- A modular template for the design of thiol-triggered sensors and prodrugs
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A unique reaction between thiols (RSH) and alkyl sulfonylbenzothiazole was discovered. This reaction was specific for thiols and produced a sulfinic acid (RSO2H) as the intermediate, which further triggered an intramolecular cyclization to release a -OH containing payload. This reaction was used to develop thiol-triggered fluorescent sensors and prodrugs. The modular design of this template provides tunability of the release profiles of the payloads.
- Berkman, Clifford E.,Chen, Wei,Knight, Jessica Renee,Wang, Yingying,Xian, Ming,Xu, Shi
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- New Taste-blind Substances. Studies on the Sensory Divergence of Bitterness to the Taste-blindness of 2-Mercaptoimidazoline, 2-Mercaptobenzothiazole and Their Derivatives, with Special Reference to Their Molecular Structure
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In order to investigate the relationship between taste-blindness and its chemical structure, sensory tests on thioureas, guanidines, imidazoles and thiazoles, which are widely used as vulcanizing agents for rubber, were carried out.It was found that new compounds, which had an intermediate characteristic between bitter and taste-blind substances, were present in benzimidazole and benzothiazole compounds.When it is considered that these compounds have structural similarities and only slight structural changes were present in them, these results provide an indication of the bitter exhibition mechanism on a taste receptor.
- Kouge, Katsushige,Koizumi, Tatsuya,Ishibashi, Norio,Okai, Hideo
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p. 1941 - 1946
(2007/10/02)
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- BENZAZOLIN-2-THIONES IN THE MICHAEL REACTION. 1. REACTION OF BENZOTHIAZOLIN- AND BENZOXAZOLIN-2-THIONES WITH ACRYLONITRILE, ACRYLAMIDE, AND METHACRYLATE IN THE PRESENCE OF ACID CATALYST
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The reaction of benzothiazolin- and benzoxazolin-2-thiones with acrylonitrile, acrylamide, and methylacrylate under conditions of acid catalysis takes place at the sulfur atom.The formation of minor amounts of N-derivatives is attributed to izomerization of the principal reaction products.
- Anan'eva, K.V.,Rozhkov, N.K.
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p. 456 - 459
(2007/10/02)
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- BENZAZOLIN-2-THIONES IN THE MICHAEL REACTION. 2. REACTION OF BENZOTHIAZOLIN- AND BENZOXAZOLIN-2-THIONES WITH ACRYLONITRILE, ACRYLAMIDE, AND METHYL ACRYLATE IN THE PRESENCE OF BASIC CATALYSTS
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Depending on the structure of the reagents and the kind of basic catalyst, the addition of benzazolin-2-thiones to an activated double bond takes place at either nitrogen or sulfur.Acrylonitrile, regardless of the catalyst, reacts at the nitrogen atom.In the presence of sodium methylate, addition to acrylamide takes place only, and to methyl acrylate predominantly at nitrogen.In the presence of triethylamine, a mixture of compounds with a high content of S-derivatives forms.
- Anan'eva, K. V.,Rozhkova, N. K.
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p. 564 - 567
(2007/10/02)
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- Synthesis and Reactions of 2-Mercaptobenzothiazole Derivatives of Expected Biological Activity. 2
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The amides and anilides of benzothiazol-2-ylthioacetic acid and 3-(benzothiazol-2-ylthio)propanoic acid were prepared by the reaction of the corresponding acid chlorides with amines and anilines.Also the arylhydrazones, the cycloalkanone hydrazones, and pyrazoline derivatives were prepared.
- Hammam, Abou El-Fotooh G.,Youssif, Nabil M.
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p. 207 - 208
(2007/10/02)
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