62-55-5Relevant articles and documents
A convenient synthesis of derivatives of 1,3,2-dioxaphosphocane-2-sulfide with bioacitivity via Lawesson's reagent
Luo, Yanping,He, Liangnian,Ding, Mingwu,Yang, Guangfu,Luo, Aihong,Liu, Xiaopeng,Wu, Tianjie
, p. 37 - 41 (2001)
Lawesson's reagent, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disufide, reacted with the substituted 1,5-bisphenol 1to afford derivatives of 1,3,2-dioxaphosphocane-2-sulfide 2, which were found to possess selective herbicidal activity against rape.
Multicomponent synthesis of diphenyl-1,3-thiazole-barbituric acid hybrids and their fluorescence property studies
Mahata, Alok,Bhaumick, Prabhas,Panday, Anoop Kumar,Yadav, Rahul,Parvin, Tasneem,Choudhury, Lokman H.
, p. 4798 - 4811 (2020/04/03)
A series of novel diphenyl-1,3-thiazole linked barbituric acid hybrids (4) were prepared by two catalyst-free methods from readily available starting materials. The reaction of arylglyoxal, barbituric acid and aryl thioamides in the presence of 3-4 drops of water and liquid assisted grinding (LAG) provides the corresponding trisubstituted thiazoles tethered with a barbituric acid moiety within 30 minutes. Alternatively, a sequential two-step one-pot process involving aryl nitriles, ammonium sulphide, arylglyoxal and barbituric acid in water medium was developed. In this second method, in situ thioamides were prepared at room temperature from the reaction of alkyl/aryl nitriles and ammonium sulphide in aqueous medium. Arylglyoxal and barbituric acid were added to the in situ thioamides after neutralizing the reaction medium to provide trisubstituted thiazoles linked with barbituric acid derivatives. Some of our synthesized molecules showed fluorescent properties with very good quantum yields in DMSO medium. We also observed that fluorescent quantum yields of these thiazole derivatives depend on the type of electron donating/withdrawing character of R1 and R3. R2 has a very small effect on tuning the fluorescent properties. The salient features of this work are catalyst-free reactions, wide substrate scope, green reaction conditions (liquid assisted grinding and room temperature reactions in water medium) as well as the presence of more than one pharmaceutically important heterocyclic moiety with fluorescent properties.
Evaluation of thioamides, thiolactams and thioureas as hydrogen sulfide (H2S)donors for lowering blood pressure
Zaorska, Ewelina,Hutsch, Tomasz,Gawry?-Kopczyńska, Marta,Ostaszewski, Ryszard,Ufnal, Marcin,Koszelewski, Dominik
supporting information, (2019/04/29)
Hydrogen sulfide (H2S)is a biologically important gaseous molecule that exhibits promising protective effects against a variety of pathological processes. For example, it was recognized as a blood pressure lowering agent. Aligned with the need for easily modifiable platforms for the H2S supply, we report here the preparation and the H2S release kinetics from a series of structurally diversified thioamides, thiolactams and thioureas. Three different thionation methods based on the usage of a phosphorus pentasulfide and Lawesson reagent were applied to prepare the target thioamides and thiolactams. Furthermore, obtained H2S donors were evaluated both in in vivo and in vitro studies. The kinetic parameters of the liberating H2S was determined and compared with NaHS and GYY4137 using two different detection technics i.e.; fluorescence labeling 7-azido-4-methyl-2H-chromen-2-one and 5,5‘-dithiobis (2-nitrobenzoic acid), sulfhydryl probe, also known as the Ellman's reagent. We have proved that the amount of releasing H2S from these compounds is controllable through structural modifications. Finally, the present study shows a hypotensive response to an intravenous administration of the developed donors in the anesthetized rats.
Synthesis and biological evaluation of 2,4,5-trisubstituted thiazoles as antituberculosis agents effective against drug-resistant tuberculosis
Karale, Uttam B.,Krishna, Vagolu Siva,Krishna, E. Vamshi,Choudhari, Amit S.,Shukla, Manjulika,Gaikwad, Vikas R.,Mahizhaveni,Chopra, Sidharth,Misra, Sunil,Sarkar, Dhiman,Sriram, Dharmarajan,Dusthackeer, V.N. Azger,Rode, Haridas B.
, p. 315 - 328 (2019/06/14)
The dormant and resistant form of Mycobacterium tuberculosis presents a challenge in developing new anti-tubercular drugs. Herein, we report the synthesis and evaluation of trisubstituted thiazoles as antituberculosis agents. The SAR study has identified a requirement of hydrophobic substituent at C2, ester functionality at C4, and various groups with hydrogen bond acceptor character at C5 of thiazole scaffold. This has led to the identification of 13h and 13p as lead compounds. These compounds inhibited the dormant Mycobacterium tuberculosis H37Ra strain and M. tuberculosis H37Rv selectively. Importantly, 13h and 13p were non-toxic to CHO cells. The 13p showed activity against multidrug-resistant tuberculosis isolates.
COMPOUNDS FOR THIOL-TRIGGERED COS AND/OR H2S RELEASE AND METHODS OF MAKING AND USING THE SAME
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Page/Page column 35, (2019/12/25)
Disclosed herein are embodiments of a compound that is capable of releasing COS and/or H2S upon reaction with a thiol-containing compound. The compound embodiments also can produce a detectable signal (e.g., a fluorescent signal) substantially concomitantly with COS and/or H2S release and/or can release an active agent, such as a therapeutic agent. Methods of making and using the compound embodiments also are disclosed.
Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling
Bonfio, Claudia,Caumes, Cécile,Duffy, Colm D.,Patel, Bhavesh H.,Percivalle, Claudia,Tsanakopoulou, Maria,Sutherland, John D.
supporting information, p. 3934 - 3939 (2019/03/08)
The main aim of origins of life research is to find a plausible sequence of transitions from prebiotic chemistry to nascent biology. In this context, understanding how and when phospholipid membranes appeared on early Earth is critical to elucidating the prebiotic pathways that led to the emergence of primitive cells. Here we show that exposing glycerol-2-phosphate to acylating agents leads to the formation of a library of acylglycerol-phosphates. Medium-chain acylglycerol-phosphates were found to self-assemble into vesicles stable across a wide range of conditions and capable of retaining mono- and oligonucleotides. Starting with a mixture of activated carboxylic acids of different lengths, iterative cycling of acylation and hydrolysis steps allowed for the selection of longer-chain acylglycerol-phosphates. Our results suggest that a selection pathway based on energy-dissipative cycling could have driven the selective synthesis of phospholipids on early Earth.
Process method for synthesizing thioamide
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Paragraph 0049-0052, (2017/08/30)
The invention discloses a process method for synthesizing thioamide. The process method comprises the step of synthesizing a thioamide compound from aliphatic nitrile or aromatic nitrile as raw materials and sodium sulfide metal salt or ammonium sulfide salt and amine salt or ammonium salt in one step in a certain solvent. The method for synthesizing thioamide is high in safety and low in environmental pollution, and expensive raw materials are not used, so that the method is economic and environment-friendly.
Method for preparing thioacetamide
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Paragraph 0025; 0026, (2017/01/02)
The invention discloses a method for preparing thioacetamide.The method includes the steps that 1, sulfuric acid reacts with NaHS to prepare H2S, wherein the chemical equation is shown as following: 2NaHS+H2SO4 (dilute)=2H2S+Na2SO4; 2, H2S obtained in the step1 and acetonitrile (CH3CN) are catalyzed by an organic amine catalyst to prepare a thioacetamide crude product, wherein the chemical equation is shown as following: CH3CN+H2S=CH3CSNH2; 3, the thioacetamide crude product obtained in the step2 is distilled, residual CH3CN and the residual catalyst are removed, then filtrate is dissolved in anhydrous alcohol, and the thioacetamide finished product is obtained through crystallization, recrystallization and vacuum drying.The yield of the product is high, the production technology is simple, and thioacetamide is suitable for industrialized large-scale production; the purity of the obtained product is high, and the using requirements for a biological medicine intermediate are met.
Decomposition of S-nitroso species
Dorado,Dlugogorski,Kennedy,MacKie,Gore,Altarawneh
, p. 29914 - 29923 (2015/05/13)
Nitrosation reactions and subsequent decomposition of S-nitroso (RSNO+) species remain important in many biochemical processes as well as in industrial applications such as chemical gassing of emulsion explosives. This paper develops kinetic mechanisms of gas formation pathways in the decomposition of RSNO+ species, particularly S-nitrosothioacetamide and S-nitrosothiourea, providing new kinetic and thermodynamic constants. At pH levels of 1 and below, decomposition proceeds exclusively via NO formation pathways. With decreasing acidity, molecular nitrogen formation emerges as an equally important product of S-nitrosothiourea, while NO remains the only product for S-nitrosothioacetamide. Theoretical calculations for reaction enthalpies further elucidate the gas formation pathways and proposed mechanisms, fitted to experimental data, afford kinetic rate constants. In both species, the S-N bonds split homolytically with activation energies of 70.9 and 118 kJ mol-1 for S-nitrosothioacetamide and S-nitrosothiourea, respectively. The electron donating effect of methyl substitution in S-nitrosothioacetamide engenders lower activation energies with the bimolecular reaction of RSNO+ and RS occurring within the diffusion controlled regime at an activation energy of 17.6 kJ mol-1. For S-nitrosothiourea, a further bimolecular reaction of two RSNO+ molecules occurs irreversibly with an activation energy of 84.4 kJ mol-1.
Ammonium phosphorodithioate: A mild, easily handled, efficient, and air-stable reagent for the conversion of amides into thioamides
Kaboudin, Babak,Malekzadeh, Leila
experimental part, p. 2807 - 2810 (2012/01/02)
A simple, efficient, and new method has been developed for the synthesis of thioamides from amides. As described below, the reaction of a variety of aromatic and aliphatic amides in the presence of ammonium phosphorodithioate as an efficient reagent proceeded effectively to afford the corresponding thioamides in high yields. This method is easy, rapid, and high-yielding for the synthesis of thioamides from amides using an easily handled reagent. Georg Thieme Verlag Stuttgart · New York.
