Synthesis, antiviral and antibacterial activities and action mechanism of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety

Xia, Rongjiao; Guo, Tao; Chen, Mei; Su, Shijun; He, Jun; Xu, Tao; Jiang, Shichun

doi:10.1039/c9nj03019k

Cited by 39 publications

(27 citation statements)

References 33 publications

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“…The agricultural chemicals derived from natural products are environmentally friendly and have unique bioactivities. Xia et al [57] synthesized a series of penta-1,4-dien-3-one oxime comprising a quinoxaline moiety, equivalent to curcumin isolated from plant Curcuma Longa L. The synthesized compounds displayed antibacterial and antiviral activities, with distinct activity against TMV. As revealed in Scheme 13, 2-chloroquinoxaline (43) and penta-1,4-dien-3-one oxime ether (44) were stirred for 30 min and refluxed for 4 h at 80 • C to get the target compound (45).…”

Section: Synthesis Of Penta-14-dien-3-one Oxime Containing a Quinoxaline Nucleus As Antiviral Agentsmentioning

confidence: 99%

Novel Synthetic Routes to Prepare Biologically Active Quinoxalines and Their Derivatives: A Synthetic Review for the Last Two Decades

Khatoon

Abdulmalek

2021

Molecules

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Quinoxalines, a class of N-heterocyclic compounds, are important biological agents, and a significant amount of research activity has been directed towards this class. They have several prominent pharmacological effects like antifungal, antibacterial, antiviral, and antimicrobial. Quinoxaline derivatives have diverse therapeutic uses and have become the crucial component in drugs used to treat cancerous cells, AIDS, plant viruses, schizophrenia, certifying them a great future in medicinal chemistry. Due to the current pandemic situation caused by SARS-COVID 19, it has become essential to synthesize drugs to combat deadly pathogens (bacteria, fungi, viruses) for now and near future. Since quinoxalines is an essential moiety to treat infectious diseases, numerous synthetic routes have been developed by researchers, with a prime focus on green chemistry and cost-effective methods. This review paper highlights the various synthetic routes to prepare quinoxaline and its derivatives, covering the literature for the last two decades. A total of 31 schemes have been explained using the green chemistry approach, cost-effective methods, and quinoxaline derivatives’ therapeutic uses.

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Section: Synthesis Of Penta-14-dien-3-one Oxime Containing a Quinoxaline Nucleus As Antiviral Agentsmentioning

confidence: 99%

Novel Synthetic Routes to Prepare Biologically Active Quinoxalines and Their Derivatives: A Synthetic Review for the Last Two Decades

Khatoon

Abdulmalek

2021

Molecules

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“…As an example, tobacco mosaic virus is the most persistent plant virus and can survive in dry plant debris for up to 100 years. Individuals in more than 100 plant families can infect the virus, significant loss of crops each year globally due to plant diseases caused by tobacco mosaic virus . Hence, the development of novel antiviral molecules against tobacco mosaic virus has attracted an increasing amount of attention.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Guo

Xia

Liu

et al. 2020

Chemistry & Biodiversity

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A series of novel chalcone malonate derivatives were synthesized and their antibacterial and antiviral activities were evaluated. All target compounds were characterized by spectral data. The results of antimicrobial bioassay showed that one compound (diethyl [3-(naphthalen-2-yl)-1-(3-nitrophenyl)-3-oxopropyl]propanedioate) showed excellent antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo), with an EC 50 value of 10.2 μg/mL, which is significantly superior to bismerthiazol (71.7 μg/mL) and thiodiazole copper (97.8 μg/mL). At the same time, the mechanism of two compounds was confirmed by scanning electron microscopy. In addition, another compound (diethyl [3-(naphthalen-2-yl)-1-(4-nitrophenyl)-3-oxopropyl]propanedioate) showed significant curative activity to tobacco mosaic virus, with a value of 74.3 %, which was superior to 53.3 % of ningnanmycin. The results of microscale thermophoresis also showed that the Kd value of the combination of two compounds with the coat protein of tobacco mosaic virus was 0.211 and 0.166 μmol/L, which was better than 0.596 μmol/L of ningnanmycin. At the same time, the molecular docking of two compounds with tobacco mosaic virus-coat protein shows that the compound is well embedded in the pocket between the two subunits of tobacco mosaic virus-coat protein. These results show that chalcone derivatives containing malonate group can be considered as activators in the design of antibacterial and antiviral agents.

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“…Notably, these N‐heterocycles play an interesting role as basic skeleton for the synthesis of many other pharmacologically and biologically active agents. A large number of synthetic quinoxalines have been reported to exhibit Ant amoebic, anticancer, antifungal, antiviral and antibacterial, antimicrobial, antitumoral, anticonvulsant, antidiabetic, antinomic, antioxidant, antitubercular, and antileptospiral agents and neuroprotective activity . Also, some quinoxalines were used in agricultural field as pesticides and chemical controllable switches, corrosion inhibitor, and insecticides .…”

Section: Introductionmentioning

confidence: 99%

A newly synthesized nitrogen‐rich derivative of bicyclic quinoxaline—Structural and conceptual DFT reactivity study

Abad¹,

Hajji

Ramli

et al. 2020

J of Physical Organic Chem

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Novel nitrogen-rich compound featured bicyclic quinoxaline as a basic core structure has been synthesized, 1-{[1-(3-azido-2-hydroxypropyl)-1H-1,-2,3-triazol-4-yl]methyl}-3-methyl-1,2-dihydroquinoxalin-2-one with formula C 15 H 16 N 8 O 2 , and their structural and chemical reactivity aspects have been comprehensively discussed. Nature, role, and relative contribution of weak noncovalent interactions in supramolecular assembly have been assessed through single-crystal analysis and computational approaches. Useful information about the global and local reactivity were obtained from Conceptual Density Functional Theory at wB97X-D/cc-pVDZ level. Studied system could act as strong electrophile and/or moderate nucleophile in polar organic reactions. We hope this study will provide deeper insight in the knowledge of the synthesis and chemistry of the quinoxaline and quinoxaline derivatives. K E Y W O R D SDFT, chemical reactivity theory, Hirshfeld surfaces, NCI topological analysis, quinoxaline derivatives, weak noncovalent interactions

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Synthesis, antiviral and antibacterial activities and action mechanism of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety

Abstract: A series of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety were synthesized, and their bioactivities and action mechanism were evaluated.

Cited by 39 publications

References 33 publications

Novel Synthetic Routes to Prepare Biologically Active Quinoxalines and Their Derivatives: A Synthetic Review for the Last Two Decades

Novel Synthetic Routes to Prepare Biologically Active Quinoxalines and Their Derivatives: A Synthetic Review for the Last Two Decades

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

A newly synthesized nitrogen‐rich derivative of bicyclic quinoxaline—Structural and conceptual DFT reactivity study

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