Amberlite IRA-400 Cl Resin Catalyzed Multicomponent Organic Synthesis in Water: Synthesis, Antimicrobial and Docking Studies of Spiroheterocyclic 2-Oxindoles and Acenaphthoquinone

Harichandran, G.; Devi, Krishnan Sarojini; Shanmugam, P.; Jesse, Michael Immanuel; Kathiravan, K.

doi:10.2174/2213337205666180316170023

Cited by 17 publications

(7 citation statements)

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“…Spirooxindoles containing a pyran ring have drawn noteworthy attention to organic as well as medicinal chemists due to their varied range of pharmacological activities including antimicrobial, antimycobacterial, antifungal, anticancer, antioxidant, and photochromic properties . Similarly, 4 H -pyran fused with dimedone/chromenes containing isatins showed a broad range of biological properties such as anticoagulant, spasmolytic, antioxidant, antibacterial, and diuretic activities. − Recently, Zarei et al synthesized mono- and bis-spiro-4 H -pyran and reported biological studies of the synthesized compounds . They have also described that the spiro-4 H -pyran derivatives bearing dimedone and isatin motifs have eminent antioxidant efficacies and exhibited strong antibacterial activities against the Escherichia coli bacterial strain compared to the positive control gentamicin.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel Fused Spiro-4H-Pyran Derivatives as Bacterial Biofilm Disruptor

et al. 2019

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This study aims to synthesize novel fused spiro-4H-pyran derivatives under green conditions to develop agents having antimicrobial activity. The synthesized compounds were initially screened for in vitro antibacterial activity against two Gram-positive and three Gram-negative bacterial strains, and all the compounds exhibited moderate to potent antibacterial activity. However, compound 4l showed significant inhibition toward all the bacterial strains, particularly against Streptococcus pneumoniae and Escherichia coli with minimum inhibitory concentration values of 125 μg/mL for each. The toxicity studies of selected compounds (4c, 4e, 4l, and 4m) using human red blood cells as well as human embryonic kidney (HEK-293) cells showed nontoxic behavior at desired concentration. Growth kinetic and time–kill curve studies of 4l against S. pneumoniae and E. coli supported its bactericidal nature. Interestingly, compound 4l showed a synergistic effect when used in combination with ciprofloxacin against selected strains. Biofilm formation in the presence of a lead compound, as assessed by XTT assay, showed complete disruption of the bacterial biofilm visualized by scanning electron microscopy. Overall, the findings suggest 4l to be considered as a promising lead for further development as an antibacterial agent.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel Fused Spiro-4H-Pyran Derivatives as Bacterial Biofilm Disruptor

et al. 2019

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“…The catalytic potency of our novel catalyst (PC/AgNPs) was compared with the same recently reported MCR, involving acenaphthenequinone, malononitrile and dimedone for the preparation of 2′-amino-tetrahydro-2 H -spiro[acenaphthylene-1,4′-chromene]-3′-carbonitrile ( 12b ) with various catalysts such as CaCl 2 , 164 Fe 3 O 4@ Cs-SO 3 H, 163 Na 2 EDTA, 165 HAuCl 4 .3H 2 O, 166 Meglumine, 135 Fe 2 O 3, 167 HEAA, 168 Cu(OAc) 2 . H 2 O, 169 Amb-400Cl (IRA-400 Cl), 170 Fe 3 O 4 @CS-SO 3 H NPs, 171 C 4 (DABCO-SO 3 H) 2 . 4Cl, 172 1-butyl-3-methylimidazolium hydroxide ([bmim][OH], 173 Carbon–SO 3 H, 174 DBU, 175 (SB-DBU)Cl, 176 PEG-Ni nanoparticle-catalyzed, 177 trisodiumcitrate dehydrate, 178 with that of PC/AgNPs novel catalyst.…”

Section: Resultsmentioning

confidence: 99%

Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite as a novel and efficient catalyst for the synthesis of 2-amino-4H-pyrans and spirochromenes

Saneinezhad

Mohammadi

Zadsirjan

et al. 2020

Sci Rep

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Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite (PC/AgNPs) was prepared and fully characterized by FTIR, UV–vis, SEM, and TEM techniques. The preparation of PC/AgNPs was studied systematically to optimize the processing parameters by Taguchi method using the amount of PC, reaction temperature, concentration of silver nitrate and pH of medium. Taguchi’s L9 orthogonal (4 parameters, 4 level) was used for the experimental design. The SEM analysis confirmed the presence of the Preyssler as a white cloud as well as spherical AgNPs on the surface of cellulose. The formation of AgNPs on the surface was observed by changing of the color from yellow to deep brown and confirmed by UV–vis spectroscopy. The best yield of AgNPs forming was obtained in pH 12.5 at 80 ºC in 20 min. TEM analysis confirmed the formation of spherical AgNPs with a size of 50 nm, at the 1% wt. loading of Preyssler. This easily prepared PC/AgNPs was successfully employed as an efficient, green, and reusable catalyst in the synthesis of a wide range of 2-amino-4 H -pyran and functionalized spirochromene derivatives via a one-pot, multicomponent reaction. The chief merits realized for this protocol were the utilization of commercially available or easily accessible starting materials, operational simplicity, facile work-up procedure, obtaining of high to excellent yields of the products and being done under green conditions. The catalyst could be easily separated from the reaction mixture and reused several times without observing any appreciable loss in its efficiency.

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“…reported its use as an efficient catalyst to access spirooxindole derivatives in water (Scheme 41A). Reduced reaction times, good reaction scope and reusability of the catalyst (up to four cycles) makes this protocol efficient and eco‐friendly [76] . Allahresani et al .…”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Amberlite IRA-400 Cl Resin Catalyzed Multicomponent Organic Synthesis in Water: Synthesis, Antimicrobial and Docking Studies of Spiroheterocyclic 2-Oxindoles and Acenaphthoquinone

Cited by 17 publications

References 0 publications

Design, Synthesis, and Biological Evaluation of Novel Fused Spiro-4H-Pyran Derivatives as Bacterial Biofilm Disruptor

Design, Synthesis, and Biological Evaluation of Novel Fused Spiro-4H-Pyran Derivatives as Bacterial Biofilm Disruptor

Silver nanoparticles-decorated Preyssler functionalized cellulose biocomposite as a novel and efficient catalyst for the synthesis of 2-amino-4H-pyrans and spirochromenes

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

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