3-Methyl-2-phenyl-1-substituted-indole derivatives as indomethacin analogs: design, synthesis and biological evaluation as potential anti-inflammatory and analgesic agents

Abdellatif, Khaled R.A.; Lamie, Phoebe F.; Omar, Hany A.

doi:10.3109/14756366.2015.1022174

Cited by 67 publications

(32 citation statements)

References 21 publications

(24 reference statements)

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“…Furthermore, the 4-substituted-1-phenylpyrazolo [3,4-d]pyrimidine derivative (9) showed considerable anti-inflammatory activity 16 . Guided by the previously mentioned studies and as a continuation of our previous work [17][18][19][20][21] for the development of safe anti-inflammatory derivatives,here wedescribe the synthesis, in vitro evaluation as COX-1/COX-2 inhibitors, in vivo antiinflammatory (AI) activity and ulcerogenic liability for some new 1-phenylpyrazolo [3,4-d]pyrimidine derivatives (14a-d-21) with the hope of realizing compounds with improved anti-inflammatory activity and diminished side effects.…”

Section: Introductionmentioning

confidence: 91%

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

Bakr

Azouz

Abdellatif

2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A new group of 1-phenylpyrazolo [3,4-d]pyrimidine derivatives 14a-d-21 were synthesized from 2-(6-methyl-1-phenyl-1H-pyrazolo [3,4-d]pyrimidin-4-yloxy)acetohydrazide (12). All the synthesized compounds were evaluated for their cyclooxygenase (COX) inhibition, antiinflammatory activity and ulcerogenic liability. All the target compounds were more potential in inhibiting COX-2 than COX-1. Compounds having pyrazolyl moiety in a hybrid structure with pyrazolo[3,4-d]pyrimidine scaffold (14a-d, 16 and 17) showed higher edema inhibition percentage activities (34-68%) and the 5-aminopyrazole derivative (14c, ED 50 ¼ 87.9 mmol/kg) was the most potent one4celecoxib (ED 50 ¼ 91.9 mmol/kg). While, the in vivo potent compounds (14a-d, 16, 17 and 21) caused variable ulceration effect (ulcer index ¼ 0.33-4.0) comparable to that of celecoxib (ulcer index ¼ 0.33), the pyrazol-3-one derivative (16) and the acetohydrazide (21) were the least ulcerogenic derivatives showing the same ulcerogenic potential of celecoxib.

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Section: Introductionmentioning

confidence: 91%

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

Bakr

Azouz

Abdellatif

2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Indole, a privileged scaffold, is widely known for its significance not only in the area of synthetic chemistry but also in biological, pharmaceutical, and material science . Indole derivatives have shown a wide range of biological activities such as plant growth regulation and antifungal, antibacterial, antitubercular, anticancer, antiulcer, antiviral, antioxidant, antidepressant, anti‐inflammatory, antidiabetic, antimalarial, anti‐HIV, insecticidal, and analgesic activities …”

Section: Introductionmentioning

confidence: 99%

An efficacious synthesis of N‐1–, C‐3–substituted indole derivatives and their antimicrobial studies

Jain

Utreja

Sharma

2019

Journal of Heterocyclic Chem

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A novel series of 11 C-3-and N-1-substituted oxoacetamide indole derivatives were synthesized by reacting with various aromatic amines and alkyl halides. These compounds were characterized by using various spectral techniques, ie, 1 HNMR, 1 HNMR-D 2 O, 13 CNMR, UV, elemental analysis, IR, and mass spectrometery. In vitro, antimicrobial studies of resultant compounds were carried out against two bacterial strains, Pseudomonas aeruginosa and Pseudomonas oryzihabitans using disc plate method. All the tested compounds showed vital efficiency as antimicrobial agents against both the bacterial strains. The results revealed that synthesized indole derivative 2-(1-(3bromopropyl)-1H-indol-3-yl)-N-(2-nitrophenyl)-2-oxoacetamide displayed the best antimicrobial activity as compared with all other synthesized compounds.

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“…Indole derivatives have been reported to possess significant pharmacological activities. Derivatives of indole have been used as anti-inflammatory, analgesic and antipyretic agents [ 11 , 12 , 13 ]. Schiff bases have been reported to possess various pharmacological activities e.g., anti-inflammatory activity [ 14 ], anti-tubercular activity [ 15 ] and anticonvulsant activity [ 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Indole Derivatives as Cyclooxygenase Inhibitors: Synthesis, Biological Evaluation and Docking Studies

et al. 2018

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A new series of 2-(5-methoxy-2-methyl-1H-indol-3-yl)-N′-[(E)-(substituted phenyl) methylidene] acetohydrazide derivatives (S1–S18) were synthesized and evaluated for their anti-inflammatory activity, analgesic activity, ulcerogenic activity, lipid peroxidation, ulcer index and cyclooxygenase expression activities. All the synthesized compounds were in good agreement with spectral and elemental analysis. Three synthesized compounds (S3, S7 and S14) have shown significant anti-inflammatory activity as compared to the reference drug indomethacin. Compound S3 was further tested for ulcerogenic index and cyclooxygenase (COX) expression activity. It was selectively inhibiting COX-2 expression and providing the gastric sparing activity. Docking studies have revealed the potential of these compounds to bind with COX-2 enzyme. Compound S3 formed a hydrogen bond between OH of Tyr 355 and NH2 of Arg 120 with carbonyl group and this hydrogen bond was similar to that formed by indomethacin. This study provides insight for compound S3, as a new lead compound as anti-inflammatory agent and selective COX-2 inhibitor.

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3-Methyl-2-phenyl-1-substituted-indole derivatives as indomethacin analogs: design, synthesis and biological evaluation as potential anti-inflammatory and analgesic agents

Cited by 67 publications

References 21 publications

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo[3,4-d]pyrimidine derivatives

An efficacious synthesis of N‐1–, C‐3–substituted indole derivatives and their antimicrobial studies

Indole Derivatives as Cyclooxygenase Inhibitors: Synthesis, Biological Evaluation and Docking Studies

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