Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles

Thotla, Krishna; Noole, Venkatagiri; Kedika, Bhavani; Reddy, C. H. Krishna

doi:10.1134/s1070428020060172

Cited by 8 publications

(6 citation statements)

References 26 publications

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“…Furthermore, a solution of 3 in DCM, propargyl bromide followed by TBAB in TEA stirred for 4 h at rt to get 4-methyl-2-((5-(prop-2-yn-1ylthio)-1,3,4-oxadiazol-2-yl)methyl)phthalazin-1(2H)-one 4. [43] The desired phthalazines with triazolo-oxadiazoles 5 a-f were obtained by the reaction of compound 4, an appropriate azide, sodium ascorbate and copper sulphate pentahydrate in DCM for 45 min À 1 h at ambient temperature (70-89 % yield).…”

Section: Resultsmentioning

confidence: 99%

“…The desired final products of phthalazine with triazolo‐thiadiazoles 7(a – f) were obtained by refluxing the mixture of compound 6 , corresponding aromatic acids in phosphorus oxychloride for 6–8 h (72–89 % yield). Furthermore, a solution of 3 in DCM, propargyl bromide followed by TBAB in TEA stirred for 4 h at rt to get 4‐methyl‐2‐((5‐(prop‐2‐yn‐1‐ylthio)‐1,3,4‐oxadiazol‐2‐yl)methyl)phthalazin‐1(2 H )‐one 4 [43] . The desired phthalazines with triazolo‐oxadiazoles 5 a – f were obtained by the reaction of compound 4 , an appropriate azide, sodium ascorbate and copper sulphate pentahydrate in DCM for 45 min −1 h at ambient temperature (70‐89 % yield).…”

Section: Resultsmentioning

confidence: 99%

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New triazole based oxadiazolo/thiadiazolo–phthalazines as potent antimycobacterial agents: Design, synthesis, molecular modelling and in silico ADMET profiles

Reddy,

Avuthu,

Kishore

et al. 2024

ChemistrySelect

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The study of the chemical and biological properties of molecules simultaneously comprising various heterocycles, such as fused 1,3,4–oxadiazolyl–1,2,3–triazoles and 1,2,4–triazolyl–1,3,4–thiadiazole have been conducted as part of our ongoing research in the field of medicinal and organic chemistry. In this study, we performed ligand–based pharmacophore modelling as a promising design strategy of substituted phthalazinone derivatives (5 and 7). These were synthesized from key intermediate mercapto‐containing oxadiazo‐phthalazinone derivative 2. The synthesized compounds were characterized by IR, 1H and 13C NMR, elemental analysis and mass spectrometric techniques. In preliminary antibacterial studies, analogues 5 d, 5 f, 7 a and 7 d were found to be most effective against S. epidermidis, whereas 5 d displayed excellent activity against P. aeruginosa microorganism. Later, explored the probable key active site and inhibitors of Cytochrome P450 CYP121A1 interactions from M. tuberculosis H37Rv based antitubercular drug candidate with 5O4K protein and ligand 7 b possesses highest hydrophobic amino acid residues. The physicochemical and medicinal properties were also evaluated using SwissADME and ADMETlab2.0 web to function as effective oral bioavailability medications.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

New triazole based oxadiazolo/thiadiazolo–phthalazines as potent antimycobacterial agents: Design, synthesis, molecular modelling and in silico ADMET profiles

Reddy,

Avuthu,

Kishore

et al. 2024

ChemistrySelect

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“…A series of 1phenylsubstituted-5-(prop-2-yn-1-ylthio)-1H-tetrazoles 3a-j was synthesized as per the reported literature from starting from substituted phenyl isothiocyanate which was reacted with sodium azide to give 1-phenylsubstituted-1H-tetrazole-5thiol. [44] Then the solution of 1-phenylsubstituted-1H-tetrazole-5-thiol, propargyl bromide, and tetrabutylammonium bromide in a mixture of triethylamine and dichloromethane was stirred for 4 h to obtain the tetrazole derivatives (80-87 %). In the final step, the synthesis of novel tetrazolyl 1,2,3-triazole linked indazole scaffolds was accomplished via Click chemistry of appropriate alkyne 3a (7.6 mmol), a mixture of 5-azido-1methyl-1H-indazole 2 (10 mmol) in 20 mL of DMF: water (1 : 1) was added to a solution of copper sulphate (6.2 mmol) and followed by the dropwise addition of sodium ascorbate (8.3 mmol) under a nitrogen atmosphere at 10-15 °C.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and in Silico Studies of Some New 1,2,3‐Triazolyltetrazole Bearing Indazole Derivatives as Potent Antimicrobial Agents

Gujja,

Sadineni,

Epuru

et al. 2023

Chemistry & Biodiversity

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Abstract1,2,3‐Triazole and tetrazole derivatives bearing pyrrolidines are found to exhibit notable biological activity and have become useful scaffolds in medicinal chemistry for application in lead discovery and optimization. Novel indazole bearing 1,2,3‐triazolyltetrazoles were designed as potential antimicrobial candidates. The structure of duel heterocyclics was validated by a spectroscopic technique of infrared (IR), nuclear magnetic resonance (1H and 13C NMR), and mass spectral data. Compounds 4b, 4c, 4d, and 4h were found to have a stronger antibacterial effect against Gram‐positive (S. aureus, B. subtilis, M. Luteus) and Gram‐negative (E. coli, P. aeruginosa) microorganisms with MICs ranging from 5±0.03–18±0.02 μM, respectively. Moreover, scaffolds 4a, 4h showed potent antifungal activity against A. flavus, M. gypsuem strains with MIC values of 10±0.02, 11±0.01 μM, which are similar activity that of the standard Itraconazole (MIC=8±0.02, 10±0.01 μM). The binding mode for compound 4 inside the catalytic pocket of S. aureus complexed with nicotinamide adenine dinucleotide phosphate and trimethoprim and produced a network of hydrophobic and hydrophilic interactions (3FRE). From in silico results, 4b demonstrated highly stable hydrogen binding amino acids Leu62(X) [N18…O, 2.47 Å], Arg44(X) [N17…N, 3.11 Å], Thr96(X) [N10…OG1, 3.05 Å], Gly94(X) [F7…N, 2.82 Å], and Gly43(X) [F7…N, 2.90 Å], which are plays a crucial role in ensuring efficient binding of the ligand in a crystal structure of antibacterial receptor. Furthermore, the physicochemical and ADME filtration molecular properties, estimation of toxicity, and bioactivity scores of these novel scaffolds were evaluated by using SwissADME and ADMETlab2.0 online protocols. Thus, the significant antimicrobial activity of indazole linked to duel heterocyclic compounds can be used for development of new antimicrobial agents with further modifications.

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“…Both classes show several biological and pharmacological activities, including antibacterial, antiviral, antifungal, anticancer, analgesic, antioxidant, anti-inflammatory, anti-HIV, etc. [46] Ahmed et al [4] synthesized six triazole inhibitors (ATT 1 -ATT 6 ) by the fusion of thiocarbohydrazide and substituted benzoic acid. The authors studied all six inhibitors for their anticorrosion efficiency toward carbon steel (CS) in 0.5 M HCl using gravimetric weight loss (WL) methods.…”

Section: Triazoles and Tetrazoles As Hcismentioning

confidence: 99%

“…Triazoles and tetrazoles have enormous importance in medicinal chemistry. Both classes show several biological and pharmacological activities, including antibacterial, antiviral, antifungal, anticancer, analgesic, antioxidant, anti‐inflammatory, anti‐HIV, etc [46] . Ahmed et al [4] .…”

Section: Bioinspired Heterocyclic Compounds As Corrosion Inhibitorsmentioning

confidence: 99%

Bioinspired Heterocyclic Compounds as Corrosion Inhibitors: A Comprehensive Review

Goni

Mazumder

Quraishi

et al. 2021

Chemistry An Asian Journal

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Corrosion is a phenomenon that devastatingly affects innovative, industrial, and mechanical applications, especially in the oil and gas industries. The corrosion conceivably influences industrial equipment; it deteriorates the environment and lessens the equipment/infrastructure's lifetime. Considering the significant impact of corrosion in our daily lives, this review article aims to briefly discuss the significance of corrosion and different control methods with special attention on corrosion inhibitors. The classification of corrosion inhibitors based on types and their advantage/ limitations, and heterocyclic compounds as potential corrosion inhibitors, mainly nitrogen-based compounds (pyridine (1N), pyrimidine (2N), and triazines (3N) fused ring benzimidazole, etc.), and their biological significance has been discussed in detail. The mechanism, challenges, and applications of heterocyclic compounds as corrosion inhibitors in various industrial relevant corrosive environments such as acid pickling, descaling operation in the desalination plant, oil gas industry, etc., have also been highlighted in the review.

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Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles

Cited by 8 publications

References 26 publications

New triazole based oxadiazolo/thiadiazolo–phthalazines as potent antimycobacterial agents: Design, synthesis, molecular modelling and in silico ADMET profiles

New triazole based oxadiazolo/thiadiazolo–phthalazines as potent antimycobacterial agents: Design, synthesis, molecular modelling and in silico ADMET profiles

Synthesis and in Silico Studies of Some New 1,2,3‐Triazolyltetrazole Bearing Indazole Derivatives as Potent Antimicrobial Agents

Bioinspired Heterocyclic Compounds as Corrosion Inhibitors: A Comprehensive Review

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