- Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents
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Abstract Benzoxazolone and benzothiazolone were used as template blocks to develop two series of dimers as anti-inflammatory and analgesic agents based on the concept of bivalent ligands. The first series (I) involved varying the carbon chain lengths extending from the piperazine core to the nitrogen atom of the dibenzo[d]oxazol-2(3H)-one or dibenzo[d]thiazol-2(3H)-one. The second series (II) was designed by changing the attachment point. All compounds were screened for their in vitro anti-inflammatory activity in terms of the inhibition of inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-κB). Seventeen compounds inhibited both targets. Eleven of them exhibited IC50 values below 3 μM while five compounds showed IC50 values of 1 μM or below. Most of the compounds were found to be devoid of cytotoxicity against mammalian kidney and solid tumors cell lines up to 25 μg/mL. In vivo anti-inflammatory and antinociceptive studies revealed that compounds 3j, 5t and 8b have significant anti-inflammatory and analgesic activity comparable to that of indomethacin and ketorolac, respectively.
- Abdelazeem, Ahmed H.,Khan, Shabana I.,White, Stephen W.,Sufka, Kenneth J.,McCurdy, Christopher R.
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Read Online
- A convenient metal-free method for the synthesis of benzothiazolethiones from o-haloanilines and carbon disulfide
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A convenient method has been developed for the preparation of a variety of 1,3-benzothiazole-2(3H)-thiones. The reaction proceeds from an o-haloaniline derivative and carbon disulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 80-140 °C to g
- Wang, Fei,Xi, Chanjuan,Zhao, Peng
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Read Online
- 9-Fluorenylmethyl (Fm) Disulfides: Biomimetic Precursors for Persulfides
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The development of a functional disulfide, FmSSPy-A (Fm = 9-fluorenylmethyl; Py = pyridinyl), is reported. It can effectively convert small molecule and protein thiols (-SH) to form -S-SFm adducts under mild conditions. This method allows for a H2S-free and biomimetic protocol to generate highly reactive persulfides (in their anionic forms). The high nucleophilicity of persulfides toward a number of thiol-blocking reagents is also demonstrated. The method holds promise for further understanding the chemical biology of persulfides and S-sulfhydration.
- Park, Chung-Min,Johnson, Brett A.,Duan, Jicheng,Park, Jeong-Jin,Day, Jacob J.,Gang, David,Qian, Wei-Jun,Xian, Ming
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Read Online
- Purification of high-purity 2-mercaptobenzothiazole by two-steps
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High-purity 2-mercaptobenzothiazole (2-MBT) is prepared from crude 2-MBT by aniline method under high pressure by solvent crystallization and deep impurity removal. For the first step of toluene purification, the semi-finished 2-MBT with excellent purity and yield can be obtained when the temperature of toluene solution reaches 100 oC and the content of toluene is about 1.5 times of that of crude 2-MBT. For the second step of deep purification, the by-products of semi-finished 2-MBT could be further removed by Na2SO3 when the mass ratio of water, the 2-MBT and Na2SO3 is 2: 1: 0.12 and the reaction condition is under 100 oC for 0.75 h. As a result, the purity and yield of 2-MBT can reach 99.9% and 97.3%, respectively. The preparation of high-purity 2-MBT would further optimize the market demand and meet the quality standard requirements for the development of other pharmaceutical intermediates or fine chemicals. This strategy solves the current problem of purification 2-MBT, and develops a new process technology route for the production of high-purity 2-MBT.
- Zhao, Zengbing,Chen, Bo,Cheng, Lanxing,Zhao, Yili,Chai, Yongli,Yang, Shucheng
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p. 851 - 859
(2021/05/19)
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- PROCESS FOR THE PURIFICATION OF 2 MERCAPTOBENZOTHIAZOLE
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The present disclosure relates to a process for the purification of a crude 2-mercaptobenzothiazole. The process comprises purifying the crude 2-mercaptobenzothiazole by using a suitable fluid medium to obtain pure 2-mercaptobenzothiazole and filtrate. The filtrate containing a dissolved portion of 2-mercaptobenzothiazole is further treated with a base and neutralized by using an acid to obtain pure 2-mercaptobenzothiazole. The process of the present disclosure is simple, economical, and produces pure 2-mercaptobenzothiazole with comparatively high yields.
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Page/Page column 7-13
(2021/11/26)
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- Cleaner and greener synthesis of 3H-benzothiazole-2-thione and its derivatives
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A cleaner and greener method of synthesis of 3H-benzothiazole-2-thione is being reported in this communication. In this method, various o-iodoaniline derivatives are reacted with carbon disulfide in the presence of Cs2CO3 and tetramethyl ammonium bromide (TMAB) to give 3H-benzothiazole-2-thione and its derivatives in higher yields.
- Srivastava, Nitin,Kishore, Ram
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- A new strategy for the synthesis of 2-mercaptobenzazole derivatives by green chemistry metrics
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A green and efficient method has been developed for the synthesis of 2-mercaptobenzazole derivatives via the reaction of commercially available aniline derivatives with low-cost and nontoxic potassium thiocyanate in water. The reactions proceeded smoothly under catalyst- and ligand-free conditions to give the corresponding products in good to excellent yields. The versatility, low cost, and environmental friendliness, in combination with high yields and easy work-up makes the procedure noteworthy.
- Vessally, Esmail,Monfared, Aazam,Eskandari, Zahra,Abdoli, Morteza,Hosseinian, Akram
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supporting information
p. 1 - 5
(2020/08/25)
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- A green approach for the synthesis of benzazolyl pyrimidinyl carbamothioates under ultrasonication and their antimicrobial activity
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A library of benzazolyl pyrimidinyl carbamothioates were prepared by the reaction of benzazolyl carbonothioates with pyrimidinyl-2-amine in the presence of an ionic liquid- 1-butyl-3-methylimidazolium hydroxide ([bmim]OH) under ultrasonication at a frequency of 35?kHz and tested for antimicrobial activity. Chloro- and nitro-substituted benzothiazolyl/benzimidazolyl pyrimidinyl carbamothioates displayed prominent antibacterial activity against Bacillus subtilis, while nitro-substituted benzothiazolyl/benzimidazolyl pyrimidinyl carbamothioates showed excellent antifungal activity against Aspergilus niger. Graphic abstract: [Figure not available: see fulltext.].
- Kayathi, Narendra Babu,Panga, Siva Sankar,Adivireddy, Padmaja,Venkatapuram, Padmavathi
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p. 2931 - 2943
(2021/07/26)
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- Developing a scaffold for urease inhibition based on benzothiazoles: Synthesis, docking analysis, and therapeutic potential
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The synthesis, in silico molecular docking, and in vitro urease inhibition studies of a novel series of benzothiazole derivatives are reported. The title compounds in the two series, namely, 2-({5-[(benzothiazol-2-ylthio)methyl]-1,3,4-oxadiazol-2-yl}thio)-1-(4-substituted-phenyl)ethan-1-one and 2-(benzothiazol-2-ylthio)-1-(4-substituted-phenyl)ethan-1-one oxime, were synthesized by the reaction of benzo[d]thiazole-2-thiol with different kinds of intermediates in several steps using both conventional and microwave techniques. All compounds were found to have an excellent degree of urease-inhibitory potential ranging between 16.16 ± 0.54 and 105.32 ± 2.10 μM when compared with the standard inhibitor acetohydroxamic acid with IC50 = 320.70 ± 4.24 μM. The structure–activity relationship was established in detail. The binding interactions of the compounds with the enzyme were confirmed through molecular docking. Further, 100 -ns molecular dynamics simulations were performed to investigate the stability and structural perturbations experienced by the most potent compound over the urease active site.
- ?zil, Musa,Tuzcuo?lu, ?zge,Emirik, Mustafa,Balta?, Nimet
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- Preparation method of mercapto-substituted nitrogen heterocyclic compound
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The invention discloses a preparation method of sulfhydryl substituted nitrogen heterocyclic compounds. The preparation method comprises the following steps: a substituted aniline compound and a disulfide compound are subjected to a stirring reaction in an organic solvent at 60-150 DEG C for 1-15 h, after the reaction, a product is cooled to room temperature and dissolved and diluted by ethanol and water, then acid is added for acidification until pH reaches 1-6, and filtering and drying are performed finally. The preparation process is simple, low in cost and easy to operate and produces little environmental pollution.
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Paragraph 0041-0043
(2021/06/02)
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- PdCl2/DMSO-Catalyzed Thiol-Disulfide Exchange: Synthesis of Unsymmetrical Disulfide
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Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals. Disulfide-containing organic dyes have also been prepared. This transformation could be extended to thiol-diselenide or thiol-ditelluride exchange affording RS-SeR′ or RS-TeR′.
- Guo, Jimin,Zha, Jianjian,Zhang, Tao,Ding, Chang-Hua,Tan, Qitao,Xu, Bin
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supporting information
p. 3167 - 3172
(2021/05/05)
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- Benzo[d]thiazole-2-thiol bearing 2-oxo-2-substituted-phenylethan-1-yl as potent selectivelasBquorum sensing inhibitors of Gram-negative bacteria
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Quorum sensing is a well-known term for describing bacterial cell-cell communication. Bacteria use quorum sensing pathways to respond to external factors such as nutrient availability, defense mechanisms, and coordinate host toxic behaviors such as biofilm formation, virulence production, and other pathogenesis. Discovery of novel compounds which inhibit quorum sensing without being antibiotic are currently emerging fields. Herein, the library of fifteen benzo[d]thiazole/quinoline-2-thiol bearing 2-oxo-2-substituted-phenylethan-1-yl compounds was designed, synthesized and evaluated to find novel quorum sensing inhibitors. Firstly, compounds were evaluated for their growth inhibitory activities at high concentrations up to 1000 μg mL?1towardPseudomonas aeruginosa. Under our conditions, twelve compounds showed moderate growth inhibitory activities in the concentration tested. To our delight, three compounds3,6and7do not affect the growth of the bacteria which were chosen for the evaluation of quorum sensing inhibitor activities. In theLasBsystem, our compounds3,6,7showed promising quorum-sensing inhibitors with IC50of 115.2 μg mL?1, 182.2 μg mL?1and 45.5 μg mL?1, respectively. In thePqsRsystem, no activity observed suggesting that the selectivity of the compound toward theLasBsystem. In addition,7showed the moderate anti-biofilm formation ofPseudomonas aeruginosa. Docking studies revealed that3,6and7binding to the active site ofPseudomonas aeruginosaquorum sensingLasRsystem with better affinity compared to reference compounds4-NPO. Finally, computation calculations suggest that compounds are a good template for further drug development.
- Quoc, Thang Nguyen,Thanh, Tung Truong,Xuan, Huy Luong
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p. 28797 - 28808
(2021/09/22)
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- Synthesis of thiocarbamoyl fluorides and isothiocyanates using amines with CF3SO2Cl
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A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.
- Jiang, Lvqi,Yi, Wenbin,Wei, Jingjing,Liang, Shuaishuai
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p. 12374 - 12381
(2020/11/10)
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- K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles
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We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.
- Deng, Guobo,Kuang, Daizhi,Liang, Yun,Yang, Yuan,Yu, Jiangxi,Zhang, Fuxing,Zhu, Xiaoming
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supporting information
p. 3789 - 3793
(2020/06/04)
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- A chemical looping technology for the synthesis of 2,2′-dibenzothiazole disulfide
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A novel chemical looping technology for the synthesis of 2,2′-dibenzothiazole disulfide (MBTS) with zero emissions has been developed. Through chemical cycling between carbonate and bicarbonate in the reaction system, the insoluble 2-mercaptobenzothiazole (MBT) can become soluble in the aqueous phase of sodium carbonate and then be oxidized efficiently by hydrogen peroxide and the absorption of CO2 with high selectivity. The mother liquor can be totally recycled by the desorption of CO2 without any generation of salt-containing wastewater. With the new synthesis technology, the product has high purity and reaches the standard of a superior product that can be applied as a vulcanization accelerator. When 5.0 wt% hydrogen peroxide was added dropwise over 40 min at 50 °C, the conversion ratio of MBT was over 98%. The mother liquor was recycled 5 times and no side-products were found. The whole process is clean and pollution-free, which greatly reduces the burden of hazardous waste treatment and brings great environmental benefits.
- Tian, Jiaxin,Jiayu Hu,Wang, Kai,Deng, Jian,Luo, Guangsheng
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p. 2778 - 2785
(2020/06/17)
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- Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media
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A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C-S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.
- Chen, Jin-Quan,Dong, Zhi-Bing,Guo, Jia
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p. 1927 - 1933
(2020/07/03)
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- Preparation method of cefepime hydrochloride having content of genotoxic impurity 2-mercaptobenzothiazole reduced
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The invention belongs to the field of medicinal chemistry, and relates to a preparation method of cefepime hydrochloride. The preparation method comprises the steps: in a dichloromethane solvent, in the presence of triethylamine, carrying out acylation reaction on a cefepime side chain compound and AE active ester; after the reaction, adding water into the reaction liquid, and extracting to obtaina water phase; adding hydrochloric acid into the water phase to adjust the pH value of the water phase to 2.0-2.5, then adding a water-insoluble organic solvent, extracting, standing for layering, and separating out the water phase; adjusting the pH value of the water phase to 1.0-1.5 with hydrochloric acid after activated carbon decoloration, and adding a crystallization solvent to obtain cefepime hydrochloride. According to the cefepime hydrochloride prepared by the preparation method disclosed by the invention, the content of a genotoxic impurity 2-mercaptobenzothiazole in the cefepime hydrochloride is reduced to 1-5 mmp, even 1-3 mmp, so that the safety of a cefepime hydrochloride medicine is improved.
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Paragraph 0031-0050
(2020/01/25)
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- Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source
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A facile and effective C–H functionalization strategy for the synthesis of 2-mercaptobenzothiazoles and 2-mercaptobenzoxazoles is described. 1,3-Propanedithiol was employed to convert benzothiazoles and benzoxazoles to the corresponding heteroarylthiols in the presence of potassium hydroxide and DMSO. This novel protocol is featured by direct C–H mercaptalization of heteroarenes and a simple reaction system.
- Xiao, Yan,Jing, Bing,Liu, Xiaoxia,Xue, Hongyu,Liu, Yajun
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supporting information
p. 279 - 284
(2019/02/20)
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- A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from: O -iodoanilines, DMSO and potassium sulfide
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Under catalyst-free and additive-free conditions, a novel, convenient, eco-friendly method for the synthesis of benzothiazolethiones has been developed. The three-component reaction of o-iodoanilines and K2S with DMSO proceeded smoothly and the corresponding benzothiazolethiones were obtained with good isolated yields. Meanwhile, this method could be used for the synthesis of thioureas from primary diamines. Furthermore, mechanism research showed that DMSO not only functioned as a carbon source, but also as a mild oxidant in this reaction.
- Zhu, Xiaoming,Li, Wenguang,Luo, Xiai,Deng, Guobo,Liang, Yun,Liu, Jianbing
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p. 1970 - 1974
(2018/05/23)
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- Preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as mercapto source
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The invention belongs to the synthesis field of medicine chemical intermediate, and provides a preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as a mercapto source. According to the preparation method, under inert gas protection, in dimethyl sulphoxide solvent, substituted benzoxazole(thiazole) and 1,3-dimercaptopropane are subjected to 120 to 140 DEG Cheating stirring in the presence of an alkali, after 12 to 24h of reaction, an obtained reaction solution is cooled to room temperature, and is subjected to acidifying post-treatment so as to obtaina product. The reaction conditions are simple; function group compatibility is excellent; yield is relatively high; the obtained 2-mercaptobenzoxazole(thiazole) compounds are important organic synthesis intermediates; application range in the field of chemical raw material, pesticide, and medicine is wide; and practical value and social and economic benefit are excellent.
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Paragraph 0024; 0025
(2018/10/02)
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- Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water
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An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.
- Liu, Xing,Zhang, Shi-Bo,Zhu, Hui,Dong, Zhi-Bing
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p. 11703 - 11711
(2018/10/02)
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- Preparation and application of coumarin 2-hydrazinobenzothiazole Schiff base Cd fluorescent probe
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The invention relates to the field of fluorescent probes, and in particular relates to a coumarin 2-hydrazinobenzothiazole Schiff base fluorescent probe and an application thereof. The fluorescent probe has a specific structure shown in the description. The fluorescent probe provided by the invention can recognize Cd in an EtOH-H2O (95:5, v/v, and HEPES 20 mmol/L) solution, and has the advantages of exhibiting excellent selectivity in competition with other ions, and having higher fluorescence sensing properties, low detection limit, high detection sensitivity and a high fluorescence quantum yield.
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Paragraph 0039-0042; 0060-0061; 0067-0068
(2018/09/11)
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- AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate
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A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.
- Liu, Xing,Zhang, Shi-Bo,Dong, Zhi-Bing
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p. 5406 - 5411
(2018/10/20)
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- SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
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The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017
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Paragraph 0032; 0033; 0063; 0067; 0069; 0070
(2017/09/02)
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- Metal sulfide: An efficient promoter for the synthesis of 2-mercaptobenzothiazoles from 2-haloanilines and carbon disulfide
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A convenient method has been developed for the preparation of a variety of 2-mercaptobenzothiazoles from 2-haloanilines and CS2 mediated by metal sulfide. In this reaction, 2-haloanilines reacted with CS2 in the presence of Na2S · 9H2O to form 2-mercaptobenzothiazoles. Na2S · 9H2O functioned both as an activator of CS2 and as a base. Furthermore, NMR analysis was used to identify the different reaction mechanisms of 2-haloanilines and CS2 mediated by Na2S or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which demonstrated that Na2S interacted only with CS2, while DBU reacted with both 2-iodoaniline and CS2.
- Zhang, Tianmiao,Qin, Weijing,Zhu, Ning,Han, Limin,Wang, Liubo,Hong, Hailong
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supporting information
p. 1916 - 1925
(2017/09/27)
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- A preparing method of a rubber vulcanization accelerator 2-mercaptobenzothiazole
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A preparing method of a rubber vulcanization accelerator 2-mercaptobenzothiazole is disclosed. The method includes adding benzothiazole and sulfur which are raw materials into a reaction kettle, starting stirring and heating, heating to 200 DEG C +/- 5 DEG C, maintaining the temperature, and preparing a 2-mercaptobenzothiazole crude product after a reaction at a maintained temperature is finished, refining the 2-mercaptobenzothiazole crude product with a composite solvent process to obtain a 2-mercaptobenzothiazole high-quality product. The method does not adopt toxic dangerous aniline or carbon disulfide, and can greatly reduce harms to body health of operators. The method is free of generation of hydrogen sulfide that is a highly toxic product in a preparation process, thus reducing harms to bodies of operators and pollution to the environment. The method has significant economic benefit and social benefit.
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Paragraph 0040; 0041; 0042; 0043; 0044; 0045; 0046-0081
(2017/03/08)
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- Elemental sulfur as a sulfuration agent in the copper-catalyzed C-H bond thiolation of electron-deficient arenes
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By utilizing elemental sulfur as the thiolation agent and oxidant, a copper-catalyzed direct C-H bond thiolation of electron-deficient arenes was demonstrated. Various electron-deficient arenes were proved to be suitable for this transformation. Preliminary mechanistic studies indicated that this reaction underwent a radical pathway, in which the trisulfur radical anion (S3-) might play a vital role. Meanwhile, KIE experiments suggested that C-H bond cleavage was not involved in the rate-determining step.
- Yan, Haiming,Huang, Zhiliang,Chen, Meng,Li, Cuiting,Chen, Ya,Gao, Meng,Lei, Aiwen
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supporting information
p. 8276 - 8279
(2017/10/23)
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- Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: Metal sulfide-disulfide dynamic interchange reaction
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A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS2 mediated by a metal sulfide in water is described. This synthetic methodology could be used to prepare diverse 2-mercaptobenzothiazole derivatives in good to excellent yields. In this paper, the concept of metal sulfide-disulfide dynamic interchange reaction was put forward. Then the intermediates of the interchange reaction between NaHS and a disulfide were detected by LC-MS, which demonstrated that the S-S bond of the disulfide could be broken by the metal sulfide through the dynamic interchange reaction. In addition, NaHS was eventually transformed into sulfur S8 by the dynamic interchange reaction. Moreover, the underlying mechanism of 2-mercaptobenzothiazole formation is proposed, in which NaHS not only acts as an S-S bond cleaving agent but also as an activator of CS2. As a result, a novel synthetic route for the preparation of sulfur-containing heterocycles from a disulfide is developed.
- Lou, Chunqing,Zhu, Ning,Fan, Ronghua,Hong, Hailong,Han, Limin,Zhang, Jianbin,Suo, Quanling
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p. 1102 - 1108
(2017/08/15)
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- Coordination modes of 2-mercapto-1,3-benzothiazolate in gallium and indium complexes
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2-Mercapto-1,3-benzothiazole (mbztH) may act as a chelating or bridging ligand. In this study, reactions of mbztH with Me3Ga and Me3In were examined. The products were characterized by NMR spectroscopy, elemental analyses, melting point, and molecular weight determinations. Formation of mononuclear chelating complexes Me2M(mbzt) (M?=?Ga, In) was observed in solutions. Crystallization of Me2M(mbzt) yielded uncommon non-symmetrical dinuclear complexes Me4M2(mbzt)2, in which one metal is bonded to two sulfurs and the other to two nitrogens.
- Basiak, Dariusz,Ziemkowska, Wanda,Socha, Pawe?,Dobrzycki, ?ukasz,Ochal, Zbigniew,Pindelska, Edyta
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p. 1528 - 1535
(2017/05/15)
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- Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles
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The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.
- Mallikarjuna Reddy,Lavanya,Lakshmi Teja,Padmaja,Padmavathi
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p. 2755 - 2766
(2017/09/26)
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- Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of novel benzothiazole-triazole derivatives
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Benzothiazole-triazole derivatives 6a–6s have been synthesized and characterized by1H-NMR and13C-NMR. All synthetic compounds were screened for their in vitro α-glucosidase inhibitory activity by using Baker’s yeast α-glucosidase enzyme. The majority of compounds exhibited a varying degree of α-glucosidase inhibitory activity with IC50 values between 20.7 and 61.1 μM when compared with standard acarbose (IC50 = 817.38 μM). Among the series, compound 6s (IC50 = 20.7 μM) bearing a chlorine group at the 5-position of the benzothiazole ring and a tert-butyl group at the para position of the phenyl ring, was found to be the most active compound. Preliminary structure-activity relationships were established. Molecular docking studies were performed to predict the binding interaction of the compounds in the binding pocket of the enzyme.
- Gong, Zipeng,Peng, Yaping,Qiu, Jie,Cao, Anbai,Wang, Guangcheng,Peng, Zhiyun
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- An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water
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An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.
- Liu, Xing,Liu, Min,Xu, Wan,Zeng, Meng-Tian,Zhu, Hui,Chang, Cai-Zhu,Dong, Zhi-Bing
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p. 5591 - 5598
(2017/12/06)
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- Green synthesis method of 2-mercaptobenzothiazoles derivatives
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The invention provides a green synthesis method of 2-mercaptobenzothiazoles derivatives. The method comprises the step of enabling o-amino aromatic disulfide, CS2 and metal sulfide to be in contact with a solvent to obtain the 2-mercaptobenzothiazoles derivatives, wherein the solvent is at least one of water, low carbon alcohol, dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), N-methyl pyrrolidone (NMP) and 1, 4-dioxane. Compared with the prior art, the method enables the o-amino aromatic disulfide to react with the CS2, thus rapidly and efficiently synthesizing the 2-mercaptobenzothiazoles derivatives; the raw materials used by the method are stable, easy to obtain and low in cost; the synthesis method is simple and convenient in operation, short in step, high in yield and easy in purification of a product.
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Paragraph 0050; 0051
(2018/02/04)
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- MANUFACTURING METHOD OF ANTIOXIDANT OR VULCANIZATION ACCELERATOR
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PROBLEM TO BE SOLVED: To manufacture an antioxidant or a vulcanization accelerator by a method with industrially excellent productivity while using plant as a raw material. SOLUTION: A manufacturing method includes a process of heat decomposing indigo extracted from plant in absence of a solvent to convert into aniline and/or N-alkyl aniline and a process of synthesizing an amine-based antioxidant, a benzimidazole-based antioxidant, a thiazole-based vulcanization accelerator, a sulfenamide-based vulcanization accelerator, a guanidine-based vulcanization accelerator or an alkylphenyl dithiocarbamate-based vulcanization accelerator from the resulting aniline or N-alkyl aniline. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0035
(2017/08/14)
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- MANUFACTURING METHOD OF ANTIOXIDANT OR VULCANIZATION ACCELERATOR
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PROBLEM TO BE SOLVED: To manufacture an antioxidant or a vulcanization accelerator by a method with industrially excellent productivity while using plant as a raw material. SOLUTION: A manufacturing method includes a process of hydrolyzing indigo extracted from plant to obtain 2-aminobenzoic acid, a process of decarbonating the resulting 2-aminobenzoic acid to obtain aniline, a process of synthesizing an amine-based antioxidant, a benzimidazole-based antioxidant, a thiazole-based vulcanization accelerator, a sulfenamide-based vulcanization accelerator, a guanidine-based vulcanization accelerator or an alkylphenyl dithiocarbamate-based vulcanization accelerator from the resulting aniline. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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Paragraph 0037
(2017/10/11)
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- Inorganic metal sulfide neighbouring halogen promoting the reaction of aniline with carbon disulfide synthesis of 2-mercaptobenzothiazole method
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The invention provides a method for synthesizing a 2-mercaptobenzothiazole derivate by utilizing 2-halogen phenylamine, carbon disulfide and inorganic metal sulfide as raw materials and relates to the field of medicines, industry and agriculture and the like. The synthesizing method comprises the steps of dissolving 2-halogen phenylamine and inorganic metal sulfide in an appropriate solvent, adding carbon disulfide to react for a certain time under the conditions of 90-130 DEG C, and performing purification treatment to obtain the product. The 2-mercaptobenzothiazole derivate can be synthesized rapidly and efficiently through the method, the raw materials used for the method are non-toxic, cheap and free of pollution, reaction conditions are moderate, aftertreatment is simple, and the yield is high.
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Paragraph 0015-0016
(2017/03/17)
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- Benzothiazole compound and use thereof
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The invention belongs to the technical field of medicine and relates to novel benzothiazole compounds capable of inhibiting gastric acid secretion and resisting Helicobacter pylori. The compounds effectively bind with the H+K+-ATP enzyme in vivo so as to eventually inhibit gastric acid secretion, and the compounds have good gastric acid inhibiting and anti-gastric ulcer activity. The structural formula (I) of the compounds is described in the specification, and R, m and n in the formula (I) are defined in claim 1.
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Paragraph 0077; 0087; 0088
(2016/10/10)
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- Chalcogen containing heterocyclic scaffolds: New hybrids with antitumoral activity
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In this work, 27 novel hybrid derivatives containing diverse substituents with chalcogen atoms (selenium or sulfur) and several active heterocyclic scaffolds have been synthesized. Compounds were tested against two human cancer cells lines (MCF7 and PC-3) and a normal human mammary epithelial cell line (184B5) in order to determine their activity and selectivity against malignant cells. Ten compounds showed GI50values below 10?μM in at least one of the cancer cell lines and six of them exhibited a selectivity index higher than 9. In general, selenium-containing compounds were more active than their corresponding sulfur analogs but we found some thiocyanate derivatives with comparable or higher activity and selectivity. Among the different substituents, the seleno- and thio-cyanate groups showed the most promising results. On the basis of their potent activity and high selectivity index, compounds 7e and 8f (containing a thiocyanate and a selenocyanate group, respectively) were selected for further biological evaluation. Both the compounds induced caspase-dependent cell death and cell cycle arrest in G2/M phase. In addition, these compounds do not violate any of the Lipinski's Rule of Five and thus possess good potential to become drugs, compound 7e being particularly promising.
- Alcolea, Verónica,Plano, Daniel,Encío, Ignacio,Palop, Juan Antonio,Sharma, Arun K.,Sanmartín, Carmen
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p. 407 - 418
(2016/08/04)
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- An efficient copper-catalyzed synthesis of 2-mercaptobenzothiazole through S-arylation/heterocyclization of 2-haloaniline with potassium xanthate
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A mild and efficient methodology to produce 2-mercaptobenzothiazoles in DMF via ortho-haloaniline coupling with potassium O-ethyl dithiocarbonate catalyzed by copper without a ligand has been developed.
- Liu, Lei,Zhu, Ning,Gao, Min,Zhao, Xiaole,Han, Limin,Hong, Hailong
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p. 699 - 701
(2016/05/09)
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- Liquid chromatography/mass spectrometry identification of intermediates and vulcanization products by using squalene as vulcanization model compound
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Rationale Sulfur-vulcanized rubber is a three-dimensional polymer network, insoluble in all organic solvents. For this reason, vulcanization products are difficult to study and identify by conventional analytical techniques. To simplify this task, low molecular weight olefins have been used as model compounds (MCs) in place of rubber in vulcanization experiments. Methods In this work, the vulcanization process was investigated using squalene (SQ) as MC. By-products, intermediates and products were separated by semipreparative reversed-phase liquid chromatography (RPLC) with UV detection. Each fraction was collected, concentrated and characterized by flow injection analysis (FIA) and non-aqueous reversed-phase (NARP) LC coupled to positive atmospheric pressure chemical ionization mass spectrometry (APCI-MS). Under the latter conditions, an Information-Dependent Acquisition (IDA) was performed on a linear ion trap mass spectrometer to obtain structural information. Results Several vulcanized compounds containing up to three SQ molecules, cross-linked with chains involving up to 14 sulfur atoms overall, have been identified along with some of their oxidized products (epoxides and hydroperoxides). The FIA-MS spectra showed peak clusters, each of which included two-three subclusters; the interpretation was complicated by the occurrence of more ion species per product, by the unsaturation grade and by the characteristic isotopic distribution of sulfur. The enhanced product ion scan (EPI) spectra, acquired during the IDA experiments, supported the FIA-MS identification allowing one to count the number of sulfur atoms. Conclusions The sensitivity of the developed analytical strategy was due to the enrichment factor achieved via semipreparative chromatography and the very good response of the APCI detection. Pattern fragmentation and chromatographic behavior simplified the identification of the cured compounds and their oxidized products, whose occurrence was related to the grade of oxidation of SQ used as reagent.
- Giansanti, Luisa,Aleandri, Simone,Altieri, Barbara,Caretti, Fulvia,Mancini, Giovanna,Morosetti, Stefano,Ventura, Salvatore,Pérez-Fernández, Virginia,Gentili, Alessandra
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p. 1339 - 1348
(2016/05/24)
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- STABLE COMPOSITIONS OF THIABENDAZOLE AND IODINE-CONTAINING FUNGICIDES
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The present invention relates to stable compositions for the fungicidal equipment of thermoplastic polymers, in particular PVC, comprising thiabendazole, at least one iodine-containing fungicide and at least one epoxide and optionally further fungicidally active compounds, and also to methods for preparing these formulations and to uses thereof for the protection of thermoplastic polymers against attack and destruction by microorganisms. Moreover, the invention relates to mold-resistant PVC materials equipped with the compositions according to the invention.
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- Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
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A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.
- Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun
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supporting information
p. 2205 - 2212
(2015/07/27)
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- Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o-Iodoanilines, Isocyanide, and Potassium Sulfide
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An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.
- Dang, Pan,Zeng, Weilan,Liang, Yun
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supporting information
p. 34 - 37
(2015/07/28)
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- Sulfenylation of β-Diketones Using C- H Functionalization Strategy
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Sulfenylation of β-diketones is challenging as β-diketones undergo deacylation after sulfenylation in the reaction medium. The sulfenylation of β-diketones without deacylation under metal-free conditions at ambient temperature via a cross dehydrogenative coupling (CDC) strategy is reported. The resultant products can be further manipulated to form α,α-disubstituted β-diketones and pyrazoles.
- Varun, Begur Vasanthkumar,Gadde, Karthik,Prabhu, Kandikere Ramaiah
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p. 2944 - 2947
(2015/06/30)
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- Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S-Arylation/Heterocyclization of 2-Haloaniline with Potassium Xanthate
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A mild and practical method for the synthesis of 2-mercaptobenzothiazole has been developed by using iron as an efficient catalyst. The present tandem reaction process allows access to a wide range of 2-mercaptobenzothiazoles in good to excellent yields by the reaction of 2-haloaniline with potassium O-ethyl dithiocarbonate in the presence of FeF3 as a catalyst and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as a ligand under an atmosphere of argon.
- Gao, Min,Lou, Chunqing,Zhu, Ning,Qin, Weijing,Suo, Quanling,Han, Limin,Hong, Hailong
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supporting information
p. 2378 - 2385
(2015/10/12)
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- Synthesis of Benzoxazolylthiomethyl and Benzthiazolylthiomethyl Quinazolin-4(3 h)-ones
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o-Aminophenol (1a, X = O) or o-aminothiophenol (1b, X = S) was reacted with carbon disulfide in ethanol containing KOH under reflux to obtain 2-mercaptobenzoxazole (2a, X = O) and 2-mercaptobenzthiazole (2b, X = S), respectively. Condensation of 2a and 2b each with chloroacetic acid gave 2-(benzoxazol-2-ylthio)acetic acid (3a, X = O) and 2-(benzthiazol-2-ylthio)acetic acid (3b, X = S) respectively which with anthranilamide gave 2-((benzoxal-2-ylthio)methyl) quinazolin-4(3H)-one (5a, X = O) and 2-((benzthiazol-2-ylthio)methyl)quinazolin-4(3H)-one (5b, X = S) respectively. The products 5a,b could be prepared in three other routes involving the general sequences 6→2→5, 6→7→5 and 8→9→5.
- Rafeeq, Mohammad,Ramana Reddy, Chittireddy Venkata,Dubey, Pramod Kumar
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p. 1857 - 1864
(2015/12/12)
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- FUNGICIDAL PENFLUFEN MIXTURES
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The invention relates to mixtures comprising penflufen, to the use of these mixtures for protecting industrial materials and to a method for treating industrial materials with the penflufen mixtures.
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- Regioselective thiolation of arenes and heteroarenes: C-H functionalization strategy for C-S bond formation
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A facile transition-metal-free oxidative cross-dehydrogenative coupling reaction involving selective formation of a C-S bond leading to the synthesis of arylthiobenzoxazoles, heteroarylthiobenzoxazoles, and arylthiobenzothiazoles has been described. This highly regioselective C-H functionalization reaction with electron-rich aromatic systems including heteroaromatics is achieved by reversing the reactivity of sulfur in the presence of a suitable oxidant and strong acid. (Chemical Equation Presented).
- Varun, Begur Vasanthkumar,Prabhu, Kandikere Ramaiah
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p. 9655 - 9668
(2015/01/16)
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- Lanthanide-catalyzed cyclocarbonylation and cyclothiocarbonylation: A facile synthesis of benzannulated 1,3-diheteroatom five- and six-membered heterocycles
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La[N(SiMe3)2]3 proves to be an efficient catalyst system for the cyclocarbonylation of 1,2-disubstituted benzenes with isocyanates. In this approach, aryl/alkyl isocyanates react with o-phenylenediamine, o-aminophenol, o-aminothiophenol, catechols and anilines ortho-substituted by CH2NH2 and CONH2 to form, respectively, the corresponding benzimidazolones, benzoxazolones, benzothiazolones, benzodioxolones, 3,4-dihydroquinazolin-2(1H)-one, and quinazolinediones. These results represent the first example of lanthanide-catalyzed carbonylation. This methodology is also applicable for the preparation of various benzannulated 1,3-diheteroatom cyclic thioketones starting from aryl/alkyl isothiocyanates or CS2 in good to excellent yields. Based on the results of experiments performed using an o-aminobenzamido dianion lanthanide complex, a general mechanism, involving the tandem reaction of two lanthanide-ligand bonds with one heterocumulene molecule, is proposed as well.
- Jing, Yufeng,Liu, Ruiting,Lin, Yanghui,Zhou, Xigeng
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p. 1117 - 1125
(2014/08/18)
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- Studies and X-ray determinations with 2-(acetonylthio)benzothiazole: Synthesis of 2-(benzothiazol-2-ylthio)-1-phenylethanone and 2-(acetonylthio) benzothiazole by C - S bond cleavage of 2-(acetonylthio)benzothiazole in KOH
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New route for the synthesis of 2-(benzothiazol-2-ylthio)-1-phenylethanone (6) and 2-(acetonylthio)benzothiazole (1) by using phenacyl bromide and α-chloroacetone, respectively, through carbon-sulfur bond cleavage reactions in a basic medium has been generated. Treatment of 1 with malononitrile and elemental sulfur afforded the corresponding derivative of 2-amino-3-cyanothiophene (12), whereas treatment of 1 with cyanoacetohydrazide afforded the corresponding derivative of cyanoacetylhydrazone derivative (13). The structure of the synthesis compounds has been established on the basis of elemental analyses, 1H-NMR, 13C-NMR, correlation spectroscopy, heteronuclear single quantum coherence, MS spectra, and X-ray crystallographic investigations.
- Al-Omran, Fatima,El-Khair, Adel Abou
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