Synthesis and antiviral activity of 2-[aryl(hetaryl)]quinoline-4-carboxylic acids

Belen'kaya, R. S.; Бореко, Е. И.; Земцова, М. Н.; Kalinina, M. I.; Timofeeva, M. M.; Trakhtenberg, P. L.; Chelnov, V. M.; Lipkin, A. E.; Votyakov, V. I.

doi:10.1007/bf00758458

Cited by 6 publications

(6 citation statements)

References 11 publications

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“…Meanwhile, by employing well‐known Pfitzinger reaction condition, [29–31] substituted acetophenones/appropriate ethanones (R 4 ‐COCH 3 ) and isatin 5 were treated with sodium hydroxide in a mixture of ethanol: water (7 : 1) under reflux to form 2‐substituted cinchonic acids 6a – aj . Synthesis of nitro substituted cinchonic acid 6j , 6v was carried out through weak base assisted condensation of isatin and corresponding nitro acetophenone, followed by acid catalyzed cyclization of resultant intermediate as reported in literature [32] . The above formed cinchonic acids 6a – aj were treated with intermediate aniline 4a using EDCI⋅HCl and HOBt to afford desired product 7a – aj .…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of nitro substituted cinchonic acid 6j, 6v was carried out through weak base assisted condensation of isatin and corresponding nitro acetophenone, followed by acid catalyzed cyclization of resultant intermediate as reported in literature. [32] The above formed cinchonic acids 6a-aj were treated with intermediate aniline 4a using EDCI•HCl and HOBt to afford desired product 7a-aj. Synthesis of modified analogs of hit compound was achieved as illustrated in Scheme 1.…”

Section: Chemistrymentioning

confidence: 99%

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Exploration of Isoxazole‐Carboxylic Acid Methyl Ester Based 2‐Substituted Quinoline Derivatives as Promising Antitubercular Agents

Sahoo

Ahmad

Kaul

et al. 2022

Chemistry & Biodiversity

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In pursuit of potent anti‐TB agents active against drug resistant tuberculosis (DR‐TB), herein we report synthesis and bio‐evaluation of a new series of isoxazole‐carboxylic acid methyl ester based 2‐substituted quinoline derivatives. Preliminary evaluation indicated selectivity towards Mtb H37Rv, with no inhibition of non‐tubercular mycobacterial (NTM) & bacterial pathogen panel. Out of 36 synthesized compounds, majority exhibited substantial inhibition of Mtb H37Rv (MIC 0.5–8 μg/mL). Cell viability test against Vero cells revealed no significant cytotoxicity. Further, screening against drug resistant strains (DR‐Mtb) found hit compound displaying promising potency (MIC 1–4 μg/mL). Structure optimization of the hit led to the identification of lead compound demonstrating potent inhibition of both drug‐susceptible Mtb (MIC 0.12 μg/mL) and drug‐resistant Mtb (MIC 0.25–0.5 μg/mL) along with a high selectivity index (SI) >80. Taken together, with appreciable selectivity and potent activity, these chemotypes show prospect to be turned into a potential anti‐TB candidate.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Exploration of Isoxazole‐Carboxylic Acid Methyl Ester Based 2‐Substituted Quinoline Derivatives as Promising Antitubercular Agents

Sahoo

Ahmad

Kaul

et al. 2022

Chemistry & Biodiversity

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“…The error of mea surements was ±2 cm -1 . The 1 H NMR spectra were recorded on a Varian VXR 200 Mercury spectrometer operating at 200 MHz in DMSO d 6 with SiMe 4 as the internal standard; the δ scale was used in all cases.…”

Section: Methodsmentioning

confidence: 99%

Dimerization of 3-(2-aryl-2-oxoethylidene)oxindoles

et al. 2008

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6 Aroyl 7 arylindolo[3,4 jk]phenanthridin 5(4H) ones (2a-i) were synthesized by heating 3 (2 aryl 2 oxoethylidene) 2,3 dihydroindol 2 ones (1a-i) in DMF. Compounds 2a-i are formed via the dimerization of two molecules of unsaturated ketones 1a-i proceeding as the [2+4] cycloaddition through the formation of intermediate spiro adducts. The further Pfitzinger rearrangement, decarboxylation, and heteroaromatization afford compounds 2a-i. The structures of the reaction products were established by spectroscopic methods and X ray diffraction.

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“…Several communications reported on the synthesis ofquinoline derivatives from 3-substituted oxindoles [77][78][79]. …”

Section: Syntheses Of 2-lndolinone Based Heterocycles Including Mmentioning

confidence: 99%

Heterocyclization of 2-indolinone derivatives (A review)

Граник¹,

Graevskaya²,

Ryabova³

1997

Pharm Chem J

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At present, only a few summarizing papers devoted to the synthesis of varions heterocycles on the basis of oxindole (2indolinone) are available in the literature. The well-known monograph [ I] considered the synthesis of condensed indoles based on the 2-indolinone derivatives. Unfortunately, a recent review [2] paid little attention to the problem of heteroeyclization in these systems. We believed that it would be importaat to fill the gap, thus stimulating investigations in this direction. This review summarizes data published doting the past two decades on the annelation of various heterocycles at different "edges" of the indole cycle using substituted indoles as the initial compounds. In addition, Section IV concerns some problems related to the possible expansions of the fivemembered oxindole ring.

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Synthesis and antiviral activity of 2-[aryl(hetaryl)]quinoline-4-carboxylic acids

Cited by 6 publications

References 11 publications

Exploration of Isoxazole‐Carboxylic Acid Methyl Ester Based 2‐Substituted Quinoline Derivatives as Promising Antitubercular Agents

Exploration of Isoxazole‐Carboxylic Acid Methyl Ester Based 2‐Substituted Quinoline Derivatives as Promising Antitubercular Agents

Dimerization of 3-(2-aryl-2-oxoethylidene)oxindoles

Heterocyclization of 2-indolinone derivatives (A review)

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