Heterocyclic Building Blocks-Naphthyridine

Vinpocetine attenuates thioacetamide-induced liver fibrosis in rats was written by Elnfarawy, Ahmed A.;Nashy, Asmaa E.;Abozaid, Alaa M.;Komber, Ibrahim F.;Elweshahy, Rawan H.;Abdelrahman, Rehab S.. And the article was included in Human & Experimental Toxicology in 2021.HPLC of Formula: 42971-09-5 This article mentions the following:

Liver fibrosis is associated with increased mortality and morbidity. However, there is not effective treatment so far. Vinpocetine (Vinpo) is a synthetic derivative of vinca alkaloid vincamine. Limited previous reports have shown some beneficial effects of Vinpo in different organ fibrosis, but the ability of Vinpo to inhibit liver fibrosis induced by thioacetamide (TAA) has not been reported, that is why we investigate the potential ability of this vinca alkaloid derivative to attenuate liver fibrosis. Hepatic fibrosis was induced in male Sprague Dawley rats by TAA (200 mg/kg; i.p.; 3 times/wk) for 6 wk. Daily treatments with Vinpo (10-20 mg/kg/day; orally) ameliorated TAA-induced hepatic oxidative stress and histopathol. damage as indicated by a decrease in liver injury markers, LDH, hepatic MDA, and NOx levels, as well as increase anti-oxidative parameters. Besides, the anti-fibrotic efficacy of Vinpo was confirmed by decreasing hydroxyproline, and α-SMA. Also, the anti-inflammatory effect of Vinpo was explored by decreasing IL-6 and TNF-α levels. Our novel findings were that Vinpo decreased VEGF/Ki-67 expression in the liver confirming its effect on angiogenesis and proliferation. These findings reveal the anti-fibrotic effect of Vinpo against TAA-induced liver fibrosis in rats, and suggest the modulation of oxidative stress, inflammation, angiogenesis and proliferation as mechanistic cassette underlines this effect. 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: 42971-09-5HPLC of Formula: 42971-09-5).

(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 and their derivatives exhibit various types of biological activity, and the organic chemistry has been frequently reviewed. 1,6-Naphthyridine and some of its derivatives have been reported to have medicinal, electronic, and catalytic properties. But none of these investigations has yet resulted in any practical applications. Very few metal complexes of naphthyridines other than 1,8-naphthyridine have been described.HPLC of Formula: 42971-09-5

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

Successful partnerships: exploring the potential of immunogenic signals triggered by TMZ, CX-4945, and combined treatment in GL261 glioblastoma cells was written by Villamanan, Lucia;Martinez-Escardo, Laura;Arus, Carles;Yuste, Victor J.;Candiota, Ana P.. And the article was included in International Journal of Molecular Sciences in 2021.COA of Formula: C19H12ClN3O2 This article mentions the following:

The relevance of the cancer immune cycle in therapy response implies that successful treatment may trigger the exposure or the release of immunogenic signals. Previous results with the preclin. GL261 glioblastoma (GB) showed that combination treatment of temozolomide (TMZ) + CX-4945 (protein kinase CK2 inhibitor) outperformed single treatments, provided an immune-friendly schedule was followed. Our purpose was to study possible immunogenic signals released in vitro by GB cells. Methods: GL261 GB cells were treated with TMZ and CX-4945 at different concentrations (25 μM-4 mM) and time frames (12-72 h). Cell viability was measured with Trypan Blue and propidium iodide. Calreticulin exposure was assessed with immunofluorescence, and ATP release was measured with bioluminescence. TMZ showed cytostatic rather than cytotoxic effects, while CX-4945 showed remarkable cytotoxic effects already at low concentrations Calreticulin exposure after 24 h was detected with TMZ treatment, as well as TMZ/CX-4945 low concentration combined treatment. ATP release was significantly higher with CX-4945, especially at high concentrations, as well as with TMZ/CX-4945. Combined treatment may produce the simultaneous release of two potent immunogenic signals, which can explain the outperformance over single treatments in vivo. A word of caution may be raised since in vitro conditions are not able to mimic pharmacokinetics observed in vivo fully. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6COA of Formula: C19H12ClN3O2).

5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6) belongs to naphthyridine derivatives. The naphthyridines and their derivatives exhibit various types of biological activity, and the organic chemistry has been frequently reviewed. 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.COA of Formula: C19H12ClN3O2

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

Chiral 1,8-naphthyridine based ligands: Syntheses and characterization of Di- and tetranuclear copper(I) and silver(I) complexes was written by Sarkar, Mithun;Pandey, Pragati;Bera, Jitendra K.. And the article was included in Inorganica Chimica Acta in 2019.Application In Synthesis of (S)-4-Benzyl-2-(1,8-naphthyridin-2-yl)-4,5-dihydrooxazole This article mentions the following:

Oxazoline and camphor-pyrazole units are introduced on the 1,8-naphthyridine scaffold to access chiral ligands C₈H₅N₂C₃H₃NOR (R = Ph (L¹), CH₂Ph (L²)) and L³ (C₈H₄N₂(C₁₁H₁₆N₂)₂). Metalation of these chiral ligands with Cu(I) and Ag(I) precursors afforded di- and tetranuclear [Cu₄I₄(L¹)₂] (1), [Cu₄I₄(L²)₂] (2), [Cu₂I₂(L³)] (3), [Cu₂I(L²)₂](OTf) (4), [Ag₂(L¹)₂](OTf)₂ (5) and [Ag₄(L²)₄Br](OTf)₃ (6), containing [M₄X_n] (n = 1,4 and X = Br, I) or [M₂X_n] (n = 0, 1, 2 and X = I) core. All complexes are structurally characterized. Naphthyridine-derived ligands reveal a bridge-chelate coordination motif and hold two metal centers in close proximity. The tetranuclear complexes are dimers of dinuclear complexes bridged by the halides. Electronic absorption and emission spectra of the Cu complexes are reported. Catalytic utilities of all complexes were examined for asym. transformations but they showed poor activity probably due to limited solubility and coordinative saturation at the metal centers. The best results were obtained with [L³/Cu salt] combination for cyclopropanation of styrene, N-H bond insertion and nitroaldol (Henry) reactions with very low enantioselectivity. In the experiment, the researchers used many compounds, for example, (S)-4-Benzyl-2-(1,8-naphthyridin-2-yl)-4,5-dihydrooxazole (cas: 1772625-41-8Application In Synthesis of (S)-4-Benzyl-2-(1,8-naphthyridin-2-yl)-4,5-dihydrooxazole).

(S)-4-Benzyl-2-(1,8-naphthyridin-2-yl)-4,5-dihydrooxazole (cas: 1772625-41-8) 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.Application In Synthesis of (S)-4-Benzyl-2-(1,8-naphthyridin-2-yl)-4,5-dihydrooxazole

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

Protein kinase CK2 controls T-cell polarization through dendritic cell activation in response to contact sensitizers was written by de Bourayne, Marie;Gallais, Yann;El Ali, Zeina;Rousseau, Philippe;Damiens, Marie-Helene;Cochet, Claude;Filhol, Odile;Chollet-Martin, Sylvie;Pallardy, Marc;Kerdine-Roemer, Saadia. And the article was included in Journal of Leukocyte Biology in 2017.COA of Formula: C19H12ClN3O2 This article mentions the following:

Allergic contact dermatitis (ACD) represents a severe health problem with increasing worldwide prevalence. It is a T-cell-mediated inflammatory skin disease caused by chems. present in the daily or professional environment. NiSO₄ and 2,4-dinitrochlorobenzene (DNCB) are 2 chems. involved in ACD. These contact sensitizers are known to induce an up-regulation of phenotypic markers and cytokine secretion in dendritic cells (DCs; professional APCs), leading to the generation of CD8⁺ Tc1/Tc17 and CD4⁺ Th1/Th17 effector T cells. In the present study, using a peptide array approach, we identified protein kinase CK2 as a novel kinase involved in the activation of human monocyte-derived DCs (MoDCs) in response to NiSO₄ and DNCB. Inhibition of CK2 activity in MoDCs led to an altered mature phenotype with lower expression of CD54, PDL-1, CD86, and CD40 in response to NiSO₄ or DNCB. CK2 activity also regulated proinflammatory cytokine production, such as TNF-α, IL-1β, and IL-23 in MoDCs. Moreover, in a DC/T cell coculture model in an allogeneic setup, CK2 activity in MoDCs played a major role in Th1 polarization in response to NiSO₄ and DNCB. CK2 inhibition in MoDCs led to an enhanced Th2 polarization in the absence of contact sensitizer stimulation. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6COA of Formula: C19H12ClN3O2).

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. 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.COA of Formula: C19H12ClN3O2

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

Identification of novel regulators of STAT3 activity was written by Parri, Elina;Kuusanmaki, Heikki;van Adrichem, Arjan J.;Kaustio, Meri;Wennerberg, Krister. And the article was included in PLoS One in 2020.Electric Literature of C19H12ClN3O2 This article mentions the following:

STAT3 mediates signalling downstream of cytokine and growth factor receptors where it acts as a transcription factor for its target genes, including oncogenes and cell survival regulating genes. STAT3 has been found to be persistently activated in many types of cancers, primarily through its tyrosine phosphorylation (Y705). Here, we show that constitutive STAT3 activation protects cells from cytotoxic drug responses of several drug classes. To find novel and potentially targetable STAT3 regulators we performed a kinase and phosphatase siRNA screen with cells expressing either a hyperactive STAT3 mutant or IL6-induced wild type STAT3. The screen identified cell division cycle 7-related protein kinase (CDC7), casein kinase 2, alpha 1 (CSNK2), discoidin domain-containing receptor 2 (DDR2), cyclin-dependent kinase 8 (CDK8), phosphatidylinositol 4-kinase 2-alpha (PI4KII), C-terminal Src kinase (CSK) and receptor-type tyrosine-protein phosphatase H (PTPRH) as potential STAT3 regulators. Using small mol. inhibitors targeting these proteins, we confirmed dose and time dependent inhibition of STAT3-mediated transcription, suggesting that inhibition of these kinases may provide strategies for dampening STAT3 activity in cancers. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6Electric Literature of C19H12ClN3O2).

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. Very few metal complexes of naphthyridines other than 1,8-naphthyridine have been described.Electric Literature of C19H12ClN3O2

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

Expression of concern: autophagosome- mediated EGFR down-regulation induced by the CK2 inhibitor enhances the efficacy of EGFR-TKI on EGFR-mutant lung cancer cells with resistance by T790M [Erratum to document cited in CA163:608659] was written by Anonymous. And the article was included in PLoS One in 2019.Related Products of 1009820-21-6 This article mentions the following:

In Fig 1C, the actin bands are duplicated in the PC-9/GR and PC-9/ER panels. In Fig 1B and 1F, the images of cellular morphol. are the same in the PC-9/ER CT panels. The corrected version of Fig.1 is provided. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6Related Products of 1009820-21-6).

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. 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.Related Products of 1009820-21-6

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

Structural analysis of PIM1 kinase complexes with ATP-competitive inhibitors was written by Bogusz, Jozefina;Zrubek, Karol;Rembacz, Krzysztof P.;Grudnik, Przemyslaw;Golik, Przemyslaw;Romanowska, Malgorzata;Wladyka, Benedykt;Dubin, Grzegorz. And the article was included in Scientific Reports in 2017.Application of 1009820-21-6 This article mentions the following:

PIM1 is an oncogenic kinase overexpressed in a number of cancers where it correlates with poor prognosis. Several studies demonstrated that inhibition of PIM1 activity is an attractive strategy in fighting overexpressing cancers, while distinct structural features of ATP binding pocket make PIM1 an inviting target for the design of selective inhibitors. To facilitate development of specific PIM1 inhibitors, in this study we report three crystal structures of ATP-competitive inhibitors at the ATP binding pocket of PIM1. Two of the reported structures (CX-4945 and Ro-3306) explain the off-target effect on PIM1 of resp. casein kinase 2 and cyclin-dependent kinase 1 dedicated inhibitors. In turn, the structure with CX-6258 demonstrates a binding mode of a potent, selective inhibitor of PIM1, PIM2, PIM3 and Flt-3 kinases. The consequences of our findings for future inhibitor development are discussed. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6Application of 1009820-21-6).

5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6) 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. 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.Application of 1009820-21-6

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

Efficient hole transport materials based on naphthyridine core designed for application in perovskite solar photovoltaics was written by Vatanparast, Morteza;Shariatinia, Zahra. And the article was included in Journal of Molecular Graphics & Modelling in 2022.Synthetic Route of C8H6N2 This article mentions the following:

Naphthyridine-based compounds with a donor-acceptor-donor (D-A-D) skeleton were considered as hole transport materials (HTMs) for perovskite solar cells (PSCs). The optical characteristics, stability, solubility, Hirshfeld surface anal., crystal structure, and hole transport properties of the HTMs were studied systematically. The HOMO energies of all HTMs were higher than valence band of CH₃NH₃PbI₃ (MAPbI₃) perovskite signifying naphthyridine-based HTMs had appropriate energy alignments for usage in PSCs. The LUMO level of designed HTMs were higher than MAPbI₃ conduction band ensuring prevention of backward electronic movement from MAPbI₃ to the cathode. The λ^maxabs amounts of all HTMs were close 400 nm, which showed their competition with perovskite was impossible. The 18NP and 26NP HTMs had higher hole mobilities compared to that of the Spiro-OMeTAD. Considering aligned HOMO energies, suitable hole mobilities, satisfactory stability and solubility, 18NP (1,8-Naphthyridine) and 26NP (2,6-Naphthyridine) were introduced as the best HTM materials for PSCs which could replace Spiro-OMeTAD. In the experiment, the researchers used many compounds, for example, 2,6-Naphthyridine (cas: 253-50-9Synthetic Route of C8H6N2).

2,6-Naphthyridine (cas: 253-50-9) belongs to naphthyridine derivatives. The naphthyridines and their derivatives exhibit various types of biological activity, and the organic chemistry has been frequently reviewed. 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.Synthetic Route of C8H6N2

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

Vinpocetine inhibits RANKL-induced osteoclastogenesis and attenuates ovariectomy-induced bone loss was written by Zhu, Meipeng;Liu, Hui;Sun, Kai;Liu, Jian;Mou, Yan;Qi, Dahu;Zhou, Chuankun;Abudunaibi, Maihaiti;Tasiken, Bahebieergan;Li, Jianwen;Cheng, Hao;Huang, Hui. And the article was included in Biomedicine & Pharmacotherapy in 2020.Reference of 42971-09-5 This article mentions the following:

Osteoporosis is a result of impaired bone formation and/or excessive bone resorption. Osteoclasts are the only cells in the body that have a bone resorption function. Inhibiting osteoclast activity and differentiation is a way to treat osteoporosis. The current pharmacol. treatment for osteoporosis has many shortcomings, and more effective treatments are needed. Vinpocetine (Vinp), a derivative of the alkaloid vincamine, has been used to treat cerebrovascular disorders and cognitive impairment for a long time. Vinp inhibits mitogen-activated protein kinase (MAPK) and nuclear factor-kappa B (NF-kappa B)-dependent inflammatory responses and oxidative damage in which osteoclasts are often involved. However, the effects of Vinp on the regulation of osteoclast activity remain unknown. In this study, we found that Vinp significantly inhibited receptor activator of NF-kappa B ligand (RANKL)-induced osteoclast and F-actin formation and decreased osteoclastic bone resorption in vitro. Vinp also suppressed the expression of osteoclast-specific genes, including NFATc1, c-Fos, tartrate-resistant acid phosphatase (TRAP), matrix metalloproteinase-9 (MMP-9), and cathepsin K (CTSK) at both the mRNA and protein levels. Vinp reduced activation of NF-kappa B, MAPK, and AKT signaling during osteoclastogenesis and prevented the production of reactive oxygen species with increased nuclear factor erythroid 2-related factor 2, heme oxygenase 1, and NAD(P)H:quinone acceptor oxidoreductase 1 expression. Animal experiments consistently demonstrated that Vinp treatment significantly attenuated ovariectomy-induced bone loss with a decrease in the osteoclast number and decreases in serum levels of RANKL, TRAP, interleukin-1beta, and tumor necrosis factor-alpha, as well as increased serum levels of osteoprotegerin. Taken together, our findings reveal that Vinp may be a potential pharmacol. choice for preventing and treating osteoporosis. 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: 42971-09-5Reference of 42971-09-5).

(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. 1,6-Naphthyridine and some of its derivatives have been reported to have medicinal, electronic, and catalytic properties. But none of these investigations has yet resulted in any practical applications.Reference of 42971-09-5

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

D11-mediated inhibition of protein kinase CK2 impairs HIF-1α-mediated signaling in human glioblastoma cells was written by Schaefer, Susanne;Svenstrup, Tina H.;Fischer, Mette;Guerra, Barbara. And the article was included in Pharmaceuticals in 2017.Synthetic Route of C19H12ClN3O2 This article mentions the following:

Compelling evidence indicates that protein kinase CK2 plays an important role in many steps of cancer initiation and progression, therefore, the development of effective and cell-permeable inhibitors targeting this kinase has become an important objective for the treatment of a variety of cancer types including glioblastoma. We have recently identified 1,3-dichloro-6-[(E)-((4-methoxyphenyl)imino)methyl]dibenzo(b,d)furan-2,7-diol (D11) as a potent and selective inhibitor of protein kinase CK2. In this study, we have further characterized this compound and demonstrated that it suppresses CK2 kinase activity by mixed type inhibition (KI 7.7 nM, KI’ 42 nM). Incubation of glioblastoma cells with D11 induces cell death and upon hypoxia the compound leads to HIF-1α destabilization. The anal. of differential mRNA expression related to human hypoxia signaling pathway revealed that D11-mediated inhibition of CK2 caused strong down-regulation of genes associated with the hypoxia response including ANGPTL4, CA9, IGFBP3, MMP9, SLC2A1 and VEGFA. Taken together, the results reported here support the notion that including D11 in future treatment regimens might turn out to be a promising strategy to target tumor hypoxia to overcome resistance to radio- and chemotherapy. In the experiment, the researchers used many compounds, for example, 5-((3-Chlorophenyl)amino)benzo[c][2,6]naphthyridine-8-carboxylic acid (cas: 1009820-21-6Synthetic Route of C19H12ClN3O2).

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.Synthetic Route of C19H12ClN3O2

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