scholarly journals Synthesis of 3-acyltetramates by side chain manipulation and their antibacterial activity

2014 ◽  
Vol 12 (11) ◽  
pp. 1711-1716 ◽  
Author(s):  
Song Wei Benjamin Tan ◽  
Christina L. L. Chai ◽  
Mark G. Moloney
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Side Chain ◽  
Efficient Approach ◽  
Nucleophilic Displacement ◽  
Acyl Side Chain

An efficient approach for the introduction of 3-acyl side chain groups onto a core tetramate system, which are suitable for further manipulation by nucleophilic displacement or Horner–Wadsworth–Emmons coupling, provides access to a diverse library of substituted tetramates related to two distinct classes of natural products, equisetin and pramanicin.

Antibacterial and Cytotoxic Natural and Synthesized Hydroquinones from Sponge Ircinia spinosula

1999 ◽  
Vol 54 (5-6) ◽  
pp. 417-423 ◽  
Author(s):  
Nikos Mihopoulos ◽  
Constantinos Vagias ◽  
Ioanna Chinou ◽  
Christos Roussakis ◽  
Michael Scoullos ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Antibacterial Effect ◽  
Antibacterial Activities ◽  
Activity Relationship ◽  
Side Chain ◽  
Structure Activity ◽  
Biological Studies ◽  
Wide Range ◽  
Derivatives Of

Abstract In order to check the structure-activity relationship and find more potent derivatives of the natural products 1 and 2 obtained from sponge Ircinia spinosula, a series of oxidation, hydrogenation, acetylation and methylation derivatives was prepared. All compounds (natural and synthetic ones) were screened for their cytotoxic and antibacterial activities. The biological studies showed a wide range of antibacterial activity even though only 2 and 2d showed a moderate cytotoxicity against the clone C98. The oxidation of the hydroquinone to quinone and the hydrogenation of the side-chain increased the antibacterial effect of the molecules.

In vivo modulated N -acyl side chain of N -acetylneuraminic acid modulates the cell contact-dependent inhibition of growth

FEBS Letters ◽  
1996 ◽  
Vol 395 (2-3) ◽  
pp. 170-173 ◽  
Author(s):  
J.Raimund Wieser ◽  
Anja Heisner ◽  
Peer Stehling ◽  
Franz Oesch ◽  
Werner Reutter
Keyword(s):  
Side Chain ◽  
Cell Contact ◽  
Acetylneuraminic Acid ◽  
Inhibition Of Growth ◽  
Acyl Side Chain ◽  
Dependent Inhibition

scholarly journals Degradation of the Acyl Side Chain of the Steroid Compound Cholate in Pseudomonas sp. Strain Chol1 Proceeds via an Aldehyde Intermediate

2012 ◽  
Vol 195 (3) ◽  
pp. 585-595 ◽  
Author(s):  
J. Holert ◽  
Z. Kulic ◽  
O. Yucel ◽  
V. Suvekbala ◽  
M. J.- F. Suter ◽  
...  
Keyword(s):  
Side Chain ◽  
Pseudomonas Sp ◽  
Steroid Compound ◽  
Acyl Side Chain

Rashes with Ampicillin

1980 ◽  
Vol 1 (7) ◽  
pp. 197-201
Author(s):  
Michael J. Kraemer ◽  
Arnold L. Smith
Keyword(s):  
Penicillin G ◽  
Side Chain ◽  
Gram Negative Bacteria ◽  
Acid Moiety ◽  
Structure Activity ◽  
Body Tissues ◽  
The Family ◽  
Acyl Side Chain ◽  
Penicillanic Acid ◽  
Lactam Ring

Ampicillin, first introduced in 1961, has probably become the most widely used penicillin in clinical pediatrics. STRUCTURE ACTIVITY RELATIONSHIPS All penicillins contain the 6-amino penicillanic acid moiety (Fig 1). Its structure includes a thiazolidine ring (A), a β-lactam ring (B), the source of antibacterial activity, and an acyl side chain (R), containing a variety of substitutions creating the family of semisynthetic penicillins. The only difference between ampicillin and penicillin G is the presence of an amino group in the acyl side chain (Fig 1). PHARMACOLOGY AND BACTERIOLOGY Ampicillin is a semisynthetic penicillin, active against Streptococus pneumoniae and certain Gram-negative bacteria, including most Haemophilus influenzae, Escherichia coli, and certain Proteus species. Compared to penicillin G, it has increased stability in acid solutions: a property facilitating oral administration and absorption. It penetrates into most body tissues; effective entry into CSF, however, occurs only with inflamed meninges. The serum half-life with normal renal function varies from four hours in newborns1 to 1.3 hours in adults.2 Ampicillin can cause an allergic, or nonallergic skin rash (Fig 2). ALLERGY Allergy (for the purposes of this discussion) is defined as a specific immunologic interaction, between either antigen and antibody, or antigen with a sensitized lymphocyte, resulting in a clinically deleterious effect. Implicit is a prior contact with the antigen.

Critical Review of Biotransformational Studies on Steroids by Using Culture of Cunninghamella blakesleeana

2021 ◽  
Vol 18 ◽  
Author(s):  
Azizuddin ◽  
Muhammad Iqbal ◽  
Syed Ghulam Musharraf
Keyword(s):  
Double Bond ◽  
Critical Review ◽  
Structural Modification ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Side Chain ◽  
Synthetic Compounds ◽  
Efficient Approach ◽  
Cunninghamella Blakesleeana ◽  
Different Strains

: For several decades, biotransformational studies on steroidal compounds have gained a lot of attention because it is an efficient approach for the structural modification of complicated natural or synthetic compounds with high regio-, chemo- and stereoselectivity at environmentally friendly conditions. This review summarizes the use of different strains of Cunninghamella blakesleeana for the biotransformation of sixteen steroids 1-16 into a variety of transformed products. The transformed products may be important as a drug or precursor for the production of important pharmaceuticals. The types of reactions performed by C. blakesleeana include hydroxylation, epoxidation, reduction, demethylation, oxidation, glycosidation, double bond formation, side-chain degradation, isomerisation and opening of an isoxazol ring, which would be difficult to produce by traditional synthesis.

scholarly journals Peniginsengins B–E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11

Marine Drugs ◽  
2018 ◽  
Vol 16 (10) ◽  
pp. 358 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wei Xu ◽  
Lijun Liu ◽  
Shumin Li ◽  
Wangjun Yuan ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Nuclear Magnetic Resonance ◽  
Antibacterial Activity ◽  
Magnetic Resonance ◽  
Deep Sea ◽  
Dienoic Acid ◽  
Side Chain ◽  
Chemical Examination ◽  
Etoac Extract ◽  
Penicillium Sp

Chemical examination of the EtOAc extract of the deep sea-derived fungus Penicillium sp. YPGA11 resulted in the isolation of four new farnesylcyclohexenones, peniginsengins B–E (1–4), and a known analog peniginsengin A (5). The structures of compounds 1–4 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1, 2, and 4 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compounds 1–5, characterized by a highly oxygenated 1-methylcyclohexene unit and a (4E,8E)-4,8-dimethyldeca-4,8-dienoic acid side chain, are rarely found in nature. Compounds 2–4 exhibited antibacterial activity against Staphylococcus aureus.

scholarly journals Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

2014 ◽  
Vol 10 ◽  
pp. 1228-1232 ◽  
Author(s):  
Jens Schmidt ◽  
Zeinab Khalil ◽  
Robert J Capon ◽  
Christian B W Stark
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Joint Effort ◽  
Natural Product Biosynthesis ◽  
New Members ◽  
Degree Of Oxidation ◽  
Rare Class

The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.

Synthesis and antibacterial activity evaluation of C-5 side chain modified analogues of FYL-66, a potential agent against methicillin-resistant Staphylococcus aureus

MedChemComm ◽  
2015 ◽  
Vol 6 (6) ◽  
pp. 1156-1172 ◽  
Author(s):  
Xiaoyan Yang ◽  
Zicheng Li ◽  
Zhenling Wang ◽  
Zitai Sang ◽  
Haiyue Long ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Animal Models ◽  
Antibacterial Agent ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Biological Activities ◽  
Side Chain ◽  
Methicillin Resistant ◽  
Activity Evaluation

Monofluoro- (39), difluoro- (40) and trifluoro- (41) substituted analogues showed different biological activities, and 40 is a potent antibacterial agent in animal models.

scholarly journals Synthesis and antibacterial activity of monocyclic 3-carboxamide tetramic acids

2013 ◽  
Vol 9 ◽  
pp. 1899-1906 ◽  
Author(s):  
Yong-Chul Jeong ◽  
Mark G Moloney
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Chemical Library ◽  
Rapid Construction ◽  
Tetramic Acids

A chemical library of carboxamide-substituted tetramates designed by analogy with antibacterial natural products, a method for their rapid construction, and the evaluation of their antibacterial activity is reported.

scholarly journals Potentially Effective and Safe Anti-Helicobacter pylori Natural Products: Chemometric Study

2020 ◽  
Vol 71 (6) ◽  
pp. 267-273 ◽  
Author(s):  
Branislava D. Kocic ◽  
Dobrila M. Stankovic Dordevic ◽  
Marija V. Dimitrijevic ◽  
Marija S. Markovic ◽  
Dragoljub L. Miladinovic
Keyword(s):  
Helicobacter Pylori ◽  
Antibacterial Activity ◽  
Natural Products ◽  
Chemical Composition ◽  
Essential Oils ◽  
Principal Component ◽  
Synergistic Activity ◽  
Agglomerative Hierarchical Clustering ◽  
Naturally Occurring ◽  
H Pylori

The susceptibility of Helicobacter pylori to three essential oils (EOs), 12 naturally occurring monoterpene hydrocarbons, oxygenated and phenolic monoterpenes and three reference antibiotics were studied. Classification and comparison of essential oils and monoterpenes on the basis of their chemical composition and antibacterial activity were made by the utilization of principal component analyses (PCA) and agglomerative hierarchical clustering (AHC). The most abundant compound in the Thymus glabrescens Willd. and Thymus pulegioides L. EOs is geraniol (33.8% and 52.5%), while the main constituent in Satureja kitaibelii Wierzb. ex Heuff. EO is limonene (16,1%). The compound that was the most active against H. pylori was carvacrol. EOs of T. glabrescens and S. kitaibelii exhibit higher antibacterial ability in comparison with all monoterpenes, except carvacrol, probably based on the concept of synergistic activity of essential oil components. PCA separated essential oils based on chemical composition and explain 96.5% of the total variance in the first two principal components. Essential oils, phenolic monoterpenes and two antibiotics were classified in the same sub-cluster within AHC analyses. EOs of T. glabrescens and S. kitaibelii can be used to treat infections caused by H. pylori, as a potentially effective, cheap and safe natural products. Further research of antibacterial activity of selected monoterpenes, essential oils and standard antibiotic combinations, as well as clinical study are required.

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