Synthesis, antifungal studies, molecular docking, ADME and DNA interaction studies of 4-hydroxyphenyl benzothiazole linked 1,2,3-triazoles

Nehra, Nidhi; Tittal, Ram Kumar; Ghule, Vikas D.; Naveen, _______; Lal, Kashmiri

doi:10.1016/j.molstruc.2021.131013

Cited by 34 publications

(23 citation statements)

References 52 publications

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“…The signal at 159.2 ppm and the one at 171.0 ppm were assigned to carbonyl groups of β-lactam ring and isatin ring, respectively. The 13 CNMR spectra of 4e also con rmed the presence of methyl and methylene carbons, as well as vinylic and aromatic carbons at 40.5, 42.8, and 110.0-155.1 ppm, respectively.…”

Section: Chemistrymentioning

confidence: 74%

“…Thin layer chromatography (TLC) and column chronatgraphy were performed on silica gel 254 and Merk Kieselgel (230-270 mesh), respectively. To determine the structure of synthesized compounds different methods were applied suuch as FT-IR, 1 HNMR, 13 CNMR, GC-Mass as well as Elemental analysis. 1 HNMR and 13 CNMR spectra were performed on Bruker Avance DPX instrument (250 MHz for 1 H and 62.9 MHz for 13 C) in CDCl 3 or DMSO-d 6 with tetramethylsilane (TMS) as the internal standard.…”

Section: Experimental Materialsmentioning

confidence: 99%

“…To determine the structure of synthesized compounds different methods were applied suuch as FT-IR, 1 HNMR, 13 CNMR, GC-Mass as well as Elemental analysis. 1 HNMR and 13 CNMR spectra were performed on Bruker Avance DPX instrument (250 MHz for 1 H and 62.9 MHz for 13 C) in CDCl 3 or DMSO-d 6 with tetramethylsilane (TMS) as the internal standard. All the chemical shifts were reported in ppm and coupling constants (J) are in Hz.…”

Section: Experimental Materialsmentioning

confidence: 99%

“…In this concept, such hybrid molecules by combination of two or more active pharmacophoric fragments have been developed as antimalarial agents [5][6][7][8][9][10]. The synthesis of hybrid molecules, as well as, evaluation of their biological activity [11,12] such as antimicrobial [13][14][15], anti-cancer [16,17], anti-in ammatory [18,19], anti-malarial [20,21], antihyperglycemic [22], anti-tubercular [23], anti-oxidant activities [24] and so on have been increasingly investigated for the last two decades. Based on the mentioned content, a diversity of natural products such as taxoids, peptides, carbohydrates and steroids have been hybridized by other pharmacologically active molecules such as β-lactams, anthraquinones, C 60 -fullerenes, porphyrin and enediyne and their properties have been evaluated [12,25].…”

Section: Introductionmentioning

confidence: 99%

“…J=7.7, 1.2 Hz, Ar), 6.78-6.87 (3H, m, Ar), 6.93-7.07 (3H, m, Ar), 7.19-7.28 (3H, m, Ar), 7.39-7.47 (2H, m, Ar);13 C-NMR (CDCl 3 , 62.5 MHz) δ 48.0 (CH 2 -N),86.5 (C-3), 70.9 (C-4), 106.7-147.5 (aromatic and C=C vinylic), 159.7 (CO, β-lactam), 176.5 (CO, amide); Anal. Calcd.…”

mentioning

confidence: 99%

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Synthesis, in-vitro Biological Evaluation, and Molecular Docking Study of Novel spiro-β-lactam-isatin Hybrids

Jarrahpour

Jowkar

Haghighijoo

et al. 2022

Preprint

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In our ongoing search for bioactive compounds, a class of novel spiro-β-lactam isatin hybrids have been obtained by [2+2] cycloaddition reaction from 1-allyl-3-(arylimino)indolin-2-one and ketenes from various aryloxy acetic acids. The formation of all cycloadducts were confirmed by FTIR, 1H NMR, 13C NMR, and Mass spectra as well as elemental analyses. The new β-lactams were evaluated for their biological activities. The compounds 4a-g showed moderate to good activity against P. falciparum K1 strain and showed moderate to good activity. Among them, 4b and 4e demonstrated the best results with IC50 of 5.04 and 7.18, respectively. The molecular docking simulation of 4b with P. falciparum dihydrofolate reductase enzyme (PfDHFR) binding site shown several intermolecular interactions that would be consider to design the future analogs of antimalarial agents. Moreover, all the synthesized β-lactams were evaluated against some gram positive and gram negative bacteria including E. coli ATCC 28922, P. aeruginosa ATCC 27853 and S. aureus ATCC 25923 at the MIC level of 200 µg/mL and did not possess significant activity.

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Section: Chemistrymentioning

confidence: 74%

Section: Experimental Materialsmentioning

confidence: 99%

Section: Experimental Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis, in-vitro Biological Evaluation, and Molecular Docking Study of Novel spiro-β-lactam-isatin Hybrids

Jarrahpour

Jowkar

Haghighijoo

et al. 2022

Preprint

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Nascent pharmacological advancement in adamantane derivatives

Ragshaniya,

Kumar,

Tittal

et al. 2023

Archiv der Pharmazie

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The adamantane moiety has attracted significant attention since its discovery in 1933 due to its remarkable structural, chemical, and medicinal properties. This molecule has a notable impact in the therapeutic field because of its “add‐on” lipophilicity to any pharmacophoric moieties. As in the case of molecular hybridization, in which one pharmacophore is attached to another one(s) with a probability of increasing the biological activity, adding an adamantane unit improves the absorption distribution, metabolism and excretion properties of the resultant hybrid molecule. This review summarizes various reports highlighting the biological activities of adamantane‐based synthetic compounds and their structure–activity relationship study. The information presented in this review may open up possible dimensions for adamantane‐based drug development and discovery in the pharmaceutical industry after proper structural modifications.

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Design, Synthesis and In vitro Antitubercular Effect of New Chalcone Derivatives Coupled with 1,2,3‐Triazoles: A Computational Docking Techniques

Sadineni,

Reddy Basireddy,

Rao Allaka

et al. 2024

Chemistry & Biodiversity

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A very interesting foundation for this study is the creation of new methods for modifying compounds with a 1,2,3‒triazole and chalcones, as these compounds are significant in organic synthesis as bioactive organic compounds. To contribute to the development of an efficient method for the conversion of antimicrobial and anti‐TB drugs, a novel series of cyclohepta pyridinone fused 1,2,3–triazolyl chalcones were designed and synthesized. All the newly prepared scaffolds were characterized by IR, NMR (1H & 13C) and mass spectrometry. Among the tested compounds, hybrids 8b, 8d, and 8f exhibited exceptional antibacterial susceptibilities with zone of inhibition 27, 32, and 38 mm against the tested E. faecalis bacteria, whereas 8d had better antitubercular potency against M. tuberculosis H37Rv strain with MIC value 5.25 µg/mL. All the synthesized compounds were initially assessed in silico against the targeted protein i.e., DprE1 that indicated compound 8d, 8f and 8h along with several other 1,2,3‐triazole compounds as possible inhibitors. Based on docking results, 8d showed that the amino acids His74(A), Lys76(A), Cys332(A), Asp331(A), Val307(A), Tyr357(A), ect., exhibited highly stable binding to DprE1 receptor of M. tuberculosis (4G3U). Moreover, these scaffolds physicochemical characteristics, filtration molecular properties, assessment of toxicity, and bioactivity scores were assessed.

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Synthesis, antifungal studies, molecular docking, ADME and DNA interaction studies of 4-hydroxyphenyl benzothiazole linked 1,2,3-triazoles

Cited by 34 publications

References 52 publications

Synthesis, in-vitro Biological Evaluation, and Molecular Docking Study of Novel spiro-β-lactam-isatin Hybrids

Synthesis, in-vitro Biological Evaluation, and Molecular Docking Study of Novel spiro-β-lactam-isatin Hybrids

Nascent pharmacological advancement in adamantane derivatives

Design, Synthesis and In vitro Antitubercular Effect of New Chalcone Derivatives Coupled with 1,2,3‐Triazoles: A Computational Docking Techniques

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