Isatin-semicarbazone linked acetamide 1,2,3-triazole hybrids: Synthesis, antimicrobial evaluation and docking simulations

Kumar, Aman; Lal, Kashmiri; Yadav, Monika; Kumar, Sunil; Singh, Madhur Babu; Kumari, Kamlesh

doi:10.1016/j.molstruc.2023.135660

Cited by 9 publications

(5 citation statements)

References 35 publications

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“…Kumar et al [81] . created a new library of isatin‐semi carbazone tethered acetamide 1,2,3‐triazoles conjugates and demonstrated their antimicrobial evaluation as well as docking simulations.…”

Section: Biological Assessment Of 123‐triazole Tethered Isatin Hybridsmentioning

confidence: 99%

“…Kumar et al [81] created a new library of isatin-semi carbazone tethered acetamide 1,2,3-triazoles conjugates and demonstrated their antimicrobial evaluation as well as docking simulations. Conjugate 149 exhibited the best potency against E. coli having a MIC value of 0.0108 μmol/mL and it also showed the highest efficacy towards A. niger having a MIC value of 0.0072 μmol/mL.…”

Section: Miscellaneous Activitymentioning

confidence: 99%

“…(Reproduced from ref. [81] Copyright (2023), with permission from Elsevier) Scheme 48. Synthetic strategy for the synthesis of isatin-semi carbazonelinked 1,2,3-triazoles hybrids.…”

Section: Miscellaneous Activitymentioning

confidence: 99%

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A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

Rohila,

Sebastian,

Ansari

et al. 2024

Chemistry & Biodiversity

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Heterocyclic compounds containing 1,2,3‐triazole and isatin as core structures have emerged as promising drug candidates due to their diverse biological activities such as anti‐cancer, antifungal, antimicrobial, antitumor, anti‐epileptic, antiviral, and more. The presence of 1,2,3‐triazoles and isatin heterocycles in these hybrids, both individually known for their medicinal significance, has increasingly piqued the interest of drug discovery researchers, as they seek to delve deeper into their extensive pharmacological potential for enhancing therapeutic efficacy. Moreover, these hybrid compounds are synthetically accessible using readily available materials. Therefore, there is a pressing need to provide a comprehensive overview of the existing knowledge in this field, offering valuable insights to readers and paving the way for the discovery of novel 1,2,3‐triazole‐linked isatin hybrids with therapeutic potential.

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Section: Biological Assessment Of 123‐triazole Tethered Isatin Hybridsmentioning

confidence: 99%

Section: Miscellaneous Activitymentioning

confidence: 99%

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A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

Rohila,

Sebastian,

Ansari

et al. 2024

Chemistry & Biodiversity

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“…In pursuit of developing novel antimicrobial agents with enhanced efficacy and safety profiles, the exploration of hetero-aryl semicarbazones has emerged as a promising avenue within medicinal chemistry [5]. Semicarbazones, characterized by a hydrazine-derived moiety, exhibit diverse pharmacological properties and their structural modification with heteroaryl substituents holds promise for imparting unique bioactive features [6][7][8][9]. Studies on semicarbazones have unveiled their potential as antimicrobial [10,11], antiviral [12], anticancer [13], anticonvulsant [14], analgesic and anti-inflammatory [15] agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in silico Assessment of Heteroaryl Semicarbazones: Towards Understanding Antimicrobial Activities and Safety Profiles

Rao,

Chitrapu,

Singh

et al. 2024

ajc

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Seven semicarbazone derivatives incorporating either substituted furan or thiophene were synthesized by reacting phenylurea with semicarbazide and various heteroaryl aldehydes. The newly synthesized compounds were characterized using IR, NMR, mass spectrometry and elemental analysis. Additionally, their antibacterial and anti-tubercular activities were also evaluated. In silico tools such as Swiss ADME and Pro Tox II were employed to assess molecular targets, medicinal chemistry properties, as well as toxicity and safety profiles. Compounds 3a-g demonstrated significant antibacterial activity at a 100 µg/mL when compared to the standard ciprofloxacin. Notably, compounds 3c, 3d, 3f and 3g exhibited the highest activity against all bacterial strains. Furthermore, compound 3d demonstrated anti-tubercular activity at all tested concentrations.

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“…In general terms, isatinketo group is condensed with various aromatic primary amines to produce isatin Schiff bases. Schiff base containing marketed drug include thiacetazone (antituberculosis), dantrolene (muscle relaxant) and nifuroxazide (antibiotic) [40][41][42] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial and In Silico Studies of Isatin Schiff Base Linked 1,2,3‐Triazole Hybrids

Kumar,

Bhukal,

Raman

et al. 2024

Chemistry & Biodiversity

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A new series of isatin‐Schiff base linked 1,2,3‐triazole hybrids has been synthesized using CuAAC approach from (E)‐3‐(phenylimino)‐1‐(prop‐2‐yn‐1‐yl)indolin‐2‐one derivatives in high yield (73‐91 %). These synthesized derivatives were characterized using FT‐IR, 1H NMR, 13C NMR, 2D‐NMR and HRMS spectral techniques. The in vitro antimicrobial activity assay proposed that most of the tested hybrids exhibited promising activity. Compound 5j displayed good significant antibacterial efficacy against P. aeruginosa and B. subtilis with MIC value of 0.0062 µmol/mL. While, 5j showed better antifungal potency against A. niger with MIC value of 0.0123 µmol/mL. The docking studies of most promising compounds were also performed with the well‐known antibacterial and antifungal targets i.e. 1KZ1, 5TZ1. Molecular modelling investigations demonstrated that hybrids 5h and 5l exhibited good interactions with 1KZN and 5TZ1, with binding energies of ‐9.6 and ‐11.0 kcal/mol, respectively. Further, molecular dynamics studies of the compounds showing promising binding interactions were also carried out to study the stability of complexes of these hybrids with both the targets.

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Isatin-semicarbazone linked acetamide 1,2,3-triazole hybrids: Synthesis, antimicrobial evaluation and docking simulations

Cited by 9 publications

References 35 publications

A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

Synthesis and in silico Assessment of Heteroaryl Semicarbazones: Towards Understanding Antimicrobial Activities and Safety Profiles

Synthesis, Characterization, Antimicrobial and In Silico Studies of Isatin Schiff Base Linked 1,2,3‐Triazole Hybrids

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