- 3-(benzo[d]thiazol-2-YL)phenol and 4-(benzo[d]thiazol-2-YL)phenol: Crystal Structure Determination, DFT Calculations and Visualizing Intermolecular Interactions Using Hirshfeld Surface Analysis
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This article describes the synthesis and X-ray crystal structure analysis of 3-(benzo[d]thiazol-2-yl) phenol (I) and 4-(benzo[d]thiazol-2-yl)phenol (II), crystallized in centrosymmetric triclinic and orthorhombic space groups respectively. The packing in
- Mudsainiyan,Jassal
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- Discovery of new and highly effective quadruple FFA1 and PPARα/γ/δ agonists as potential anti-fatty liver agents
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Non-alcoholic fatty liver disease (NAFLD) has become the most common hepatic disease, while no drug was approved until now. The previous study reported that the quadruple FFA1/PPAR-α/γ/δ agonist RLA8 provided better efficacy than obeticholic acid on NASH. In the present study, two design strategies were introduced to explore better quadruple FFA1/PPAR-α/γ/δ agonists with improved metabolic stability. These efforts ultimately resulted in the identification of ZLY18, a quadruple FFA1/PPAR-α/γ/δ agonist with twice higher metabolic half-life than RLA8 in the liver microsome. In the triton-1339W-induced hyperlipidemic model, ZLY18 reversed hyperlipidemia to an almost normal level, which exhibited far stronger lipid-lowering effects than that of RLA8. Moreover, ZLY18 significantly decreased steatosis, hepatocellular ballooning, inflammation and liver fibrosis in NASH model even better than RLA8. Further mechanism studies suggested that ZLY18 exerts stronger effects than RLA8 on the regulation of the gene related to lipid synthesis, oxidative stress, inflammation and fibrosis. In addition, ZLY18 is more effective than pirfenidone in the prevention of CCl4-induced liver fibrosis. Besides, ZLY18 has an acceptable safety profile in the acute toxicity study at a high dose of 500 mg/kg. Therefore, ZLY18 represents a novel and highly promising quadruple FFA1/PPAR-α/γ/δ agonist worth of further investigation and development.
- Zhou, Zongtao,Ren, Qiang,Jiao, Shixuan,Cai, Zongyu,Geng, Xinqian,Deng, Liming,Wang, Bin,Hu, Lijun,Zhang, Luyong,Yang, Ying,Li, Zheng
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supporting information
(2021/12/27)
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- Tuning the Excited State of Tetradentate Pd(II) and Pt(II) Complexes through Benzannulated N-Heteroaromatic Ring and Central Metal
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A series of tetradentate Pd(II) and Pt(II) complexes containing fused 5/6/6 metallocycles with phenyl N-heteroaromatic benzo[d]imidazole (pbiz), benzo[d]oxazole (pboz) or benzo[d]thiazole (pbthz)-containing ligands was developed. Systematic studies by exp
- Fang, Xiaoli,Guo, Hua,Li, Guijie,Lou, Weiwei,She, Yuanbin,Sun, Yulu,Yang, Yun-Fang,Zhang, Qisheng
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p. 223 - 234
(2021/12/16)
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- Pentafluorophenylammonium Triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach
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In this work, one pot, simple and environmentally benign effective synthesis of 2-substituted benzothiazole and benzothiazoline derivatives are described in presence of PFPAT (pentafluorophenylammonium triflate) catalyst in water successfully. A series of benzothiazole derivative were synthesized by the reaction between 2-aminothiophenol and various aldehydes in good yields. Recyclability of the catalyst is observed for four times without loss of its activity in aqueous medium.
- Datta, Arup
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- Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents
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Oxidative stress is the product or aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized via condensation reaction between 2-aminothiophenols and different benzaldehydes. SAR study, particularly in position 2 and 6 of benzothiazoles, led to the identification of 4g and 4k as very interesting potential compounds for the design of multifunctional drugs. In particular, compound 4g is the best blocker of hERG potassium channels expressed in HEK 293 cells exhibiting 60.32percent inhibition with IC50 = 4.79 μM.
- Andreotti, Elisa,Baldisserotto, Anna,Balzarini, Jan,Buzzi, Raissa,Dissette, Valeria,Djuidje, Ernestine Nicaise,Liekens, Sandra,Manfredini, Stefano,Sciabica, Sabrina,Serra, Elena,Vertuani, Silvia
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- Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase
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The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.
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Paragraph 0013; 0049
(2019/02/13)
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- Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions
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The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.
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Paragraph 0062; 0141
(2019/01/21)
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- SPIRO-CONTAINING PLATINUM (II) EMITTERS WITH TUNABLE EMISSION ENERGIES AND SYNTHESES THEREOF
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An asymmetric tetradentate metal complex of a N^C^C^N comprising tetradentate ligand has a metal connected to binding sites which are connected to each other via three or four covalent bonds that can be either single or double bonds with bridging linkers reside between C^C and C^N moieties. These linkers result in three-dimension metal complexes with distorted square planar geometries. The four donor atoms coordinate to a metal center. Upon metal binding a 5-6-6 membered metallocycle is formed upon chelation including a first nitrogen donor bond, a first metal-carbon bond, a second metal-carbon bond, and a second nitrogen donor bond. The light emission from these metal complexes can be tuned by the ligand structure over the entire visible spectrum.
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Page/Page column 23; 24
(2019/08/12)
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- Synthesis and insecticidal activity of novel benzothiazole derivatives containing the coumarin moiety
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A series of novel benzothiazole derivatives containing a coumarin moiety was designed and synthesized. Their structures were characterized in detail via 1H NMR, 13C NMR, HRMS spectra and single-crystal X-ray diffraction analysis. The bioassay results indicated that some compounds showed encouraging insecticidal activity against Plutella xylostella and Aphis fabae at 400 mg/L. The preliminary structure-activity relationships were also discussed.
- Si, Wei-Jie,Chen, Min,Wang, Xue-Lun,Wang, Meng-Qi,Jiao, Jian,Fu, Xin-Can,Yang, Chun-Long
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- 2-Arylation/alkylation of benzothiazoles using superparamagneticgraphene oxide-Fe3O4 hybrid material as a heterogeneous catalystwith diisopropyl azodicarboxylate (DIAD) as an oxidant
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In this report, we introduced Graphene oxide-iron oxide (GO-Fe3O4) nanocomposites as a heterogeneous catalyst for arylation/alkylation of benzothiazoles with aldehydes and benzylic alcohols in the presence of diisopropyl azodicarboxylate (DIAD) as an oxidant which exclusively produced 2-aryl (alkyl)-1H–benzothizoles in moderate to excellent yields. The absence of precious metals and toxic solvent, easy product isolation, and recyclability of the GO-Fe3O4 with no loss of activity are notable advantages of this method.
- Khalili, Dariush,Etemadi-Davan, Elham,Banazadeh, Ali Reza
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- Chromium(III)-salen complex nanoparticles on AlPO4: as an efficient heterogeneous and reusable nanocatalyst for mild synthesis of highly functionalized piperidines, 2-arylbenzimidazoles, and 2-arylbenzothiazoles
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Abstract: A simple, convenient, and highly efficient multicomponent one-pot synthesis of highly functionalized piperidines has been developed via tandem reactions of β-keto esters, aromatic aldehydes, and various amines in ethanol at room temperature using catalytic amount (10?mol%) of a chromium(III)-salen complex nanoparticles supported on AlPO4. The heterogeneous catalyst exhibited excellent activity and reusability (up to 8 times) in the synthesis of highly functionalized piperidines. Also, synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles have been efficiently developed under mild condition from o-phenylenediamines or 2-aminothiophenol with aryl aldehydes via one-step process using catalytic amount (2.0?mol%) of nanocatalyst in air atmosphere as a green oxidant. The heterogeneous catalyst was characterized by scanning electron microscopy, atomic force microscopy, inductively coupled plasma spectrometry, thermogravimetry for analysis of nitrogen adsorption, and FT-IR spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].
- Sharghi, Hashem,Aberi, Mahdi,Doroodmand, Mohammad Mahdi,Shiri, Pezhman
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p. 1557 - 1573
(2017/06/06)
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- Synthesis of some benzothiazoles by developing a new protocol using urea nitrate as a catalyst and their antimicrobial activities
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The present communication demonstrates the development of urea nitrate as an effective and efficient catalyst for the synthesis of some 2-substituted benzothiazoles. Instant progress of reaction at room temperature under solvent-free condition, very high catalytic activity, inexpensive, clean reaction profile, operational simplicity, large-scale synthesis and appreciable yields are the main advantages of this protocol. These synthesized benzothiazoles have been evaluated for their antibacterial and antifungal activities against Gram-positive bacterium (Bacillus subtilis MTCC 121); two Gram-negative bacteria (Escherichia coli MTCC 1652 and Pseudomonas aeruginosa MTCC 741) and two fungi (Candida albicans MTCC 3017 and Saccharomyces cerevisiae MTCC 170). Compound 3n was found the most active against all the tested microbes.
- Kumar, Parvin,Bhatia, Rimpy,Khanna, Radhika,Dalal, Aarti,Kumar, Dinesh,Surain, Parveen,Kamboj, Ramesh C.
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p. 585 - 596
(2017/10/05)
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- Green and Highly Efficient Synthesis of Mono- and Bis-Benzothiazoles in the Presence of Fe(SD)3 under Ultrasound Irradiation
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A convenient, practical, green, and environmentally friendly method was developed for the synthesis of benzothiazoles from 2-aminothiophenol and various aldehydes. Bis-benzothiazoles were synthesized in high yield under mild reaction conditions. Products
- Pirbasti, Fateme Ghanbari,Mahmoodi, Nosrat Ollah
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- The immunomodulation potential of the synthetic derivatives of benzothiazoles: Implications in immune system disorders through in vitro and in silico studies
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Benzothiazole and its natural or synthetic derivatives have been used as precursors for several pharmacological agents for neuroprotective, anti-bacterial, and anti-allergic activities. The objecctive of the present study was to evaluate effects of benzot
- Khan, Khalid Mohammed,Mesaik, Mohammad A.,Abdalla, Omer M.,Rahim, Fazal,Soomro, Samreen,Halim, Sobia A.,Mustafa, Ghulam,Ambreen, Nida,Khalid, Ahmad Shukralla,Taha, Muhammad,Perveen, Shahnaz,Alam, Muhammad Tanveer,Hameed, Abdul,Ul-Haq, Zaheer,Ullah, Hayat,Rehman, Zia Ur,Siddiqui, Rafat Ali,Voelter, Wolfgang
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- Yttrium-catalyzed heterocyclic formation via aerobic oxygenation: A green approach to benzothiazoles
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The YCl3-catalyzed aerobic oxidative cyclization reaction for the synthesis of benzothiazoles has been developed. This method provides a practical, effective and green synthetic approach to benzothiazoles which are important units in many biologically active compounds.
- Fan, Li-Yan,Shang, Ying-Hui,Li, Xiang-Xiong,Hua, Wen-Jun
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supporting information
p. 77 - 80
(2015/01/30)
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- An economic, simple and convenient synthesis of 2-aryl/heteroaryl/styryl/alkylbenzothiazoles using SiO2-HNO3
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The present work was undertaken to develop an economic method for the synthesis of 2-aryl/heteroaryl/styryl/alkylbenzothiazoles mediated by SiO2-HNO3. In this report, we have demonstrated the catalytic potential of SiO2-HN
- Kumar, Parvin,Bhatia, Rimpy,Kumar, Dinesh,Kamboj, Ramesh C.,Kumar, Suresh,Kamal, Raj,Kumar, Ramesh
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p. 4283 - 4292
(2015/06/30)
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- Graphene oxide as a heterogeneous reagent promoted synthesis of 2-substituted 1,3-benzazoles in water
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An efficient chemical method for the synthesis of benzimidazoles, benzothiazoles, and benzoxazoles has been developed through the condensation of various aldehydes with o-phenylenediamine, o-aminothiophenol, and o-aminophenol using graphene oxide (GO) as an oxidant in water. These benzazoles are also prepared through a one-pot oxidation/condensation tandem process by reacting alcohols with 2-amino-(thio)phenol/aniline in the presence of GO in poly(ethylene glycol) as a safe media. Moreover, this carbonaceous material could be readily separated using a simple filtration.
- Khalili, Dariush,Banazadeh, Ali Reza
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p. 1693 - 1706
(2016/01/26)
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- Antileishmanial activities of benzothiazole derivatives
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Benzothiazole derivatives 1-22 were synthesized from 2-aminothiophenol and all synthetic compounds were screened for in vitro antileishmanial activity. These compound showed different types activities against leishmania with IC50 values ranging
- Rahim, Fazal,Samreen,Taha, Muhammad,Saad, Syed Muhammad,Perveen, Shahnaz,Khan, Momin,Alam, Muhammad Tanveer,Khan, Khalid Mohammed,Choudhary, M. Iqbal
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p. 157 - 161
(2015/05/20)
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- Magnetically separable nano CeO2: A highly efficient catalyst for ligand free direct C-H arylation of heterocycles
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An efficient, ligand free, nano CeO2-Fe3O4 catalyzed direct C-H arylation of heteroarenes such as benzoxazole and benzothiazole has been carried out with aryl halides in DMSO or arenediazonium salts in water. The catalyst exhibited high activity with moderate to excellent product yields under mild reaction conditions. Nano CeO2-Fe3O4 was synthesized and characterized by SEM, TEM, EDAX, XRD, FTIR, DSC-TGA, and ICP-MS analyses. The catalytic activity and stability of the catalyst were excellent, even after the ten cycle of recyclability
- Shelkar, Radheshyam S.,Balsane, Kishor E.,Nagarkar, Jayashree M.
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supporting information
p. 693 - 699
(2015/01/30)
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- A ball-milling strategy for the synthesis of benzothiazole, benzimidazole and benzoxazole derivatives under solvent-free conditions
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A convenient solvent-free method for the synthesis of benzothiazole, benzimidazole, and benzoxazole derivatives has been developed using recyclable ZnO-NPs via a ball-milling strategy. The method affords environmentally friendly reaction conditions that score high on the ecoscale with the low E-factor. The process is also highly efficient even on a multi-gram scale and provides easy product isolation.
- Sharma, Hemant,Singh, Narinder,Jang, Doo Ok
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p. 4922 - 4930
(2015/01/08)
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- IMMUNOSUPPRESSIVE COMPOUNDS
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The invention feature series of benzothiazole derivatives as potent immunosuppressive and antiinflammatory agents. Eight compounds 2, 4, 5, 8, 9, 10, 12, and 18 showed potent inhibitory activity on PHA-activated T-cell proliferation. Compounds 2, 4, 8, and 18 were found to have a potent inhibitory activity with IC50 values ranging 50 values 1.9, 5050), respectively.
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Paragraph 0023
(2015/01/07)
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- Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media
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A series of substituted benzimidazoles, benzothiazoles, and benzoxazoles was synthesized by combining 1,2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, heteroaryl, aliphatic, α,β-unsaturated aldehydes in the presence of nano ceria (CeO2) as an efficient heterogeneous catalyst.
- Shelkar, Radheshyam,Sarode, Sachin,Nagarkar, Jayashree
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supporting information
p. 6986 - 6990
(2013/12/04)
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- Synthesis and antibacterial evaluation of benzazoles tethered dihydro[1,3]oxazines
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Synthesis of various benzazoles tethered 1,3-oxazines such as 1H-benzo[d]azolophenyl-3,4-dihydro-2H-benzo- [e][1,3]oxazines 2a-j, 2-(3-(1H-benzo[d]oxazol-2-yl)phenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 3, 2-(3-(1Hbenzo-[ d]imidazol-2-yl)phenyl)-2,3
- Prasada, Davinder,Kumar Rohilla, Rajesh,Roy, Nilanjan,Nath, Mahendra
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body text
p. 739 - 745
(2012/07/01)
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- Hybrid thiophosphoryl-benzothiazole palladium SCN-pincer complexes: Synthesis and effect of structure modifications on catalytic performance in the suzuki cross-coupling
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The novel hybrid pincer-type ligands 3, 6, 9, and 11, bearing, as donating sites, a thiophosphoryl group and an imine moiety of the benzothiazole ring bound either directly to the central benzene core or attached to the latter one via O or NHlinkers, unde
- Kozlov, Vladimir A.,Aleksanyan, Diana V.,Nelyubina, Yulia V.,Lyssenko, Konstantin A.,Petrovskii, Pavel V.,Vasil'ev, Andrei A.,Odinets, Irina L.
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experimental part
p. 2920 - 2932
(2011/07/31)
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- Thiophosphoryl-, thiophosphoryloxy-, and thiophosphorylamino-benzene derivatives as novel classes of hybrid pincer ligands
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The synthetic approaches to novel families of SCE (E = S',N,O) hybrid pincertype ligands bearing thophosphoryl, thiophosphoryloxy, and thiophosphorylamino groups in various combinations with thiophosphoryl-, thiocarbamoyl-, and imine- (including that of benzothiazole ring) donating functions have been developed. All of the ligands readily undergo direct cyclometallation (metal = Pd(II), Pt(II)) to afford 5,5- or 5,6-membered pincer complexes. Palladium complexes displayed from high to excellent catalytic performance in the Suzuki cross-coupling reaction of aryl bromides and phenylboronic acid and the higher asymmetry for a complex served as a factor of its higher catalytic activity. Copyright Taylor & Francis Group, LLC.
- Kozlov, Vladimir A.,Aleksanyan, Diana V.,Vasilev, Andrei A.,Odinets, Irina L.
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scheme or table
p. 626 - 637
(2011/06/22)
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- Rapid and convenient thermal or microwave-assisted synthesis of substituted 2-phenylbenzothiazoles
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A simple one-step method for the synthesis of biologically relevant 2-phenylbenzothiazoles has been developed, using sodium metabisulfite as an oxidant following condensation between 2-aminothiophenol and substituted benzaldehydes. Attractive features of
- Weekes, Ashley A.,Dix, Matthew C.,Bagley, Mark C.,Westwell, Andrew D.
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experimental part
p. 3027 - 3032
(2010/11/05)
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- Water-promoted dowex 50W catalyzed highly efficient green protocol for 2-arylbenzothiazole formation
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2-Aminothiophenol and a variety of aryl aldehydes were allowed to react in one-pot operation to give 2-aryl-benzothiazoles in excellent yields in the presence of Dowex 50W in water. Very high yields coupled with the ease of work-up procedure, formation of no side products, employment of "reusable" catalyst, and "green" synthesis in aqueous medium without maintaining anhydrous reaction conditions are the most important aspects of this methodology.
- Mukhopadhyay, Chhanda,Datta, Arup
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scheme or table
p. 91 - 95
(2009/05/07)
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- Methanesulfonic acid/SiO2 as an efficient combination for the synthesis of 2-substituted aromatic and aliphatic benzothiazoles from carboxylic acids
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Methanesulfonic acid/SiO2 (1 mL/0.3 g) was found to be as an expeditious mixture in the synthesis of 2-substituted aromatic and aliphatic benzothiazoles at 140° using carboxylic acids. After a simple workup, benzothiazoles were obtained in good yields. Simplicity, use of widely available and diverse carboxylic acids, and easy handling of the reaction conditions are among the benefits of the method. Copyright Taylor & Francis Group, LLC.
- Sharghi, Hashem,Asemani, Omid
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experimental part
p. 860 - 867
(2009/08/08)
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- A green method for the synthesis of 2-arylbenzoles
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Aromatic aldehydes with both electron withdrawing and electron donating substituents were smoothly converted to the corresponding 2-arylbenzothiazoles by direct condensation of aromatic aldehydes with 2-aminothiophenol in one pot in a microoven under solv
- Mukhopadhyay, Chhanda,Datta, Amp
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p. 1837 - 1842
(2008/03/14)
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- An efficient and green synthesis of 2-arylbenzothiazoles in an ionic liquid, [pmIm]Br under microwave irradiation
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An efficient and green procedure for the synthesis of 2-arylbenzothiazoles has been developed by a simple condensation of 2-aminothiophenol and aromatic aldehyde in an inexpensive ionic liquid, 1-pentyl-3-methylimidazolium bromide ([pmIm]-Br) by microwave irradiation under solvent and catalyst-free condition. The ionic liquid is recycled for subsequent reactions.
- Ranu, Brindaban C.,Jana, Ranjan,Dey, Suvendu S.
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p. 274 - 275
(2007/10/03)
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- Compounds enhancing antitumor activity of other cytotoxic agents
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This invention relates to certain heterocyclic compounds and their pharmaceutically acceptable salts, which are useful for sensitizing multidrug-resistant tumor cells to anticancer agents and multidrug resistant forms of malaria, tuberculosis, leishmania and amoebic dysentery to chemotherapeutants. The compounds and their pharmaceutically acceptable salts are also inhibitors of the active drug transport capability of P-glycoprotein which is encoded by the human MDR1 gene, as well as of certain other related ATP-binding-cassette transporters from eukaryotic and prokaryotic organisms (e.g., pfmdr from Plasmodium falciprum, and murine mdr1 and mdr3 gene products).
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- Solid-state Fluorescent Photophysics of Some 2-Substituted Benzothiazoles
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The solid-state fluorescence properties of a series of benzothiazoles with phenyl, napthalene, and coumarin moieties substituted at the 2-position have been investigated.The necessity for a 2'-OH substituent for fluorescence has been confirmed and the effects of further substitution in the 2-phenyl ring are reported.
- Anthony, Kevin,Brown, Robert G.,Hepworth, John D.,Hodgson, Kevin W.,May, Bernadette,West, Michael A.
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p. 2111 - 2118
(2007/10/02)
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