o-Nitrobenzylidene compounds. Part 3. Formation of 4-arylamino-3-methoxycinnoline 1-oxides from N-o-nitrobenzylideneanilines, cyanide ion, methanol: the intermediacy of 2-aryl-3-cyano-2H-indazole 1-oxides

Johnston, David B.; Smith, David M.; Shepherd, T. M.; Thompson, David

doi:10.1039/p19870000495

Cited by 18 publications

(5 citation statements)

References 6 publications

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“…Yellow solid (92% yield); m.p. : 79.1–79.9 °C (lit [ 36 ]: 81–82 °C); 1 H-NMR (600 MHz, CDCl 3 ) δ 8.97 (s, 1H), 8.32 (dd, J = 7.8, 1.4 Hz, 1H), 8.06 (dd, J = 8.2, 1.1 Hz, 1H), 7.75–7.70 (m, 1H), 7.62–7.57 (m, 1H), 7.35–7.29 (m, 2H), 6.98–6.94 (m, 2H), 3.85 (s, 3H); 13 C-NMR (151 MHz, CDCl 3 ) δ 159.09, 153.31, 143.88, 133.48, 131.36, 130.81, 129.55, 124.53, 122.78, 114.50, 55.53.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents

et al. 2017

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Indazole is considered a very important scaffold in medicinal chemistry. It is commonly found in compounds with diverse biological activities, e.g., antimicrobial and anti-inflammatory agents. Considering that infectious diseases are associated to an inflammatory response, we designed a set of 2H-indazole derivatives by hybridization of cyclic systems commonly found in antimicrobial and anti-inflammatory compounds. The derivatives were synthesized and tested against selected intestinal and vaginal pathogens, including the protozoa Giardia intestinalis, Entamoeba histolytica, and Trichomonas vaginalis; the bacteria Escherichia coli and Salmonella enterica serovar Typhi; and the yeasts Candida albicans and Candida glabrata. Biological evaluations revealed that synthesized compounds have antiprotozoal activity and, in most cases, are more potent than the reference drug metronidazole, e.g., compound 18 is 12.8 times more active than metronidazole against G. intestinalis. Furthermore, two 2,3-diphenyl-2H-indazole derivatives (18 and 23) showed in vitro growth inhibition against Candida albicans and Candida glabrata. In addition to their antimicrobial activity, the anti-inflammatory potential for selected compounds was evaluated in silico and in vitro against human cyclooxygenase-2 (COX-2). The results showed that compounds 18, 21, 23, and 26 display in vitro inhibitory activity against COX-2, whereas docking calculations suggest a similar binding mode as compared to rofecoxib, the crystallographic reference.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents

et al. 2017

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“…Chemistry. The 9,11-dihydroindolizino[1,2- b ]quinolines 10 and 11 were synthesized on the basis of the Friedländer reaction, requiring the appropriate 2-aminobenzaldehydes 3a , b (and the imine surrogate 4 , ) and the enolizable indolizinones 8 and 9 (Scheme ). The 2-aminobenzaldehydes 3a , b were obtained in two steps by O-alkylation of phenols 1a and 1b (K 2 CO 3 , DMF) followed by a Bechamp reduction of the nitro group of 2a , b .…”

Section: Resultsmentioning

confidence: 99%

“…General Procedure for the Synthesis of 9,11-Dihydroindolizino[1,2-b]quinolines 10a-c and 11a-c. Tetrahydroindolizine 8 or 9 and 2-aminobenzaldehyde 3a, 3b, or 4 8,9 were added to acetic acid (20 mL) and heated while stirring under reflux for 8 h. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. Methanol saturated HCl was added to the residual solid dissolved in MeOH.…”

Section: N-(7-methyl-15-dioxo-1235-tetrahydroindolizin-6-ylmethyl)ace...mentioning

confidence: 99%

Formaldehyde-Induced DNA Cross-Link of Indolizino[1,2-b]quinolines Derived from the A−D Rings of Camptothecin

et al. 2002

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Camptothecin consists of a lactone E ring adjacent to tetracyclic A-D rings of a planar chromophore, which are essential for topoisomerase I inhibition and DNA interaction. The A-D rings can be exploited to develop DNA-sequence-reading molecules. Indolizino[1,2-b]quinoline derivatives substituted with a piperidinoethyloxy side chain and an aminomethyl function on rings A and D, respectively, were synthesized, and their DNA binding and formaldehyde-mediated bonding properties were investigated.

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“…This second step in the tandem reaction, formation of nitrogen–nitrogen bond, has been known for years and it was employed e.g., in the synthesis of 3,4-fused cinnolines59,60 and indazole oxides 39,40,42,44…”

Section: Discussionmentioning

confidence: 99%

Remarkably Efficient Synthesis of 2H-Indazole 1-Oxides and 2H-Indazoles via Tandem Carbon−Carbon Followed by Nitrogen−Nitrogen Bond Formation

et al. 2008

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o-Nitrobenzylidene compounds. Part 3. Formation of 4-arylamino-3-methoxycinnoline 1-oxides from N-o-nitrobenzylideneanilines, cyanide ion, methanol: the intermediacy of 2-aryl-3-cyano-2H-indazole 1-oxides

Cited by 18 publications

References 6 publications

Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents

Synthesis and Biological Evaluation of 2H-Indazole Derivatives: Towards Antimicrobial and Anti-Inflammatory Dual Agents

Formaldehyde-Induced DNA Cross-Link of Indolizino[1,2-b]quinolines Derived from the A−D Rings of Camptothecin

Remarkably Efficient Synthesis of 2H-Indazole 1-Oxides and 2H-Indazoles via Tandem Carbon−Carbon Followed by Nitrogen−Nitrogen Bond Formation

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