11 research outputs found
FACILE SYNTHESIS AND SPECTROSCOPIC CHARACTERIZATION OF SULFONAMIDE BEARING DIVERSIFIED CARBOXAMIDE AND HYDRAZINE CARBOXAMIDE MOIETIES
This current research describes the eco-friendly synthesis of N-(s-phenyl)-3-phenyl-2-(phenyl sulfonamido)
propanamides which are sulfonamide bearing diversified carboxamide moieties. The incorporation of amido
functionality into the sulfonamide moieties was herein achieved in three steps in a cost-effective manner by starting
from cheap amino acid, phenyl alanine which was reacted with benzenesulfonyl chloride to produce sulfonamide
which upon subsequent esterification followed by amidation furnished carboxamido-incorporated sulfonamide
analogs 9a-j in good to excellent yield. The completion of reaction processes was authenticated with Thin Layer
Chromatography (TLC) and the chemical structures were validated through the elemental analysis result as well as
spectroscopic means which include FT-IR, UV, 1H and 13C NMR. The technique used herein was found to be efficient
and cost-effective for the production of the series of carboxamide diversified sulfonamide derivative
Facile Synthesis, Characterization and Antimicrobial Activity of 2-Alkanamino Benzimidazole Derivatives
Benzimidazole derivatives are known to represent a class of medicinally important compounds which are extensively used in drug design and catalysis. A series of 2-substituted benzimidazole derivatives 10a-i was herein synthesized from the reaction of o-phenylenediamine with some amino acids using ameliorable pathway. The chemical structures of the synthesized compounds were con rmed by IR, UV, 1H-NMR, 13C-NMR, Mass spectral and analytical data. The compounds were investigated for their antimicrobial activity alongside gentamicin clinical standard. The results showed that this skeletal framework exhibited marked potency as antimicrobial agents. The most active compound was 1H-benzo[d]imidazol-2-yl)methanamine, 10a
Comparative Study of the Antibacterial Activity of N, N-Diethylamido Substituted p-Toluenesulfonamides to their α-Toluenesulfonamide Counterparts
Reaction of p-toluenesulfonyl chloride with amino acids gave sulfonamides p-T1a-k which upon amidation afforded p-T2a-k. Similarly, treatment involving α-toluenesulfonyl chloride and amino acids afforded the sulfonamides α-T1a-k.
These two classes of sulfonamides were synthetically modified at their COOH end position to achieve N,N-diethylamido substituted p-toluenesulfonamides p-T2a-k
and α-toluenesulfonamides α-T2a-k, respectively. The chemical structures of the compounds were validated with IR, Mass spectra, NMR as well as elemental analytical data. Both classes of compounds were screened against Escherichia coli and Staphylococcus aureus and their activity were compared. It was remarkable to note that the α-toluene sulfonamides α-T2a-k were more active than their p-toluenesulfonamide counterparts p-T2a-k. Compound 1-(benzylsulfonyl)-N,Ndiethylpyrrolidine-2-carboxamide α-T2a was the most potent antibacterial compound on S. aureus with MIC value of 3.12 μg mLG1 while N,N-Diethyl-3-
phenyl-2-(phenylmethylsulfonamide) propanamide α-T2j emerged as the best antibacterial motif against E. coli with MIC value of 12.5 μg mLG1. Hence, these compounds especially the α-toluenesulfonamide core structural templates are good candidates for further study for future drug discovery
Comparative Study of the Antibacterial Activity of N, N-Diethylamido Substituted p-Toluenesulfonamides to their α-Toluenesulfonamide Counterparts
Reaction of p-toluenesulfonyl chloride with amino acids gave sulfonamides
p-T1a-k which upon amidation afforded p-T2a-k. Similarly, treatment involving
α-toluenesulfonyl chloride and amino acids afforded the sulfonamides α-T1a-k.
These two classes of sulfonamides were synthetically modified at their COOH end
position to achieve N,N-diethylamido substituted p-toluenesulfonamides p-T2a-k
and α-toluenesulfonamides α-T2a-k, respectively. The chemical structures of the
compounds were validated with IR, Mass spectra, NMR as well as elemental
analytical data. Both classes of compounds were screened against Escherichia coli
and Staphylococcus aureus and their activity were compared. It was remarkable
to note that the α-toluene sulfonamides α-T2a-k were more active than their
p-toluenesulfonamide counterparts p-T2a-k. Compound 1-(benzylsulfonyl)-N,Ndiethylpyrrolidine-
2-carboxamide α-T2a was the most potent antibacterial
compound on S. aureus with MIC value of 3.12 μg mLG1 while N,N-Diethyl-3-
phenyl-2-(phenylmethylsulfonamide) propanamide α-T2j emerged as the best
antibacterial motif against E. coli with MIC value of 12.5 μg mLG1. Hence, these
compounds especially the α-toluenesulfonamide core structural templates are good
candidates for further study for future drug discovery
Microwave-assisted synthesis and antibacterial propensity of N0-s-benzylidene-2-propylquinoline- 4-carbohydrazide and N0-((s-1H-pyrrol- 2-yl)methylene)-2-propylquinoline- 4-carbohydrazide motifs
Microwave-assisted approach was utilized as green approach to access a series of 2-pro
pylquinoline-4-carbohydrazide hydrazone derivatives 10a-j of aromatic and heteroaromatic aldehydes
in highly encouraging yields. It involved four steps reaction which was initiated with ring opening
reaction of isatin in a basified environment and subsequent cross-coupling with pentan-2-one to
produce compound 7. Esterification of 7 in acid medium led to the formation of compound 8 which
was reacted with hydrazine hydrate to access 9 which upon microwave-assisted condensed with aromatic
and heteroaromatic aldehydes furnished the targeted compounds 10a-j. The structures of 10aj
were confirmed by physico-chemical, elemental analyses and spectroscopic characterization which
include UV, FT-IR, 1H and 13C NMR as well as DEPT-135. The targeted compounds 10a-j, alongside
with gentamicin clinical standard, were investigated for their antibacterial efficacies using agar
diffusion method. 2-Propyl-N0-(pyridine-3-ylmethylene) quinoline-4-carbohydrazide 10j emerged a
Structure-based design of functionalized 2-substituted and 1,2- disubstituted benzimidazole derivatives and their in vitro antibacterial efficacy
The aim of this present study was to synthesize 2-substituted and 1,2-disubstituted benzimidazole
derivatives to investigate their antibacterial diversity for possible future drug design. The structurebased
design of precursors 2-(1H-benzimidazol-2-yl)aniline 1, 2-(3,5-dinitro phenyl)-1Hbenzimidazole
3 and 2-benzyl-1H-benzimidazole 5 were achieved by the condensation reaction of ophenylenediamine
with anthranilic acid, 3,5-dinitrophenylbenzoic acid, and phenylacetic acid, respectively.
The precursors 1, 3 and 5, upon reaction with six different electrophile-releasing agents, furnished
the corresponding 2-substituted benzimidazole, 2a-f and 1,2-disubstituted benzimidazole derivatives
4a-f and 6a-f, respectively. The structural identity of the targeted compounds was authenticated by elemental
analytical data and spectral information from FT-IR, UV, 1H, and 13C NMR. The outcome of the
findings from the in vitro screening unveiled 2-benzyl-1-(phenylsulfonyl)-1H-benzimidazole 6b as the
most active derivative with lowest MIC value of 15.63 mg/m
Dimethylformamide-mediated synthesis and characterization of novel pyrazole- and pyrimidine-based 3,4- dihydropyrimidine-2(1H)-thione derivatives
Pyrimidine, an essential component of nucleic acid is currently reported for its
potential application in Acquired Immune Deficiency Syndrome (AIDS) chemotherapy. Also,
pyrazole nucleus, a versatile heterocyclic compound is gaining more attention in drug designs
owing to its pharmacological therapeutic potentials. Hence, this present study deals with cost
effective synthesis of 6-methyl-4-phenyl-5-(substituted-5-phenyl-4H-pyrazol-3-yl)-3,4-
dihydropyrimidine-2(1H)-thione derivatives which are concisely known as pyrazole-based
pyrimidine scaffolds. The multicomponent reaction of benzaldehyde, acetyl acetone and
thiourea in the presence of catalytic amount of hydrochloric acid (HCl)ab initio produced 5-
aceto-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine, 1. Later, room temperature Claisen-
Schmidt condensation of precursor 1 with diverse aromatic aldehydes which were
benzaldehyde derivatives led to the formation of α,β-unsaturated carbonyl side chain, 2a-h.
Finally, the thermal annellation through synthetic cyclization furnished crude products which
were purified by recrystallization to afford 6-methyl-4-phenyl-5-(substituted-5-phenyl-4Hpyrazol-
3-yl)-3,4-dihydropyrimidine-2(1H)-thione derivatives 3a-h in a cheap condition. The
chemical structures were authenticated using IR, UV, 1H-NMR and 13C-NMR as well as
analytical data. The final products 3a-h possessed good candidature for further investigation
regarding their biological activities and pharmacological potential for new drug discovery
Facile Synthesis, Characterization and in vitro Antibacterial Efficacy of Functionalized 2-Substituted Benzimidazole Motifs
A series of functionalized 2-substituted benzimidazole motifs was
designed and successfully synthesized via thermal cyclization of 1,2-diaminobenzene
on COOH end of L- leucine to achieve benzimidazole derivatives 6 as the essential
precursor. The coupling of the precursor 6 with benzaldehyde derivatives a-h, ketone
series i-k, and aryl sulfonyl chlorides l-n led to the formation of the targeted 2-
substituted benzimidazole motifs 7a-n in improved yields. The targeted
benzimidazole motifs were structurally authenticated through their spectral data
and microanalytical parameters. The targeted final moieties were investigated for
potential antimicrobial activity using the agar diffusion method with gentamicin as
the clinical standard. All the compounds had a broad spectrum of activity with
compound 7k having the highest remarkable activity with MIC of 0.98 ± 0.02 μg/mL
and MBC value of 3.91 ± 0.10 μg/mL. These findings suggest that compound 7k
containing camphor might be a good candidate for the design of new antimicrobial
small-molecule drugs