- MECHANISM OF THE REACTION OF DIPHENYLPHOSPHINODITHIOIC ACID WITH NITRILES
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Kinetic studies of the reaction of diphenylphosphinodithioic acid with nitriles support a two step mechanism, the first step being an "ene" reaction.
- Benner, Steven A.
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Read Online
- Simple microwave-assisted method for the synthesis of primary thioamides from nitriles
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Primary thioamides are prepared in excellent yield from the corresponding nitrile by treatment with ammonium sulfide in methanol, at room temperature for electron-deficient aromatic nitriles or under microwave irradiation at 80 °C or 130 °C in 15-30 minutes for other aromatic and aliphatic nitriles. This procedure avoids the use of gaseous H2S under high pressure, proceeds in the absence of base and provides thioamides usually without the need for chromatographic purification.
- Bagley, Mark C.,Chapaneri, Krishna,Glover, Christian,Merritt, Eleanor A.
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Read Online
- Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
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A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.
- Chen, Xinzhi,Ge, Xin,Jin, Hao,Qian, Chao,Zhou, Shaodong
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supporting information
p. 3403 - 3406
(2021/06/25)
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- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
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Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
- Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
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supporting information
p. 3398 - 3402
(2021/06/25)
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- An efficient, one-pot, regioselective synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles under solvent-free conditions
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In this article, we present an efficient, one-pot regioselective approach towards the synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles obtained during the reaction of α-bromo-1,3-diketones generated in situ by triturating unsymmetrical 1,3-diketones with N-bromosuccinimide, with various thioamides under solvent-free conditions. This environmentally benign protocol showed large functional group tolerance, resulted in the exclusive formation of a single isomer, out of the two possible regioisomers in admirable yields. The structure of the isomeric thiazole was assigned unambiguously on the basis of multinuclear NMR [(1H-13C) HMBC, (1H-13C) HMQC, (1H-15N) HMBC] and X-ray crystallographic studies. The entire protocol is ecologically desirable as it employs no organic solvent.
- Aggarwal, Ranjana,Claramunt, Rosa M.,Hooda, Mona,Jain, Naman,Rozas, Isabel,Sanz, Dionisia,Twamley, Brendan
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- Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents
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The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.
- Chiarelli, Laurent R.,Fan, Dongguang,Han, Quanquan,Lu, Yu,Qiao, Chunhua,Shi, Rui,Stelitano, Giovanni,Wang, Bin,Huszár, Stanislav,Miku?ová, Katarína,Savková, Karin
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supporting information
p. 14526 - 14539
(2021/10/26)
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- Method for preparing aryl thioamide compound
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The invention discloses a method for preparing an aryl thioamide compound. The method comprises the following steps: under the protection of inert gas, performing stirring to react for 6-12 hours at the reaction temperature of room temperature to 60 DEG C by taking aryl methanol as a substrate, sublimed sulfur as a sulfur source, an alkali metal complex formed by combining alkali metal salt and ligand as a catalyst, alkali as an accelerant, formamide as a solvent and an amine source; and carrying out post-treatment on the reaction product to obtain the aryl thioamide compound. According to theinvention, cheap and easily available aryl methanol is used as a substrate for three-component reaction to prepare the corresponding thioamide compound; the method for preparing the aryl thioamide compound has the technical advantages of simple technological process, high yield, less pollution, safety, environmental protection, greenness, mildness and the like.
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Paragraph 0044-0046
(2021/03/31)
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- Multicomponent synthesis of diphenyl-1,3-thiazole-barbituric acid hybrids and their fluorescence property studies
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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.
- Mahata, Alok,Bhaumick, Prabhas,Panday, Anoop Kumar,Yadav, Rahul,Parvin, Tasneem,Choudhury, Lokman H.
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p. 4798 - 4811
(2020/04/03)
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- Thiazole amide derivative and application thereof in antitumor drugs
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The invention belongs to the technical field of medicines, and provides a thiazole amide derivative shown as a general formula and a preparation method thereof. The invention further discloses use ofthe thiazole amide derivative as a wnt inhibitor, and the thiazole amide derivative has obvious antitumor activity.
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Paragraph 0024-0026
(2020/07/13)
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- Compound containing dithiazolothiadiazole double heterocycles and preparation method of compound
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The invention discloses a compound containing dithiazolothiadiazole double heterocycles and a preparation method of the compound; the structural formula of the compound is shown in the specification,wherein R1 and R2 are respectively and independently selected from any one of alkyl, substituted alkyl, aryl, substituted aryl, silicon base, substituted silicon base, aliphatic heterocycle and aromatic heterocycle. The compound is prepared by cycloaddition reaction of a compound shown in the specification and isonitrile under the action of a catalyst. The obtained compound provides a new choice for research and development of new drugs. The preparation method disclosed by the invention is simple to operate, mild in system, low in cost and high in yield, and has great popularization and application values.
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Paragraph 0070-0072
(2020/10/14)
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- Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2-phenylthiazole or oxazole skeletons
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A series of novel pyridazinone derivatives were designed and synthesized by replacing 4-(tert-butyl)phenyl moiety of pyridaben with 2-phenylthiazole or oxazole fragments via activity substructure connecting approach. The structures of all target compounds were characterized through NMR, MS, and elemental analysis. Bioassay results exhibit that most compounds showed potent bioactivities against Aphis fabae, Tetranychus urticae, Erysiphe graminis, and/or Puccinia polysora. Among the newly synthesized compounds, 2-(tert-butyl)-4-chloro-5-(((2-phenylthiazol-4-yl)methyl)thio)pyridazin-3(2H)-one (12b) displays remarkable insecticidal activity against A fabae. Its LC50 value (2.73 mg/L) is better than that of pyridaben (5.46 mg/L), although inferior to that of imidacloprid (0.51 mg/L). In addition to its extraordinary insecticidal activity, compound 12b also exerts 96.9% fungicidal activities against P polysora at 500 mg/L in vivo, significantly superior to that of pyridaben (50.0%), while slightly lower than that of tebuconazole (100%). This article discusses the synthesis, bioassay results, and structure-activity relationship of this series of novel pyridazinone derivatives.
- Dang, Mingming,Liu, Minhua,Huang, Lu,Ou, Xiaoming,Long, Chuyun,Liu, Xingping,Ren, Yeguo,Zhang, Ping,Huang, Mingzhi,Liu, Aiping
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p. 4088 - 4098
(2020/10/02)
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- Preparation method of 2, 4-disubstituted thiazole compound
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The invention discloses a preparation method of a 2, 4-disubstituted thiazole compound. The method comprises the following steps: carrying out heating reflux reaction on substituted carboxylic acid inthionyl chloride to obtain yellow transparent liquid, and adding dichloromethane to dilute for later use; in an ice bath, slowly dropwise adding the substituted acyl chloride solution into ammonia water while stirring, stirring at room temperature to separate out a white solid, and after the reaction is finished, carrying out suction filtration, washing and drying to obtain substituted amide; carrying out reflux on substituted amide and Lawesson in tetrahydrofuran, carrying out rotary evaporation to remove the solvent after the reaction is finished, and carrying out column purification on thecrude product to obtain substituted sulfamide. The preparation method comprises the following steps: putting substituted sulfamide, ethanol, triethylamine and an alpha-bromocarbonyl compound into a pressure reaction tank, putting the pressure reaction tank into an annular focusing single-mode microwave synthesizer for irradiation, and cooling with compressed air to obtain a target compound. Basedon microwave synthesis, the invention has the advantages of short reaction time, high yield, high heating speed, environment friendliness and the like, and provides a microwave synthesis method of a2, 4-disubstituted thiazole compound.
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Paragraph 0034; 0039-0040
(2020/11/23)
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- Thiazole hydrazide derivatives and application thereof as agricultural bactericides
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The invention relates to the field of organic chemistry and pesticide science, and discloses a derivative containing a thiazole hydrazide structure and application of the derivative. The general chemical structural formula of the thiazole hydrazide derivative is shown in the specification, wherein R1 and R2 are respectively and independently selected from hydrogen, halogen, C1-6 alkyl, hydroxyl, amino, nitro, difluoromethyl, trifluoromethyl, C1-6 alkoxy, C1-6 alkyl substituted by 1-3 halogens and C1-6 alkoxy substituted by 1-3 halogens. The compound has good antibacterial activity on phytopathogens, and can be used as an agricultural bactericide for plant disease control.
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Paragraph 0038-0040
(2020/11/22)
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- COMPOUNDS FOR THIOL-TRIGGERED COS AND/OR H2S RELEASE AND METHODS OF MAKING AND USING THE SAME
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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.
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Page/Page column 34; 35
(2019/12/25)
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- Cyclic Sulfenyl Thiocarbamates Release Carbonyl Sulfide and Hydrogen Sulfide Independently in Thiol-Promoted Pathways
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Hydrogen sulfide (H2S) is an important signaling molecule that provides protective activities in a variety of physiological and pathological processes. Among the different types of H2S donor compounds, thioamides have attracted attention due to prior conjugation to nonsteroidal anti-inflammatory drugs (NSAIDs) to access H2S-NSAID hybrids with significantly reduced toxicity, but the mechanism of H2S release from thioamides remains unclear. Herein, we reported the synthesis and evaluation of a class of thioamide-derived sulfenyl thiocarbamates (SulfenylTCMs) that function as a new class of H2S donors. These compounds are efficiently activated by cellular thiols to release carbonyl sulfide (COS), which is quickly converted to H2S by carbonic anhydrase (CA). In addition, through mechanistic investigations, we establish that COS-independent H2S release pathways are also operative. In contrast to the parent thioamide-based donors, the SulfenylTCMs exhibit excellent H2S releasing efficiencies of up to 90percent and operate through mechanistically well-defined pathways. In addition, we demonstrate that the sulfenyl thiocarbamate group is readily attached to common NSAIDs, such as naproxen, to generate YZ-597 as an efficient H2S-NSAID hybrid, which we demonstrate releases H2S in cellular environments. Taken together, this new class of H2S donor motifs provides an important platform for new donor development.
- Pluth, Michael D.,Steiger, Andrea K.,Zhao, Yu
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supporting information
(2019/09/06)
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- Optimization, Structure-Activity Relationship, and Mode of Action of Nortopsentin Analogues Containing Thiazole and Oxazole Moieties
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Plant diseases seriously endanger plant health, and it is very difficult to control them. A series of nortopsentin analogues were designed, synthesized, and evaluated for their antiviral activities and fungicidal activities. Most of these compounds displayed higher antiviral activities than ribavirin. Compounds 1d, 1e, and 12a, with excellent antiviral activities, emerged as novel antiviral lead compounds, among which 1e was selected for further antiviral mechanism research. The mechanism research results indicated that these compounds may play an antiviral role by aggregating viral particles to prevent their movement in plants. Further fungicidal activity tests revealed that nortopsentin analogues displayed broad-spectrum fungicidal activities. Compounds 2p and 2f displayed higher antifungal activities against Alternaria solani than the commercial fungicides carbendazim and chlorothalonil. Current research has laid a foundation for the application of nortopsentin analogues in plant protection.
- Guo, Jincheng,Hao, Yanan,Ji, Xiaofei,Wang, Ziwen,Liu, Yuxiu,Ma, Dejun,Li, Yongqiang,Pang, Huailin,Ni, Jueping,Wang, Qingmin
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p. 10018 - 10031
(2019/10/05)
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- Mo (CO)6-assisted Pd-supported magnetic graphene oxide-catalyzed carbonylation-cyclization as an efficient way for the synthesis of 4(3H)-quinazolinones
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In this paper, a novel catalyst is introduced based on the immobilization of palladium on modified magnetic graphene oxide nanoparticles. The catalyst is characterized by several methods, including transmission electron microscopy, scanning electron microscopy, X-ray fluorescence, vibrating-sample magnetometer, Fourier transform-infrared and dynamic light scattering (DLS) analysis. The activity of the catalyst was investigated in the synthesis of 4(3H)-quinazolinones via Pd-catalyzed carbonylation-cyclization of N-(2-bromoaryl) benzimidamides by Mo (CO)6. The Mo (CO)6 is used as a carbon monoxide source for performing the reaction under mild conditions. The catalyst showed good reusability, and no change in activity was observed after 10?cycles of recovery.
- Bahadorikhalili, Saeed,Ansari, Samira,Hamedifar, Haleh,Ma'mani, Leila,Babaei, Mohsen,Eqra, Rahim,Mahdavi, Mohammad
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- Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation
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A regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium catalysis was developed. This transformation tactically linked the 1,2,4-thiadiazoles and succinimides together, and the novel molecules formed may have potential biological activity.
- Tian, Ting,Dong, An-Shun,Chen, Dan,Cao, Xian-Ting,Wang, Guannan
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supporting information
p. 7664 - 7668
(2019/08/30)
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- Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives
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The antioxidant, antimalarial, antibacterial, and antitumor activities of thiosemicarbazones have made this class of compounds important for medicinal chemists. In addition, thiosemicarbazones are among the most potent and well-known ribonucleotide reductase inhibitors. In this study, 24 new thiosemicarbazone derivatives were synthesized, and the structures and purity of the compounds were determined by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The IC50 values of these 24 compounds were determined with an assay for ribonucleotide reductase inhibition. Compounds 19, 20, and 24 inhibited ribonucleotide reductase enzyme activity at a higher level than metisazone as standard. The cytotoxic effects of these compounds were measured on the MCF7 (human breast adenocarcinoma) and HEK293 (human embryonic kidney) cell lines. Similarly, compounds 19, 20, and 24 had a selective effect on the MCF7 and HEK293 cell lines, killing more cancer cells than cisplatin as standard. The compounds (especially 19, 20, and 24 as the most active ones) were then subjected to docking experiments to identify the probable interactions between the ligands and the enzyme active site. The complex formation was shown qualitatively. The ADME (absorption, distribution, metabolism, and excretion) properties of the compounds were analyzed using in-silico techniques.
- Ertas, Merve,Sahin, Zafer,Bulbul, Emre F.,Bender, Ceysu,Biltekin, Sevde N.,Berk, Barkin,Yurttas, Leyla,Nalbur, Aysu M.,Celik, Hayati,Demirayak, ?eref
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- Discovery of 2-phenylthiazole-4-carboxylic acid, a novel and potent scaffold as xanthine oxidase inhibitors
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The xanthine oxidase (XO) plays an important role in producing uric acid, and therefore XO inhibitors are considered as one of the promising therapies for hyperuricemia and gout. We have previously reported a series of XO inhibitors with pyrazole scaffold to extend the chemical space of current XO inhibitors. Herein, we describe further structural optimization to explore the optimal heterocycle by replacing the thiazole ring of Febuxostat with 5 heterocycle scaffolds unexplored in this field. All of these efforts resulted in the identification of compound 8, a potent XO inhibitor (IC50 = 48.6 nM) with novel 2-phenylthiazole-4-carboxylic acid scaffold. Moreover, lead compound 8 exhibited hypouricemic effect in potassium oxonate-hypoxanthine-induced hyperuricemic mice. These results promote the understanding of ligand-receptor interaction and might help to design more promising XO inhibitors.
- Xu, Xue,Deng, Liming,Nie, Lu,Chen, Yueming,Liu, Yanzhi,Xie, Rongrong,Li, Zheng
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supporting information
p. 525 - 528
(2019/01/09)
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- Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety
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Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC50 = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, T18 gave the optimal fungicidal activity, which respectively offers control effects with EC50 values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to commercial fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound T18 has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future.
- Yan, Zhongzhong,Liu, Aiping,Ou, Yingcan,Li, Jianming,Yi,Zhang, Ning,Liu, Minhua,Huang, Lu,Ren, Jianwei,Liu, Weidong,Hu, Aixi
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p. 3218 - 3228
(2019/06/05)
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- Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides
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Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.
- Peng, Xiangjun,Qin, Feng,Xu, Mengyue,Zhu, Shaojie,Pan, Yingming,Tang, Haitao,Meng, Xiujin,Wang, Hengshan
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supporting information
p. 8403 - 8407
(2019/09/30)
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- A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
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A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.
- Cao, Xian-Ting,Qiao, Li,Zheng, Hui,Yang, Hui-Yong,Zhang, Peng-Fei
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p. 170 - 175
(2018/01/17)
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- A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
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A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.
- Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
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p. 509 - 517
(2018/03/27)
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- DYNAMIN-1-LIKE PROTEIN INHIBITORS
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This application is directed to inhibitors of dynamin-l-like protein (Drpl) represented by the following structural formula (I): and methods for their use, such as to treat one or more DRPl-related diseases.
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Page/Page column 83
(2018/11/22)
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- Photocatalytic Construction of S-S and C-S Bonds Promoted by Acridinium Salt: An Unexpected Pathway to Synthesize 1,2,4-Dithiazoles
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An unexpected cyclization of thioamides with p-quinone methides promoted by acridinium salt under the irradiation of visible light furnished 1,2,4-dithiazoles in moderate to good yields. In addition, the reaction of the obtained 1,2,4-dithiazoles with isocyanides offered a new entry for the synthesis of thiazol-5(4H)-imines in moderate yields.
- Huang, Xiao-Ying,Ding, Rui,Mo, Zu-Yu,Xu, Yan-Li,Tang, Hai-Tao,Wang, Heng-Shan,Chen, Yan-Yan,Pan, Ying-Ming
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supporting information
p. 4819 - 4823
(2018/08/24)
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- Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
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Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.
- Yan, Zhongzhong,Liu, Aiping,Huang, Mingzhi,Liu, Minhua,Pei, Hui,Huang, Lu,Yi, Haibo,Liu, Weidong,Hu, Aixi
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p. 170 - 181
(2018/03/08)
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- Selective Cleavage of Inert Aryl C-N Bonds in N-Aryl Amides
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A highly selective, IBX-promoted reaction has been developed for the oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions (HFIP/H2O, 25 °C), providing facile access to various useful primary amides, some of which would be otherwise unattainable using conventional aminolysis and hydrolysis approaches.
- Zhang, Zhiguo,Zheng, Dan,Wan, Yameng,Zhang, Guisheng,Bi, Jingjing,Liu, Qingfeng,Liu, Tongxin,Shi, Lei
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p. 1369 - 1376
(2018/02/09)
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- Oxazolidinone compound containing piperazine hydrazone structure
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The invention discloses an oxazolidinone compound containing a piperazine hydrazone structure. The oxazolidinone compound comprises a compound shown as a general formula (I), or stereisomer thereof, or pharmaceutically-acceptable salt thereof, or solvate thereof or prodrug thereof, wherein R1 is hydrogen, fluorine, chlorine or trifluoromethyl, R2 is -NHCOCH3 or -OH, R3 is Ar which is C5-C10 aryl substituted by any 1-3 R4 and heteroaryl, and R4 is hydrogen, hydroxyl, halogen, nitro, amino, cyan, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl substituted by hydroxyl, amino or halogen, C1-C6 alkoxy substituted by hydroxyl, amino or halogen, amino substituted by mono- or bi-(C1-C6 alkyl), C1-C6 alkyl amido, free, salty, esterified and amidated hydroxyl, C1-C6 alkyl sulfinyl, C1-C6 alkyl sulfonyl, C1-C6 alkyl acyl and carbamoyl. The oxazolidinone compound can be used for preparing drug for treating microbial infection.
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Paragraph 0131; 0132
(2017/09/02)
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- Process method for synthesizing thioamide
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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.
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Paragraph 0059; 0060
(2017/08/30)
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- Iminothioethers as Hydrogen Sulfide Donors: From the Gasotransmitter Release to the Vascular Effects
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The gasotransmitter hydrogen sulfide (H2S) is an important tuner of the cardiovascular homeostasis, and its deficiency is etiologically associated with a number of cardiovascular diseases. Therefore, the research of original moieties able to release H2S represents a timely issue for drug discovery. In this work, we developed a collection of iminothioethers (ITEs), exhibiting H2S-releasing properties and producing vasorelaxing effects on rat aortic rings. Derivatives 4 and 11, selected as representative of slow and fast rate H2S donors, respectively, produced a complete recovery of the basal coronary flow, reverting the AngII-induced effects in isolated rat hearts. In addition, studies on human aortic smooth muscle cells (HASMCs) demonstrated membrane hyperpolarizing effects, well related to the intracellular generation of H2S. Taken together, the results obtained support ITEs 4 and 11 as new pharmacological tools, as well as effective and innovative H2S donors for cardiovascular drug discovery.
- Barresi, Elisabetta,Nesi, Giulia,Citi, Valentina,Piragine, Eugenia,Piano, Ilaria,Taliani, Sabrina,Da Settimo, Federico,Rapposelli, Simona,Testai, Lara,Breschi, Maria Cristina,Gargini, Claudia,Calderone, Vincenzo,Martelli, Alma
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p. 7512 - 7523
(2017/09/23)
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- Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents
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To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compounds (1), a series of aromatic heterocyclic derivatives were designed, synthesized and evaluated for in vitro antifungal activity. Many of the target compounds showed good inhibitory activity against Candida albicans and Cryptococcus neoformans. In particular, the isoxazole nuclei were more suited for improving the activity against Aspergillus spp. Among these compounds, 2-F substituted analogues 23g and 23h displayed the most remarkable in vitro activity against Candida spp., C. neoformans, A. fumigatus and fluconazole-resistant C.alb. strains, which is superior or comparable to the activity of the reference drugs fluconazole and voriconazole. Notably, the compounds 23g and 23h exhibited low inhibition profiles for various isoforms of human cytochrome P450 and excellent blood plasma stability.
- Zhao, Shizhen,Zhang, Xiangqian,Wei, Peng,Su, Xin,Zhao, Liyu,Wu, Mengya,Hao, Chenzhou,Liu, Chunchi,Zhao, Dongmei,Cheng, Maosheng
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- Sulfated polyborate catalyzed Kindler reaction: a rapid, efficient, and green protocol
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A rapid, green, and efficient one-pot, three-component Kindler reaction was developed using a sulfated polyborate catalyst. The method described the reaction of aldehydes, amines/ammonium acetate, and sulfur for the synthesis of thioamides using sulfated polyborate under a solvent free condition at 100?°C. The key features of the present protocol are high yields, short reaction time, easy workup, and recyclability of a catalyst which gives economical as well as ecological rewards. The present method also has an ability to tolerate a variety of functional groups. Graphical abstract: [Figure not available: see fulltext.].
- Khatri, Chetan K.,Mali, Anil S.,Chaturbhuj, Ganesh U.
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p. 1463 - 1468
(2017/07/18)
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- Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes
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The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.
- Li, Zheng,Qiu, Qianqian,Xu, Xue,Wang, Xuekun,Jiao, Lei,Su, Xin,Pan, Miaobo,Huang, Wenlong,Qian, Hai
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supporting information
p. 246 - 257
(2016/03/08)
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- Domino aryne precursor: Efficient construction of 2,4-disubstituted benzothiazoles
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An aryne precursor with a potential to perform domino aryne chemistry was proposed and synthesized. The reaction of this reagent with benzothioamide derivatives could afford 2,4-disubstituted benzothiazole with sequential incorporation of C-S, C-N, and C-C bonds on the consecutive three positions of the aryne precursor.
- Shi, Jiarong,Qiu, Dachuan,Wang, Juan,Xu, Hai,Li, Yang
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supporting information
p. 5670 - 5673
(2015/05/20)
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- Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media
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One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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supporting information
p. 408 - 416
(2014/01/06)
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- ANTIMICROBIAL SUBSTITUTED THIAZOLES AND METHODS OF USE
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Disclosed are compositions having activity against MRSA and/or VRSA, and methods of using the compositions to treat microbial infections.
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Paragraph 0049
(2014/05/08)
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- Agonists for the adenosine A1 receptor with tunable residence time. a case for nonribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines
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We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A 1 receptor (hA1AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.
- Louvel, Julien,Guo, Dong,Agliardi, Marta,Mocking, Tamara A. M.,Kars, Roland,Pham, Tan Phát,Xia, Lizi,De Vries, Henk,Brussee, Johannes,Heitman, Laura H.,Ijzerman, Adriaan P.
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supporting information
p. 3213 - 3222
(2014/05/20)
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- Discovery and characterization of potent thiazoles versus methicillin- and vancomycin-resistant Staphylococcus aureus
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Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) infections are growing global health concerns. Structure-activity relationships of phenylthiazoles as a new antimicrobial class have been addressed. We present 10 thiazole derivatives that exhibit strong activity against 18 clinical strains of MRSA and VRSA with acceptable PK profile. Three derivatives revealed an advantage over vancomycin by rapidly eliminating MRSA growth within 6 h, and no derivatives are toxic to HeLa cells at 11 μg/mL.
- Mohammad, Haroon,Mayhoub, Abdelrahman S.,Ghafoor, Adil,Soofi, Muhammad,Alajlouni, Ruba A.,Cushman, Mark,Seleem, Mohamed N.
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p. 1609 - 1615
(2014/03/21)
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- A novel process for the synthesis of 3,5-diaryl-1,2,4-thiadiazoles from aryl nitriles
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A novel and efficient process for the synthesis of 3,5-diaryl-1,2,4- thiadiazoles from aryl nitriles in 1-butyl-3-methylimidazolium bromide promoted by (NH4)2S and TCT-DMSO is described.
- Noei, Jalil,Khosropour, Ahmad Reza
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supporting information
p. 9 - 11
(2013/02/21)
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- A new application of rhodanine as a green sulfur transferring agent for a clean functional group interconversion of amide to thioamide using reusable MCM-41 mesoporous silica
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A novel thionation protocol for amide compounds, with the system rhodanine/secondary amine has been discovered. Clean and efficient synthesis of a variety of thioamides can be achieved through this simple and convenient method using MCM-41 mesoporous silica as an acid catalyst. For this purpose we have synthesized MCM-41 silica and characterized by using an array of sophisticated analytical techniques like BET, HR TEM, EDX, XRD, 29Si MAS NMR and FTIR. This reaction is therefore a very neat example of a functional group interconversion.
- Ray, Suman,Bhaumik, Asim,Dutta, Arghya,Butcher, Ray J.,Mukhopadhyay, Chhanda
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p. 2164 - 2170
(2013/05/08)
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- Sulfonic acid functionalized nano Γ-Al 2O 3: A new, efficient, and reusable catalyst for synthesis of thioamides
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Sulfonic acid functionalized nano γ-Al2O3 is easily prepared by the reaction of nano γ-Al2O3 with 1,3-propane sulfone. This reagent can be used as an eficient catalyst for the synthesis of thioamides. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered for several times.
- Yin, Zhikui,Zheng, Bin,Ai, Fang
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p. 1412 - 1420
(2013/10/08)
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- Nano n -propylsulfonated magnetic γ-Fe2O3 as an efficient and reusable catalyst for the synthesis of thioamides
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One-pot three-component reactions of aldehydes, amines, and sulfur are carried out in the presence of nano n-propylsulfonated magnetic γ-Fe2O3 as a catalyst for the synthesis of biologically interesting thioamide derivatives. The value of this catalytic method lies in its mild reaction catalyst and conditions, good yields, and ease of handling.
- Yin, Zhikui,Zheng, Bin
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p. 527 - 531
(2013/10/21)
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- Synthesis of thioamides by catalyst-free three-component reactions in water
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Three-component reactions involving amines, aldehydes, and elemental sulfur powder are reported to afford thioamides in a simple one-pot procedure in the absence of a catalyst. A variety of thioamides can be obtained in good to excellent yields up to 88 %. Three-component reactions involving amines, aldehydes, and sulfur powder afford thioamides in a simple one-pot procedure. A variety of substituted thioamides are obtained in good to excellent yields up to 88 %. Copyright
- Xu, Hualong,Deng, Hang,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
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supporting information
p. 7054 - 7057
(2013/11/06)
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- SYNTHESIS OF 2-(4-AMINOPHENYL) BENZOTHIAZOLE DERIVATIVES AND USE THEREOF
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The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R1 of formulae 1-6 is H, C1-10 alkyl, C1-10 alkoxy or C1-10 haloalkyl, and R2 of formulae 1-6 is H or C1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R1 and R2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.
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- A thiophosphoryl chloride assisted transformation of arylaldoximes to thioamides
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Primary benzothioamides were accessed from benzaldoximes (benzaldehyde oximes) via benzonitriles in a sequential tandem approach utilizing thiophosphoryl chloride as a dehydrating and thionating agent. Georg Thieme Verlag Stuttgart New York.
- Pandey, Lokesh Kumar,Pathak, Uma,Mathur, Sweta,Suryanarayana
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p. 377 - 379
(2012/03/27)
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- A THIONATION PROCESS AND A THIONATING AGENT
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A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N
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Page/Page column 12
(2012/08/27)
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- A thionation process and a thionating agent
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A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.
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Page/Page column 8
(2012/08/14)
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- Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
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Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1).
- Mayhoub, Abdelrahman S.,Marler, Laura,Kondratyuk, Tamara P.,Park, Eun-Jung,Pezzuto, John M.,Cushman, Mark
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experimental part
p. 510 - 520
(2012/03/10)
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- Microwave-assisted synthesis of thioamides with elemental sulfur
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Thioamides are prepared in moderate-to-good yields from the benzylamines or benzylamine derivatives by treatment with elemental sulfur under microwave and solvent-free conditions at 170.C in 15 min.
- Milen, Matyas,Abranyi-Balogh, Peter,Dancso, Andras,Keglevich, Gyoergy
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experimental part
p. 33 - 41
(2012/07/01)
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- O,O-Diethyl dithiophosphoric acid mediated direct synthesis of thioamides from aldehydes and ketones
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A general and convenient method for a one-pot conversion of aldehydes and ketones into thioamides has been developed. The protocol involves oximation of aldehydes and ketones followed by deoxygenative thioamidation of oximes with O,O-diethyl dithiophosphoric acid which acts as an acid as well a source of sulfur. The method is operationally simple, high yielding, and also applicable to the conversion of amides and nitriles into the corresponding thioamides.
- Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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p. 7113 - 7116
(2013/01/15)
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- Sulfated tungstate: An efficient catalyst for synthesis of thioamides via Kindler reaction
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New application of sulfated tungstate, a mildly acidic solid inorganic acid, as reusable heterogeneous catalyst for efficient Kindler reaction, a three component reactions of aldehydes, amines and sulfur, for synthesis of thioamides is discussed.
- Pathare, Sagar P.,Chaudhari, Pramod S.,Akamanchi, Krishnacharya G.
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experimental part
p. 125 - 129
(2012/07/03)
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