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135-57-9Relevant academic research and scientific papers
Preparation method of high-quality peptizer
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Paragraph 0020-0027, (2021/01/28)
The invention discloses a preparation method of a high-quality peptizer DBD, which belongs to the technical field of chemical engineering. The method comprises the following steps: after benzothiazoleis subjected to a ring-opening reaction, adding a certain volume of an organic solvent for dissolution, then carrying out an oxidation reaction, and finally carrying out an acylation reaction to prepare the peptizer DBD. In the process provided by the invention, the production efficiency and quality of an intermediate diphenyl amino disulfide are improved, the oxidation reaction and acylation reaction are facilitated, and the yield and quality of the final peptizer DBD are improved; solid-liquid separation and other treatment on the intermediate diphenyl amino disulfide are not needed, the technological process is simple, and wastewater discharge is reduced; according to the method, the organic solvent is recycled, the COD content in the produced wastewater is low, the post-treatment wastewater cost is easy to reduce, and the whole method is high in environmental friendliness.
Industrialized preparation method of rubber peptizer DBD
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Paragraph 0017; 0018; 0019; 0020, (2018/06/21)
The invention relates to a preparation method of a rubber aid, and particularly discloses a novel preparation method of a rubber peptizer DBD. The industrialized preparation method of the rubber peptizer DBD is characterized by comprising the following steps: 1) producing 2,2-dinitrodisulfide by using o-nitrochlorobenzene and sodium polysulfide under the heating reflux condition; 2) adding aceticacid to reduce the 2,2-dinitrodisulfide into diphenyl aminodisulfide; and 3) adding benzoyl chloride and an acid-binding agent into the product obtained in the step 2) in a mixed solvent to obtain theDBD. In the process, the step 1) and the step 2) are conducted continuously, and separation and purification are not needed. The step 3) can be conducted only through simple separation of the productin the step 2), purification is not needed, and the process is simplified greatly; furthermore, yield loss caused by purification is reduced; in addition, the mixed solvent and the triethylamine canbe recycled and the whole process is little in discharge.
Copper-Catalyzed Arylation of Benzothiazoles with Toluene Derivatives: Synthesis of 2-Arylbenzothiazole
Li, Chengliang,Deng, Hongmei,Jin, Tao,Liu, Zhiqiang,Jiang, Ruolan,Li, Chunju,Jia, Xueshun,Li, Jian
, p. 4350 - 4356 (2017/09/12)
A copper-catalyzed reaction of benzothiazole and readily available toluene derivatives has been disclosed. This protocol is proposed to proceed through the oxidation of toluene and ring opening of benzothiazole, thus providing a new pathway for the synthesis of 2-arylbenzothiazoles..
Discovery of new low-molecular-weight p53-Mdmx disruptors and their anti-cancer activities
Uesato, Shinichi,Matsuura, Yoshihiro,Matsue, Saki,Sumiyoshi, Takaaki,Hirata, Yoshiyuki,Takemoto, Suzuho,Kawaratani, Yasuyuki,Yamai, Yusuke,Ishida, Kyoji,Sasaki, Tsutomu,Enari, Masato
, p. 1919 - 1926 (2016/04/05)
Although several p53-Mdm2-binding disruptors have been identified to date, few studies have been published on p53-Mdmx-interaction inhibitors. In the present study, we demonstrated that o-aminothiophenol derivatives with molecular weights of 200-300 selectively inhibited the p53-Mdmx interaction. S-2-Isobutyramidophenyl 2-methylpropanethioate (K-178) (1c) activated p53, up-regulated the expression of its downstream genes such as p21 and Mdm2, and preferentially inhibited the growth of cancer cells with wild-type p53 over those with mutant p53. Furthermore, we found that the S-isobutyryl-deprotected forms 1b and 3b of 1c and S-2-benzamidophenyl 2-methylpropanethioate (K-181) (3c) preferentially inhibited the p53-Mdmx interaction over the p53-Mdm2 interaction, respectively, by using a Flag-p53 and glutathione S-transferase (GST)-fused protein complex (Mdm2, Mdmx, DAPK1, or PPID). In addition, the interaction of p53 with Mdmx was lost by replacing a sulfur atom with an oxygen atom in 1b and 1c. These results suggest that sulfides such as 1b, 3b, 4b, and 5b interfere with the binding of p53-Mdmx, resulting in the dissociation of the two proteins. Furthermore, the results of oral administration experiments using xenografts in nude mice indicated that 1c reduced the volume of tumor masses to 49.0% and 36.6% that of the control at 100 mg/kg and 150 mg/kg, respectively, in 40 days.
Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives
Castanheiro, Thomas,Suffert, Jean,Gulea, Mihaela,Donnard, Morgan
, p. 2588 - 2591 (2016/06/15)
An unprecedented three-component reaction involving a 2,2′-diaminodiaryl disulfide, copper cyanide, and an electrophile is described. This transformation is based on an oxidative copper-mediated S-cyanation as a key step and involves a cyanation/cyclization/acylation domino sequence enabling a rapid and efficient synthesis of diversely substituted 2-aminobenzothiazole derivatives. Notably, this reaction proceeds via an original mechanism involving an intermolecular migration of the acyl group.
3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) mediated metal-free mild oxidation of thiols to disulfides in aqueous medium
Samanta, Suvendu,Ray, Shounak,Ghosh, Abhisek Brata,Biswas, Papu
, p. 39356 - 39363 (2016/06/01)
Thiols are efficiently oxidized to disulfides (RSSR) in the presence of 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) in aqueous medium, as well as in the absence of a solvent under mild and metal-free conditions. A broad range of alkyl, aryl and heterocyclic symmetrical disulfides can be easily obtained in almost quantitative yields. The X-ray single crystal structure of 2-aminocyclopent-1-ene-1-carbothioic dithioperoxyanhydride (disulfide obtained from 2-aminocyclopentene-1-dithiocarboxylic acid, ACDA) is reported. The reaction mechanism has been studied thoroughly. It is shown that the reaction proceeds through the formation of an organosulphur radical. Pytz interacts with thiol to accept one electron and produces an organosulphur radical. Pytz ultimately accepts two electrons to form H2pytz and is capable of oxidizing 2 equivalents of thiols.
Solid phase synthesis of benzothiazolyl compounds
Mourtas, Spyros,Gatos, Dimitrios,Barlos, Kleomenis
, p. 2201 - 2204 (2007/10/03)
2-Aminobenzenethiol, bound through its thiol function to the 2-chlorotrityl (Clt)-, trityl (Trt)-, 4-methyltrityl (Mtt)- and 4-methoxytrityl (Mmt)-resins, was acylated at the amino-function by aliphatic and aromatic acids. The obtained 2-N-acyl-aminobenzenethiols were cleaved from the resin by treatment with trifluoroacetic acid solutions in dichloromethane. The 2-N-acyl-aminobenzenethiols released from the resin were cyclised to the corresponding 2-substituted benzothiazoles, by standing in a solution of dithiothreitol in DMF or methanol for 1-3 h at room temperature.
Bis(2-(acylamino)phenyl) disulfides, 2-(acylamino)benzenethiols, and S-(2-(acylamino)phenyl) alkanethioates as novel inhibitors of cholesteryl ester transfer protein
Shinkai,Maeda,Yamasaki,Okamoto,Uchida
, p. 3566 - 3572 (2007/10/03)
A series of bis(2-(acylamino)phenyl) disulfides, 2-(acylamino)benzenethiols, S-(2-(acylamino)-phenyl) alkanethioates, and related compounds were synthesized, and their inhibitory effect on cholesteryl ester transfer protein activity in human plasma was evaluated. This study elucidated the structural requirements for inhibitory activity and determined that the optimum compound was S-(2-((1-(2-ethylbutyl)cyclohexane)carbonylamino)phenyl) 2-methylpropanethioate (27) (JTT-705). This compound achieved 50% inhibition of CETP activity in human plasma at a concentration of 9 μM and 95% inhibition of CETP activity in male Japanese white rabbits at an oral dose of 30 mg/kg. It increased the plasma HDL cholesterol level by 27% and 54%, respectively, when given at oral doses of 30 or 100 mg/kg once a day for 3 days to male Japanese white rabbits.
Cooperative redox regulation of [4Fe-4S] ferredoxin model arenethiolate complexes by NH· · ·S hydrogen bonds and an aromatic C-H···S interaction
Ueno, Takafumi,Inohara, Masahiro,Ueyama, Norikazu,Nakamura, Akira
, p. 1077 - 1083 (2007/10/03)
A series of the model complexes containing ortho-substituted arenethiolato ligands, ((Et4N)2[Fe4S4(S-2- RCONHC6H4)4] {R=Ph (1), 4-MeO-C6H4 (2), and4-F-C6H4 (3)} and (Et4N)2[Fe 4S4{S-2,6-(RCONH)2C6H 3}4] {R=Ph (4), 4-MeO-C6H4 (5), and 4-F-C6H4 (6)}) was synthesized and characterized by 1NMR, IR spectroscopy, and cyclic voltammetry. The solution structures of these complexes are discussed based on their 1NMR T1 data and moleculardynamics calculations. Complex 4 has a shorter distance (av. 4.3 A) between the protons of the benzoyl group and the inorganic sulfur atom of the [4Fe-4S] cluster than the corresponding ones of 1 (av. 6.2 A). These results indicate the C-H · · · S interaction between the protons of the benzoyl group and the sulfur atom of the [4Fe-4S] cluster. The [Fe4S4(SAr)4] 2-/[Fe4S4(SAr)4]3- redox potential for 1 and 4 are-0.86 and-0.65 V, respectively. The difference between 1 and 4 is Δ0.21 V. This is larger than the value Δ0.11 V between [Fe4S4(S-2-t-BuCONHC6H4)4] 2- (-0.91 V) and [Fe4S4{S-2,6-(t-BuCONH) 2C6H3}4]2- (-0.80 V), considered to be the difference between singly and doubly NH· · ·S hydrogen-bonded complexes. The redox potentials for 1-6 follow the trend of the Hammett σ mvalues, showing that the aromatic ring of the benzoyl group interacts with the [4Fe-4S] cluster directly. A cooperative effect between the C-H· · ·S interaction and the NH ·· · S hydrogen bond is thus found to regulate the redox potential of the model complexes.
