40167-20-2Relevant academic research and scientific papers
Syntheses of carbocyclic uracil polyoxin C analogs: Application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone
Cesario, Cara,Miller, Marvin J.
, p. 5730 - 5733 (2009)
(Figure Presented) Carbocyclic uracil polyoxin C analogs are prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct in fewer than nine steps. Pd(0)/InI-mediated allylation of 4-acetoxy-2-azetidinone is used to install the β-amino acid side ch
Synthesis method of N-methylthio phthalimide
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Paragraph 0008; 0010-0017, (2020/07/21)
The invention provides a synthesis method of N-methylthio phthalimide. N-hydroxyphthalimide (NOP) and methyl mercaptan are used as initial reaction raw materials, and subjected to a condensation reaction to obtain the N-methylmercapto phthalimide. The method has the advantages of being simple in production, free of pollution, safe, easy to control and the like. The molar yield of the process disclosed by the invention can reach 96% or above, and the product content is more than 98%. The method provides a green raw material guarantee for the organic synthesis industry in China in the directionof introducing methylthio.
Allicin-inspired thiolated fluoroquinolones as antibacterials against ESKAPE pathogens
Sheppard, Jordan G.,Long, Timothy E.
, p. 5545 - 5549 (2016/11/05)
Thiolated fluoroquinolones were synthesized from ciprofloxacin and evaluated for antimicrobial activity against a panel of pathogenic bacteria. Gram-positive species including methicillin-resistant Staphylococcus aureus (MRSA) exhibited the highest level of increased sensitivity toward ciprofloxacin bound with a N-propylthio substituent. Evidence was found that the antibiotics form disulfides with low molecular weight thiols in bacteria and potentiate generation of cytosolic reactive oxygen species (ROS). In final analysis, the enhanced anti-MRSA activity of thiolated fluoroquinolones was attributed to increased cell permeability and reaction with cytosolic thiols that yields an inactive disulfide metabolite and the parent drug ciprofloxacin as an inhibitor of DNA synthesis.
N-Thiolated β-lactam antibacterials: Effects of the N-organothio substituent on anti-MRSA activity
Heldreth, Bart,Long, Timothy E.,Jang, Seyoung,Reddy, G. Suresh Kumar,Turos, Edward,Dickey, Sonja,Lim, Daniel V.
, p. 3775 - 3784 (2007/10/03)
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 we examined, the N-sec-butylthio β-lactam derivative 5g 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. Stereochemistry within the organothio chain does not seem to be a significant factor, although for N-sec-butylthio β-lactams 15a-d, the 3R,4S-lactams 15c, d are more active than the 3S,4R-stereoisomers 15a, b 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.
Preparation of 2-(2-cyanoethyl)sulfanyl-1H-isoindole-1,3-(2H)-dione and related sulfur-transfer agents
Klose, Jana,Reese, Colin B.,Song, Quanlai
, p. 14411 - 14416 (2007/10/03)
The title compound 3 and 4-[(2-cyanoethyl)sulfanyl]morpholine-3,5-dione 12 are both conveniently prepared in good yield from 2-cyanoethyl disulfide, which itself is readily prepared in one step from S-(2-cyanoethyl)isothiouronium chloride 4. In the same way, dimethyl and diphenyl disulfides are converted, into 2-methylsulfanyl- and 2-phenylsulfanyl-1H-isoindole-1,3-(2H)-diones 8a and 8b, respectively, also in good yields.
