Convergent synthesis of new N -substituted 2-{[5-(1H -indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as suitable therapeutic agents

Rubab, Kaniz; Abbasi, Muhammad Athar; Aziz-Ur-Rehman, -; Siddiqui, Sabahat Zahra; Ashraf, Muhammad; Shaukat, Ayesha; Ahmad, Irshad; Lodhi, Muhammad Arif; Khan, Farman Ali; Shahid, Muhammad Furqan; Akhtar, Muhammad Nadeem

doi:10.1590/s1984-82502015000400019

Cited by 8 publications

(7 citation statements)

References 24 publications

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“…The indole–1,3,4‐oxadiazole hybrid 48 (Figure 8; MIC: 9.15–12.22 μg/ml) showed potential activity against B. subtilis , S. aureus , S. typhi , E. coli , and P. aeruginosa , and the activity was slightly lower than that of ciprofloxacin (MIC: 7.29–8.54 μg/ml). [ 108 ] The 1,2,4‐triazole‐tethered indole–1,3,4‐oxadiazole hybrid 49 (MIC: 1.0–16 μg/ml) was comparable to amoxicillin (MIC: 2–16 μg/ml) against S. aureus , B. subtilis , E. coli , and P. aeruginosa , so this hybrid is a promising antibacterial compound for further study. [ 109 ] Further study revealed that the replacement of the 1,2,4‐triazole linker by 1,3,4‐oxadiazole could not improve the activity.…”

Section: Indole/isatin–azole Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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The emergence and worldwide spread of drug-resistant bacteria have already posed a serious threat to human life, creating the urgent need to develop potent and novel antibacterial drug candidates with high efficacy. Indole and isatin (indole-2,3-dione) present a wide structural and mechanistic diversity, so their derivatives possess various pharmacological properties and occupy a salient place in the development of new drugs. Indole/isatin-containing hybrids, which demonstrate a promising activity against a panel of clinically important Gram-positive and Gram-negative bacteria, are privileged scaffolds for the discovery of novel antibacterial candidates. This review, covering articles published between January 2015 and May 2020, focuses on the development and structure-activity relationship (SAR) of indole/isatincontaining hybrids with potential application for fighting bacterial infections, to facilitate further rational design of novel drug candidates.

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Section: Indole/isatin–azole Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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“…Hemolytic activity of the samples was studied by the method used by (Rubab et al, 2015) Three millimeter human red blood cells were collected from Department of Clinical Medicine and Surgery, University of Agriculture, Faisalabad, Pakistan. Blood centrifuged for 5 min at 1000 ×g plasma was discarded and cells were washed with thrice witha5 mL ofachilled (4 o C) sterile isotoniccPhosphate-buffered saline (PBS) pH 7.4.…”

Section: Hemolytic Activityimentioning

confidence: 99%

Antibacterial, antibiofilm, hemolytic activity and phytochemical study of various aerial parts of Moringa oleifera in Pakistan

Dilawar

Shah

Khan

et al. 2018

Asian J. Med. Biol. Res

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Theamethanolicoextractsaofffiveeaerial parts ofaMoringa oleifera Lamwwereascreened for their antibacterial, antibiofilm and hemolytic activity."Theaphytochemical screening of the methanolic extracts of aerial parts was also evaluated. The antibacterial, antibiofilmiactivityiof the extractssof various aerial parts of M. oleifera was evaluated by disc diffusion and micro titer plate assay method against two selected bacterial species. Hemolyticaactivity of the methanoliciextracts was screened against normal human erythrocytes. Comparatively the methanolic extracts of all aerial parts were more effective against Gram positive bacteria Bacillus subtilis and Gram negative bacteria Escherichia coli (E. coli) .The present study suggests that all aerial parts of this plant can be used as an antibacterial, anti-biofilm agent in treating ailments caused by the tested organisms (Bacillus subtilis and Escherichia coli). Methanolic extracts of aerial parts possessed minimum hemolytic activity. Significant antimicrobial, antibiofilm activity of the extract was found in this study.

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“…α-Glucosidase is a membrane-bound enzyme at the epithelium of the small intestine and hydrolyzes terminal nonreducing 1–4 linked α-glucose residues to release monomeric glucose molecules, which is mainly responsible for causing hyperglycemia . The inhibition of α-glucosidase can delay the carbohydrate absorption and has been used as one of the therapeutic approaches for the treatment of diabetes. , Therefore, design and synthesis of small hybrid molecules as α-glucosidase inhibitors is an important research area in medicinal chemistry …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Molecular Docking Studies of Novel Biheterocyclic Propanamides as Antidiabetic Agents Having Mild Cytotoxicity

et al. 2023

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The aim of this work was to bring forth some new hybrid molecules having pharmacologically potent indole and 1,3,4-oxadiazole heterocyclic moieties unified with a propanamide entity. The synthetic methodology was initiated by esterification of 2-(1H-indol-3-yl)acetic acid (1) in a catalytic amount of sulfuric acid and ethanol in excess, to form ethyl 2-(1H-indol-3-yl)acetate (2), which was converted to 2-(1H-indol-3-yl)acetohydrazide (3) and further transformed to 5-(1H-indole-3-yl-methyl)-1,3,4oxadiazole-2-thiol (4). 3-Bromopropanoyl chloride (5) was reacted with various amines (6a−s) in aqueous alkaline medium to generate a series of electrophiles, 3-bromo-N-(substituted)propanamides (7a−s), and these were further reacted with nucleophile 4 in DMF and NaH base to yield the targeted N-(substituted)-3-{(5-(1H-indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl)sulfanyl}propanamides (8a−s). The chemical structures of these biheterocyclic propanamides were confirmed by IR, 1 H NMR, 13 C NMR, and EI-MS spectral techniques. These compounds were evaluated for their enzyme inhibitory potentials against the αglucosidase enzyme, where the compound 8l showed promising enzyme inhibitory potential with an IC 50 value less than that of the standard acarbose. Molecular docking results of these molecules were coherent with the results of their enzyme inhibitory potentials. Cytotoxicity was assessed by the percentage of hemolytic activity method, and these compounds generally exhibited very low values as compared to the reference standard, Triton-X. Hence, some of these biheterocyclic propanamides might be considered as salient therapeutic agents in further stages of antidiabetic drug development.

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Convergent synthesis of new N -substituted 2-{[5-(1H -indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as suitable therapeutic agents

Cited by 8 publications

References 24 publications

Indole/isatin‐containing hybrids as potential antibacterial agents

Indole/isatin‐containing hybrids as potential antibacterial agents

Antibacterial, antibiofilm, hemolytic activity and phytochemical study of various aerial parts of Moringa oleifera in Pakistan

Synthesis and Molecular Docking Studies of Novel Biheterocyclic Propanamides as Antidiabetic Agents Having Mild Cytotoxicity

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