Synthesis, cyclooxygenase inhibition, and anti-inflammatory evaluation of novel diarylheterocycles with a central pyrazole, pyrazoline, or pyridine ring

Abdellatif, Khaled R.A.; Abdelall, Eman K. A.; Fadaly, Wael A.A.; Kamel, Gehan M.

doi:10.1007/s00044-015-1327-7

Cited by 39 publications

(19 citation statements)

References 19 publications

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“…The compounds TP2 , TP4 , TP6 , TP9, and TP10 were reported for the first time in this study. The compounds TP1 , TP3 , TP5 , TP7, and TP8 were registered in literatures as racemates, and their several bioactivities such as antidiabetic, anticancer, anti‐inflammatory, and COX inhibitory activities were reported . The compounds synthesized in this study were also obtained as pure racemates, and they were directly used for CA and AChE inhibition studies.…”

Section: Resultsmentioning

confidence: 96%

Synthesis, molecular modeling, and biological evaluation of 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

et al. 2017

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In this study, 4-[5-aryl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl] benzenesulfonamides were synthesized, and inhibition effects on AChE, hCA I, and hCA II were evaluated. K values of the compounds toward hCA I were in the range of 24.2 ± 4.6-49.8 ± 12.8 nm, while they were in the range of 37.3 ± 9.0-65.3 ± 16.7 nm toward hCA II. K values of the acetazolamide were 282.1 ± 19.7 nm and 103.60 ± 27.6 nm toward both isoenzymes, respectively. The compounds inhibited AChE with K in the range of 22.7 ± 10.3-109.1 ± 27.0 nm, whereas the tacrine had K value of 66.5 ± 13.8 nm. Electronic structure calculations at M06-L/6-31 + G(d,p)//AM1 level and molecular docking studies were also performed to enlighten inhibition mechanism and to support experimental findings. Results obtained from calculations of molecular properties showed that the compounds obey drug-likeness properties. The experimental and computational findings obtained in this study might be useful in the design of novel inhibitors against hCA I, hCA II, and AChE.

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Section: Resultsmentioning

confidence: 96%

Synthesis, molecular modeling, and biological evaluation of 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

et al. 2017

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“…Pyrazoles were also found to possess inhibitory activities against xanthine oxidase, cyclooxygenase, and alkaline phosphatases [5][6][7]. Particular substituents at the pyrazole provide additional biological activities [8,9].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of methyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C₁₈H₁₅FN₂O₂

Sheng-Yue

You

Zhang

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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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: 90%

“…The most potent anti-inflammatory compounds (14a-d, 16, 17 and 21) were subjected to ulcerogenic liability in comparison with celecoxib, low ulcerogenic reference drug, which was reported 18,22 by our group to be about seven folds less ulcerogenic than ibuprofen as traditional NSAID and the results are shown in Table 3. It was clear that the tested compounds caused variable ulceration effect (ulcer index ¼ 0.33-4.0) comparable to that of celecoxib (ulcer index ¼ 0.33).…”

Section: Ulcerogenic Liabilitymentioning

confidence: 99%

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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Synthesis, cyclooxygenase inhibition, and anti-inflammatory evaluation of novel diarylheterocycles with a central pyrazole, pyrazoline, or pyridine ring

Cited by 39 publications

References 19 publications

Synthesis, molecular modeling, and biological evaluation of 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

Synthesis, molecular modeling, and biological evaluation of 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

Crystal structure of methyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C₁₈H₁₅FN₂O₂

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

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Synthesis, cyclooxygenase inhibition, and anti-inflammatory evaluation of novel diarylheterocycles with a central pyrazole, pyrazoline, or pyridine ring

Cited by 39 publications

References 19 publications

Synthesis, molecular modeling, and biological evaluation of 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

Synthesis, molecular modeling, and biological evaluation of 4‐[5‐aryl‐3‐(thiophen‐2‐yl)‐4,5‐dihydro‐1H‐pyrazol‐1‐yl] benzenesulfonamides toward acetylcholinesterase, carbonic anhydrase I and II enzymes

Crystal structure of methyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C18H15FN2O2

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

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Crystal structure of methyl 1-(4-fluorobenzyl)-3-phenyl-1H-pyrazole-5-carboxylate, C₁₈H₁₅FN₂O₂