Design, synthesis and biological evaluation of diarylpyrazole/triazole bearing 1,3,4- oxadiazole moiety as coxs inhibitors endowed with potential anti-inflammatory and analgesic activities

Abdelazeem, Ahmed H.; El-Din, Asmaa G. Safi; El‐Saadi, Mohammed T.; El-Moghazy, Samir M.; Amin, Noha H.

doi:10.5958/0974-360x.2020.00751.9

Cited by 5 publications

(2 citation statements)

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“…Compound 33 induced a lower antiedematogenic effect than the reference drug celecoxib (39 and 82% of edema inhibition, respectively). Celecoxib exhibited higher potency of cyclooxygenase (COX)-2 inhibition than compound 33 (IC 50 = 0.95 and 2.52 µM, respectively) ( Abdelazeem et al, 2020 ). New azomethine compounds with an electron-withdrawing group like nitrogen ( 34 ) or chlorine ( 35 ) at the ortho position of phenyl ring with a satisfactory anti-inflammatory effect (ED 50 = 0.86 and 0.92 mmol/kg, respectively) elicited weak COX-2 inhibition (IC 50 = 38.12 and 32.11) as compared with celecoxib (ED 50 = 8.03 mmol/kg; IC 50 = 0.34) ( Murahari et al, 2019 ).…”

Section: Selected Activitiesmentioning

confidence: 99%

Heterocyclic Compounds: Pharmacology of Pyrazole Analogs From Rational Structural Considerations

et al. 2021

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Low quality of life and life-threatening conditions often demand pharmacological screening of lead compounds. A spectrum of pharmacological activities has been attributed to pyrazole analogs. The substitution, replacement, or removal of functional groups on a pyrazole ring appears consistent with diverse molecular interactions, efficacy, and potency of these analogs. This mini-review explores cytotoxic, cytoprotective, antinociceptive, anti-inflammatory, and antidepressant activities of some pyrazole analogs to advance structure-related pharmacological profiles and rational design of new analogs. Numerous interactions of these derivatives at their targets could impact future research considerations and prospects while offering opportunities for optimizing therapeutic activity with fewer adverse effects.

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Section: Selected Activitiesmentioning

confidence: 99%

Heterocyclic Compounds: Pharmacology of Pyrazole Analogs From Rational Structural Considerations

et al. 2021

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“…Hence, in the recent years, many chemist focused and developed these derivatives to enhance the efficiency of anti‐HIV drug activity compared to Efavirenz 3–6 . Benzoxazolone derivatives exhibit important biological activities like neurological, 7–9 allergy, 10 autoimmune, 11 anti‐inflammatory, 12–15 psychiatric, 16 antitumor, 17 metabolic disorders, 18 cytotoxicity activities, 19 antimalarial activity, 20,21 anti‐AIDS, 22–26 cardiovascular, 27 anticancer, 28 cerebrovascular diseases, 29 antimicrobial agents, 30 antifungal, 31 and acetylcholinesterase inhibitors 32 (Figure 1). These derivatives are used for the treatment of several cardiovascular diseases 27,33,34 control of hypertension and offered good oral pharmacological development in rats.…”

Section: Introductionmentioning

confidence: 99%

Convenient method for the synthesis of some novel chiral methyl 2‐(2‐oxo‐2H‐benzo[e][1,3]oxazin‐3(4H)‐yl)propanoate derivatives and biological evaluation of their antioxidant, cytotoxic, and molecular docking properties

Sivakumar

Prabakaran

Selvaraj

et al. 2020

Journal of Heterocyclic Chem

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Ten chiral methyl 2‐(2‐oxo‐2H‐benzo[e][1,3]oxazin‐3(4H)‐yl)propanoate derivatives 6a‐6j have been synthesized from optically pure amino methyl phenol 5 and 4‐nitrophenyl chloroformate. These derivatives 6a‐6j are characterized by 1H NMR, 13C NMR, FT‐IR, and HRMS spectral techniques. Optical purity of these derivatives was confirmed by chiral HPLC method. Ten synthesized ester derivatives 6a‐6j were screened for their in vitro antioxidant activity. Among the compounds 6b‐d and 6h‐j have exhibited comparable antioxidant activity with ascorbic acid as a standard. Compounds 6a and 6e‐g have shown moderate antioxidant activity. Further, the in vitro cytotoxicity of these compounds were studied through MTT cell proliferation assay in addition the effect on LDH leakage and NO release. Among the derivatives, 6j showed extremely best activity and the IC50 value (12.54 ± 0.71 μM) is very close to doxorubicin (7.2 ± 0.58 μM) as a standard. Compounds 6b, 6h, and 6i showed better inhibition next to compound 6j on the viability of HepG2 cells with an IC50 value (μM) of 56.02 ± 1.4, 41.76 ± 0.58, and 38.17 ± 0.34, respectively. Also, molecular docking studies have been carried out with STAT‐3 (PDB ID: 1BG1) and BCL‐2 (PDB ID: 4AQ3) proteins against the four active compounds 6b, 6h, 6i, and 6j. The binding energies of the tested compounds were in the range of −7.76 to −8.41 kcal/mol, which is very close to doxorubicin (−8.53 kcal/mol) as a standard. These molecular docking results are in good agreement with the in vitro studies.

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Emerging Aspects of Triazole in Organic Synthesis: Exploring its Potential as a Gelator

Das

Jenifer

Pradhan

2024

COS

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Cu(I)-catalyzed azide−alkyne 1,3-dipolar cycloaddition (CuAAC) — commonly known as the “click reaction” — serves as the most effective and highly reliable tool for facile construction of simple to complex designs at the molecular level. It relates to the formation of carbon heteroatomic systems by joining or clicking small molecular pieces together with the help of various organic reactions such as cycloaddition, conjugate addition, ring-opening, etc. Such dynamic strategy results in the generation of triazole and its derivatives from azides and alkynes with three nitrogen atoms in the five-membered aromatic azole ring that often form gel assembled structures having gelating properties. These scaffolds have led to prominent applications in designing advanced soft materials, 3D printing, ion sensing, drug delivery, photonics, separation, and purification. In this review, we mainly emphasize on the different mechanistic aspects of triazole formation which includes synthesis of sugar-based and non-sugar-based triazoles, and their gel applications reported in the literature for the past ten years, as well as the upcoming scope in different branches of applied sciences.

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Design, synthesis and biological evaluation of diarylpyrazole/triazole bearing 1,3,4- oxadiazole moiety as coxs inhibitors endowed with potential anti-inflammatory and analgesic activities

Cited by 5 publications

References 0 publications

Heterocyclic Compounds: Pharmacology of Pyrazole Analogs From Rational Structural Considerations

Heterocyclic Compounds: Pharmacology of Pyrazole Analogs From Rational Structural Considerations

Convenient method for the synthesis of some novel chiral methyl 2‐(2‐oxo‐2H‐benzo[e][1,3]oxazin‐3(4H)‐yl)propanoate derivatives and biological evaluation of their antioxidant, cytotoxic, and molecular docking properties

Emerging Aspects of Triazole in Organic Synthesis: Exploring its Potential as a Gelator

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