Variability of the antibacterial potential among analogue diterpenes against Gram-positive bacteria: considerations on the structure–activity relationship

2019 ◽  
Vol 97 (7) ◽  
pp. 568-575 ◽  
Author(s):  
Ana Carolina Ferreira Soares ◽  
Priscilla Mendonça Matos ◽  
Herbert Júnior Dias ◽  
Gabriela de Paula Aguiar ◽  
Eliene Silvério dos Santos ◽  
...  
Keyword(s):  
Antimicrobial Agents ◽  
Public Health Problem ◽  
Antibacterial Activities ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Gram Positive ◽  
Structure Activity ◽  
Esterification Reactions ◽  
Relationship Of ◽  
Synthetic Derivatives

The search for new antibacterial agents and a better comprehension of substances with antimicrobial behavior is mandatory nowadays due to the serious public health problem of infection diseases. In the present work, 30 diterpenes were studied, with 2 natural derivatives, named ent-16-kauren-19-oic acid and ent-pimara-8(14),15-dien-19-oic acid, and 28 semi-synthetic derivatives. The natural diterpenes were isolated from Mikania glomerata and Viguiera arenaria, respectively. All diterpenes were submitted to antimicrobial assays against six different Gram-positive microorganisms to better understand the structure–activity relationship of antimicrobial diterpenes. The semi-synthetic derivatives were all obtained from the two natural derivatives by structural modifications, mainly esterification reactions. Both natural derivatives, together with the derivative ent-8(14)-pimaren-19-oic acid, displayed the most relevant antibacterial activities, with minimal inhibitory concentration (MIC) values that were less than 10 μg mL–1 for most pathogens; thus, they were considered promising antimicrobial agents. Moreover, in light of the hypothesis of Urzúa and colleagues, several considerations about the structure–activity relationship of antimicrobial diterpenes could be stated.

scholarly journals Chemical Synthesis and Structure-Activity Relationship Study Yield Desotamide a Analogues with Improved Antibacterial Activity

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 303
Author(s):  
Run Xu ◽  
Yongxiang Song ◽  
Jun Li ◽  
Jianhua Ju ◽  
Qinglian Li
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Fold Increase ◽  
Antibacterial Activities ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Gram Positive ◽  
Methicillin Resistant ◽  
Structure Activity ◽  
Relationship Of

Desotamides A, a cyclohexapeptide produced by the deep-sea-derived Streptomyces scopuliridis SCSIO ZJ46, displays notable antibacterial activities against strains of Streptococcus pnuemoniae, Staphylococcus aureus, and methicillin-resistant Staphylococcus epidermidis (MRSE). In this study, to further explore its antibacterial potential and reveal the antibacterial structure-activity relationship of desotamides, 13 cyclopeptides including 10 new synthetic desotamide A analogues and wollamides B/B1/B2 were synthesized and evaluated for their antibacterial activities against a panel of Gram-positive and -negative pathogens. The bioactivity data reveal that residues at position II and VI greatly impact antibacterial activity. The most potent antibacterial analogues are desotamide A4 (13) and A6 (15) where l-allo-Ile at position II was substituted with l-Ile and Gly at position VI was simultaneously replaced by d-Lys or d-Arg; desotamides A4 (13) and A6 (15) showed a 2–4-fold increase of antibacterial activities against a series of Gram-positive pathogens including the prevalent clinical drug-resistant pathogen methicillin-resistant Staphylococcus aureus (MRSA) with MIC values of 8–32 μg/mL compared to the original desotamide A. The enhanced antibacterial activity, broad antibacterial spectrum of desotamides A4 and A6 highlighted their potential as new antibiotic leads for further development.

scholarly journals INDANYL ANALOGS AS POTENTIAL ANTIMICROBIAL AGENTS

2018 ◽  
Vol 11 (5) ◽  
pp. 278 ◽  
Author(s):  
Sudip Kumar Mandal
Keyword(s):  
Antimicrobial Agents ◽  
Biological Activities ◽  
Antibacterial Activities ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Dilution Method ◽  
Pathogenic Microorganisms ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Structure Activity

 Objective: The wide variety of biological activities of different indane derivatives makes them an interesting moiety in the field of medicinal chemistry. The objective of the study was to identify and develop novel antimicrobial agents from indanyl analogs.Methods: Recently synthesized indanyl analogs (4a-c and 5a-o) were examined against various pathogenic microorganisms (Gram-positive and Gram-negative bacteria and fungi) using serial dilution method. These analogs were found to possess antibacterial and antifungal activities with minimum inhibitory concentration values ranging between 1.56 and 100 μg/mL.Results: The results revealed that the entire compounds showed mild-to-moderate antibacterial activities and moderate-to-excellent antifungal activities against the pathogenic microorganisms as compared to the standard drugs ciprofloxacin and fluconazole, respectively. Compounds 4a, 5a, 5b, 5d, 5e, 5i, and 5j exhibited antifungal activities superior to the reference drug.Conclusion: Based on the structure-activity relationship, it can conclude that the indan-3-oxo-1-acetic acid moiety is essential for the activities and lipophilic alkoxy substituents on indane ring have enhanced the biological activity. Further, structure-activity relationship studies of the compounds 4a, 5a, and 5b are needful to find the new lead as antimicrobial agent.

SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP OF NEW BENZIMIDAZOLE DERIVATIVES AS ANTIMICROBIAL AGENTS

INDIAN DRUGS ◽  
2012 ◽  
Vol 49 (03) ◽  
pp. 25-29
Author(s):  
S. G Jadhav ◽  
◽  
S. R. Pattan
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Data ◽  
Antimicrobial Agents ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Benzimidazole Derivatives ◽  
Structure Activity ◽  
Relationship Of

A new series of substituted benzimidazole derivatives were synthesized and the structures of these compounds were established on the basis of spectral data. The title compounds were evaluated for antimicrobial activity. Some of these compounds have shown excellent antimicrobial activity.

scholarly journals Synthesis and Antibacterial Analysis of Analogues of the Marine Alkaloid Pseudoceratidine

Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2713
Author(s):  
David Barker ◽  
Stephanie Lee ◽  
Kyriakos G. Varnava ◽  
Kevin Sparrow ◽  
Michelle van Rensburg ◽  
...  
Keyword(s):  
Structure Activity Relationship ◽  
Structural Features ◽  
Secondary Amines ◽  
Activity Relationship ◽  
Gram Positive ◽  
Gram Negative ◽  
Structure Activity ◽  
Escherichia Coli Bacteria ◽  
Anti Fungal ◽  
Relationship Of

In an effort to gain more understanding on the structure activity relationship of pseudoceratidine 1, a di-bromo pyrrole spermidine alkaloid derived from the marine sponge Pseudoceratina purpurea that has been shown to exhibit potent biofouling, anti-fungal, antibacterial, and anti-malarial activities, a large series of 65 compounds that incorporated several aspects of structural variation has been synthesised through an efficient, divergent method that allowed for a number of analogues to be generated from common precursors. Subsequently, all analogues were assessed for their antibacterial activity against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Overall, several compounds exhibited comparable or better activity than that of pseudoceratidine 1, and it was found that this class of compounds is generally more effective against Gram-positive than Gram-negative bacteria. Furthermore, altering several structural features allowed for the establishment of a comprehensive structure activity relationship (SAR), where it was concluded that several structural features are critical for potent anti-bacterial activity, including di-halogenation (preferable bromine, but chlorine is also effective) on the pyrrole ring, two pyrrolic units in the structure and with one or more secondary amines in the chain adjoining these units, with longer chains giving rise to better activities.

scholarly journals Synthesis and Structure–Activity Relationship of Palmatine Derivatives as a Novel Class of Antibacterial Agents against Helicobacter pylori

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1352
Author(s):  
Tianyun Fan ◽  
Xixi Guo ◽  
Qingxuan Zeng ◽  
Wei Wei ◽  
Xuefu You ◽  
...  
Keyword(s):  
Helicobacter Pylori ◽  
Lethal Dose ◽  
Antibacterial Activities ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
New Family ◽  
Structure Activity ◽  
Resistant Strains ◽  
H Pylori ◽  
Relationship Of

Taking palmatine (PMT) as the lead, 20 new PMT derivatives were synthesized and examined for their antibacterial activities against six tested metronidazole (MTZ)-resistant Helicobacter pylori (H. pylori) strains. The structure–activity relationship (SAR) indicated that the introduction of a suitable secondary amine substituent at the 9-position might be beneficial for potency. Among them, compound 1c exhibited the most potent activities against MTZ-resistant strains, with minimum inhibitory concentration (MIC) values of 4–16 μg/mL, better than that of the lead. It also exhibited a good safety profile with a half-lethal dose (LD50) of over 1000 mg/kg. Meanwhile, 1c might exert its antimicrobial activity through targeting H. pylori urease. These results suggested that PMT derivatives might be a new family of anti-H. pylori components.

scholarly journals Synthesis and Structure-Activity Relationship of Some New Thiophene-Based Heterocycles as Potential Antimicrobial Agents

Molecules ◽  
2016 ◽  
Vol 21 (8) ◽  
pp. 1036 ◽  
Author(s):  
Yahia Mabkhot ◽  
Fatima Alatibi ◽  
Nahed El-Sayed ◽  
Nabila Kheder ◽  
Salim Al-Showiman
Keyword(s):  
Antimicrobial Agents ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Structure Activity ◽  
Relationship Of
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