Bisheterocycles: Synthesis of some novel 1,2,3-triazolyl oxadiazole and 4(3H)-quinazolinones via azide cycloaddition reaction

Komaraiah, A.; Ramakrishna, Kallaganti V. S.; Sailu, B.; Reddy, P. Sambasiva

doi:10.3998/ark.5550190.0008.e11

Cited by 9 publications

(3 citation statements)

References 4 publications

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“…Unless otherwise specied, solvents and reagents were of analytical grade from commercial suppliers and were used without further purication. Compounds 1 21 and 2 22 were prepared according to reported methods. 1 H NMR and 13 C NMR spectra were performed on an Agilent 400 MR spectrometer, and the chemical shis (d) were expressed in ppm and coupling constants (J) in Hertz.…”

Section: Materials and Instrumentsmentioning

confidence: 99%

Multi-analyte, ratiometric and relay recognition of a 2,5-diphenyl-1,3,4-oxadiazole-based fluorescent sensor through modulating ESIPT

et al. 2015

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Section: Materials and Instrumentsmentioning

confidence: 99%

Multi-analyte, ratiometric and relay recognition of a 2,5-diphenyl-1,3,4-oxadiazole-based fluorescent sensor through modulating ESIPT

et al. 2015

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“…They have excellent applications in organic chemistry, medicinal chemistry, drug discovery, agrochemicals, and dyes . Besides, these compounds were demonstrated to have a wide scope of pharmaceutical properties involving anti‐HIV, antimicrobial, and b 3 ‐adrenergic receptor agonists . The Indole nucleus is an important nitrogen heterocyclic compound, derivatives of this compound possess a variety of biological properties such as antipyretic, anticonvulsant, analgesic, antidepressant, antiestrogen, cytotoxic and antimitotic activities .…”

Section: Introductionmentioning

confidence: 99%

“…[6][7][8][9] Besides, these compounds were demonstrated to have a wide scope of pharmaceutical properties involving anti-HIV, [10] antimicrobial, [11] and b 3 -adrenergic receptor agonists. [12] The Indole nucleus is an important nitrogen heterocyclic compound, derivatives of this compound possess a variety of biological properties such as antipyretic, anticonvulsant, analgesic, antidepressant, antiestrogen, cytotoxic and antimitotic activities. [13][14][15][16][17] 1,2,4-Triazines and their analogues play important roles in pharmaceutical chemistry, due to their high potential of biological properties including antifungal, [18] antimicrobial, [19] anti-HIV, [20] and antiproliferative, [21] activities.…”

Section: Introductionmentioning

confidence: 99%

Click Synthesis of 1,2,3‐Triazoles‐Linked 1,2,4‐Triazino[5,6‐b]indole, Antibacterial Activities and Molecular Docking Studies

et al. 2020

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The reaction of 4,5-dihydro- 3H-1,2,4-triazino[5,6-b]indole-3-thion with propargyl bromide, in EtOH at 80°C, produces monopropargylated 3-(prop-2-one-1-ylthio)-5H-1,2,4-triazino[5,6-b] indole. Further reaction of this compound with propargyl bromide, in DMF in the presence of K 2 CO 3 at room temperature, produced successfully double-propargylated 5-The Cu(I)-catalyzed click reaction of these propargylated compounds with different aromatic azides at room temper-ature, afforded new derivatives of 1,2,3-triazoles-linked 1,2,4triazino [5,6-b]indole with high yields. The in vitro antibacterial activities of the novel 1,2,3-triazoles were screened. The binding modes of these compounds to three enzyme active sites were determined by a molecular docking study. Docking studies demonstrated the most potent compounds; and binding maps revealed that the activities might be attributed to the hydrophobic interactions, hydrogen bonds, cation-π and π-π contacts with the active sites. Figure 7. Binding mode of compound 7 a (A), 7 b (B) and 7 c (C) in the active site. ChemistrySelectFull Papers

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Synthesis and Biological Evaluation of New Tetra‐aza Macrocyclic Scaffold Constrained Oxadiazole, Thiadiazole and Triazole Rings

Kumar

Naik

Girija

et al. 2011

Archiv der Pharmazie

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A new series of N,N'-(benzene-1,3-diyldi-1,3,4-oxadiazole-5,2-diyl)bis{2-[(5-benzene-1,3-diyl-1,3,4-oxadiazol-2-yl)amino]acetamide}(macrocycle 1), N,N'-(benzene-1,3-diyldi-1,3,4-thiadiazole-5,2-diyl)bis{2-[(5-benzene-1,3-diyl-1,3,4-thiadiazol-2-yl)amino]acetamide} (macrocycle 2) and S,S'-[benzene-1,3-diylbis(4H-1,2,4-triazole-5,3-diyl)]bis{[(5-benzene-1,3-diyl-4H-1,2,4-triazol-3-yl)sulfanyl]ethanethioate}(macrocycle 3) was synthesized from isophthalic dihydrazide (4) through a multistep reaction sequence. All the synthesized compounds were screened for their inhibitory effect against four different bacterial strains: P. aeruginosa ATCC-20852, K. pneumoniae MTCC-618, S. aureus ATCC- 29737, S. typhi MTCC- 3214. The synthesized compounds showed a significant zone of inhibition and the results were comparable with that of the standard drug ciprofloxacin. The synthesized compounds were further studied for their possible in vitro antioxidant effects by DPPH scavenging, total antioxidant capacity, total reductive capacity and H(2) O(2) scavenging activity. The results indicated that the in vitro antioxidant activity for all the three molecules was efficient when compared to the standards. The DNA interaction behavior of macrocycles 1-3 with CT-DNA was investigated by the absorption spectra obtained (K(b) constant for 1 is 4.53 × 10(4) M(-1) , for 2 is 5.75 × 10(4) M(-1) and for 3 is 5.86 × 10(4) M(-1) ). Based on the results it can be interpreted that the reducing power effect of the newly synthesized compounds demonstrates a direct effect on DNA binding and hence inhibiting the bacterial growth through their action on DNA by inhibiting DNA replication or DNA transcription.

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Bisheterocycles: Synthesis of some novel 1,2,3-triazolyl oxadiazole and 4(3H)-quinazolinones via azide cycloaddition reaction

Cited by 9 publications

References 4 publications

Multi-analyte, ratiometric and relay recognition of a 2,5-diphenyl-1,3,4-oxadiazole-based fluorescent sensor through modulating ESIPT

Multi-analyte, ratiometric and relay recognition of a 2,5-diphenyl-1,3,4-oxadiazole-based fluorescent sensor through modulating ESIPT

Click Synthesis of 1,2,3‐Triazoles‐Linked 1,2,4‐Triazino[5,6‐b]indole, Antibacterial Activities and Molecular Docking Studies

Synthesis and Biological Evaluation of New Tetra‐aza Macrocyclic Scaffold Constrained Oxadiazole, Thiadiazole and Triazole Rings

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