or 2,7 positions. Imidazonaphthyridines have been prepared through a ‘one-pot’ three-component ‘domino’ reaction between the keto-ester, acrolein, and ethylenediamine in presence of 4 Å molecular sieves. The corresponding thiazolonaphthyridine is obtained from a similar reaction using 2-aminoethanethiol and Dowex basic anion-exchange resin.Computed Properties of C8H6N2

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Aromaticity of heterocycles containing the imine nitrogen was written by Hess, B. A. Jr.;Schaad, L. J.;Holyoke, C. W. Jr.. And the article was included in Tetrahedron in 1975.Recommanded Product: 2,6-Naphthyridine This article mentions the following:

The method of predicting aromaticity based on simple Heuckel calculations was applied to heterocyclic systems containing imine N. The necessary heteroatomic integrals were determined from thermochem. data. Replacement of C by N in alternant systems, e.g. benzene and pyridine, produced little change but in nonalternants, e.g. pentalene and azapentalene, the effect was large, and interesting synthetic possibilities were suggested. In the experiment, the researchers used many compounds, for example, 2,6-Naphthyridine (cas: 253-50-9Recommanded Product: 2,6-Naphthyridine).

2,6-Naphthyridine (cas: 253-50-9) belongs to naphthyridine derivatives. The naphthyridines have 10 delocalized π-electrons located in five molecular orbitals, each of which is distorted by the presence of the nitrogen atoms causing an electron drift in that direction. Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones.Recommanded Product: 2,6-Naphthyridine

Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem