scholarly journals Structural and Spectral Investigation of a Series of Flavanone Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1298
Author(s):  
Anna Sykuła ◽  
Agnieszka Kowalska-Baron ◽  
Krystian Gałęcki ◽  
Paulina Błazińska ◽  
Elżbieta Łodyga-Chruścińska

Four flavanone Schiff bases (E)-1-(2-phenylchroman-4-ylidene)thiosemicarbazide (FTSC) (1), N′,2-bis((E)-2-phenylchroman-4-ylidene)hydrazine-1-carbothiohydrazide (FTCH) (2), (E)-N’-(2-phenylchroman-4-ylidene)benzohydrazide (FHSB) (3) and (E)-N′-(2-phenylchroman-4-ylidene)isonicotinohydrazide (FIN) (4) were synthesized and evaluated for their electronic and physicochemical properties using experimental and theoretical methods. One of them, (2), consists of two flavanone moieties and one substituent, the rest of the compounds (1, 3, 4) comprises of a flavanone-substituent system in relation to 1:1. To uncover the structural and electronic properties of flavanone Schiff bases, computational simulations and absorption spectroscopy were applied. Additionally, binding efficiencies of the studied compounds to serum albumins were evaluated using fluorescence spectroscopy. Spectral profiles of flavanone Schiff bases showed differences related to the presence of substituent groups in system B of the Schiff base molecules. Based on the theoretically predicted chemical descriptors, FTSC is the most chemically reactive among the studied compounds. Binding regions within human and bovine serum albumins of the ligands studied are in the vicinity of the Trp residue and a static mechanism dominates in fluorescence quenching.

2020 ◽  
Vol 41 (1) ◽  
pp. 26-35
Author(s):  
Kishor Devkota ◽  
Govinda Pathak ◽  
Bhushan Shakya

Triazole ring system has attracted a continuously growing interest of synthetic organic chemists and those dealing with the medicinal compounds due to its versatile potential to interact with biological systems. Schiff bases are also considered as one of the most biologically active compounds.  The aim of the present study was to synthesize new Schiff bases bearing triazole nucleus and to assess their antimicrobial activities. Four new Schiff base derivatives of 1,2,4-triazole-3-thione were synthesized by combining two different pharmacophores viz. triazole nucleus and Schiff base moiety and were characterized by spectral techniques (UV, FT-IR, and NMR). The Schiff bases were evaluated for antibacterial (Staphylococcus aureus, Escherichia coli, and Klebsiella pneumoniae) and antifungal (Candida albicans) activities. The synthesized compounds exhibited good to moderate activities against different strains of bacteria and fungi tested.


2007 ◽  
Vol 62 (6) ◽  
pp. 807-817 ◽  
Author(s):  
Mohammed Enamullah ◽  
A.K.M. Royhan Uddin ◽  
Anne-Christine Chamayou ◽  
Christoph Janiak

Condensation of salicylaldehyde with enantiopure (R)-(1-aryl-ethyl)amines yields the enantiopure Schiff bases (R)-N-(1-aryl-ethyl)salicylaldimine (HSB*; aryl = phenyl, 2-methoxyphenyl, 3- methoxyphenyl, 4-methoxyphenyl (4), 4-bromophenyl (5), 2-naphthyl). These Schiff bases readily react with dinuclear (acetato)(η4-cycloocta-1,5-diene)rhodium(I), [Rh(μ-O2CMe)(η4-cod)]2, to afford the mononuclear complexes, cyclooctadiene-((R)-N-(1-aryl-ethyl)salicylaldiminato-κ2N,O)- rhodium(I), [Rh(SB∗)(η4-cod)] (SB* = deprotonated chiral Schiff base = salicylaldiminate; aryl = phenyl (7), 2-methoxyphenyl, 4-methoxyphenyl, 4-bromophenyl, 2-naphthyl). The complexes have been characterized by IR, UV/vis, 1H/13C NMR and mass spectrometry, optical rotation as well as by single-crystal X-ray structure determination for 4, 5 and 7. The structure of 5 shows C-Br· · ·π contacts. Compound 7 is only the second example of a Rh(η4-cod) complex with a six-membered Rh-N,O-chelate ring


1974 ◽  
Vol 29 (7-8) ◽  
pp. 565-566 ◽  
Author(s):  
R. N. Prasad ◽  
J. P. Tandon

The magnetic susceptibilities of some newly syntesized Al(III) and Si(IV) complexes of Schiff bases derived from the condensation of o-hydroxyacetophenone or 2-dydroxy-1-naphthaldehyde with hydroxyalkylamines or diamines have been measured and the data indicate their diamagnetic character.


1958 ◽  
Vol 80 (13) ◽  
pp. 3475-3478 ◽  
Author(s):  
Gardner W. Stacy ◽  
Richard I. Day ◽  
Richard J. Morath

1977 ◽  
Vol 32 (5) ◽  
pp. 551-561 ◽  
Author(s):  
John R. Wasson ◽  
H. Wayne Richardson ◽  
William E. Hatfield

Copper(II) complexes with the Schiff bases formed by condensing t-butyl-, isopropyl-, cyclohexyl- and diphenylmethylamines with salicylaldehyde and 3-methoxy- and 5-nitrosalicyl-aldehyde have been prepared and characterized. The isotropic nuclear hyperfine coupling constants increase in the order t-butyl < isopropyl < cyclohexyl < diphenylmethyl for the N-substituents in the three series of complexes while isotropic g-values increased in the opposite direction. Spectra structure correlations were examined and discussed.


2016 ◽  
Vol 81 (10) ◽  
pp. 1111-1119 ◽  
Author(s):  
Fatemeh Bagheri ◽  
Abolfazl Olyaei

A novel method was developed for synthesizing a series of new three dentate Schiff base ligands starting from hydroxynaphthalidene pyrimidinyl amines with o-phenylenediamines or o-aminophenol or 2-amino-3-hydroxy-pyri-dine in the presence of formic acid catalyst under solvent-free conditions. In these reactions [1+1] condensation product as half-unit ligand was obtained. Moreover, the reaction of hydroxynaphthalidene pyrimidinyl amines with 3,4-diamino-pyridine and 1,8-naphthalenediamine lead to the formation of C2-naphthylated imidazopyridine and dihydropyrimidine, respectively. The attractive features of this protocol are: use of inexpensive catalyst, operationally simple, short reaction times, easy handling, and good yields.


2018 ◽  
Vol 42 (6) ◽  
pp. 4646-4652 ◽  
Author(s):  
Hua Zhang ◽  
Junyang Xing ◽  
Yanhong Dong ◽  
Shangqing Xie ◽  
Shishuai Ren ◽  
...  

The sp2 C–H bond activation of the HCN moiety in diphenylphosphino benzalimines was realized using CoMe(PMe3)4 with the elimination of methane.


1975 ◽  
Vol 6 (15) ◽  
pp. no-no
Author(s):  
G. CONDORELLI ◽  
I. FRAGALA ◽  
S. GIUFFRIDA ◽  
A. CASSOL

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