![ethyl 2-(benzo[d]thiazol-2-ylthio)acetate](/Databaselist/images/loading.webp)
6295-57-4Relevant academic research and scientific papers
Enhanced reactive oxygen species levels by an active benzothiazole complex-mediated fenton reaction for highly effective antitumor therapy
You, Chaoqun,Wu, Hongshuai,Gao, Zhiguo,Chen, Fanghui,Ning, Like,Zhang, Yu,Dong, Yixin,Sun, Baiwang,Wang, Fei
, p. 4929 - 4939 (2019)
Breaking the threshold of intracellular reactive oxygen species (ROS) levels can cause nonspecific oxidative damage to proteins and lead to the Fenton reaction-mediated exogenous ROS production to be a new promising anticancer strategy. However, the problems, including the inefficient transport of metal catalysts and insufficient endogenous hydrogen peroxide (H2O2) content in cells, still need to be improved. In this study, a functional nanosystem encapsulated with benzothiazole complexes (FeTB2) and the photosensitizer indocyanine green (ICG) was designed for highly effective antitumor therapy. The surface of the nanocarriers was modified with dihydroartemisinin (DHA)-grafted polyglutamic acid. The induced hyperthermia enables the lipid-polymer shell to depolymerize, releasing FeTB2. The released FeTB2 could kill tumor cells in two different ways by inhibiting DNA replication and catalyzing H2O2 to produce active a OH. Moreover, the conjugated DHA could increase the amount of peroxides in tumor cells and significantly enhance the ROS yield. This work has provided solid evidence that the present nanosystem enables a significant effect on tumor killing through the combined inhibition of DNA replication and ROS-mediated oxidative damage by regulation of the tumor microenvironment, providing a ROS-mediated high-efficiency antitumor strategy.
A novel anti-tumor agent, Ln(III) 2-thioacetate benzothiazole induces anti-angiogenic effect and cell death in cancer cell lines
Hussein, Belal H.M.,Azab, Hassan A.,El-Azab, Mona F.,El-Falouji, Abdullah I.
, p. 99 - 109 (2012)
New complexes with a potent DNA-binding anti-tumor agent, europium(III)- and terbium(III)-2-thioacetate benzothiazole were synthesized and characterized. These complexes showed strong binding affinity to calf thymus DNA using fluorometric and electronic absorption spectroscopy. The synthesized complexes resulted in inhibition of proliferation of EAC cells and ascites formation. Their anti-tumor effect was found to be through anti-angiogenic activity as was evident by the reduction of microvessel density and down-regulation of VEGF receptor type-2 (Flk-1). It was found that EAC cells had distinct DNA fragmentation patterns analyzed by capillary electrophoresis in the treated animals. Moreover, the synthesized complexes exhibited significant cytotoxic activity against HepG2 and MCF7 cell lines. Furthermore, complexes showed a potent anti-bacterial activity against two pathogenic bacteria Escherichia coli and Salmonella.
Head-to-head bisbenzazole derivatives as antiproliferative agents: design, synthesis, in vitro activity, and SAR analysis
Ersan, Ronak Haj,Alagoz, Mehmet Abdullah,Ertan-Bolelli, Tugba,Duran, Nizami,Burmaoglu, Serdar,Algul, Oztekin
, p. 2247 - 2259 (2020/06/27)
Abstract: In the present work, a series of bisbenzazole derivatives were designed and synthesized as antiproliferative agents. The antiproliferative activity of these compounds was investigated using MTT assay. Bisbenzazole derivatives showed significant antiproliferative activity against all the four tested cancer cell lines. Among the various bisbenzazole derivatives, bisbenzoxazole derivatives exhibited the most promising anticancer activity followed by bisbenzimidazole and bisbenzothiazole derivatives. All the derivatives were found to be less toxic as compared to methotrexate (positive control) in normal human cells, indicating selective and efficient antiproliferative activity of these bisbenzazole derivatives. The structure–activity relationships of heteroaromatic systems and linkers present in bisbenzazole derivatives were analyzed in detail. In silico ADMET prediction revealed that bisbenzazole is a drug-like small molecule with a favorable safety profile. Compound 31 is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from methotrexate. Graphic abstract: Twenty-one bisbenzoxazole derivatives have been designed synthesized and evaluated to be an antiproliferative activity against four human tumor cell lines.[Figure not available: see fulltext.]
Mercaptobenzothiazole imidazoline derivative and its preparation method and application (by machine translation)
-
Paragraph 0010; 0022; 0023, (2019/05/04)
The invention relates to a containing imidazole group of 2 - mercaptobenzothiazole derivative synthesis process and its application. Its synthesis is 2 - mercaptobenzothiazole as raw materials, with chloroacetic acid, diethylenetriamine, N - hydroxy ethylene diamine, ethylene diamine, triethylene tetramine and tetraethylene pentamine reaction, xylene or toluene as the aqua, 2 - mercaptobenzothiazole and di-ethylene triamine, N - hydroxy ethylene diamine such as the molar ratio of amine reaction to 1: 1.1 reaction, the reaction temperature is 130 - 160 °C and 180 - 220 °C, the reaction time for each of the 4 hour and 2 hours. The operation of this invention is simple, high yield, the reaction conditions are easy to control. The product is 2 - mercaptobenzothiazole imidazoline derivatives can be applied to the copper corrosion inhibitor, anti-rust agent, water-based lubricating oil additive and the like. (by machine translation)
Novel bisphosphonates with antiresorptive effect in bone mineralization and osteoclastogenesis
Savino, Salvatore,Toscano, Annamaria,Purgatorio, Rosa,Profilo, Emanuela,Laghezza, Antonio,Tortorella, Paolo,Angelelli, Mariacristina,Cellamarea, Saverio,Scala, Rosa,Tricarico, Domenico,Thomas Marobbio, Carlo Marya,Perna, Filippo,Vitale, Paola,Agamennone, Mariangela,Dimiccoli, Vincenzo,Tolomeo, Anna,Scilimati, Antonio
, p. 184 - 200 (2018/09/18)
Bisphosphonates such as zoledronic, alendronic and risedronic acids are a class of drugs clinically used to prevent bone density loss and osteoporosis. Novel P-C-P bisphosphonates were synthesized for targeting human farnesyl pyrophosphate synthase (hFPPS) and human geranylgeranyl pyrophosphate synthase (hGGPPS), key enzymes of the mevalonate pathway, and capable of anti-proliferative action on a number of cell lines (PC3, MG63, MC3T3, RAW 264.7, J774A.1, bone marrow cells and their co-colture with PC3) involved in bone homeostasis, bone formation and death. Among sixteen compounds, [1-hydroxy-2-(pyrimidin-2-ylamino)ethane-1,1-diyl]bis(phosphonic acid) (10) was effective in reducing PC3 and RAW 264.7 cell number in crystal-violet and cell-dehydrogenase activity assays at 100 μM concentration. 10 reduced differentiated osteoclasts number similarly with zoledronic acid in osteoclastogenesis assay. At nanomolar concentrations, 10 was more effective than zoledronic acid in inducing mineralization in MC3T3 and murine bone marrow cells. Further, 10 significantly inhibited the activity of hFPPS showing an IC50 of 0.31 μM and a remarkable hydroxyapatite binding of 90%. Docking calculations were performed identifying putative interactions between some representative novel bisphosphonates and both hFPPS and hGGPPS. Then, 10 was found to behave similarly or even better than zoledronic acid as a anti-resorptive agent.
Synthesis of novel benzimidazole and benzothiazole derivatives bearing a 1,2,3-triazole ring system and their acetylcholinesterase inhibitory activity
Faraji, Laleh,Shahkarami, Shiva,Nadri, Hamid,Moradi, Alireza,Saeedi, Mina,Foroumadi, Alireza,Ramazani, Ali,Haririan, Ismaeil,Ganjali, Mohammad Reza,Shafiee, Abbas,Khoobi, Mehdi
, p. 30 - 35 (2017/02/15)
A series of 20 novel benzimidazole and benzothiazole derivatives linked to a 1,2,3-triazole ring system was synthesised, characterised and evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity. Several copper catalysts and solvents were screened to establish the optimal conditions for the preparation of the target compounds. Three different linkers were used to optimise the enzyme inhibitory effect. Out of the 20 compounds, 13 showed some AChE inhibition. The most potent compound, which showed 84% inhibition at 100 μM, contained a 1-(2-fluorobenzyl)-1,2,3-triazole linked to a benzimidazole group. A docking simulation study showed that the most active compound bound preferentially to the catalytic anionic subsite of the AChE enzyme.
Bivalent SIRT1 inhibitors
Wang, Juan,Zang, Wenwen,Liu, Jiajia,Zheng, Weiping
supporting information, p. 180 - 186 (2016/12/27)
In the current study, bivalent compounds 1–17 constructed by covalently linking the ?-amino group of lysine in a tripeptidic scaffold to a functionality via a linker were prepared and examined for their inhibitory potencies against SIRT1, a prototypical member of the β-nicotinamide adenine dinucleotide (β-NAD+)-dependent sirtuin family of protein Nε-acyl-lysine deacylases. A few of them were found to be stronger SIRT1 inhibitors than the N?-acetyl-lysine-containing monovalent counterparts 18 and 19. As exemplified with compounds 6 and 18, a bivalent SIRT1 inhibitor could exhibit a greater degree of inhibitory selectivity among SIRT1/2/3 than the corresponding monovalent counterpart. This study has laid a foundation for the future development of superior bivalent inhibitors against the (patho)physiologically and therapeutically important sirtuin family of deacylase enzymes.
Synthesis of Benzoxazolylthiomethyl and Benzthiazolylthiomethyl Quinazolin-4(3 h)-ones
Rafeeq, Mohammad,Ramana Reddy, Chittireddy Venkata,Dubey, Pramod Kumar
, p. 1857 - 1864 (2015/12/12)
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.
One-pot, three-component reaction using modified Julia reagents: A facile synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles in a wet organic solvent
Chai, Huihui,Guo, Ruiqiang,Yin, Wei,Cheng, Lingping,Liu, Renhua,Chu, Changhu
supporting information, p. 147 - 151 (2015/03/18)
A new one-pot, three component reaction involving the use of Julia reagent, aldehyde, and sodium azide was developed for the efficient synthesis of N-unsubstituted 1,2,3-triazoles. This reaction could be carried out under mild reaction conditions without any precaution, and broad scope of substrates, both respect to Julia reagents and aldehydes, could be applied in this reaction system in generation of a small library of title compounds.
CYCLIC AMIDE DERIVATIVES AS INHIBITORS OF 11 - BETA - HYDROXYSTEROID DEHYDROGENASE AND USES THEREOF
-
Paragraph 0485, (2015/06/17)
The present invention relates to certain amide derivatives that have the ability to inhibit 11-β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) and which are therefore useful in the treatment of certain disorders that can be prevented or treated by inhibition of this enzyme. In addition the invention relates to the compounds, methods for their preparation, pharmaceutical compositions containing the compounds and the uses of these compounds in the treatment of certain disorders. It is expected that the compounds of the invention will find application in the treatment of conditions such as non-insulin dependent type 2 diabetes mellitus (NIDDM), insulin resistance, obesity, impaired fasting glucose, impaired glucose tolerance, lipid disorders such as dyslipidemia, hypertension and as well as other diseases and conditions.
