- Synthesis and antimicrobial activities of structurally novel S,S′-bis(heterosubstituted) disulfides
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The central focus of this study is on the antibacterial and antifungal properties of synthetically produced S,S′-bis(heterosubstituted) disulfides as a means to control the growth of various infection-causing pathogens. Staphylococcus aureus, Francisella tularensis and Candida albicans were each found to be highly susceptible to several of these compounds by agar or broth dilution and Kirby-Bauer diffusion assays. These structurally simple, low molecular weight disulfides have shown promising bioactivities and may serve as leads to the development of effective new antibacterials for pathogenic bacteria such as methicillin-resistant S. aureus and F. tularensis.
- Ramaraju, Praveen,Gergeres, Danielle,Turos, Edward,Dickey, Sonja,Lim, Daniel V.,Thomas, John,Anderson, Burt
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experimental part
p. 3623 - 3631
(2012/07/16)
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- ANTIBACTERIAL S-HETEROSUBSTITUTED DISULFIDES
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Synthetically-derived S,S-heterodisubstituted disulfides that exhibit potent in vitro antibacterial activity against a variety of bacteria, including Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and Francisella tularensis. The present invention provides compounds, methods and compositions effective to treat microbial/bacterial infections, and, especially, infections arising from bacteria which have developed resistance to conventional antibiotics.
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Page/Page column 13; 16
(2009/05/30)
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- Substituent effects on the reactivity of benzo-1,2-dithiolan-3-one 1-oxides and their possible application to the synthesis of DNA-targeting drugs
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The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-1,2-dithiolan-3- one 1-oxides in acetonitrile-water (7:3) mixtures. The reaction is facilitated by reducing the electron density at the para position or by placing substituents bearing lone pair electrons ortho to the dithiolanone-oxide (S1) reaction center. Through-space and through-bond effects both contribute to the conversion of polysulfane products.
- Sawwan, Nahed,Brzostowska, Edyta M.,Greer, Alexander
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p. 6968 - 6971
(2007/10/03)
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- Formation of dialkyl polysulfides from vinyl ethers in the system H2S-DMSO-MOH
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The reaction of vinyl ethers with the system H2S-DMSO-MOH (30°C, 5 h) gives dialkyl polysulfides with a total yield of up to 65% instead of expected oxygen-containing thiols and sulfides. The ratio between dialkyl di-, tri-, and tetrasulfides depends on the nature of the vinyl ether and on the amount of alkali metal hydroxide in the reaction mixture. With di(propen-1-yl) ether, 4-methyl-2-ethyl-1,3-oxathiolane was also found as a by-product.
- Musorin,Sedunova,Trofimov
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p. 794 - 797
(2007/10/03)
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- Use of a sacriflcial-sulfur electrode in electroorganic chemistry. V. Formation of the sequence CSSSC from S and thiols or thiolates
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At a working potential of about +2.0 V (vs SCE) the carbon-sulfur electrode is a source of the electrogenerated cation S2+. In organic media, this electrophile reacts with thiols (or thiolates) to give a mixture of polysulfides of which the trisulfide is the main product. The reaction between electrogenerated Sy2- and alkyl halides is less selective. Elsevier,.
- Do, Quang Tho,Elothmani, Driss,Simonet, Jacques,Guillanton, Georges Le
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p. 273 - 281
(2007/10/03)
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- Reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide: Studies related to the reaction of antitumor antibiotic leinamycin with DNA
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We have studied the reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide. The major products isolated from these reactions are the corresponding dithio carboxylic acids. In the case of 3H-1,2-benzodithiol-3-one 1-oxide, an unstable hydrodisulfide that decomposes to polysulfides under the reaction conditions is formed. A mechanism involving an unstable oxathiolanone intermediate is proposed for these reactions. We believe that these reactions may serve as useful models for some aspects of the thiol-activated DNA-cleavage chemistry of the antitumor antibiotic leinamycin, a natural product that contains a 1,2-dithiolan-3-one 1-oxide heterocycle.
- Behroozi,Kim,Gates
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p. 3964 - 3966
(2007/10/02)
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- REACTION OF SULFUR DIOXIDE WITH THIOLS CATALYZED BY BORON TRIFLUORIDE ETHERATE. EVIDENCE FOR A POSSIBLE INTERVENTION OF DITHIOSULFITE AS A REACTION INTERMEDIATE.
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The reaction of sulfur dioxide (SO//2) with 1-propanethiol (NPT), 2-propanethiol (IPT), or 2-methyl-2-propanethiol (TBT) catalyzed by boron trifluoride ethrate (BF//3OEt//2) was investigated. The ratios of dialkyl trisulfide to dialkyl disulfide obtained (RSSSR/RSSR) at an early stage of the reaction were larger than 1 for the reaction of TBT and less than 1 for the reaction of NPT or IPT. The reaction of dithiosulfites with BF//3OEt//2 in the presence or absence of thiol was investigated. From a consideration of the similarity of the composition of the sulfides formed in the reaction of dithiosulfites with BF//3OEt//2 to those in the reaction of SO//2 witn thiol in the presence of BF//3OEt//2, the possibility of the intervention of dithiosulfite as a reaction intermediate in the reaction of SO//2 with thiol is discussed.
- Akiyama
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p. 2657 - 2660
(2007/10/02)
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