Synthesis of a new class of antimicrobial agents incorporating the indolin-2-one moiety

Kandile, Nadia G.; Zaky, Howida T.; Saleh, Yassmin G; Ahmed, Nashwa A.

doi:10.3109/14756366.2012.689298

Cited by 9 publications

(4 citation statements)

References 32 publications

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“…On the other hand, the heterocyclic compounds indolin-2-one and 3-halooxindoles have been the subject of extensive research in various fields of organic chemistry. [28][29][30] Traditionally, the synthesis of 3-halooxindoles was relied on multi-step and iterative manipulations of functional groups to incorporate both oxygen and halogen functionalities. [31] At present, the direct 3-halooxidation [30,32] of an indole derivative (using more than two equivalents of NCS and a large amount of solvent) has emerged as a supplementary approach that has been extensively utilised (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

“…However, the divulged methodologies have several downsides, such as low yield, wide adaptability, the formation of multiple products, a multistep process, and the accessibility and stability of the reagents (Scheme 1a). On the other hand, the heterocyclic compounds indolin‐2‐one and 3‐halooxindoles have been the subject of extensive research in various fields of organic chemistry [28–30] . Traditionally, the synthesis of 3‐halooxindoles was relied on multi‐step and iterative manipulations of functional groups to incorporate both oxygen and halogen functionalities [31] .…”

Section: Introductionmentioning

confidence: 99%

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Selective Functionalization of Indole: Synthesis of Bioinspired 2,2′‐thiobisindoles, 3‐substituted Oxindoles, and 1‐(chloromethyl) Indoline‐2‐dione in One‐pot manner

Sharma,

Kumar,

Erande

2024

ChemistrySelect

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Indolyl thioethers and indolin‐2‐one motifs are extremely common in pharmaceuticals and organic materials, therefore developing a method to create these scaffolds is considered to be a vital endeavour in the chemical sciences. Here we have reported a unified strategy developed by the fine‐tuning of catalyst‐solvent combination [SOCl2 /AlCl3 in CHCl3 and SOCl2/DMSO (1 : 1) in CHCl3 at 25 °C] towards selective functionalization of Indole to synthesize 2,2′‐thiobisindoles and 3‐chloro‐3‐alkyl substituted oxindoles selectively in one‐pot manner with good to satisfactory yield (52‐86 %; 26 Examples). In application, reactions of 3‐subsituted indole and isatin derivatives produced the 1‐(chloromethyl) indoline‐2,3‐diones by just changing the reaction condition (60 °C), which shows the synthetic utility of the developed method.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selective Functionalization of Indole: Synthesis of Bioinspired 2,2′‐thiobisindoles, 3‐substituted Oxindoles, and 1‐(chloromethyl) Indoline‐2‐dione in One‐pot manner

Sharma,

Kumar,

Erande

2024

ChemistrySelect

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“…Moreover, N.G. Kandile et al, [82] synthesized a series of indolyl-pyrrolones and tested their antibacterial activity. Compound 92 exhibited equipotent activity to chloramphenicol against E. coli with MIC of 2.5 µg/ML.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Pyridazinones and pyrrolones as promising Scaffolds in Medicinal Chemistry

Abdelbaset

Abdel‐Aziz

Abuo‐Rahma

et al. 2018

Journal of advanced Biomedical and Pharmaceutical Sciences

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Pyridazinones and pyrrolones are important building blocks for some important drugs such as the naturally occurring antibacterial pyrrolone, althiomycin; the cardiotonic pyridazinones, pimobendan and levosimendan and the analgesic anti-inflammatory, emorfozan. Therefore, researchers all over the world paid attention to prepare various pyridazinones and pyrroolones derivatives. The variability in the biological response and ease of preparation from the corresponding furanones attracted attention of researchers to explore these two nuclei in the design and synthesis of different analogues. This review article focuses on different biological activities, structure activity relationship and mechanism of action of pyridazinones and pyrrolones derivatives.

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“…Due to the important biological activities of pyridazines and pyrans, we hypothesized that the synthesis of new heterocycles containing both pyridazine and pyran moieties might result in the design of new drug candidates. Therefore, in continuation of our efforts on the design and efficient synthesis of new biologically active compounds and in particular pyridazines [18][19][20][21][22][23][24][25][26][27] , herein we report a new and simple method for the synthesis of polyfunctionalized pyrano-fused pyridazine systems.…”

Section: Introductionmentioning

confidence: 99%

New pyrano[2,3-c]pyridazine derivatives with antimicrobial activity synthesized using piperidine as the organocatalyst

Kandile

Zaky

2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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A simple and efficient method for the synthesis of highly diverse pyrano [2,3-c]pyridazines was achieved by a one pot multicomponent reaction using piperidine as the organocatalyst. The synthesis of a series of heterocyclic derivatives with varying functionality (e.g. thiazine, tetrazole and pyrimidine) incorporating the pyrano[2,3-c]pyridazine moiety were achieved via reaction of 2a-e with different reagents. The structures of the synthesized derivatives were elucidated by FTIR, MS, 1 H and 13 C NMR spectroscopy. A number of the newly synthesized targeted compounds 2b-e, 3a-c and 4a-c were evaluated for their in vitro antibacterial activity and were compared with chloramphenicol and nystatin as broad spectrum reference standard antibiotics. Tests were carried out against Staphylococcus aureus (MTCC3160) and Enterococcusi fecalis as Gram-positive bacteria, and Escherichia coli (MTCC1652) and Klebsiella pneumonia as Gram-negative bacteria. Antifungal potential against Candida albicans, and Aspergillus albicans strains were also evaluated. The results revealed that compounds 3a and 3c showed strong significant activity relative to the reference against these bacterial and fungal strains.

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Synthesis of a new class of antimicrobial agents incorporating the indolin-2-one moiety

Cited by 9 publications

References 32 publications

Selective Functionalization of Indole: Synthesis of Bioinspired 2,2′‐thiobisindoles, 3‐substituted Oxindoles, and 1‐(chloromethyl) Indoline‐2‐dione in One‐pot manner

Selective Functionalization of Indole: Synthesis of Bioinspired 2,2′‐thiobisindoles, 3‐substituted Oxindoles, and 1‐(chloromethyl) Indoline‐2‐dione in One‐pot manner

Pyridazinones and pyrrolones as promising Scaffolds in Medicinal Chemistry

New pyrano[2,3-c]pyridazine derivatives with antimicrobial activity synthesized using piperidine as the organocatalyst

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