scholarly journals An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity

2020 ◽  
pp. 144
Author(s):  
Ismiarni Komala ◽  
Supandi Supandi ◽  
Ahmad Thantow ◽  
Andrianopsyah Mas Jaya Putra
Keyword(s):  
Structural Modification ◽  
Structure Activity Relationship ◽  
Inflammatory Activity ◽  
Activity Relationship ◽  
Efficient Procedure ◽  
Kaempferia Galanga ◽  
Structure Activity ◽  
Anti Inflammatory ◽  
Natural Ester ◽  
Direct Amidation

Ethyl p-methoxycinnamate (EPMC) (1) is a major natural ester found in the rhizome of Kaempferia galanga and has been reported to have anti-inflammatory activity. Some of the structural modification of this compound has been carried out in order to study the structure-activity relationship on its anti-inflammatory activity. In the present study, we report a new, simple and efficient procedure in the conversion of the ethyl p-methoxycinnamate into N,N-dimethyl-p-methoxycinnamamide (5) and then study the structure-activity relationship on its anti-inflammatory activity. The reaction was carried out through a microwave-assisted direct amidation between (EPMC) (1) with dimethylformamide (DMF) in the basic condition. The mixture was irradiated by using unmodified microwave-oven at 300 W for 1 minute to obtain compound (5) in 88.8% yields. The extensive analysis of the GCMS and NMR data supported that the product of synthesis is N,N-dimethyl-p-methoxycinnamamide (5). Evaluation of the anti-inflammatory activity of compound 5 by using anti-denaturation of heat bovine serum albumin (BSA) assay indicated that N,N-dimethyl-p-methoxycinnamamide (5) still have anti-denaturation activity. Compound 5 has an amide functional group which is more slowly hydrolyzed if compared to 1. Hence, the reaction has successfully produced a more stable compound which still has anti-inflammatory activity

scholarly journals Structure–Activity Relationship Analysis of Benzimidazoles as Emerging Anti-Inflammatory Agents: An Overview

2021 ◽  
Vol 14 (7) ◽  
pp. 663
Author(s):  
Ravichandran Veerasamy ◽  
Anitha Roy ◽  
Rohini Karunakaran ◽  
Harish Rajak
Keyword(s):  
Cannabinoid Receptors ◽  
Transient Receptor Potential ◽  
Structure Activity Relationship ◽  
Inflammatory Activity ◽  
Activity Relationship ◽  
Transient Receptor Potential Vanilloid ◽  
Relationship Analysis ◽  
Structure Activity ◽  
Inflammatory Drugs ◽  
Anti Inflammatory

A significant number of the anti-inflammatory drugs currently in use are becoming obsolete. These are exceptionally hazardous for long-term use because of their possible unfavourable impacts. Subsequently, in the ebb-and-flow decade, analysts and researchers are engaged in developing new anti-inflammatory drugs, and many such agents are in the later phases of clinical trials. Molecules with heterocyclic nuclei are similar to various natural antecedents, thus acquiring immense consideration from scientific experts and researchers. The arguably most adaptable heterocyclic cores are benzimidazoles containing nitrogen in a bicyclic scaffold. Numerous benzimidazole drugs are broadly used in the treatment of numerous diseases, showing promising therapeutic potential. Benzimidazole derivatives exert anti-inflammatory effects mainly by interacting with transient receptor potential vanilloid-1, cannabinoid receptors, bradykinin receptors, specific cytokines, 5-lipoxygenase activating protein and cyclooxygenase. Literature on structure–activity relationship (SAR) and investigations of benzimidazoles highlight that the substituent’s tendency and position on the benzimidazole ring significantly contribute to the anti-inflammatory activity. Reported SAR analyses indicate that substitution at the N1, C2, C5 and C6 positions of the benzimidazole scaffold greatly influence the anti-inflammatory activity. For example, benzimidazole substituted with anacardic acid on C2 inhibits COX-2, and 5-carboxamide or sulfamoyl or sulfonyl benzimidazole antagonises the cannabinoid receptor, whereas the C2 diarylamine and C3 carboxamide substitution of the benzimidazole scaffold result in antagonism of the bradykinin receptor. In this review, we examine the insights regarding the SARs of anti-inflammatory benzimidazole compounds, which will be helpful for researchers in designing and developing potential anti-inflammatory drugs to target inflammation-promoting enzymes.

scholarly journals Structure-Activity Relationship Study on the Ethyl p-Methoxycinnamate as an Anti-Inflammatory Agent

2018 ◽  
Vol 18 (1) ◽  
pp. 60
Author(s):  
Ismiarni Komala ◽  
Supandi Supandi ◽  
Nurhasni Nurhasni ◽  
Ofa Suzanti Betha ◽  
Eka Putri ◽  
...  
Keyword(s):  
Active Sites ◽  
Structural Modification ◽  
Inflammatory Activity ◽  
Esterification Reaction ◽  
Inflammatory Agent ◽  
Kaempferia Galanga ◽  
Structure Activity ◽  
Anti Inflammatory

Ethyl p-methoxycinnamate (EPMC) (1) has been isolated as a major compound from the rhizome of Kaempferia galanga together with the other compound ethyl cinnamate (2). As reported in the literature, EPMC (1) exhibited a significant in vitro and in vivo anti-inflammatory activity. In this research, we investigated the anti-inflammatory activity of compounds 1 and 2 by using anti-denaturation of heat bovine serum albumin (BSA) method. In order to analyze active sites that are responsible for the anti-inflammatory activity, therefore, it is necessary to conduct structural modification of EPMC (1). The structural modification was performed through re-esterification reaction by using conventional and assistance of the unmodified microwave oven. Evaluation of the results of the bioassay indicated that the ester and methoxy functional groups of EPMC (1) play an important role for the anti-inflammatory activity.

Structure-Activity Relationship Study of Androstene Steroids with Respect to Local Anti-inflammatory Activity

2011 ◽  
Vol 56 (06) ◽  
pp. 394-398 ◽  
Author(s):  
Rohini Chaubal ◽  
Arvind Mujumdar ◽  
Ashwini Misar ◽  
Vishnu Deshpande ◽  
Nirmala Deshpande
Keyword(s):  
Structure Activity Relationship ◽  
Inflammatory Activity ◽  
Activity Relationship ◽  
Structure Activity ◽  
Relationship Study ◽  
Anti Inflammatory

Antineoplastic Activity, Structural Modification, Synthesis and Structure-activity Relationship of Dammarane-type Ginsenosides: An Overview

2019 ◽  
Vol 23 (5) ◽  
pp. 503-516 ◽  
Author(s):  
Qiang Zhang ◽  
Xude Wang ◽  
Liyan Lv ◽  
Guangyue Su ◽  
Yuqing Zhao
Keyword(s):  
Structural Modification ◽  
Gastrointestinal Disease ◽  
Structure Activity Relationship ◽  
Cerebrovascular Diseases ◽  
Activity Relationship ◽  
Cycle Arrest ◽  
Structure Activity ◽  
Wide Range ◽  
Structural Association ◽  
Relationship Of

Dammarane-type ginsenosides are a class of tetracyclic triterpenoids with the same dammarane skeleton. These compounds have a wide range of pharmaceutical applications for neoplasms, diabetes mellitus and other metabolic syndromes, hyperlipidemia, cardiovascular and cerebrovascular diseases, aging, neurodegenerative disease, bone disease, liver disease, kidney disease, gastrointestinal disease and other conditions. In order to develop new antineoplastic drugs, it is necessary to improve the bioactivity, solubility and bioavailability, and illuminate the mechanism of action of these compounds. A large number of ginsenosides and their derivatives have been separated from certain herbs or synthesized, and tested in various experiments, such as anti-proliferation, induction of apoptosis, cell cycle arrest and cancer-involved signaling pathways. In this review, we have summarized the progress in structural modification, shed light on the structure-activity relationship (SAR), and offered insights into biosynthesis-structural association. This review is expected to provide a preliminary guide for the modification and synthesis of ginsenosides.

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