Synthesis and evaluation of [N-(Substituted phenyl)-2-(3-substituted) sulfamoyl) phenyl)] acetamide derivatives as anticancer agents

Pawar, Chandrakant D.; Sarkate, Aniket P.; Karnik, Kshipra S.; Shinde, Devanand B.

doi:10.1016/j.ejbas.2017.09.001

Cited by 6 publications

(5 citation statements)

References 27 publications

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“…In step f, we have used peptide coupling condition for the reaction of compound 6 and 3-flouro aniline to obtain 88% of compound 7. [36,37] In step g, we have used Buchwald coupling reaction condition to obtain different compounds as 9a-9j with >70% yields. [38] We have optimized Buchwald coupling reaction by modifying catalyst, ligand, base, solvent, and temperature to get suitable condition.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and anti‐proliferative activity studies of 2‐(2‐(trifluoromethyl)‐6‐(substituted)imidazo[1,2‐b]pyridazin‐3‐yl)‐N‐(substituted)acetamide derivatives

Gaikwad

Pawar

Chavan

et al. 2020

Journal of Heterocyclic Chem

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A series of novel imidazo[1,2‐b]pyridazin‐3‐yl acetamide derivatives (9a‐9j) were synthesized from a 3,6‐dichloropyridazine. We have developed a simple strategy for the synthesis of functionally diverse imidazole, and pyridiazine derivatives were reported via a series of steps. The work involves bicyclic imidazo‐pyridazine ring formation, halogenation, cynation, hydrolysis, peptide coupling, and Buchwald reaction. The structure of the synthesized compounds was confirmed by IR, 1H NMR, 13C NMR,19F NMR, mass spectra, and elemental analysis, and purity is checked by HPLC. All synthesized compounds were screened for anticancer activity against A‐549 and Du‐145 cancer cell lines by MTT assay. The preliminary bioassay suggests that most of the compounds show anti‐proliferation with different degrees; doxorubicin was used as positive control. The synthesized compound shows IC50 values in the range of 1.74μM to 16.17μM in both cell lines. The compounds 9e, 9g, and 9h were active compared with doxorubicin in both the cell lines. The compounds having cyclopentyl ring are active compared with higher and lower carbon analogues.

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Section: Resultsmentioning

confidence: 99%

Synthesis and anti‐proliferative activity studies of 2‐(2‐(trifluoromethyl)‐6‐(substituted)imidazo[1,2‐b]pyridazin‐3‐yl)‐N‐(substituted)acetamide derivatives

Gaikwad

Pawar

Chavan

et al. 2020

Journal of Heterocyclic Chem

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“…[21][22][23] For example, benzodifuran scaffold can be easily utilized as dyes in solar cells, 24 building blocks for optoelectronic devices 25 and transistors. 26 By considering the varied biological importance of furanes and sulfonamides and in continuation of research on heterocyclic compounds in our group for the development of antimicrobial and anticancer agent [27][28][29] we have synthesized a series of 5-(substituted phenyl)-N-(2-oxo-2-(substituted phenyl)ethyl)-N-methylfuran-2-sulfonamide derivatives (4a-4m) depicted in Scheme 1 and tested their antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Screening of 5-(Substituted Phenyl)-N-(2-Oxo-2-(Substituted Phenyl)ethyl)-N-Methylfuran-2-Sulfonamide Derivatives

Desmukh¹,

Pawar²,

Pansare³

et al. 2019

ECB

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We synthesized substituted furansulfonamide compounds and developed reaction conditions for a series of 5-(substituted phenyl)-N-(2oxo-2-(substituted phenyl)ethyl)-N-methylfuran-2-sulfonamide derivatives (4a-4m). We have optimized methodology for targets from milligram scale to multi gram scale. The structure of synthesized compounds were elucidated and confirmed by 1H NMR, 13C NMR, LCMS and purity was checked by HPLC. All the synthesized final compounds (4a-4m) are screened for antimicrobial activity (minimum inhibitory concentration) against a series of strains of Bacillus subtillis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus niger for antifungal activity. The results of antimicrobial screening data revealed most of compounds (4a-4m) showed moderate to promising microbial inhibitions.

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“…Moreover, recently particular attention was given to numerous derivatives of acetamides by the researchers as these molecules exhibit different biological activity such as antibacterial and antifungal (Ertan et al, 2007, Jamkhandi and Disouza, 2012, Hamad et al, 2017, antiinflammatory (de Castro Barbosa et al, 2009), antilieshmania (Pacheco et al, 2013), antituberculosis (Yadav et al, 2018), insecticide (Kalyanasundaram and Mathew, 2006), anthelmintic (Sawant and Kawade, 2011), antioxidant and anticancer (Özkay et al, 2010, Chen et al, 2013, Pawar et al, 2017, anticonvulsant and antidepressant (Soyer et al, 2004, Tarikogullari et al, 2010, Guan et al, 2016. In this study, various NSAIDs 2a-f were attached to N-(2,6-dimethyl phenyl) acetamide 1 to decrease the gastric irritation by masking the acidic carboxylic group through ester linkage as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs

hamadameen

Ameen

2019

ZJPAS

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Non steroidal anti-inflammatory drugs (NSAIDs) are among the most used analgesic and anti-inflammatory drugs. However inhibition of cyclooxygenase1 and acidic groups such as carboxylic groups in most NSAIDs cause gastrointestinal (GI) side effects. Therefore masking the acidic groups till it pass through the GI tract will decrease the direct GI side effects and because N-(2,6-dimethylphenyl)-acetamide 1 also has anti-inflammatory activity so the synthesized ester prodrugs might act as mutual prodrugs. Moreover, because of emerging of new strains of bacteria and resistance of bacteria to the available antibacterial agents, new antibacterial agents are needed. The NSAIDs have antibacterial activity and N-(2,6-dimethylphenyl) acetamide 1 also has antibacterial activity so binding of these molecules with each other might give more potent antibacterial agent. 2-Chloro-N-(2,6dimethyl phenyl) acetamide 1 was utilized to synthesize ester prodrug of various NSAIDs 2a-f. The 2-Chloro-N-(2,6dimethylphenyl)-acetamide 1 undergo substitution reaction at α position with various sodium carboxylate of NSAIDs 2a-f in DMSO. The constitution of the newly synthesized ester prodrugs of NSAIDs 3a-f had been confirmed on the basis of their IR, ¹H and ¹³C-NMR spectral data. All the synthesized ester prodrugs 3a-f were screened for their in vitro antibacterial activities against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 however, their antibacterial activity decreased compared with their starting 1 and 2a-f.

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Synthesis and evaluation of [N-(Substituted phenyl)-2-(3-substituted) sulfamoyl) phenyl)] acetamide derivatives as anticancer agents

Abstract: Shinde (2017) Synthesis and evaluation of [N-(Substituted phenyl)-2-(3-substituted) sulfamoyl) phenyl)] acetamide derivatives as anticancer agents,

Cited by 6 publications

References 27 publications

Synthesis and anti‐proliferative activity studies of 2‐(2‐(trifluoromethyl)‐6‐(substituted)imidazo[1,2‐b]pyridazin‐3‐yl)‐N‐(substituted)acetamide derivatives

Synthesis and anti‐proliferative activity studies of 2‐(2‐(trifluoromethyl)‐6‐(substituted)imidazo[1,2‐b]pyridazin‐3‐yl)‐N‐(substituted)acetamide derivatives

Synthesis and Antimicrobial Screening of 5-(Substituted Phenyl)-N-(2-Oxo-2-(Substituted Phenyl)ethyl)-N-Methylfuran-2-Sulfonamide Derivatives

Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs

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