Benzo[f]naphtyridones: a new family of topical antibacterial agents active on multi-resistant Gram-positive pathogens

Tabart, Michel; Picaut, Guy; Lavergne, Marc; Wentzler, Sylvie; Malleron, Jean-Luc; Dutka‐Malen, Sylvie; Berthaud, Nadine

doi:10.1016/s0960-894x(03)00057-x

Cited by 16 publications

(5 citation statements)

References 12 publications

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“…Among 1,7-naphthyridine derivatives, substances have been found that show bronchodilator activity, 5a some are PARp-1 inhibitors, 5b and antibacterial agents. 5c These substances have also shown to be strong neurokinin NK1-receptor antagonists. 5d 1,7-Naphthyridine and pyrazolo[3,4- b ]pyridine derivatives have played an important role in organic and medicinal chemistry due to their therapeutic and pharmacological properties.…”

Section: Table 1 Antioxidant Activity Of 5-aminopyrazol...mentioning

confidence: 99%

New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

Fisyuk,

Shuvalov,

Shatsauskas

et al. 2023

Synthesis

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Reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole with azlactones under solvent-free conditions with heating furnished tetrahydro-1H-pyrazolo[3,4-b]pyridines. The latter were converted to oxazolo[5,4-b]pyrazolo[4,3-e]pyridines by the action with POCl3 on air. Further reaction of oxazolo[5,4-b]pyrazolo[4,3-e]pyridines with hydrazine hydrate and alkali led to the formation of 5-amino-1,7-dihydro-6H-pyrazolo[3,4-b]pyridin-6-ones, which reacted with aluminum chloride to yield 3,4-dihydro-5H-pyrazolo[4,3-f][1,7]naphthyridin-5-ones. Some of the synthesized compounds show antioxidant activity or are effective phosphors.

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Section: Table 1 Antioxidant Activity Of 5-aminopyrazol...mentioning

confidence: 99%

New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

Fisyuk,

Shuvalov,

Shatsauskas

et al. 2023

Synthesis

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“…Quinolines are privileged motifs that are abundantly found in natural products, pharmaceuticals, and agrochemicals . Of note, 3-aminoquinoline derivatives are an important class of quinolines and widely appear in many medicinal drugs . For instance, AZD2624/AZD4901, Jusbetonin, c-Met inhibitor, and pyronaridine were shown to exhibit diverse biological activities (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Rhodium-Catalyzed [4 + 2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines

2023

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Efficient synthesis of 3-aminoquinolines has been demonstrated from readily accessible N-sulfonyl-1,2,3-triazoles and oacylaniline derivatives. This transformation involves the generation of C−C and C−N bonds through insertion of rhodium azavinyl carbenoid into a N−H bond followed by cyclization and aromatization. The important features include good functional group tolerance, synthesis of indoloquinoline, and isolation of N−H-inserted product, a potential intermediate.

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“…[15,16] Recently, 1,4-dihydro-4-oxo-1,6-naphthyridine analogues have been described as antibacterial agents. [16][17][18][19][20] 5-Substituted-8-hydroxy-1,6-naphthyridine-7-carboxamides are useful as HIV integrase inhibitors for the treatment of HIV infection (AIDS). [21,22] A series of novel 1,6naphthyridine derivatives have been prepared as potential inhibitors of human topoisomerase I, [23] antiproliferative, antitumor, [24,25] anticonvulsive agents, [26] p38 mitogen-activated protein kinase inhibitors, [27] JAK2 inhibitors, [28,29] and spleen tyrosine kinase inhibitors.…”

Section: Introductionmentioning

confidence: 99%

“…Among all nitrogen heterocycles, 1,6‐naphthyridine analogues [13,14] are important class of compounds possessing diverse types of biological properties [15,16] . Recently, 1,4‐dihydro‐4‐oxo‐1,6‐naphthyridine analogues have been described as antibacterial agents [16–20] . 5‐Substituted‐8‐hydroxy‐1,6‐naphthyridine‐7‐carboxamides are useful as HIV integrase inhibitors for the treatment of HIV infection (AIDS) [21,22] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, In Vitro Cytotoxicity, and DFT Studies of Novel 2‐Amino Substituted Benzonaphthyridines as PDK1 Inhibitors

Prabha¹,

Satheeshkumar

Nasif

et al. 2022

ChemistrySelect

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The present work emphasizes the utility of 2,4‐dichloro‐5‐methylbenzo[h][1,6]naphthyridine as starting precursors. The reaction of 2,4‐dichloro‐5‐methylbenzo[h][1,6]naphthyridine with a variety of aliphatic and aromatic amines yielded 2‐amino substituted 2,4‐dichlorobenzo[h]naphthyridines. All the compounds were examined for their in vitro anticancer activity against six human cancer lines and docked with PDK1 inhibitors. The structure‐activity relationship studies are revealed that the compounds holding aminocarbazole moiety and triazole amine moiety improve the activity profile. All the structures of synthesized compounds were optimized at B3LYP‐D3/6‐31G(d) level in the water. Furthermore, the electronic properties and biological reactivity of the synthesized compounds are explored using computational techniques.

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Benzo[f]naphtyridones: a new family of topical antibacterial agents active on multi-resistant Gram-positive pathogens

Cited by 16 publications

References 12 publications

New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

Rhodium-Catalyzed [4 + 2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines

Synthesis, In Vitro Cytotoxicity, and DFT Studies of Novel 2‐Amino Substituted Benzonaphthyridines as PDK1 Inhibitors

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