Synthesis of Quinoline Analogs: Search for Antimalarial Agents

Babu, Konda Ramesh; Eeshwaraiah, B.; Aravind, D.; Meshram, H. M.; Raju, R. Madhusudan; Bhattacharya, Apurba; Bandichhor, Rakeshwar

doi:10.1007/s00706-007-0772-5

Cited by 11 publications

(7 citation statements)

References 4 publications

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“…Series of fifteen (E)-Substituted-N-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)benzeneamine derivative (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) was aimed for the synthesis, following the three step procedure (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

“…In the second step the Schiff bases undergoes cyclization to yield pyrazole carboxaldehyde (b1-b5) nucleus by using dimethylformamide (DMF) and the desired compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) by the condensation reaction between pyrazole carboxaldehyde (b1-b5) and substituted amines in ethanol and drop of acetic acid under reflux. The prepared derivatives (a1-a5), (b1-b5) and (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) were then analyzed for structural confirmation by variety of analytical techniques such as FTIR, NMR, Mass Spectroscopy, Elemental analysis. The FTIR bands around 1590-1602 and 3190-3222 cm −1 due to the presence of C=N and NH functional groups confirmed the formation of compounds (a1-a5), the singlet around 1098-11.18 ppm in 1 H-NMR spectra due to the NH proton and a strong signal around 166.08-166.90 ppm in 13 C-NMR spectra due to C=N carbon further confirmed the formation of compounds (a1-a5).…”

Section: Resultsmentioning

confidence: 99%

“…Screening of the antimicrobial therapeutic effect of the synthesized compounds was carried out employing the disc diffusion method. The stock solution of the test compounds was prepared by dissolving one mg of each compound (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) to the 100 mL of dimethysulphoxide (DMSO). The microbes [S. aureus (ATCC-25923), S. epidermidis (ATCC-29887), E. coli (ATCC-25922), P. mirabilis (ATCC-25933) were sub-cultured in nutrient agar media, following by the McFarland Protocol and transferred to the agar plate.…”

Section: Antimicrobial Screeningmentioning

confidence: 99%

“…The antimicrobial resistance (pathogens developed resistance to the available chemotherapeutic agents) has been a matter of great concern and reported the cause of 700,000 Deaths/Annum globally [1]. The pathogenic resistance has been a threat to the global community that once again become the major cause of the death due to the infectious disease [2].…”

Section: Introductionmentioning

confidence: 99%

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(E)-Substituted-N-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)benzeneamine: synthesis, characterization, antibacterial, and MTT assessment

et al. 2019

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To find out some novel antimicrobial chemotherapeutic agents, fifteen (E)-Substituted-N-(1,3-diphenyl-1H-pyrazol-4-yl) methylene)benzeneamine derivative (1-15) were synthesized. Structural elucidation of the prepared derivatives (1-15) was achieved by FTIR, NMR ( 1 H or 13 C), Mass spectroscopy and elemental analysis. After structural analyses the derivatives were subjected for biological assessment to estimate the antimicrobial therapeutic potential as well as the percent viability of the cells by disk diffusion methods and MTT assay. All the experiments were performed in triplicate; Ciprofloxacin and DMSO were used as positive and negative control. The results exhibited that the compounds 3, 4, 7-14 were found to exhibit significant antimicrobial therapeutic effect against all microorganisms, while some compounds of the series like 5, 6, 15, possessed moderate and compound 1 was found less significant potential. The percent viability of the cells were observed in the range 91-96% at lowest concentration 3.125 µM while 70-75% at the highest 100 µM.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Antimicrobial Screeningmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

(E)-Substituted-N-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)benzeneamine: synthesis, characterization, antibacterial, and MTT assessment

et al. 2019

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“…Global increase of multi‐drug‐resistant (MDR) pathogens including methicillin‐resistant Staphylococci aureus (MRSA), penicillin resistant Streptococcus pneumoniae (PRSP), vancomycin resistant enterrococci (VRE) and intolerance of first line drugs pose serious problem in therapeutics . Throughout the world, millions of people suffer from MDR bacterial infections such as of food poisoning, rheumatic fever, salmonellosis, and diarrhea, however so many people die as a direct consequence of this infection .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure‐Activity Relationship and Antimicrobial Evaluation of Methyl‐Substituted Tetrazoloquinoline‐Based Pyrazolinethioamides

et al. 2016

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A new series of pyrazolinethioamide and intermediate chalcone were synthesized from the tetrazoloqunoline molecule and the effect of these compounds on in-vitro growth of microorganisms is studied. In-vitro anti-microbial activity was performed against S.aureus, S.epidermidis, P.mirabilis and E.coli. A number of analogues exhibited potent activity against all the bacterial strains. The SAR results indicate that the thioamide, methoxy group at C-4 of phenyl ring and tetrazole unit play key roles for their bacterial inhibitory effect. This is further supported by the molecular modeling study of the crystal structure of PDB: 4Z7 M with compounds 5 b and 5 g. Compound 5 b showed potent antibacterial activity against S.aureus, S.epidermidis and moderate activity against E.coli with MIC values 6.25, 3.125, and 6.25 mg/mL, respectively. Compound 5 g showed potent antibacterial activity against S.epidermidis with MIC value 3.125 mg/mL but moderate activity against P.mirabilis and E. coli. Most promising compounds were tested for cytotoxic study by MTT assay on HepG2 cell line and the results showed that all the compounds offered remarkable > 70 % viability up to the concentration of 100 mg/mL.

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Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

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Synthesis of Quinoline Analogs: Search for Antimalarial Agents

Cited by 11 publications

References 4 publications

(E)-Substituted-N-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)benzeneamine: synthesis, characterization, antibacterial, and MTT assessment

(E)-Substituted-N-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)benzeneamine: synthesis, characterization, antibacterial, and MTT assessment

Synthesis, Structure‐Activity Relationship and Antimicrobial Evaluation of Methyl‐Substituted Tetrazoloquinoline‐Based Pyrazolinethioamides

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

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