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1.

001-es BibID:BIBFORM086917
Első szerző:Borazjani, Nassim
Cím:Cytotoxicity, anticancer, and antioxidant properties of mono and bis-naphthalimido β-lactam conjugates / Nassim Borazjani, Maryam Behzadi, Marzieh Dadkhah Aseman, Aliasghar Jarrahpour, Javad Ameri Rad, Sedigheh Kianpour, Aida Iraji, S. Masoud Nabavizadeh, Mohammad Mehdi Ghanbari, Gyula Batta, Edward Turos
Dátum:2020
ISSN:1054-2523
Megjegyzések:This article reports the diastereoselective synthesis of some novel naphthalimido and bis-naphthalimido beta-lactam derivatives and a preliminary evaluation of their anticancer properties. The reactions were completely diastereoselective, leading exclusively to the formation of cis-beta-lactams 11a-l and trans-bis-beta-lactams 16a-g. All of these compounds were obtained in good to excellent yields and their structures were established based on IR, H-1 NMR, C-13 NMR spectral data, and elemental analysis. Each of the beta-lactams was screened for antioxidant and anticancer activities. Our results showed that all the compounds lacked cytotoxicity against HepG2 cells, whereas 16a and 16b exhibited excellent anticancer activity with IC50 values below 191.57 mu M on MCF-7 cell line and also, bis-beta-lactams 16a-g showed excellent antitumor activity against the TC-1 cell line. Antioxidant experiments of 16a-d by the diphenylpicrylhydrazyl (DPPH) assay showed IC50 values ranging from 7 to 32.3 mu g/ml. Interaction of 16a, 16b, 16d-g with calf-thymus DNA (CT-DNA) was also supported by absorption titration studies. The compounds exhibit good binding propensity to CT-DNA and the DNA binding affinity (K-b) of the compounds varies as 16a; 16b; 16e; 16g > 16d; 16f. Interaction of 16d with CT-DNA was also investigated by fluorescence spectroscopy. The results support an intercalative interaction of 16d and 16f and non-intercalation mechanism for 16a, 16b, 16e, and 16g.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Anticancer
Antioxidant
Cytotoxicity
Diastereoselective
β-lactam
Megjelenés:Medicinal Chemistry Research. - 29 : 8 (2020), p. 1355-1375. -
További szerzők:Behzadi, Maryam Dadkhah Aseman, Marzieh Jarrahpour, Aliasghar Rad, Javad Ameri Kianpour, Sedigheh Iraji, Aida Nabavizadeh, S. Masoud Ghanbari, Mohammad M. Batta Gyula (1953-) (molekula-szerkezet kutató) Turos, Edward
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2.

001-es BibID:BIBFORM084070
Első szerző:Borazjani, Nassim
Cím:Three-component synthesis of chromeno β-lactam hybrids for inflammation and cancer screening / Nassim Borazjani, Saghi Sepehri, Maryam Behzadi, Aliasghar Jarrahpour, Javad Ameri Rad, Maryam Sasanipour, Milad Mohkam, Younes Ghasemi, Amin Reza Akbarizadeh, Carole Digiorgio, Jean Michel Brunel, Mohammad Mehdi Ghanbari, Gyula Batta, Edward Turos
Dátum:2019
ISSN:0223-5234
Megjegyzések:Highly diastereoselective synthesis of chromeno b-lactam hybrids was achieved by an efficient one-pot three-component reaction. With this procedure, the desired b-lactam products were obtained in good yields and with exclusive cis stereoselection, by combining a variety of benzaldehydes, malononitrile, and either 5,5-dimethylcyclohexane-1,3-dione or 4-hydroxycoumarin in the presence of 1,4-diazabicyclo [2.2.2]octane under reflux conditions. These adducts were structurally characterized on the basis of IR, 1D and 2D NMR spectra, X-ray analysis, HeH COSY and HeC HSQC two-dimensional NMR experiments, and elemental analysis. Each of the synthesized compounds was screened for anti-inflammatory and anticancer activities. b-Lactams 5b and 8b showed a 53.4 and 19.8 anti-inflammatory ratio, respectively, and 5b appeared more active than the well-known dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation. b-Lactams 5a, 5b, 5e, 5f, 5g, 8c, 8j and 8p also showed good antitumor activity against the SW1116 (colon cancer) cell line without notable cytotoxicity towards the HepG2 control cell line.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Anticancer
Anti-inflammatory
β-lactam
Colon cancer
Cytotoxicity
DABCO
Megjelenés:European Journal of Medicinal Chemistry. - 179 (2019), p. 389-403. -
További szerzők:Sepehri, Saghi Behzadi, Maryam Jarrahpour, Aliasghar Rad, Javad Ameri Sasanipour, Maryam Mohkam, Milad Ghasemi, Younes Akbarizadeh, Amin Reza Digiorgio, Carole Brunel, Jean Michel Ghanbari, Mohammad M. Batta Gyula (1953-) (molekula-szerkezet kutató) Turos, Edward
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3.

001-es BibID:BIBFORM078606
Első szerző:Borazjani, Nassim
Cím:Design, synthesis and biological evaluation of some novel diastereoselective β-lactams bearing 2-mercaptobenzothiazole and benzoquinoline / Nassim Borazjani, Aliasghar Jarrahpour, Javad Ameri Rad, Milad Mohkam, Maryam Behzadi, Younes Ghasemi, Somayyeh Mirzaeinia, Hamid Reza Karbalaei-Heidari, Mohammad Mehdi Ghanbari, Gyula Batta, Edward Turos
Dátum:2019
ISSN:1054-2523
Megjegyzések:We report the synthesis of some novel β-lactam hybrids of 2-mercaptobenzothiazole and benzoquinoline. These compounds were synthesized by a [2 + 2]-cycloaddition reaction of imines 8a-d and ketenes derived from substituted acetic acids. The reaction was totally diastereoselective leading exclusively to the formation of cis-β-lactams 10a-m. All products were obtained in good to excellent yields and their structures were established based on IR, 1H NMR, 13C NMR spectral data and elemental analysis. Schiff bases 8a-d and β-lactam hybrids 10a-m were evaluated for antimicrobial activities against six bacterial species. The minimum inhibitory concentration (MIC) values indicate that two of the β-lactams, 10k and 10m, have good activities against the two Gram-negative bacteria, E. coli and P. aeruginosa, while three of the Schiff bases, 8a-c, are active against P. aeruginosa and the Gram-positive pathogen S. aureus. The molecular and cellular basis for these observed antibacterial properties are not determined. Moreover, the five most active compounds showed acceptably low cytotoxicity (less than 25% cell growth inhibition after 72 h of incubation) against the MCF-7 cell line, and below 10% in vitro hemolytic activity at 50 and 200 ?M concentrations. These results suggest a need for further inquiry into the reason for why these compounds are bioactive, and as to what their full biological activities and antibiotic potential may be. The cis stereochemistry of β-lactam 10a was confirmed by X-ray crystallographic studies.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
β-Lactam
Hybrid
2-Mercaptobenzothiazole
Benzoquinoline
Antimicrobial
Hemolysis
Mammalian cell toxicity
Megjelenés:Medicinal Chemistry Research. - 28 : 3 (2019), p. 329-339. -
További szerzők:Jarrahpour, Aliasghar Rad, Javad Ameri Mohkam, Milad Behzadi, Maryam Ghasemi, Younes Mirzaeinia, Somayyeh Karbalaei-Heidari, Hamid Reza Ghanbari, Mohammad M. Batta Gyula (1953-) (molekula-szerkezet kutató) Turos, Edward
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4.

001-es BibID:BIBFORM085168
Első szerző:Ghanbari, Mohammad M.
Cím:Solvent-free, mild, facile, and rapid one-pot three-component synthesis of some novel imidazo[2,1-b]naphtho[1,2-e][1,3] thiazin-10-ones using p-TSA / Mohammad M. Ghanbari, Marzieh Jamali, Gyula Batta
Dátum:2014
ISSN:1741-5993 1741-6000
Megjegyzések:Novel [2,1-b]naphtho[1,2-e][1,3]thiazin-10-ones were synthesized in 63-89% yield via a three-component reaction of an aromatic aldehyde, [beta]-naphthol, and thiohydantoin in the presence of 10 mol% p-toluene sulfonic acid under solvent-free conditions. This is the first protocol to be reported for the synthesis of the title compounds. The significant features of the present protocol are simplicity, high yields, eco-friendliness, and convenient purification that does not require chromatography.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
thiohydantoins
aldehyde
beta-naphthol
one-pot reaction
solvent-free
Megjelenés:Journal of Sulfur Chemistry. - 35 : 4 (2014), p. 394-398. -
További szerzők:Jamali, Marzieh Batta Gyula (1953-) (molekula-szerkezet kutató)
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5.

001-es BibID:BIBFORM085167
Első szerző:Ghanbari, Mohammad M.
Cím:Reaction of alkyl isocyanides and dialkyl acetylenedicarboxylates in the presence of 5,5-diaryl thiohydantoins : synthesis of functionalized imidazo[2,1-b][1,3]thiazines / Mohammad Mehdi Ghanbari, Issa Yavari, Gyula Batta
Dátum:2014
ISSN:1741-5993 1741-6000
Megjegyzések:The reaction of stoichiometric amounts of dialkyl acetylenedicarboxylates with alkyl isocyanides in the presence of 5,5-diaryl thiohydantoins afforded imidazo[2,1-b][1,3]thiazines in good overall yields.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
thiohydantoin
imidazo[2,1-b][1,3]thiazine
isocyanide
acetylenedicarboxylate
zwitterionic
Megjelenés:Journal of Sulfur Chemistry. - 35 : 3 (2014), p. 312-317. -
További szerzők:Yavari, Issa Batta Gyula (1953-) (molekula-szerkezet kutató)
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6.

001-es BibID:BIBFORM071612
Első szerző:Ghanbari, Mohammad M.
Cím:Synthesis and dynamic NMR studies of novel hydantoin and thiohydantoin derivatives. Crystal structure of diethyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl) fumarate and diethyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1H-imidazol-1-yl)fumarate / Mohammad M. Ghanbari, Marzieh Jamali, Batta Gyula, Bényei Attila C.
Dátum:2017
ISSN:1747-5198
Megjegyzések:The reaction of stoichiometric amounts of dialkyl acetylenedicarboxylates with triphenylphosphine in the presence of hydantoins or thiohydantoins afforded stable crystalline phosphorus ylides. These compounds undergo smooth elimination of PPh 3 to produce dialkyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl)fumarate, 4 or dialkyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1H-imidazol-1-yl)fumarate, 7. Single crystal X-ray diffraction study on 4b and 7b proved the structures unambiguously with C=O and SH functionality at the 2-position of the imidazole ring, respectively. Dynamic effects were observed in the NMR spectra of these compounds and were attributed to restricted rotation around the carbon-nitrogen single bonds. Rotational energy barrier (?G#) for their interconversion process of rotational isomersequals to (53.6 and 17.2) ? 2 kcal mol-1.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
dynamic 1H NMR
hydantoin
thiohydantoin
phosphorus ylides
X-ray diffraction
Megjelenés:Journal of Chemical Research 41 : 5 (2017), p. 309-313. -
További szerzők:Jamali, Marzieh Batta Gyula (1953-) (molekula-szerkezet kutató) Bényei Attila (1962-) (vegyész)
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