One-Pot Regioselective Synthesis of Some Novel Isoxazole-Phenothiazine Hybrids and Their Antibacterial Activity

Guguloth, Veeranna; Thirukovela, Narasimha Swamy; Suresh, Palaniswamy; Vadde, Ramakrishna

doi:10.1134/s1070363220030214

Cited by 12 publications

(7 citation statements)

References 22 publications

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“…In this group, compounds 46 and 47 ( Figure 25 ) presented higher effects against all bacteria tested than the observed activity from antimicrobial penicillin-G (for Gram-positive bacteria) and streptomycin (for Gram-negative bacteria). Compound 46 , possessing a 4-trifluoromethyl group on the phenyl ring, also presents the best docking score in in silico simulations of the interaction with Staphylococcus aureus Murb, which express a homologous E. coli enzyme UDP- N -acetylenolpyruvylglucosamine reductase that is related with the synthesis of UDP- N -acetylmuramic acid in the bacterial cell wall [ 71 , 72 ].…”

Section: Antimicrobial Hybridsmentioning

confidence: 99%

Development of Phenothiazine Hybrids with Potential Medicinal Interest: A Review

et al. 2022

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The molecular hybridization approach has been used to develop compounds with improved efficacy by combining two or more pharmacophores of bioactive scaffolds. In this context, hybridization of various relevant pharmacophores with phenothiazine derivatives has resulted in pertinent compounds with diverse biological activities, interacting with specific or multiple targets. In fact, the development of new drugs or drug candidates based on phenothiazine system has been a promising approach due to the diverse activities associated with this tricyclic system, traditionally present in compounds with antipsychotic, antihistaminic and antimuscarinic effects. Actually, the pharmacological actions of phenothiazine hybrids include promising antibacterial, antifungal, anticancer, anti-inflammatory, antimalarial, analgesic and multi-drug resistance reversal properties. The present review summarizes the progress in the development of phenothiazine hybrids and their biological activity.

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Section: Antimicrobial Hybridsmentioning

confidence: 99%

Development of Phenothiazine Hybrids with Potential Medicinal Interest: A Review

et al. 2022

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“…Several new isoxazole phenothiazine hybrids 7 were regio-selectively prepared in high yields by a Cu (I) catalyzed one-pot reaction of 10-(prop-2yn-1-yl) phenothiazines 3 using various aromatic aldehydes 4 in aqueous butanol solution [32]. Preparation of these target isoxazole phenothiazine hybrids was continued through two steps as shown in Scheme 10.…”

Section: 3 Cycloaddition Reaction Routementioning

confidence: 99%

“…S C H E M E 1 0 Preparation of isoxazolephenothiazine hybrids 5-[(phenothiazin-10-yl) methyl]-3-phenylisoxazole derivatives [32] S C H E M E 1 1 Preparation of 3-(quinolin-2-yl)isoxazoles from TBN using 1,3-dipolar cycloaddition and alkenes or alkynes in metal-free conditions [33] S C H E M E 1 2 Synthesis route and mechanism of regioselective synthesis of 3,5-disubstituted isoxazoles [34] S C H E M E 1 3 The regioselective preparation of 3,5-disubstituted isoxazoles by 1,3-dipolar cycloaddition [35] Very interesting and novel synthesis starting with potassium poly(heptazine imide) (K-PHI) triplet excited states to O 2 and succeeding quenching with aldoximes 1, subsequently, the interface of 1O 2 by aldoximes produces nitrile oxides 2 were employed in the preparation of isoxazoles 3 by dipolar [3 + 2]-cycloaddition. The reaction has been depicted as shown in Scheme 17 [39].…”

Section: [3 + 2] Cycloaddition Routementioning

confidence: 99%

“…Furthermore, the overview of an electron scavenging group (F, Cl, Br, and NO) on the phenyl ring leads to a substantial decrease in inhibitory activity. S C H E M E 5 2 Synthesis of a new class of isoxazole-naphthalene analogues as tubulin polymerization inhibitors [73] The screening displayed some derivatives confirmed respectable to high inhibition activity, and those containing 4-trifluoromethyl group on the phenyl ring that is, S C H E M E 5 4 Preparation of some innovative isoxazolephenothiazine derivatives [32] these compounds were also tested against fungal species such as Aspergillus niger (ATCC1015) and Aspergillus fumigates (ATCC 1022) and Cycloheximide was used as a standard drug. Further, molecular modeling studies were also performed.…”

Section: Other Synthetic Routesmentioning

confidence: 99%

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A review of recent synthetic strategies and biological activities of isoxazole

Pandhurnekar¹,

Pandhurnekar

Mungole³

et al. 2022

Journal of Heterocyclic Chem

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Among different heterocyclic compounds, isoxazole and their analogues are very important classes of heterocyclic compounds as they display an extensive range of biological actions. This makes such scaffolds very important structures in the field of medicinal chemistry. From an extensive literature assessment, isoxazole is clinically proven to be very effective as an anti‐bacterial, anti‐fungal, anti‐inflammatory, anti‐cancer, anti‐tubercular, and anti‐neoplastic agent. The different derivatives of isoxazole which exhibits adjustment in their structure have shown a high degree of variety in their medicinal properties which makes evident them as very beneficial in the progress of novel bioactive drugs which show enhanced effectiveness along with minor harmfulness. Structural aspects of isoxazole having aromaticity with weaker nitrogen‐oxygen bonding provide a potential site for the ring cleavage. Thus, this isoxazole ring system allows easier modifications of substituents in their ring structure which consequently make isoxazole very useful intermediates in various synthetic routes of bioactive compounds. Hence, the synthesis and evaluation of isoxazole‐containing molecules with wider therapeutic consequences are always the topic of interest for chemists. Hence, in light of this comprehensive research on isoxazole, it is thought worthwhile to review various pathways for the synthesis of isoxazole analogues and having a broad spectrum of bioactive actions.

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“…Isoxazole derivatives play an interesting role in the development of heterocyclic chemistry; they are widely used as intermediates in organic synthesis. [ 1 ] In the quest for a new antibacterial agent, we found isoxazoles core to be a privileged structure in modern medicinal chemistry, possessing a wide range of pharmacological properties like antimicrobial, [ 2 ] anticancer, [ 3 ] anti‐HIV, [ 4 ] antituberculosis, [ 5 ] and anti‐inflammatory [ 6 ] activities. For instance, muscimol extracted from Amanita muscaria is an agonist of γ‐aminobutyric acid A (GABA‐A) receptor, which plays a role in regulating neuronal excitability in the central nervous system.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel isoxazole derivatives from acridone

Aarjane

Slassi

Tazi

et al. 2020

Archiv der Pharmazie

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The present study was carried out in an attempt to synthesize a new class of potential antibacterial agents. In this context, novel isoxazoles were synthesized and evaluated for their potential antibacterial behavior against four pathogenic bacterial strains. The synthesized compounds exhibited moderate‐to‐good antibacterial activity against these strains. The highest antibacterial activity was observed against the Escherichia coli strains, particularly for compounds 4a and 4e with phenyl and para‐nitrophenyl groups on the isoxazole–acridone skeleton; they showed promising minimum inhibitory concentration values of 16.88 and 19.01 μg/ml, respectively, compared with the standard drug chloramphenicol (22.41 µg/ml). The synthesized compounds were subjected to in silico docking studies to understand the mode of their interactions with the DNA topoisomerase complex (PDB ID: 3FV5) of E. coli. The molecular docking results showed that compounds 4a–l occupy the active site of DNA topoisomerase (PDB ID: 3FV5), stabilized via hydrogen bonding and hydrophobic interactions, which may be the reason behind their interesting in vitro antibacterial activity.

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One-Pot Regioselective Synthesis of Some Novel Isoxazole-Phenothiazine Hybrids and Their Antibacterial Activity

Cited by 12 publications

References 22 publications

Development of Phenothiazine Hybrids with Potential Medicinal Interest: A Review

Development of Phenothiazine Hybrids with Potential Medicinal Interest: A Review

A review of recent synthetic strategies and biological activities of isoxazole

Synthesis and biological evaluation of novel isoxazole derivatives from acridone

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