- Synthesis and preliminary evaluation of the anti-cancer activity on A549 lung cancer cells of a series of unsaturated disulfides
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We synthesized a series of small symmetrical unsaturated disulfides by a multi-step reaction starting from organic alcohols, and we performed a preliminary test to evaluate the effect of these compounds on the viability of A549 lung cancer cells. The garlic-derived natural compound diallyl disulfide, known for its anticancer activity, was used as the lead compound in this study. We synthesized five DADS analogues having different carbon chain lengths and different positions of the double bonds. Two analogues exhibited a promising antitumor activity in vitro, and the allylic double bond did not seem to be the main driving force.
- Olivito, Fabrizio,Amodio, Nicola,Di Gioia, Maria Luisa,Nardi, Monica,Oliverio, Manuela,Juli, Giada,Tassone, Pierfrancesco,Procopio, Antonio
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supporting information
p. 116 - 119
(2019/01/30)
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- Efficient synthesis of organic thioacetates in water
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Thioacetates as precursors of thiols are interesting starting points for synthesizing other organosulfur compounds. Herein, we propose a simple, efficient and fast method to obtain organic thioacetates using water as a solvent. Taking into account the great attention that has been paid toward environmentally friendly synthetic procedures in the past decades, we prove the role and the strength of the thioacetate anion as a nucleophile for nucleophilic displacement reactions in an aqueous medium. The reactions were carried out under pH control, to prevent the decomposition of the mesylate starting materials, using potassium carbonate as a safe and mild base. A simple work up allows products to be obtained with excellent yield and acceptable purity.
- Olivito,Costanzo,Di Gioia,Nardi,Oliverio,Procopio
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supporting information
p. 7753 - 7759
(2018/11/02)
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- Allyl sulphides in olefin metathesis: Catalyst considerations and traceless promotion of ring-closing metathesis
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Allyl sulphides are reactive substrates in ruthenium-catalysed olefin metathesis reactions, provided each substrate is matched with a suitable catalyst. A profile of catalyst activity is described, along with the first demonstration of allyl sulphides as traceless promoters in relayed ring-closing metathesis reactions. This journal is
- Edwards, Grant A.,Culp, Phillip A.,Chalker, Justin M.
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supporting information
p. 515 - 518
(2015/02/19)
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- Method of manufacturing compds. Allylnaphthol
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PROBLEM TO BE SOLVED: To provide a production method of an allyl compound of carrying out the dehydration allylation of a substrate having S, C or N which is a nucleophilic atom, especially S under the presence of a catalyst system consisting of a catalyst precursor having a specific structure and a specific ligand. SOLUTION: The production method of allyl compounds comprises as follow. A catalyst precursor chosen from Formula (1) and Formula (2) and a ligand are mixed, or a catalyst precursor, an allyl alcohol, and a ligand are mixed, then allyl alcohols and a substrate are blended and made to react. The ligand is quinaldic acid or picolinic acid, and the substrate is thiols, thiocarboxylic acids or the like. [Ru(C5H5)(CH3CN)3]PF6(1). [Ru[C5(CH3)5](CH3CN)3]PF6(2). COPYRIGHT: (C)2012,JPOandINPIT
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Paragraph 0057; 0062
(2018/06/26)
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- OLEFIN METATHESIS REACTIONS OF AMINO ACIDS, PEPTIDES AND PROTEINS CONTAINING ALLYL SULFIDE GROUPS
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A method for the modification of an amino acid, protein or peptide is disclosed. The method comprises reacting a carbon-carbon double bond-containing compound with an amino acid, a protein or a peptide containing an allyl sulfide group in the presence of a catalyst which promotes olefin metathesis, to form a modified amino acid, protein or peptide. Preferred carbon-carbon double bond-containing compounds include carbohydrates.
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Page/Page column 9
(2012/07/27)
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- Highly efficient catalytic dehydrative S-allylation of thiols and thioic S-acids
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A SH-selective allylation method using [CpRu(2-quinolinecarboxylato) (η3-C3H5)]PF6 has been realized in various solvents including aqueous media to give allyl sulfides and allyl S-thioates, demonstrating the potential applicability to lipopeptide chemistry.
- Tanaka, Shinji,Pradhan, Prasun Kanti,Maegawa, Yusuke,Kitamura, Masato
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supporting information; experimental part
p. 3996 - 3998
(2010/07/06)
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- Allyl sulfides are privileged substrates in aqueous cross-metathesis: Application to site-selective protein modification
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Allyl sulfides undergo efficient cross-metathesis in aqueous media with Hoveyda-Grubbs second generation catalyst 1. The high reactivity of allyl sulfides in cross-metathesis was exploited in the first examples of cross-metathesis on a protein surface. S-Allylcysteine was incorporated chemically into the protein, providing the requisite allyl sulfide handle. Preliminary efforts to genetically incorporate S-allylcysteine into proteins are also reported. Copyright
- Lin, Yuya A.,Chalker, Justin M.,Floyd, Nicola,Bernardes, Goncalo J. L.,Davis, Benjamin G.
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supporting information; experimental part
p. 9642 - 9643
(2009/02/04)
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- Practical preparation of esters and thioacetates from alkyl halides and carboxylates or thioacetate catalyzed by PEG400 without solvent
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Carboxylic esters and thioacetates were conveniently prepared in good to excellent yields under mild conditions by the reaction of alkyl halides with sodium carboxylates or sodium thioacetate catalyzed by PEG400 in the absence of solvents. Copyright Taylor & Francis Group, LLC.
- Cao, Yu-Qing,Wu, Guo-Qiang,Li, Ya-Bin,Dai, Zhi,Chen, Bao-Hua
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p. 3353 - 3358
(2007/10/03)
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- A facile and practical method for the preparation of thioacetates from alkyl halides and sodium thioacetate catalysed by PEG400
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Thioacetates are conveniently prepared in high yields under mild conditions by the reaction of alkyl halides and sodium thioacetate, prepared in situ from thioacetic acid and sodium carbonate, catalysed by PEG400 at room temperature.
- Cao, Yu-Qing,Du, Yun-Fei,Chen, Bao-Hua,Dai, Zhi
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p. 762 - 763
(2007/10/03)
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- A general and mild synthesis of thioesters and thiols from halides
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The conversion of a wide variety of halides to thioesters by reaction with potassium thiocetate under mild conditions is described, and the generality of the method is demonstrated.
- Zheng, Tu-Cai,Burkart, Maureen,Richardson, David E.
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p. 603 - 606
(2007/10/03)
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- A Cyclization Approach toward Five-Membered Heteroaromatic o-Quinodimethanes via Fused-3-Sulfolenes
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A general strategy involving the zincation of 4-bromo-3-chloro-2-sulfolene, in situ condensation with an α-heterosubstituted acetaldehyde, and subsequent cyclization reaction as the key steps toward the synthesis of furano- and thieno-3-sulfolenes is desc
- Chou, Ta-Shue,Tsai, Chung-Ying,Lee, Shwu-Jiuan
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p. 299 - 307
(2007/10/03)
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- Nucleophilic substitution of SN1-active halides using zinc salts: Preparation of thiolacetates
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Tertiary alkyl, allylic and benzylic halides react with zinc thiolacetate, prepared in situ, under optimised conditions to yield the corresponding thiolacetates in moderate to good yields.
- Gurudutt,Rao, Sanjay,Srinivas,Srinivas
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p. 3045 - 3050
(2007/10/02)
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- Nucleophilic Substitution of Alkyl Halides by Zinc Salts: Part 4-Synthesis of Thioethers and Thiolesters
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A variety of alkyl halides including tertiary alkyl halides react smoothly with the zinc salts of thiols and thiolcarboxylic acids yielding thioethers and thiolesters.
- Rajanikanth, B.,Ravindranath, B.
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p. 1043 - 1045
(2007/10/02)
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