Literature DB >> 33513963

New Substituted 5-Benzylideno-2-Adamantylthiazol[3,2-b][1,2,4]Triazol-6(5H)ones as Possible Anti-Inflammatory Agents.

Christophe Tratrat1, Michelyne Haroun1, Aliki Paparisva2, Charalmpos Kamoutsis3, Anthi Petrou2, Antonis Gavalas2, Phaedra Eleftheriou4, Athina Geronikaki2, Katharigatta N Venugopala1,5, Hafedh Kochkar6,7, Anroop B Nair1.   

Abstract

BACKGROUND: Inflammation is a complex response to noxious stimuli promoted by the release of chemical mediators from the damaged cells. Metabolic products of arachidonic acid, produced by the action of cyclooxygenase and lipoxygenase, play important roles in this process. Several non-steroidal anti-inflammatory drugs act as cyclooxygenase inhibitors. However, almost all of them have undesired side effects.
METHODS: Prediction of the anti-inflammatory action of the compounds was performed using PASS Program. The anti-inflammatory activity was evaluated by the carrageenan paw edema test. COX and LOX inhibitory actions were tested using ovine COX-1, human recombinant COX-2 and soybean LOX-1, respectively. Docking analysis was performed using Autodock.
RESULTS: All designed derivatives had good prediction results according to PASS and were synthesized and experimentally evaluated. The compounds exhibited in vivo anti-inflammatory action with eleven being equal or better than indomethacin. Although, some of them had no or low inhibitory effect on COX-1/2 or LOX, certain compounds exhibited COX-1 inhibition much higher than naproxen and COX-2 inhibition, well explained by Docking analysis.
CONCLUSIONS: A number of compounds with good anti-inflammatory action were obtained. Although, some exhibited remarkable COX inhibitory action this activity did not follow the anti-inflammatory results, indicating the implication of other mechanisms.

Entities:  

Keywords:  COX; LOX; NDGA; anti-inflammatory; carrageenan; docking; thiazole; triazole

Mesh:

Substances:

Year:  2021        PMID: 33513963      PMCID: PMC7866232          DOI: 10.3390/molecules26030659

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  46 in total

1.  Synthesis and in silico investigation of thiazoles bearing pyrazoles derivatives as anti-inflammatory agents.

Authors:  Rahul D Kamble; Rohan J Meshram; Shrikant V Hese; Rahul A More; Sonali S Kamble; Rajesh N Gacche; Bhaskar S Dawane
Journal:  Comput Biol Chem       Date:  2016-01-23       Impact factor: 2.877

2.  A structure-activity relationship study of thiazole derivatives with H1-antihistamine activity.

Authors:  Elzbieta Brzezińska; Justyna Stolarska; Anna Sobańska
Journal:  Acta Pol Pharm       Date:  2011 Sep-Oct       Impact factor: 0.330

3.  Design and synthesis of novel xanthone-triazole derivatives as potential antidiabetic agents: α-Glucosidase inhibition and glucose uptake promotion.

Authors:  Gao-Jie Ye; Tian Lan; Zhi-Xin Huang; Xiao-Ning Cheng; Chao-Yun Cai; Sen-Miao Ding; Min-Li Xie; Bo Wang
Journal:  Eur J Med Chem       Date:  2019-05-20       Impact factor: 6.514

4.  Design, synthesis and biological evaluation of novel pyridine-thiazolidinone derivatives as anticancer agents: Targeting human carbonic anhydrase IX.

Authors:  Mohammad Fawad Ansari; Danish Idrees; Md Imtaiyaz Hassan; Kamal Ahmad; Fernando Avecilla; Amir Azam
Journal:  Eur J Med Chem       Date:  2017-12-15       Impact factor: 6.514

5.  Histamine-induced edema in the rat paw--effect of capsaicin denervation and a CGRP receptor antagonist.

Authors:  R Amann; R Schuligoi; I Lanz; J Donnerer
Journal:  Eur J Pharmacol       Date:  1995-06-12       Impact factor: 4.432

6.  AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility.

Authors:  Garrett M Morris; Ruth Huey; William Lindstrom; Michel F Sanner; Richard K Belew; David S Goodsell; Arthur J Olson
Journal:  J Comput Chem       Date:  2009-12       Impact factor: 3.376

7.  Study of novel anticancer 4-thiazolidinone derivatives.

Authors:  Konrad A Szychowski; Marcin L Leja; Danylo V Kaminskyy; Urszula E Binduga; Oleh R Pinyazhko; Roman B Lesyk; Jan Gmiński
Journal:  Chem Biol Interact       Date:  2016-12-11       Impact factor: 5.192

8.  Computer-aided discovery of anti-inflammatory thiazolidinones with dual cyclooxygenase/lipoxygenase inhibition.

Authors:  Athina A Geronikaki; Alexey A Lagunin; Dimitra I Hadjipavlou-Litina; Phaedra T Eleftheriou; Dmitrii A Filimonov; Vladimir V Poroikov; Intekhab Alam; Anil K Saxena
Journal:  J Med Chem       Date:  2008-02-27       Impact factor: 7.446

9.  New Series of Thiazole Derivatives: Synthesis, Structural Elucidation, Antimicrobial Activity, Molecular Modeling and MOE Docking.

Authors:  Ismail Althagafi; Nashwa El-Metwaly; Thoraya A Farghaly
Journal:  Molecules       Date:  2019-05-04       Impact factor: 4.411

10.  Novel Thiazolidin-4-ones as Potential Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase.

Authors:  Anthi Petrou; Phaedra Eleftheriou; Athina Geronikaki; Melpomeni G Akrivou; Ioannis Vizirianakis
Journal:  Molecules       Date:  2019-10-23       Impact factor: 4.411

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  6 in total

Review 1.  Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents.

Authors:  Mohammed F Arshad; Aftab Alam; Abdullah Ayed Alshammari; Mohammed Bader Alhazza; Ibrahim Mohammed Alzimam; Md Anish Alam; Gulam Mustafa; Md Salahuddin Ansari; Abdulelah M Alotaibi; Abdullah A Alotaibi; Suresh Kumar; Syed Mohammed Basheeruddin Asdaq; Mohd Imran; Pran Kishore Deb; Katharigatta N Venugopala; Shahamah Jomah
Journal:  Molecules       Date:  2022-06-21       Impact factor: 4.927

2.  The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation.

Authors:  Serghei Pogrebnoi; Oleg Radul; Eugenia Stingaci; Lucian Lupascu; Vladimir Valica; Livia Uncu; Anastasia Smetanscaia; Anthi Petrou; Ana Ćirić; Jasmina Glamočlija; Marina Soković; Athina Geronikaki; Fliur Z Macaev
Journal:  Antibiotics (Basel)       Date:  2022-04-27

Review 3.  Non-steroidal anti-inflammatory drugs: recent advances in the use of synthetic COX-2 inhibitors.

Authors:  Mohsen Ahmadi; Sander Bekeschus; Klaus-Dieter Weltmann; Thomas von Woedtke; Kristian Wende
Journal:  RSC Med Chem       Date:  2022-02-14

4.  Synthesis, Characterization and In Vitro Evaluation of Novel 5-Ene-thiazolo[3,2-b][1,2,4]triazole-6(5H)-ones as Possible Anticancer Agents.

Authors:  Serhii Holota; Sergiy Komykhov; Stepan Sysak; Andrzej Gzella; Andriy Cherkas; Roman Lesyk
Journal:  Molecules       Date:  2021-02-22       Impact factor: 4.411

5.  Antitubercular, Cytotoxicity, and Computational Target Validation of Dihydroquinazolinone Derivatives.

Authors:  Katharigatta N Venugopala; Nizar A Al-Shar'i; Lina A Dahabiyeh; Wafa Hourani; Pran Kishore Deb; Melendhran Pillay; Bashaer Abu-Irmaileh; Yasser Bustanji; Sandeep Chandrashekharappa; Christophe Tratrat; Mahesh Attimarad; Anroop B Nair; Nagaraja Sreeharsha; Pottathil Shinu; Michelyne Haroun; Mahmoud Kandeel; Abdulmalek Ahmed Balgoname; Rashmi Venugopala; Mohamed A Morsy
Journal:  Antibiotics (Basel)       Date:  2022-06-21

6.  Structural and Energetic Properties of Weak Noncovalent Interactions in Two Closely Related 3,6-Disubstituted-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole Derivatives: In Vitro Cyclooxygenase Activity, Crystallography, and Computational Investigations.

Authors:  Lamya H Al-Wahaibi; Sekar Karthikeyan; Olivier Blacque; Amal A El-Masry; Hanan M Hassan; M Judith Percino; Ali A El-Emam; Subbiah Thamotharan
Journal:  ACS Omega       Date:  2022-09-16
  6 in total

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