N-Thiolated β-lactam antibacterials: Effects of the N-organothio substituent on anti-MRSA activity was written by Heldreth, Bart;Long, Timothy E.;Jang, Seyoung;Reddy, G. Suresh Kumar;Turos, Edward;Dickey, Sonja;Lim, Daniel V.. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:
A study on the structure-activity profiles of N-thiolated β-lactams 1 is reported which demonstrates the importance of the N-organothio moiety on antibacterial activity. Our results indicate that elongation of the N-alkylthio residue beyond two carbons, or extensive branching within the organothio substituent, diminishes antibacterial effects. Of the derivatives the authors examined, the N-sec-butylthio β-lactam derivative 5 g possesses the strongest growth inhibitory activity against methicillin-resistant Staphylococcus aureus strains. Sulfur oxidation state is important, as the N-sulfenyl and N-sulfinyl groups provide for the best antibacterial activity, while lactams bearing the N-sulfonyl or N-sulfonic acid functionalities have much weaker or no anti-MRSA properties. Stereochem. within the organothio chain does not seem to be a significant factor, although for N-sec-butylthio β-lactams, the 3R,4S-lactams (I, II) are more active than the 3S,4R-stereoisomers (III, IV) in agar diffusion experiments The N-methylthio lactams are the most sensitive to the presence of glutathione, followed by N-ethylthio and N-sec-butylthio lactams, which indicates that bioactivity and perhaps bacterial selectivity of the lactams may be related to the amount of organothiols in the bacterial cell. These results support the empirical model for the mechanism of action of the compounds in which the lactam transverses the bacterial membrane to deliver the organothio moiety to its cellular target. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione).
2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Recommanded Product: 2-(Phenylthio)isoindoline-1,3-dione
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles