Facile Synthesis of 1-Hydroxy-5-methoxy-Benzo[<i>f</i>][2,7]naphthyridines

Rajeev, P. V.; Rajendran, S. P.

doi:10.1080/00397910903320258

Cited by 8 publications

(5 citation statements)

References 16 publications

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“…The results indicated that the percentage of the late apoptosis is more than that of early apoptosis which a good evidence for irreversible apoptosis caused by compounds 6e (Figures 4 and 5). In accordance of IC 50 concentration duplicate (0.90 μM), the same results [49] 2a,b, [48,54] 3a,b, [50] and 5. [52] The InChI codes of the investigated compounds together with some biological activity data are provided as Supporting Information.…”

Section: Cell Cycle Analysis and Apoptosissupporting

confidence: 72%

“…The intermediates quinoline aldehydes 1a,b, 2a,b, 3a,b were synthesized through reported methods in literature, [48][49][50] Scheme 1. The 2-alkylthioquinoline-3-carbaldhyde derivatives 4a-h were prepared by stirring of compounds 1a or 1b with sodium sulfide in DMF, further alkylation in the same reaction with different alkyl halides afforded the intermediates 4a-h. [49] The structure of the new derivatives 4d-f was confirmed by 1 H NMR, mass spectroscopy, and elemental analysis.…”

Section: Chemistrymentioning

confidence: 99%

“…The most active compounds from NCI results, compounds 6c, 6e-g were selected to evaluate cytotoxicity using MTT assay and IC 50 Table 3.…”

Section: Evaluation Of Ic 50mentioning

confidence: 99%

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Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Abdelbaset

Abdel‐Aziz

Abuo‐Rahma

et al. 2018

Arch. Pharm. Chem. Life Sci.

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Novel quinoline derivatives carrying nitrones and oxime as nitric oxide donors were prepared and characterized using different spectroscopic techniques. Nitrones can release nitric oxide in larger amounts compared to corresponding oximes. Antiproliferative screening results showed that the 2-benzylthioquinoline nitrones 6e and 6f and the 2-methylthio analogues 6g and 6h exhibited promising antiproliferative activity especially against leukemia and colon cancer cell lines. Compounds 6c, 6e, and 6f exhibited higher potency as anticancer agents compared to doxorubicin, with IC 50 ranging from 0.45 to 0.91 μM. A remarkable overexpression of caspase-3 protein levels was observed in cells treated with the tested compounds. Compound 6e exhibited more pre-G1 apoptosis and cell cycle arrest at the G2/M phase than in other phases.These results revealed that the tested compounds can cause programmed cell death through overexpression of caspase 3, which may be attributed to the release of nitric oxide. K E Y W O R D S antiproliferative, apoptosis, caspase 3, nitric oxide, nitrones, oximes 1 | INTRODUCTION Quinoline is a significant nucleus which has attracted the attention of medicinal chemists due to its variable pharmacological activities. Easy functionalization of various ring positions of quinoline makes it an attractive synthetic building block for design and synthesis of new drugs. Additionally, quinolines are considered as an interesting group of compounds, many of which have widespread pharmacologicalactions such as anti-microbial, [1][2][3][4] anti-inflammatory, [5][6][7][8] antitubercular, [9][10][11][12] anti-convulsant, [13] antihypertensive, [14,15] antioxidant, [16][17][18][19] and anticancer [20] activities. Several mechanisms can explain the anticancer effect of quinoline derivatives including: topoisomerase inhibition, [21][22][23] DNA intercalation, [24] protein kinases inhibition, [25][26][27] tubulin polymerase inhibition, [28][29][30][31] and induction of apoptosis. [32,33] Quinoline derivative I exhibited potent anticancer activity against brain cancer cell line U87 with IC 50 of 1.5 nM. [31] Compound II exhibits remarkable anticancer activity against HL60 cancer cell line with IC 50 of 0.68 μM (Figure 1). [33] Incorporation of biologically active moieties into quinoline such as nitrones [34] and oximes [35] may produce biologically active anticancer agents.Compound III showed significant anticancer activity with IC 50 of 31.42 μM against Hep-G 2 cancer cell line (Figure 1). [34] Nitrones are a Arch Pharm Chem Life Sci. 2019;352:e1800270.wileyonlinelibrary.com/journal/ardp

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Section: Cell Cycle Analysis and Apoptosissupporting

confidence: 72%

Section: Chemistrymentioning

confidence: 99%

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Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Abdelbaset

Abdel‐Aziz

Abuo‐Rahma

et al. 2018

Arch. Pharm. Chem. Life Sci.

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“…Following the general procedure, reaction of 2-methoxy-6-methylquinoline-3-carbaldehyde (201 mg, 1 mmol), Na 2 SO 4 (410 mg, 3 mmol), Et 3 N (0.30 mL, 2 mmol), and N -benzylhydroxylamine hydrochloride (239 mg, 1.5 mmol) in EtOH (15 mL), after 3 h, and column chromatography (hexane/EtOAc, 9:1, v/v) gave nitrone 14 (92 mg, 30%) as a pale yellow solid: mp 142–4 °C; IR (KBr) ν max 2943, 1595, 1447, 1344, 1257 cm –1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 10.02 (s, 1H, H4), 8.03 [s, 1H, H CN(O)CH 2 C 6 H 5 ], 7.67 (d, J = 8.5 Hz, 1H, H8), 7.52–7.50 {m, 3H: 1H (H7) + 2H [HCN(O)CH 2 C 6 H 5 ], 7.42 {m, 4H: 1H (H5) + 3H [HCN(O)CH 2 C 6 H 5 ]}, 5.10 [s, 2H, HCN(O)C H 2 C 6 H 5 ], 4.07 (s, 3H, OCH 3 ), 2.45 (s, 3H, CH 3 ); 13 C NMR (101 MHz, CDCl 3 ) δ 158.3, 144.9, 137.0, 134.4, 133.6, 133.0, 129.3 (2C), 129.2, 129.1 (2C), 128.7, 128.3, 126.7, 125.2, 115.2, 71.9, 53.9, 21.5. MS (ESI) m / z : 307 [M + 1] + , 329 [M + Na] + .…”

Section: Experimental Partmentioning

confidence: 99%

New Quinolylnitrones for Stroke Therapy: Antioxidant and Neuroprotective (Z)-N-tert-Butyl-1-(2-chloro-6-methoxyquinolin-3-yl)methanimine Oxide as a New Lead-Compound for Ischemic Stroke Treatment

et al. 2019

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We describe herein the synthesis and neuroprotective capacity of an array of 31 compounds comprising quinolyloximes, quinolylhydrazones, quinolylimines, QNs, and related heterocyclic azolylnitrones. Neuronal cultures subjected to oxygen−glucose deprivation (OGD), as experimental model for ischemic conditions, were treated with our molecules at the onset of recovery period after OGD and showed that most of these QNs, but not the azo molecules, improved neuronal viability 24 h after recovery. Especially, QN (Z)-N-tert-butyl-1-(2-chloro-6-methoxyquinolin-3-yl)methanimine oxide (23) was shown as a very potent neuroprotective agent. Antioxidant analysis based on the ability of QN 23 to trap different types of toxic radical oxygenated species supported and confirmed its strong neuroprotective capacity. Finally, QN 23 showed also neuroprotection induction in two in vivo models of cerebral ischemia, decreasing neuronal death and reducing infarct size, allowing us to conclude that QN 23 can be considered as new lead-compound for ischemic stroke treatment.

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“…Recently we have reported 9 the synthesis of 2benzoylfuro [2,3-b]quinolines from quinoline-based chalcones by bromocyclization method. We report here an extension of this methodology for the synthesis of 2-acetylfuro[2,3-b]quinolines started from 2-methoxy-3-formylquinolines [10][11][12] which in turn were synthesized from 2-chloro-3-formylquinolines in single step under the Cannizzaro reaction conditions. Cannizzaro reaction is the redox disproportionative conversion of aldehydes into their corresponding alcohols and acids.…”

Section: Resultsmentioning

confidence: 99%

Cannizzaro reaction of 2-chloro-3-formylquinolines and its synthetic utility for 2-acetylfuro[2,3-b]quinolines: The alkaloid analogues

2012

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Cannizzaro reaction of 2-chloro-3-formylquinolines was investigated under two different conditions. Under both conditions, redox and methoxylation proceeded simultaneously and gave 2-methoxy-3-formylquinolines, 2-methoxyquinolin-3-yl-methanols and 2-methoxyquinoline-3-carboxylic acids. The synthesized 2-methoxy-3-formylquinolines were then condensed with acetone in the presence of sulphuric acid to give 4-(2-methoxy-quinolin-3-yl)-but-3-en-2-ones which in turn were bromocyclized and dehydrobrominated to get 2-acetylfuro[2,3-b]quinolines.

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Facile Synthesis of 1-Hydroxy-5-methoxy-Benzo[f][2,7]naphthyridines

Cited by 8 publications

References 16 publications

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

New Quinolylnitrones for Stroke Therapy: Antioxidant and Neuroprotective (Z)-N-tert-Butyl-1-(2-chloro-6-methoxyquinolin-3-yl)methanimine Oxide as a New Lead-Compound for Ischemic Stroke Treatment

Cannizzaro reaction of 2-chloro-3-formylquinolines and its synthetic utility for 2-acetylfuro[2,3-b]quinolines: The alkaloid analogues

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