Synthesis of N-Phenylanthranilic Acids Using Water as Solvent

Pellón, Raiza Texidor; Carrasco, Ramón; Rodés, Lorenzo

doi:10.1080/00397919308011235

Cited by 44 publications

(18 citation statements)

References 9 publications

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“…The acridones (2a-g) were obtained from the corresponding 2-anilinobenzoic acids (1a-g), using Ullman modifications in the presence of water as solvent according to previous reports [22,23]. The compounds 4a [24], 3a, 3c, 3e, 3f, 6a, 6c, 6e and 6f [25] were synthesized as previously reported.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Evaluation of N-Substituted Acridones as Antiviral Agents against Haemorrhagic Fever Viruses

Sepúlveda

Fascio

Mazzucco

et al. 2008

Antivir Chem Chemother

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Background: In the present study, a series of N-substituted acridone derivatives was synthesized and evaluated against two haemorrhagic fever viruses (HFV). Methods: Compounds were tested against Junin virus (JUNV), an arenavirus agent of Argentine haemorrhagic fever, and dengue virus (DENV), a flavivirus agent of the most prevalent arthropod-borne viral disease in humans. Results: Among tested compounds, two N-allyl acridones (derivatives 3c and 3f) elicited a potent and selective antiviral activity against JUNV (strain IV4454) and DENV-2 (strain NGC) with 50% effective concentration values between 2.5 and 5.5 µM, as determined by virus yield inhibition. No cytotoxicity was detected at concentrations up to 1,000 µM, resulting in selectivity indices >181.8-400.0. Both acridones were effective against a wide spectrum of arenaviruses and the four serotypes of DENV. Furthermore, 3c and 3f failed to inactivate virus before cell infection as well as to induce a refractory state by cell pretreatment, indicating that the inhibitory effect was exerted through a blockade in virus multiplication during the infectious process. Conclusion: These data are the first demonstration that acridone derivatives have a potent antiviral activity that block in vitro multiplication of HFV belonging to Arenaviridae and Flaviviridae, such as JUNV and DENV.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and Evaluation of N-Substituted Acridones as Antiviral Agents against Haemorrhagic Fever Viruses

Sepúlveda

Fascio

Mazzucco

et al. 2008

Antivir Chem Chemother

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“…The Ullmann-type condensation reaction between orthochlorobenzoic acid and aniline to form N-phenylanthranilic acid is well-known, and over the years several modifications have been made in order to provide milder, faster and more environment friendly reaction conditions with improved yields (Pellón et al 1993;Docampo Palacios and Pellón Comdom 2003;Martín et al 2006). The most recently described method uses solvent-free conditions with microwave irradiation (Martín et al 2006).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac

Svanfelt

Krönberg

2009

Environ Chem Lett

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The formation of stable and potentially hazardous compounds as a result of photochemical transformation of pharmaceutical substances in the aquatic environment implies a demand for standard compounds within environmental analysis. The major phototransformation products of diclofenac are comprised of substituted diphenylamines and carbazoles. Substituted diphenylamines were synthesized by Ullmann condensation reactions between anilines and halobenzenes. Monochlorocarbazoles were obtained from palladium-catalyzed intramolecular coupling reactions of monochlorinated diphenylamines, photocyclization of dichlorinated diphenylamines or by direct chlorination of carbazole. The availability of synthetic photoproducts of diclofenac is of critical importance for further studies on the environmental fate as well as the ecotoxicological effects of the drug in the environment.

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“…Subsequently, a copper catalyst was also considered because it was the most suitable catalyst in a water solvent. 8 As shown in Table 1, the coupling reactions of 2,4-dichlorobenzoic acid and 7 with various copper catalysts in water were tested. The results showed that a satisfying yield (%) was achieved when CuI as catalyst was used.…”

Section: Resultsmentioning

confidence: 99%

Improved Manufacturing Process for Pyronaridine Tetraphosphate

Lee¹,

Lee²,

Cho³

et al. 2014

Bulletin of the Korean Chemical Society

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Pyronaridine tetraphosphate (1) is a well-known antimalarial drug. However, it required a carefully optimized production process for the manufacture of pyronaridine tetraphosphate. Each step of its manufacturing process was reinvestigated. For the cyclization of 4-chloro-2-(6-methoxy-pyridin-3-yl-amino)-benzoic acid 6 to 7,10-dichloro-2-methoxybenzo[b]-1,5-naphthyridine 5, an improved process was developed to eliminated critical process impurity (BIA). By the redesign of the formation of triphosphate salt, the purity as API grade was increased. Thus, a robust manufacturing process with an acceptable process performance has been developed to produce high quality pyronaridine tetraphosphate.

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Synthesis of N-Phenylanthranilic Acids Using Water as Solvent

Cited by 44 publications

References 9 publications

Synthesis and Evaluation of N-Substituted Acridones as Antiviral Agents against Haemorrhagic Fever Viruses

Synthesis and Evaluation of N-Substituted Acridones as Antiviral Agents against Haemorrhagic Fever Viruses

Synthesis of substituted diphenylamines and carbazoles: phototransformation products of diclofenac

Improved Manufacturing Process for Pyronaridine Tetraphosphate

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