Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives

Odame, Felix; Hosten, Eric C.; Krause, Jason; Frost, Carminita; Lobb, Kevin A.; Tshentu, Zenixole R.

doi:10.1007/s13738-021-02158-3

Cited by 5 publications

(4 citation statements)

References 29 publications

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“…Te compound crystallized in the monoclinic space group P21/ c. Te bond distances of N1-C11 and N2-C12 are 1.409(2) and 1.406(2) Å are consistent with the bond length of an imine [40], whilst the bond distances of C1-C2 and C2-C3 which were 1.504(2) and 1.532(2) Å, respectively, are typical C-C single bonds [40]. Te bond distance of O1-C23 which is 1.364(2) Å is consistent with the hydroxyl bond length [41]. Te bond angles of N1-C11-C12, N2-C12-C13, and N2-C12-C11 were 122.3(1), 121.2(1) and 120.3(1) °,respectively, this confrmed that these carbon atoms are sp 2 hybridized [41].…”

Section: Crystal Structure Of Compoundsupporting

confidence: 71%

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Anticancer and Antimicrobial Activity of Some New 2,3-Dihydro-1,5-benzodiazepine Derivatives

Odame,

Madanhire,

Tettey

et al. 2023

Heteroatom Chemistry

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A series of 2,3-dihydro-1,5-benzodiazepine derivatives have been synthesized and characterized using IR, NMR, GC-MS, single crystal XRD, and microanalysis. The results of their antibacterial activity against methicillin-resistance Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis, Streptococcus mutans, Pseudomonas aeruginosa, Salmonella typhi, and Streptococcus pyrogens indicated that most of the compounds were bacteriostatic (0.125−4 mg/mL) and also exhibited good biofilm inhibition (0.21−72.69%). The compounds were found to be synergistic when used in combination with other antibiotics. The antiproliferative and cytotoxic effects were also investigated against PC-3 prostate cancer and RAW 264.7 macrophage cell lines, respectively, using the MTT assay. Apart from compounds 6 and 7, a good number of the compounds (1, 2, 3, 4, 5, and 8) were selectively toxic to the prostate cancer cells at 20 µM, whilst sparing the normal cells. Compound 3 demonstrated the highest antiprostate cancer effect by reducing the viability of PC-3 cells to (13.75%), which was followed by compounds 1 (47.72%), 2 (48.18%), 4 (62.61%), 5 (66.70%), and 8 (69.55%).

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Section: Crystal Structure Of Compoundsupporting

confidence: 71%

“…Te bond distance of O1-C23 which is 1.364(2) Å is consistent with the hydroxyl bond length [41]. Te bond angles of N1-C11-C12, N2-C12-C13, and N2-C12-C11 were 122.3(1), 121.2(1) and 120.3(1) °,respectively, this confrmed that these carbon atoms are sp 2 hybridized [41].…”

Section: Crystal Structure Of Compoundsupporting

confidence: 71%

Anticancer and Antimicrobial Activity of Some New 2,3-Dihydro-1,5-benzodiazepine Derivatives

Odame,

Madanhire,

Tettey

et al. 2023

Heteroatom Chemistry

Self Cite

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“…The bond distances O21-C11, O21-C20, and O22-C20 are 1.386(2), 1.373(2), and 1.214(2) Å, respectively, are consistent with carbonyls [33], while the bond distances of N1-C19, N1-C32 and N1-C36 were 1.339(2), 1.465(3) and 1.457(2) Å, respectively, are consistent with the length of the C-N single bond [34]. The bond angles of C11-O21-C20, N1-C36-C35, and C19-N1-C32 were 122.1(1), 111.1(1) and 120.6(1)°, respecttively.…”

Section: Crystal Structure Analysissupporting

confidence: 55%

Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives

et al. 2023

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Some 2H-chromen-2-one and imine derivatives have been synthesized through a one-pot condensation of aldehydes, diethyl malonate, and amine compounds. The compounds obtained have been characterized using FTIR, NMR, GC-MS, and elemental analysis. The single-crystal X-ray structure of 3-[piperidine-1-carbonyl]-2H-chromen-2-one (2) has been presented. Compound 2, recrystallized in the monoclinic space C2/c (no. 15), a = 16.654(15) Å, b = 8.789(7) Å, c = 18.460(18) Å, β = 102.89(5)°, V = 2634(4) Å3, Z = 8, T = 296(2) K, μ(MoKα) = 0.091 mm-1, Dcalc = 1.298 g/cm3, 17626 reflections measured (4.528° ≤ 2Θ ≤ 57.446°), 3321 unique (Rint = 0.0313, Rsigma = 0.0257) which were used in all calculations. The final R1 was 0.0441 (I > 2σ(I)) and wR2 was 0.1329 (all data). The experimental bond lengths, bond angles, and other topological properties of compound 2 were compared with the DFT calculated results, the comparison showed good agreement with each other with varying level deviations. The energy levels of HOMO and LUMO, as well as the global chemical reactivity descriptors of representative compound 2, have been presented. A discussion of the Hirshfeld surface analysis of compound 2 has been carried out to provide insight into its structural properties.

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“…The antioxidant activities of phenolic compounds were widely investigated and the phenolic content and the side chain functional groups had significant influences on DPPH· scavenging activities [ 29 , 30 ]. Comparing the activities of compounds 1 − 2 , when the carboxyl group at C-3′ was esterified by the methyl group, the antioxidant activity of 2 decreases significantly.…”

Section: Resultsmentioning

confidence: 99%

Antioxidative Indenone and Benzophenone Derivatives from the Mangrove-Derived Fungus Cytospora heveae NSHSJ-2

Zou

Yang

et al. 2023

Marine Drugs

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Seven new polyketides, including four indenone derivatives, cytoindenones A–C (1, 3–4), 3′-methoxycytoindenone A (2), a benzophenone derivative, cytorhizophin J (6), and a pair of tetralone enantiomers, (±)-4,6-dihydroxy-5-methoxy-α-tetralone (7), together with a known compound (5) were obtained from the endophytic fungus Cytospora heveae NSHSJ-2 isolated from the fresh stem of the mangrove plant Sonneratia caseolaris. Compound 3 represented the first natural indenone monomer substituted by two benzene moieties at C-2 and C-3. Their structures were determined by the analysis of 1D and 2D NMR, as well as mass spectroscopic data, and the absolute configurations of (±)-7 were determined on the basis of the observed specific rotation value compared with those of the tetralone derivatives previously reported. In bioactivity assays, compounds 1, 4–6 showed potent DPPH· scavenging activities, with EC50 values ranging from 9.5 to 16.6 µM, better than the positive control ascorbic acid (21.9 µM); compounds 2–3 also exhibited DPPH· scavenging activities comparable to ascorbic acid.

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Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives

Cited by 5 publications

References 29 publications

Anticancer and Antimicrobial Activity of Some New 2,3-Dihydro-1,5-benzodiazepine Derivatives

Anticancer and Antimicrobial Activity of Some New 2,3-Dihydro-1,5-benzodiazepine Derivatives

Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives

Antioxidative Indenone and Benzophenone Derivatives from the Mangrove-Derived Fungus Cytospora heveae NSHSJ-2

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