Abstract
A series of 1‐phenyl‐3‐(4‐(2‐ethanoloxy) phenyl)‐5‐aryl‐1H‐pyrazoles were synthesized from chalcones, that is, 3‐aryl‐1‐(4‐hydroxyphenyl) prop‐2‐en‐1‐ones and studied for their in vitro antibacterial activity. Chalcones 1 on reaction with phenyl hydrazine in the presence of acetic acid and few drops of hydrochloric acid yielded the corresponding 1‐phenyl‐3‐(4‐hydroxyphenyl)‐5‐aryl‐1H‐pyrazoles 2 which on further reaction with 2‐chloroethanol furnished the title compounds 3. These compounds were characterized by CHN analyses, IR, mass and 1H NMR spectral data. All the compounds were evaluated for their in vitro antibacterial activity against two Gram positive strains (Bacillus subtilis and Staphylococcus aureus) and two Gram negative strains (Escherichia coli and Pseudomonas aeruginosa), and their minimum inhibitory concentration (MIC) was determined.
Highlights
E extensive utilization of chemotherapeutic agents for the management of infectious diseases leads to the development of microbial resistance to existing drugs. e appearance of resistance to the major classes of antibacterial drugs is recognized as a major health concern of world population. is opens the gate for the medicinal chemists for the development of novel antimicrobial drugs having a different mechanism of action to combat the problem of multidrug resistance [1]
1H-pyrazoles containing phenoxy propanol [13] and phenoxy butanol [14] side chain have been reported to possess antibacterial activity by us as a part of our ongoing research program in the eld of synthesis and antimicrobial activity of medicinally important heterocyclic compounds [15, 16]. ese reports inspired us to undertake the synthesis of some 1H-pyrazoles bearing phenoxy ethanol moiety. e synthesized compounds were characterized on the basis of elemental analysis, IR, 1H NMR and mass spectral data
Chalcones 1a–g were synthesized by a base-catalyzed Claisen-Schmidt condensation reaction of appropriately substituted benzaldehydes and p-hydroxy acetophenone [17], and 1-phenyl-3(4-hydroxyphenyl)-5-aryl-1H-pyrazoles 2a–g were prepared from the chalcones 1a–g following the procedure described in the literature [18]
Summary
E extensive utilization of chemotherapeutic agents for the management of infectious diseases leads to the development of microbial resistance to existing drugs. e appearance of resistance to the major classes of antibacterial drugs is recognized as a major health concern of world population. is opens the gate for the medicinal chemists for the development of novel antimicrobial drugs having a different mechanism of action to combat the problem of multidrug resistance [1]. Heterocyclic compounds continue to attract considerable interest due to their diverse biological activities. Pyrazole derivatives have been reported to possess diverse biological activities such as antibacterial [2, 3], antifungal [4, 5], herbicidal [6], insecticidal [7], anti-in ammatory [8, 9] anticonvulsant [10], antitumor [11], anti-oxidant [12] and so forth. 1H-pyrazoles containing phenoxy propanol [13] and phenoxy butanol [14] side chain have been reported to possess antibacterial activity by us as a part of our ongoing research program in the eld of synthesis and antimicrobial activity of medicinally important heterocyclic compounds [15, 16]. All the compounds were screened for their in vitro antibacterial activity against two Gram positive strains (Bacillus subtilis and Staphylococcus aureus) and two Gram negative strains (Escherichia coli and Pseudomonas aeruginosa), respectively
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