Synthesis of (3-nitro-2-oxo-benzaldehyde thiosemicarbazonato)–zinc(ii) complexes: the position of nitro group in phenyl ring alters antimicrobial activity against K. pneumoniae 1, S. typhimurium 2, MRSA and C. albicans

2021 ◽  
Author(s):  
Tarlok S. Lobana ◽  
Shikha Indoria ◽  
Henna Sood ◽  
Daljit S. Arora ◽  
Manpreet Kaur ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Nitro Group ◽  
Phenyl Ring ◽  
Nitro Complexes

The antimicrobial activity of five coordinated 3-nitro-2-oxo-benzaldehyde-thiosemicarbazonato)zinc(ii) complexes is different from that of analogous 5-nitro-complexes.

scholarly journals Crystal structure of (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one

2014 ◽  
Vol 70 (9) ◽  
pp. o1051-o1052 ◽  
Author(s):  
Ignez Caracelli ◽  
Stella H. Maganhi ◽  
Paulo J. S. Moran ◽  
Bruno R. S. de Paula ◽  
Felix N. Delling ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Double Bond ◽  
Nitro Group ◽  
Benzene Ring ◽  
Torsion Angle ◽  
Title Compound ◽  
Phenyl Ring ◽  
Aromatic Rings ◽  
Compound C ◽  
The One

In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] isE, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in theorthoposition is twisted [O—N—C—C = 138.28 (13)°]. The molecules associateviaC—H...O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N...O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].

scholarly journals 7-Nitro-2-phenylimidazo[2,1-b][1,3]benzothiazole

2014 ◽  
Vol 70 (2) ◽  
pp. o143-o144 ◽  
Author(s):  
Alexander S. Bunev ◽  
Elena V. Sukhonosova ◽  
Vladimir E. Statsyuk ◽  
Gennady I. Ostapenko ◽  
Victor N. Khrustalev
Keyword(s):  
Nitro Group ◽  
Phenyl Ring ◽  
Three Dimensional ◽  
Interplanar Distance ◽  
Stacking Interactions ◽  
Π Stacking ◽  
The Mean ◽  
Title Molecule

In the title molecule, C15H9N3O2S, the central imidazo[2,1-b][1,3]benzothiazole heterotricyclic unit is essentially planar (r.m.s. deviation = 0.021 Å). The terminal phenyl ring and nitro group are twisted by 9.06 (1) and 11.02 (4)°, respectively, from the mean plane of the heterotricycle. In the crystal, molecules are linked by π–π stacking interactions into columns along [100]; the interplanar distance between neighboring imidazo[2,1-b][1,3]benzothiazole planes within the columns is 3.370 (2) Å. Furthermore, the columns interact with each other by secondary S...O [2.9922 (10) and 3.1988 (11) Å] interactions, forming a three-dimensional framework.

Concise Total Syntheses of Paullone and Kenpaullone via Cyanide-Catalyzed Intramolecular Imino-Stetter Reaction

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4247-4253 ◽  
Author(s):  
Cheol-Hong Cheon ◽  
Sang Lee ◽  
Seong Lee
Keyword(s):  
Nitro Group ◽  
Phenyl Ring ◽  
Amino Group ◽  
Subsequent Reduction ◽  
Stetter Reaction ◽  
Total Syntheses ◽  
Target Molecules ◽  
Acidic Conditions ◽  
Direct Use ◽  
Indole 3 Acetic Acid

Highly concise total syntheses of paullone and kenpaullone were developed. Cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines derived from methyl 2-aminocinnamate derivatives and 2-nitrobenzaldehyde provided 2-(2′-nitrophenyl)indole-3-acetic acid derivatives. Subsequent reduction of the nitro group with zinc under acidic conditions to an amino group followed by spontaneous lactam formation allowed for the total syntheses of paullone and kenpaullone to be completed in two steps starting from commercially available materials. The direct use of a nitro group as the precursor of an amino group present in the phenyl ring at the 2-position in the indole ring significantly streamlined the total syntheses of these target molecules.

Electrophilic cleavage of cyclopropanes. II. Concerning the effect of increasing electron demand upon the product-determining transition state in the reaction of 4-substituted-2-nitrobenzenesulphenyl chlorides and benzenesulphenyl chlorides with tetracyclo[3.2.0.02,7.04,6]heptane (quadricyclene)

1980 ◽  
Vol 58 (10) ◽  
pp. 1014-1020 ◽  
Author(s):  
Pierre L. Beaulieu ◽  
Ann Kabo ◽  
Dennis G. Garratt
Keyword(s):  
Transition State ◽  
Nitro Group ◽  
Phenyl Ring ◽  
Relative Proportion ◽  
Electron Demand

The effect of increasing electron demand upon the product-determining transition state in the reaction of arenesulphenyl chlorides with tetracyclo[3.2.0.02,7.04,6]heptane has been investigated. As the electron donating ability of the remote substituents on the phenyl ring of the sulphenyl chloride is varied from nitro to methoxy the relative proportion of adducts derived from edge-on attack is found to increase relative to that of adducts derived from corner attack. An ortho-nitro group was found to lead to a stabilizing interaction only in the case of 2,4-dinitrobenzenesulphenyl chloride. A mechanism involving the competition between the two conceptual modes of approach is suggested.

Antimicrobial activity of 5-membered nitroheteroaromatic compounds beyond nitrofurans and nitroimidazoles: recent progress

2021 ◽  
Vol 28 ◽  
Author(s):  
Stanislav Kalinin ◽  
Tatiana Vedekhina ◽  
Polina Paramonova ◽  
Mikhail Krasavin
Keyword(s):  
Antimicrobial Activity ◽  
Nitro Group ◽  
Recent Progress ◽  
Antimicrobial Agents ◽  
Multidrug Resistant ◽  
Drug Resistant ◽  
Reductive Activation ◽  
Resistant Tuberculosis ◽  
Multidrug Resistant Tuberculosis ◽  
Primary Focus

: The last decade has been characterized by the development and approval of pretomanid and delamanid, which are nitroimidazole based drugs for multidrug resistant tuberculosis. This attracted renewed attention to the nitroheterocyclic scaffolds as a source of safe and efficient antimicrobial agents. While the primary focus is still on nitrofurans and nitroimidazoles, well known as bioreducible prodrugs, a number of studies have been published on other 5-membered nitroheteroaromatic compounds. The latter not only show promising antimicrobial activity, but also demonstrate modes of action different from the conventional reductive activation of nitro group. Considering the potential of these efforts to impact in the continuing race against drug-resistant pathogens, herein we review non-furan/imidazole based 5-membered nitroheteroaromatics investigated as antimicrobial agents in 2010-2020.

scholarly journals Synthesis and antimicrobial activity of novel tetrabromo-α,α’-bis(substituted-benzyl)cycloalkanones

2012 ◽  
Vol 77 (6) ◽  
pp. 717-723 ◽  
Author(s):  
Rahman Motiur ◽  
Sayed Alam ◽  
Adnan Kadi
Keyword(s):  
Mass Spectrometry ◽  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Phenyl Ring ◽  
Salmonella Enteritidis ◽  
Phytophthora Capsici ◽  
Enterobacter Aerogenes ◽  
Antimicrobial Activities ◽  
Meta Position

A series of novel tetrabromo-?,??-bis(substituted-benzyl)-cycloalkanones have been synthesized through a rapid, simple, and efficient methodology in an excellent isolated yield and characterized via IR, NMR (1H 13C NMR, DEPT135, DEPT90) and Mass spectrometry. All compounds have been assayed for in vitro antimicrobial activities against eight bacteria, e. g. Staphylococcus aureus, Bacillus subtilis, and Listeria monocytogenes, Salmonella enteritidis, Pseudomonas aeruginosa, Enterobacter aerogenes, Salmonella typhimurium, and Escherichia coli and five fungi e.g. Botrytis cinerea, Rhizoctonia solani, Fusarium oxysporum, Sclerotonia sclerotiorum, and Phytophthora capsici. They showed strong antibacterial activity than antifungal activities. Compounds 4c, 4d and 4i containing methoxy or chloro substituent on the para or meta position of the phenyl ring showed comparable MIC values to streptomycin and tetracycline standard antibiotics. Among all the tested compounds 4i exhibited good to moderate antifungal activity against all fungal strains used in the present study.

Studies on the rearrangement of ortho-nitrobenzylidenemalonates and their Analogues to 2-aminobenzoate derivatives

2002 ◽  
Vol 80 (2) ◽  
pp. 192-199 ◽  
Author(s):  
Elzbieta Lewandowska ◽  
Stefan Kinastowski ◽  
Stanislaw F Wnuk
Keyword(s):  
Double Bond ◽  
Nitro Group ◽  
Phenyl Ring ◽  
Nitro Compounds ◽  
Trifluoromethyl Group ◽  
Reverse Polarity ◽  
Michael Reactions ◽  
Carbon Double Bond ◽  
Oxidative Rearrangement ◽  
Aromatic Nitro

Reaction of the diethyl 2-nitro-4-(trifluoromethyl)benzylidenemalonate with diethylamine in alcohols resulted in the reduction of the nitro group and the oxidation of the vinylic carbon attached to the phenyl ring. Simultaneous migration of the malonic fragment gave the appropriate 2-amino-4-(trifluoromethyl)benzoate esters. The presence of at least two nitro groups, or one nitro group and trifluoromethyl group on the phenyl ring, attached to the α-carbon and strongly electron withdrawing substituents at the β-carbon (CO2Et, CN) in ortho-nitrobenzylidene systems is necessary for this reductive–oxidative rearrangement to proceed. Reaction of nitrocinnamates with thiols in the presence of triethylamine in tetrahydrofuran gave Michael addition products with different regioselectivity of addition. Ethyl 2-nitrocinnamate undergoes standard β-addition of thiols to a carbon–carbon double bond. However, 2,4-dinitro- and 2,4,6-trinitrocinnamates undergo α-addition of thiols, indicating that the presence of two nitro groups on the phenyl ring can reverse polarity of the carbon–carbon double bond in cinnamate acceptors.Key words: abnormal Michael reactions, aromatic nitro compounds, benzylidene compounds, rearrangements.

scholarly journals Characterisation of twelve newly synthesised N-(substituted phenyl)-2-chloroacetamides with QSAR analysis and antimicrobial activity tests

2021 ◽  
Vol 72 (1) ◽  
pp. 70-79
Author(s):  
Aleksandra Bogdanović ◽  
Anita Lazić ◽  
Slavica Grujić ◽  
Ivica Dimkić ◽  
Slaviša Stanković ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Biological Activity ◽  
Phenyl Ring ◽  
Prediction Models ◽  
Phospholipid Bilayer ◽  
Gram Positive ◽  
Gram Negative ◽  
Qsar Analysis ◽  
Lipinski’S Rule ◽  
Gram Positive Bacteria

Abstract In this study we screened twelve newly synthesised N-(substituted phenyl)-2-chloroacetamides for antimicrobial potential relying on quantitative structure-activity relationship (QSAR) analysis based on the available cheminformatics prediction models (Molinspiration, SwissADME, PreADMET, and PkcSM) and verified it through standard antimicrobial testing against Escherichia coli, Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), and Candida albicans. Our compounds met all the screening criteria of Lipinski’s rule of five (Ro5) as well as Veber’s and Egan’s methods for predicting biological activity. In antimicrobial activity tests, all chloroacetamides were effective against Gram-positive S. aureus and MRSA, less effective against the Gram-negative E. coli, and moderately effective against the yeast C. albicans. Our study confirmed that the biological activity of chloroacetamides varied with the position of substituents bound to the phenyl ring, which explains why some molecules were more effective against Gram-negative than Gram-positive bacteria or C. albicans. Bearing the halogenated p-substituted phenyl ring, N-(4-chlorophenyl), N-(4-fluorophenyl), and N-(3-bromophenyl) chloroacetamides were among the most active thanks to high lipophilicity, which allows them to pass rapidly through the phospholipid bilayer of the cell membrane. They are the most promising compounds for further investigation, particularly against Gram-positive bacteria and pathogenic yeasts.

Sign in / Sign up

Export Citation Format

Share Document