115-08-2Relevant articles and documents
Characterization of the Simplest Thiolimine: The Higher Energy Tautomer of Thioformamide
Bernhardt, Bastian,Dressler, Friedemann,Eckhardt, André K.,Becker, Jonathan,Schreiner, Peter R.
, p. 6732 - 6739 (2021)
As sulfur-containing organic molecules thioamides and their isomers are conceivable intermediates in prebiotic chemistry, for example, in the formation of amino acids and thiazoles and resemble viable candidates for detection in interstellar media. Here, we report the characterization of parent thioformamide in the solid state via single-crystal X-ray diffraction and its photochemical interconversion to its hitherto unreported higher energy tautomer thiolimine in inert argon and dinitrogen matrices. Upon photogeneration, four conformers of thiolimine form, whose ratio depends on the employed wavelength. One of these conformers interconverts due to quantum mechanical tunneling with a half-life of 30–45 min in both matrix materials at 3 and 20 K. A spontaneous reverse reaction from thiolimine to thioformamide is not observed. To support our experimental findings, we explored the potential energy surface of the system at the AE-CCSD(T)/aug-cc-pCVTZ level of theory and computed tunneling half-lives with the CVT/SCT approach applying DFT methods.
Structure-Based Design of a Small Molecule CD4-Antagonist with Broad Spectrum Anti-HIV-1 Activity
Curreli, Francesca,Kwon, Young Do,Zhang, Hongtao,Scacalossi, Daniel,Belov, Dmitry S.,Tikhonov, Artur A.,Andreev, Ivan A.,Altieri, Andrea,Kurkin, Alexander V.,Kwong, Peter D.,Debnath, Asim K.
, p. 6909 - 6927 (2015)
Earlier we reported the discovery and design of NBD-556 and their analogs which demonstrated their potential as HIV-1 entry inhibitors. However, progress in developing these inhibitors has been stymied by their CD4-agonist properties, an unfavorable trait for use as drug. Here, we demonstrate the successful conversion of a full CD4-agonist (NBD-556) through a partial CD4-agonist (NBD-09027), to a full CD4-antagonist (NBD-11021) by structure-based modification of the critical oxalamide midregion, previously thought to be intolerant of modification. NBD-11021 showed unprecedented neutralization breath for this class of inhibitors, with pan-neutralization against a panel of 56 Env-pseudotyped HIV-1 representing diverse subtypes of clinical isolates (IC50 as low as 270 nM). The cocrystal structure of NBD-11021 complexed to a monomeric HIV-1 gp120 core revealed its detail binding characteristics. The study is expected to provide a framework for further development of NBD series as HIV-1 entry inhibitors for clinical application against AIDS.
Synthesis of bis(ethylenedithio)dithiadiazafulvalenes (BEDT-DTDAF) and generation of charge-transfer complexes with tetracyanoquinodimethane
Makowiec, Slawomir,Koczan, Wioletta,Rachon, Janusz
, p. 696 - 698 (2008)
The synthesis of bis(ethylenedithio)dithiadiazafulvalenes (BEDT-DTDAFs), in four steps via 4,5-(ethylenedithio)thiazole and 3-alkyl-4,5-(ethylenedithio) thiazolium salts, and the generation of conducting charge-transfer complexes from a new type of dithiadiazafulvalene and tetracyanoquinodimethane are reported. Georg Thieme Verlag Stuttgart.
Preparation method of 4-methyl-5-(2-acetoxyethyl) thiazole
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Paragraph 0032; 0035, (2021/07/14)
The invention relates to a preparation method of 4-methyl-5-(2-acetoxyethyl) thiazole, and discloses a preparation method of 4-methyl-5-(2-acetoxyethyl) thiazole, the 4-methyl-5-(2-acetoxyethyl) thiazole is obtained by reaction of 3-halogenated-5-acetoxy-2-pentanone and thioformamide, and the reaction takes SBA-15 molecular sieve loaded ionic liquid as a catalyst. The catalyst not only improves the reaction yield, but also improves the product purity.
Thioformamide, and preparation method and application thereof
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Paragraph 0020; 0028-0030, (2020/03/13)
The invention discloses a thioformamide, and a preparation method and an application thereof. Carbon disulfide and formamide which are used as raw materials are reacted under a pressure of 3-5 MPa under the catalytic action of an organic alkali to generate thioformamide, and the thioformamide is rectified and collected after the reaction is finished. The thioformamide prepared in the invention canbe used as an thiabendazole intermediate to synthesize thiabendazole which is applied to the fields of sterilization, corrosion prevention, fresh keeping and the like. The preparation method has theadvantages of simplicity, mild reaction conditions, safety, controllability, low production cost, high yield, no generation of wastewater or toxic gases, and reduction of environmental pollution.
Thioformamide as well as preparation method and application thereof
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Paragraph 0027-0029, (2020/03/09)
The invention discloses thioformamide as well as a preparation method and application thereof. The preparation method disclosed by the invention comprises the following steps: taking carbon disulfide,liquid ammonia and carbon monoxide as raw materials, reacting under the catalytic action of an organic alkali under the pressure of 4-6MPa to generate thioformamide, and rectifying and collecting thioformamide after the reaction is finished. Thioformamide prepared by the method can be used as a thiabendazole intermediate, is used for synthesizing thiabendazole, and is applied to the fields of sterilization, corrosion prevention, fresh keeping and the like. Thioformamide is prepared by adopting a one-step method, and the preparation method is simple, mild in reaction condition, easy to implement, safe, controllable, low in production cost, high in yield, free of generation of wastewater and toxic gas and capable of reducing environmental pollution.
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.
Tetrahydrobenzothiazol-2-acetone oxime derivative and preparation method and application thereof
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Paragraph 0037; 0039, (2018/04/21)
The invention discloses a tetrahydrobenzothiazole-2-acetone oxime derivative, and a preparation method and application thereof. A structural formula is shown in the description. R is any one of the following radical groups: 4-methylphenyl, phenyl, 2-methylphenyl, 3-methylphenyl, 2,5-dimethylphenyl, 3,5-dimethylphenyl, 4-n-propylphenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 3-methoxyphenyl, 3,4,5-trimethoxyphenyl, 3-biphenyl, 4-trifluoromethoxyphenyl, 3-fluorophenyl, 4-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 3,5-bis(trifluoromethyl)phenyl, 3-chloro-4-methylphenyl, 3-furyl, 3-thienyl, 2-pyridyl, 4-pyridyl, 2-quinolyl, and 6-quinolyl. The tetrahydrobenzothiazol-2-acetone oxime derivative has relatively high antitumor activity and is suitable for preparing antitumor drugs. The preparationmethod of the derivative has the characteristics of cheap and readily available raw materials, short steps, and high reaction efficiency.
5 - (3 - Phenyl-acryloyl) thiazole derivative and its preparation method and application (by machine translation)
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Paragraph 0043; 0045-0047, (2018/10/02)
The present invention is shown in formula I 5 - (3 - phenyl-acryloyl) thiazole derivatives and their pharmaceutically acceptable salt, pharmaceutical composition and thereof in the preparation of influenza virus neuraminidase inhibitors in the application. Wherein R is selected from: methyl, ethyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl; R1 Is selected from: hydrogen, 2 - nitro, 3 - nitro, 4 - nitro, 2 - amino, 3 - amino, 4 - amino, 2 - methylamino, 3 - methylamino, 4 - methylamino, 2 - dimethylamino, 3 - dimethylamino, 4 - dimethylamino, 2 - methoxy, 3 - methoxy, 4 - methoxy, 2 - ethoxy, 3 - ethoxy, 4 - ethoxy, 2 - hydroxy, 3 - hydroxy, 4 - hydroxy, 2, 3 - dihydroxy, 2, 4 - dihydroxy, 2, 5 - dihydroxy, 3, 4 - dihydroxy, 3, 5 - dihydroxy, 2 - hydroxy - 3 - methoxy, 3 - hydroxy - 4 - methoxy, 4 - hydroxy - 3 - methoxy, 4 - hydroxy - 3 - ethoxy, 3, 4, 5 - trimethoxy or 4 - hydroxy - 3, 5 - dimethoxy; R2 Is selected from: hydrogen, C1 - C2 Alkyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl, trifluoromethyl or chloro C1 - C4 Straight-chain alkyl. (by machine translation)
Thiophosphate - A Versatile Prebiotic Reagent?
Ritson, Dougal J.,Xu, Jiangfeng,Sutherland, John D.
, p. 64 - 67 (2016/12/27)
Described are our preliminary studies on the reactivity of thiophosphate in a setting which correlates with the cyanosulfidic systems chemistry we have previously reported. Thiophosphate adds to various nitrile groups giving the corresponding thioamides in a highly efficient manner and the mechanistic implications are briefly discussed. Thiophosphate can also act as a phosphorylating agent, which was demonstrated with adenosine. The prebiotic availability of thiophosphate must be questioned, but if a plausible synthesis can be found, the advantages it would bring to the field of prebiotic chemistry appear to be highly beneficial.
