scholarly journals Antimicrobial Properties of Volatile Phenylpropanes

2010 ◽  
Vol 5 (9) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Alexander Pauli ◽  
Karl-Heinz Kubeczka
Keyword(s):  
Antimicrobial Activity ◽  
Antimicrobial Properties ◽  
Substitution Pattern ◽  
Structure Activity Relationships ◽  
Specific Effects ◽  
Structure Activity ◽  
Microbial Characteristics ◽  
Cis And Trans Isomers ◽  
Species Specific ◽  
Cis And Trans

The examination of antimicrobial structure-activity relationships of 93 volatile phenylpropanes (VPs) and 21 related aromatic compounds revealed a dependence of antimicrobial activity from the kind and number of substituents on the aromatic ring, their substitution pattern and microbial characteristics, such as Gram coloring and strain specific factors. Eugenol isomers were predominantly inhibitory in a concentration range from 25 to 2000 mg/L against all microorganisms tested, which were three strains of Escherichia Coli and Klebsiella pneumoniae, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Listeria monocytogenes, and Candida albicans. Etherified VPs were either less active or inactive depending on the type of side chain and/or substitution pattern. Differences in the antimicrobial activity of cis- and trans-isomers were observed. Species specific structure-activity relationships exist as was demonstrated with the Gram-negative bacteria (inactivity of E-ortho-eugenol) C. albicans (activity of di- and threefold methoxylated 1-propenylbenzenes), S. aureus and B. subtilis (activity of di-ortho methoxylated phenolic allylbenzenes and hydroquinone derivatives). With regard to the variety of observed specific effects and natural variation of susceptibility towards VPs according to literature reference data, the chances for successful prediction by computational analysis (QSAR) appear to be limited.

scholarly journals The Antimicrobial Activity of Cannabinoids

Antibiotics ◽  
2020 ◽  
Vol 9 (7) ◽  
pp. 406
Author(s):  
John A. Karas ◽  
Labell J. M. Wong ◽  
Olivia K. A. Paulin ◽  
Amna C. Mazeh ◽  
Maytham H. Hussein ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Natural Products ◽  
Antimicrobial Agents ◽  
Cannabis Sativa ◽  
Antimicrobial Properties ◽  
Herbaceous Plant ◽  
Structure Activity Relationships ◽  
Modes Of Action ◽  
Structure Activity ◽  
Rapid Emergence

A post-antibiotic world is fast becoming a reality, given the rapid emergence of pathogens that are resistant to current drugs. Therefore, there is an urgent need to discover new classes of potent antimicrobial agents with novel modes of action. Cannabis sativa is an herbaceous plant that has been used for millennia for medicinal and recreational purposes. Its bioactivity is largely due to a class of compounds known as cannabinoids. Recently, these natural products and their analogs have been screened for their antimicrobial properties, in the quest to discover new anti-infective agents. This paper seeks to review the research to date on cannabinoids in this context, including an analysis of structure–activity relationships. It is hoped that it will stimulate further interest in this important issue.

scholarly journals Identification bioactive compounds from marine microorganism and exploration of structure–activity relationships (SARs)

2020 ◽  
Author(s):  
Mojdeh Dinarvand ◽  
Malcolm P. Spain
Keyword(s):  
Antimicrobial Activity ◽  
Linear Chain ◽  
Antimicrobial Properties ◽  
Antimicrobial Drug ◽  
Tertiary Amines ◽  
Quaternary Amine ◽  
Diverse Range ◽  
Structure Activity Relationships ◽  
Structure Activity

ABSTRACTMarine natural products (MNPs) have become new strong leads for antimicrobial drug discovery and an effective alternative to control drug resistant infections. Herein we report the bioassay guided fractionation of marine extracts from sponges Lendenfeldia, Ircinia and Dysidea that led us to identify novel compounds with antimicrobial properties. Tertiary amines or quaternary amine salts: anilines 1, benzylamines 2, tertiary amines 3 and 4, and quaternary amine salt 5, along with three known compounds (6-8) were isolated from a crude extract and MeOH eluent marine extracts. The absolute configurations of the new compounds were assigned based on tandem mass spectrometry (MS) analysis. Several of the compounds exhibited potent in-vitro antibacterial activity, especially against Methicillin-resistant Staphylococcus aureus (MRSA) (MICs from 15.6 to 62.5 micro g/mL). Herein, we also, report structure activity relationships of a diverse range of commercial structurally similar compounds. The structure activity relationships (SARs) results clearly demonstrate that modification of the amines through linear chain length, and inclusion of aromatic rings, modifies the observed antimicrobial activity towards different biological activity. Several commercially available compounds, which are structurally related to the molecules we discovered showed broad spectrum antimicrobial activity against different test pathogens with an MIC50 range of 50 to 0.01 microM. The results of cross-referencing antimicrobial activity and cytotoxicity establish that these compounds are promising potential lead molecules, with a favourable therapeutic index for antimicrobial drug development. Additionally, the SAR studies show that simplified analogues of the isolated compounds with increased bioactivity

STUDIES ON THE CHEMICAL BASIS FOR CHOLINOMIMETIC AND CHOLINOLYTIC ACTIVITY: PART I. THE SYNTHESIS AND CONFIGURATION OF QUATERNARY SALTS IN THE 1,3-DIOXOLANE AND OXAZOLINE SERIES

1962 ◽  
Vol 40 (6) ◽  
pp. 1201-1215 ◽  
Author(s):  
D. J. Triggle ◽  
B. Belleau
Keyword(s):  
Hydrolysis Product ◽  
Optical Purity ◽  
Large Degree ◽  
Active Member ◽  
Trans Isomers ◽  
Structure Activity Relationships ◽  
Quaternary Salts ◽  
Structure Activity ◽  
Catalytic Hydrogenolysis ◽  
Cis And Trans

Structure activity relationships in the muscarine and the quaternary 1,3-dioxolane (Fourneau series) series are briefly discussed. The most active member of the latter series (2-methyl-4-dimethylaminomethyl-1,3-dioxolane methiodide, (IX), F2268) was shown to consist of a mixture of 60% cis and 40% trans isomers. The same was found to apply to all synthetic intermediates in that series. Unequivocal assignments of configuration were made by relating various intermediates leading to (IX) and its analogs to D-cis-1,3-dimethyl-1,3-dioxolane itself, obtained by degradation of 1,6-anhydrogalactose. Attempted separation of cis–trans isomers in the 1,3-dioxolane series was not successful. However, a mixture of cis, trans-2-trichloromethyl-4-hydroxymethyl-1,3-dioxolane (XVI) could be fractionated by crystallization of the corresponding tosylates. Catalytic hydrogenolysis converted the pure cis- and trans-trichloromethyl derivatives (XVII) and (XVIII) to pure cis- and trans-2-methyl-4-hydroxymethyl-1,3-dioxolane tosylates (XIX) and (XX), which eventually afforded for the first time pure cis-F2268 and trans-F2268 (XXII) and (XXIII).Optically active members in the 1,3-dioxolane series were prepared. Members of the D(−)-series were conveniently obtained from D-isopropylidene glycerol. Members of the L(+)-series could be obtained in optically impure forms by resolution of dl-tertiary bases such as (XXXVI) with D- and L-dibenzoyltartaric acid. The best preparations had an optical purity not exceeding 32%. The resolution of the cis base (X) was unsuccessful.The synthesis of an oxazoline analog, (XLIV), of F2268 was accomplished. The reaction sequence involves solvolysis of N-acetyl-2,3-dibromo-n-propylamine (XLI) to give the 5-bromomethyl-2-methyloxazoline (XLII). This unstable intermediate was reacted with dimethylamine to give the tertiary base (XLIII), which was quaternized with methyl iodide whereupon the quaternary base (XLIV) was formed in good yield. The structure of the latter was established by an independent synthesis of the hydrolysis product (XLV).Preliminary pharmacological data are reported for the various new quaternary salts. The compounds were assayed for cholinomimetic activity. It is concluded from these studies that quaternary 1,3-dioxolanes display structure-activity relationships analogous to the muscarones. The use of triethylammonium analogs has revealed a large degree of preference of cholinergic receptors for the presence of a cis configuration in 2,4-disubstituted-1,3-dioxolanes. It was also noted that the oxazoline derivative (XLIV) ranks amongst the most active cholinomimetics thus far reported. Relationships between configuration and activity are briefly discussed.

Structure-Activity Relationships of Protoberberines Having Antimicrobial Activity

Planta Medica ◽  
1998 ◽  
Vol 64 (08) ◽  
pp. 748-751 ◽  
Author(s):  
Kinuko Iwasa ◽  
Hiroaki Nanba ◽  
Dong-Ung Lee ◽  
So-lm Kang
Keyword(s):  
Antimicrobial Activity ◽  
Structure Activity Relationships ◽  
Structure Activity

scholarly journals Synthesis and Structure-Activity Relationships of New 2-Phenoxybenzamides with Antiplasmodial Activity

2021 ◽  
Vol 14 (11) ◽  
pp. 1109
Author(s):  
Theresa Hermann ◽  
Patrick Hochegger ◽  
Johanna Dolensky ◽  
Werner Seebacher ◽  
Eva-Maria Pferschy-Wenzig ◽  
...  
Keyword(s):  
Antiplasmodial Activity ◽  
Pharmacokinetic Parameters ◽  
Log P ◽  
Partial Structure ◽  
Substitution Pattern ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Multi Stage ◽  
Different Strains

The 2-phenoxybenzamide 1 from the Medicines for Malaria Venture Malaria Box Project has shown promising multi-stage activity against different strains of P. falciparum. It was successfully synthesized via a retrosynthetic approach. Subsequently, twenty-one new derivatives were prepared and tested for their in vitro activity against blood stages of the NF54 strain of P. falciparum. Several insights into structure-activity relationships were revealed. The antiplasmodial activity and cytotoxicity of compounds strongly depended on the substitution pattern of the anilino partial structure as well as on the size of substituents. The diaryl ether partial structure had further impacts on the activity. Additionally, several physicochemical and pharmacokinetic parameters were calculated (log P, log D7.4 and ligand efficiency) or determined experimentally (passive permeability and CYP3A4 inhibition). The tert-butyl-4-{4-[2-(4-fluorophenoxy)-3-(trifluoromethyl)benzamido]phenyl}piperazine-1-carboxylate possesses high antiplasmodial activity against P. falciparum NF54 (PfNF54 IC50 = 0.2690 µM) and very low cytotoxicity (L-6 cells IC50 = 124.0 µM) resulting in an excellent selectivity index of 460. Compared to the lead structure 1 the antiplasmodial activity was improved as well as the physicochemical and some pharmacokinetic parameters.

Preparation of Racemic cis- and trans-2-(2-Alkoxyphenylcarbamoyloxy)cycloheptylmethylpiperidinium Chlorides

1994 ◽  
Vol 59 (3) ◽  
pp. 675-682 ◽  
Author(s):  
Fridrich Gregáň ◽  
Viktor Kettmann ◽  
Pavol Novomeský ◽  
Július Sivý
Keyword(s):  
Fractional Crystallization ◽  
Local Anesthetics ◽  
Conformationally Constrained ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Cis And Trans

The synthesis of two pairs of the title diastereomers, which represent conformationally constrained analogues of the phenylcarbamate local anesthetics, is described. The synthesis was accomplished by starting from cycloheptanone and 2-alkoxyanilines and the intermediate diastereomers of 2-aminomethylcycloalkanols (VI, VII) were separated as their 4-nitrobenzoyl derivatives (IV, V) by extraction and fractional crystallization. The prepared compounds (VIIIa, VIIIb, IXa, and IXb) are assumed to be of help in interpreting the structure activity relationships within this class of drugs.

scholarly journals Species-Specific Differences and Structure−Activity Relationships in the Debromination of PBDE Congeners in Three Fish Species

2011 ◽  
Vol 45 (5) ◽  
pp. 1999-2005 ◽  
Author(s):  
Simon C. Roberts ◽  
Pamela D. Noyes ◽  
Evan P. Gallagher ◽  
Heather M. Stapleton
Keyword(s):  
Fish Species ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Species Specific
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