- Development of S-Substituted Thioisothioureas as Efficient Hydropersulfide Precursors
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Because of their inherent instability, hydropersulfides (RSSH) must be generated in situ using precursors, but very few physiologically useful RSSH precursors have been developed to date. In this work, we report the design, synthesis, and evaluation of novel S-substituted thiosiothioureas as RSSH precursors. These water-soluble precursors show efficient and controllable release of RSSH under physiological conditions.
- Khodade, Vinayak S.,Toscano, John P.
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supporting information
p. 17333 - 17337
(2019/01/04)
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- Synthesis, characterization and thermal behavior of tetrakis(melamine2+) bis(melamine+) pentakis(monohydrogenphosphate) tetrahydrate
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A new organic-inorganic salt, tetrakis (2,4,6-Triamino-1,3,5-Triazin-1,3-diium) bis (2,4,6-Triamino-1,3,5-Triazin-1-ium) pentakis (monohydrogenphosphate) tetrahydrate, 4C3H8N6+2. 2C3H7N6+. 5HPO42-. 4H2O was synthesized through the reaction of melamine and phosphoric acid in an acidic medium HCl/H2O. It was then characterized by X-ray diffraction. The title compound crystallizes in monoclinic system with non-centrosymetric space group P 21 with lattice parameters a = 11.3008 ?, b = 20.9798 ?, c = 12.2679 ?, α = 90°, β = 117.236°, γ = 90°, Z = 2 and V = 2586.10 (?)3. The UV-vis absorption spectrum UV-vis showed that the crystal has a good optical transmittance in the entire visible region with a lower cut off wavelength of 290 nm. The vibrational frequencies of various functional groups present in the crystal were identified by FT-IR analysis. The chemical structure of the compound was also confirmed by 1H, 13C and 31P NMR spectroscopy. TGA-DTA analysis revealed that the materials have a good thermal stability without any melting.
- Youcef, Hakima Ait,Chafaa, Salah,Doufnoune, Rachida,Douadi, Tahar
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p. 138 - 143
(2016/07/06)
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- An approach to "escape from flatland": Chemo-enzymatic synthesis and biological profiling of a library of bridged bicyclic compounds
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A major reason for the low success rate in current drug development through chemical synthesis has been ascribed to the large fraction of quasi planar candidate molecules. Therefore, an "escape from flatland" strategy has been recommended for the generation of bioactive chemical entities. In a first attempt to test this recommendation, we synthesized a small collection of bridged bicyclic compounds possessing a rigid spherical core structure by combining a group of cyclic dienes with a collection of dienophiles. We started from planar biphenyl analogues and, by enzymatic dioxygenation, transformed them into hydroxylated diene structures. Using a small library of newly synthesized dienophiles, the dienes were converted into bridged bicycles via the Diels-Alder reaction. The resulting collection of 78 structures was first tested for bioactivity in a generic assay based on interference with the proliferation of mammalian cells. A more mechanism-targeted bioactivity profiling method, exploiting cellular impedance monitoring, was subsequently used to obtain suggestions for the mode of action exerted by those compounds that were the most active in the proliferation assay. Proteasome inhibition could be confirmed for 8 of a series of 9 respective candidates. Whilst 7 of these molecules showed relatively weak interference with proteasome activity, one candidate exerted a moderate but distinct inhibition. This result appears remarkable in view of the small size of the compound library, which was synthesized following a few basic considerations. It encourages the application of diverse synthetic approaches to further investigate the role of spherical shape for the success of compound libraries.
- Suryanarayana Birudukota,Franke, Raimo,Hofer, Bernd
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p. 3821 - 3837
(2016/05/09)
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- Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide
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A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.
- Gupta,Wagh
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p. 697 - 702
(2007/10/03)
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- On the specificity of reactions catalysed by the antibody H11
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The substrate specificity and the stereochemical course of the reactions catalysed by the antibody H11 (which was raised to a protein conjugated derivative of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyses to the corresponding dienol, the major diene component of the cycloaddition reactions observed. However, it tolerates a range of N- alkylmaleimides. The stereochemical course of cycloaddition is shown to produce a significant enantiomeric excess of the 3aR, 4S, 7aR-endo- diastereoisomer by analysis with Mosher's ester derivatives. This study also revealed that H11 is capable of slowly catalysing the hydrolysis of N- alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed. (C) 2000 Elsevier Science Ltd.
- Khalaf, Abedawn I.,Linaza, Sabin,Pitt, Andrew R.,Stimson, William H.,Suckling, Colin J.
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p. 489 - 495
(2007/10/03)
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- Antitumor chemotherapy. XIV. Cytotoxic activity of compounds possessing an ethylenic double bond substituted at the α and β positions with an electron attracting group
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The authors have previously shown that molecules possessing an ethylene double bond, activated by one or 2 electron attracting substituents, show a cytotoxic activity which must be connected with the addition of a cellular nucleophil to their double bond. This correlation has been extended to N alkylmaleinimides and different compounds with paraquinonine structure. The compounds examined possess a distinct cytotoxic antitumor activity which is, however, inferior to that of α nitro stilbenes and β nitro styrenes, the simplified analogs of aristolochic acid.
- Dore Ch.,Viel
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