- Synthesis and Antichlamydial Activity of Molecules Based on Dysregulators of Cylindrical Proteases
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Chlamydia trachomatis is the most common sexually transmitted bacterial disease globally and the leading cause of infertility and preventable infectious blindness (trachoma) in the world. Unfortunately, there is no FDA-approved treatment specific for chlamydial infections. We recently reported two sulfonylpyridines that halt the growth of the pathogen. Herein, we present a SAR of the sulfonylpyridine molecule by introducing substituents on the aromatic regions. Biological evaluation studies showed that several analogues can impair the growth of C. trachomatis without affecting host cell viability. The compounds did not kill other bacteria, indicating selectivity for Chlamydia. The compounds presented mild toxicity toward mammalian cell lines. The compounds were found to be nonmutagenic in a Drosophila melanogaster assay and exhibited a promising stability in both plasma and gastric fluid. The presented results indicate this scaffold is a promising starting point for the development of selective antichlamydial drugs.
- Seleem, Mohamed A.,Rodrigues De Almeida, Nathalia,Chhonker, Yashpal Singh,Murry, Daryl J.,Guterres, Zaira Da Rosa,Blocker, Amanda M.,Kuwabara, Shiomi,Fisher, Derek J.,Leal, Emilse S.,Martinefski, Manuela R.,Bollini, Mariela,Monge, María Eugenia,Ouellette, Scot P.,Conda-Sheridan, Martin
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p. 4370 - 4387
(2020/05/22)
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- THIOESTER COMPOUNDS AND THEIR USE IN FRAGRANCE OR FLAVOR APPLICATIONS
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The present invention relates to thioester compounds and the incorporation and use of the new chemical entities as flavor and fragrance chemicals.
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- Compounds Which Modulate The CB2 Receptor
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Compound of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful
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Page/Page column 7; 9
(2008/06/13)
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- PYROLYSIS OF α-ACYL SUBSTITUTED ETHYL PHENYL SULFOXIDE
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The effect of pyrolysis of the acyl group substituted on α-position carbon in S-ethyl group of ethyl phenyl sulfoxide was investigated by using two kinds of substrates, 1-ethoxycarbonylethyl phenyl sulfoxide (1) and 1-ethoxycarbonyl-1-methylethyl phenyl sulfoxide (2) together with 2-methoxycarbonylethyl phenyl sulfoxide (4).The rate of pyrolysis of (1) was found to be about 740 ca. 890 times faster than that of ethyl phenyl sulfoxide (5), while (2) was 5700 times faster.The rate enhancement effect on α-ethoxycarbonyl group was larger than that on β-methoxycarbonyl group.Large deuterium kinetic isotope effect (kH/kD=5.5 for PhS(O)C(CD3)2CO2Et (3)) was observed.Activation energy for (2) is about 110 kJ/mol, which is just about the same as that of (5) (108 kJ/mol), while activation entropy lies in ca. 1 Jdeg-1 mol-1.Hammett plot for substituted (2) gave ?=0.69.These kinetic results reveal that the pyrolysis of the sulfoxides proceeds via a loose transition state involving advanced C-S bond cleavage.The remarkably large rate enhancement by α-carbonyl group might be due mainly to the conjugation of that group and developing double bond acidifying the β-proton in the transition state.Key words: Pyrolysis; elimination; mechanism; isotope effect; kinetics; sulfoxide,
- Tsukurimichi, Eiichi,Yoshimura, Toshiaki,Yoshizawa, Masaki,Itakura, Hiromi,Shimasaki, Choichiro
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p. 113 - 120
(2007/10/02)
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- O,O-diethyl-O-carboxamidophosphate esters
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Mites and insects, particularly aphids, are combated by applying as pest control agents one or more compounds of the structural formula EQU1 in which R is tert.butylphenyl; tert.butyl; 3,5-dimethylphenyl; 1-methyl-1-phenylthioethyl; 1-methyl-1-methylthioethyl; 1-cyclohexylthio-1-methylethyl; 1-cyclohexylthiopropyl; 1-ethylthio-1-methylethyl; 1-ethylthiopropyl or 1-ethylthioethyl.
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