Design, synthesis and anti-inflammatory effects of novel 9-O-substituted-berberine derivatives

MedChemComm ◽  
2016 ◽  
Vol 7 (4) ◽  
pp. 658-666 ◽  
Author(s):  
Mei-Yan Huang ◽  
Jing Lin ◽  
Zhi-Jian Huang ◽  
Hong-Gui Xu ◽  
Juan Hong ◽  
...  
Keyword(s):  
Design Synthesis ◽  
Anti Inflammatory ◽  
Berberine Derivatives

A series of novel 9-O-substituted-berberine derivatives were synthesized and their anti-inflammatory activities were evaluated. Among them, compounds 3i and 5e exhibited excellent anti-inflammatory potential.

Design, Synthesis and Pharmacological Evaluation of Novel Antiinflammatory and Analgesic O-Benzyloxime Compounds Derived From Natural Eugenol

2019 ◽  
Vol 16 (10) ◽  
pp. 1157-1166
Author(s):  
Rodrigo César da Silva ◽  
Fabiano Veiga ◽  
Fabiana Cardoso Vilela ◽  
André Victor Pereira ◽  
Thayssa Tavares da Silva Cunha ◽  
...  
Keyword(s):  
Formalin Test ◽  
Docking Studies ◽  
Paw Edema ◽  
Inhibitory Effects ◽  
Structural Pattern ◽  
Design Synthesis ◽  
Drug Candidates ◽  
Anti Inflammatory ◽  
Analgesic Activities ◽  
Cox 1

Background: : A new series of O-benzyloximes derived from eugenol was synthesized and was evaluated for its antinociceptive and anti-inflammatory properties. Methods: : The target compounds were obtained in good global 25-28% yields over 6 steps, which led us to identify compounds (Z)-5,6-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one-O-(4- (methylthio)benzyloxime (8b), (Z)-5,6-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one-O-4- bromobenzyloxime (8d) and (Z)-5,6-dimethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one-O-4- (methylsulfonyl)benzyloxime (8f) as promising bioactive prototypes. Results:: These compounds have significant analgesic and anti-inflammatory effects, as evidenced by formalin-induced mice paw edema and carrageenan-induced mice paw edema tests. In the formalin test, compounds 8b and 8f evidenced both anti-inflammatory and direct analgesic activities and in the carrageenan-induced paw edema, with compounds 8c, 8d, and 8f showing the best inhibitory effects, exceeding the standard drugs indomethacin and celecoxib. Conclusion: : Molecular docking studies have provided additional evidence that the pharmacological profile of these compounds may be related to inhibition of COX enzymes, with slight preference for COX-1. These results led us to identify the new O-benzyloxime ethers 8b, 8d and 8f as orally bioactive prototypes, with a novel structural pattern capable of being explored in further studies aiming at their optimization and development as drug candidates.

scholarly journals Design, Synthesis and Anti-inflammatory Activity of Structurally Simple Anthranilic Acid Congeners Devoid of Ulcerogenic Side Effects

2012 ◽  
Vol 60 (10) ◽  
pp. 1290-1300 ◽  
Author(s):  
Amal Abdel Haleem Mohamed Eissa ◽  
Gamal Abd El-Hakeem Soliman ◽  
Moayad Hussein Khataibeh
Keyword(s):  
Side Effects ◽  
Anthranilic Acid ◽  
Inflammatory Activity ◽  
Design Synthesis ◽  
Anti Inflammatory
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