- Synthesis and evaluation of a 99mTc-BAT-phenylbenzothiazole conjugate as a potential in vivo tracer for visualization of amyloid β
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We have conjugated S,S′-bis-trityl-N-BOC-N′-acetic acid-1,2-ethylenedicysteamine, a protected bis-amino-bis-thiol (BAT) tetraligand, with 2-(4′-aminophenyl)-1,3-benzothiazole, a derivative of thioflavin-T with known affinity for amyloid. The conjugate was
- Serdons,Verduyckt,Cleynhens,Terwinghe,Mortelmans,Bormans,Verbruggen
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Read Online
- Excited state proton transfer (ESIPT) based molecular probe to sense F- and CN- anions through a fluorescence "turn-on" response
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A new chromogenic and fluorogenic hydrazone derivative of aminobenzthiazole and 2-hydroxy-1-naphthaldehyde was developed as a sensitive molecular probe, NTS, for the detection of fluoride (F-) and cyanide (CN-) anions. The photophysi
- Ali, Rashid,Gupta, Ramesh C.,Dwivedi, Sushil K.,Misra, Arvind
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Read Online
- Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles
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An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.
- Cai, Mingzhong,Hao, Wenyan,Huang, Wencheng,Ye, Qian
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- Tertiary amine derivatives and organic electroluminescent device including the same
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Provided is a tertiary amine derivative, which effectively absorbs high-energy external light source in a UV region to minimize damage to organic materials inside an organic electroluminescent device, and thus contributes to a substantial lifespan improvement of the organic electroluminescent device. An organic electroluminescent device according to the present invention comprises: a first electrode; a second electrode; an organic material layer disposed between the first electrode and the second electrode; and a capping layer, wherein the capping layer comprises a tertiary amine derivative represented by chemical formula 1 according to the present invention.
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- Novel series of benzo[d]thiazolyl substituted-2-quinolone hybrids: Design, synthesis, biological evaluation and in-silico insights
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A novel series of 3-(2-(4-(substituted-benzo[d]thiazol-2-yl)phenylamino)acetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (7a-f and 8a-f) were synthesized. Reaction of appropriately substituted-2-(4-amino phenyl)benzo[d]thiazole (4a-f) with 3-(2-bromoacetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (5/6) in the presence of glacial acetic acid resulted in desired compounds. Structures of the synthesized compounds were characterized based on their spectral (IR, 1H NMR, 13C NMR and MS) and elemental analysis. The cytotoxicity screening studies revealed that MCF-7 and WRL68 cancer cells were sensitive to all the tested compounds. Out of twelve novel hybrids, compound 8f displayed the most significant anticancer activity. Docking studies were performed in order to understand the binding mode of the title compounds at the active site of the target enzyme (EGFR tyrosine kinase, 1M17). Compounds 8f and 7f displayed prominent and conserved binding interactions against 1M17. In addition, compounds 7e, 7f, 8e, and 8f exhibited interesting in vitro antibacterial activity, especially against Gram-negative bacteria E. coli. In summary, the novel benzo[d]thiazolyl substituted-2-quinolone hybrid (8f) could be considered as promising hit and could be further exploited for developing potential anticancer/antimicrobial agents.
- Bolakatti, Girish,Palkar, Mahesh,Katagi, Manjunatha,Hampannavar, Girish,Karpoormath, Rajshekhar V.,Ninganagouda, Shilpa,Badiger, Arvind
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- Modification of 5-methylphenanthridium from benzothiazoles to indoles as potent FtsZ inhibitors: Broadening the antibacterial spectrum toward vancomycin-resistant enterococci
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The death caused by pathogenic bacteria has always been a severe threat to mankind. The prevalence of drug resistance among bacteria underscores an urgent goal for new antibacterial agents with novel mode of action. Here we first designed and synthesized a class of benzothiazolyl-5-methylphenanthridium derivatives and evaluated their antibacterial activity. On this basis, we further designed and synthesized another class of novel indolyl-5-methylphenanthridium derivatives by optimizing the benzothiazolyl-5-methylphenanthridium core and evaluated their antibacterial activity targeting the bacterial cell division protein FtsZ. The results showed that the indolyl-5-methylphenanthridium derivatives had greatly improved activity against various drug-resistant bacterial strains including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus (VRE). Among them, compound C5 displayed excellent antibacterial activity against susceptible (MIC = 1 μg/mL), methicillin-resistant and clinical isolated S. aureus (MIC = 2 μg/mL). With low hemolytic activity towards mice red blood cells, C5 exhibited good antibacterial effect in vivo in preliminary pharmacodynamic assay. More importantly, C5 was difficult to induce bacterial resistance. Further mechanism studies proved that C5 could inhibit bacterial cell division by promoting FtsZ polymerization, leading to disorderly polymerization and disordered knots. Therefore, our findings suggest that this class of novel indolyl-5-methylphenanthridium derivatives are promising for future antibacterial agents.
- Chen, Weijin,Ma, Shutao,Song, Di,Zhang, Na,Zhang, Nan,Zhang, Panpan,Zhang, Shenyan
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- Oxidant/Solvent-Controlled I2-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions
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A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols. On the other hand, when the reaction was carried out in PhNO2 or in 1,4-dioxane containing PhNO2, the condensation of aromatic methyl ketones with 2-aminobenzenethiols has priority to form imines which is followed by an oxidation of the methyl group from ketones to afford 2-arylbenzothiazoles as a sole product. The PhNO2/I2 co-catalytic system is proposed first time.
- Ma, Renchao,Ding, Yuxin,Chen, Rener,Wang, Zhiming,Wang, Lei,Ma, Yongmin
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p. 310 - 321
(2021/01/09)
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- Tertiary amine derivatives and organic electroluminescent device including the same
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A UV-region high-energy external light source is effectively absorbed to minimize damage to organic materials in the organic electroluminescent device. 1 Is a cross-sectional view of an organic electroluminescence device according to the present invention. O-2 electrode 1 Or more organic material layers disposed between the (2) and (1) th electrodes. A capping layer is included. The organic material layer and/or the capping layer may include the 1 st amine derivative represented by Formula 3. Chemical Formula 1. Wherein each substituent in Formula 1 is as defined in the description of the invention.
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- 1-Phenyl-: N -(benzothiazol-2-yl)methanimine derivatives as Middle East respiratory syndrome coronavirus inhibitors
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Middle East respiratory syndrome coronavirus (MERS-CoV) poses a serious threat to human health, and currently there are no effective or specific therapies available to treat it. Herein a series of 1-phenyl-N-(benzothiazol-2-yl)methanimine derivatives with inhibitory activity against MERS-CoV are described. The compound 4f with a 50% inhibition concentration value of 0.09 μM is a promising inhibitor that warrants further evaluation, towards the development of potential anti-MERS-CoV drugs. This journal is
- Hu, Min-Qi,Li, Heng,Lin, Ying,Tang, Jie,Tang, Wei,Tong, Xian-Kun,Yang, Fan,Yu, Li-Fang,Zhang, Ying,Zuo, Jian-Ping
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p. 43299 - 43311
(2020/12/25)
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- Liposomes Decorated with 2-(4′-Aminophenyl)benzothiazole Effectively Inhibit Aβ1-42Fibril Formation and Exhibit in Vitro Brain-Targeting Potential
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The potential of 2-benzothiazolyl-decorated liposomes as theragnostic systems for Alzheimer's disease was evaluated in vitro, using PEGylated liposomes that were decorated with two types of 2-benzothiazoles: (i) the unsubstituted 2-benzothiazole (BTH) and
- Mourtas, Spyridon,Mavroidi, Barbara,Marazioti, Antonia,Kannavou, Maria,Sagnou, Marina,Pelecanou, Maria,Antimisiaris, Sophia G.
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p. 4685 - 4698
(2020/11/13)
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- Synthesis, photophysical characterization, CASSCF/CASPT2 calculations and CT-DNA interaction study of amino and azido benzazole analogues
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This work describes the synthesis and photophysical investigation of amino and azido benzazoles. The amino derivatives were obtained by condensation reaction between ortho-substituted anilines and p-aminobenzoic in polyphosphoric acid. The respective azides were synthesized by reaction of diazonium salts from the previously prepared amines with sodium azide. These compounds present absorption maxima in the UV-A region, nm ascribed to fully spin and symmetry electronic transitions. All compounds presented a main fluorescence emission in the UV-A to the violet region with a relatively large Stokes shift. The latter related to a solvent dependence. The amino derivatives presented higher values to the fluorescence quantum yields in despite of the azido analogues. DFT, TD-DFT and multiconfigurational calculations (SA-CASSCF and MS-CASPT2) were performed in order to investigate the photophysical features of these molecules, mainly on the azide derivatives, where the main interest was the investigation of the intrinsic fluorescence quenching present in these compounds. In this sense, it was observed that the weak fluorescence emission observed in the azide compounds could be related to the dissociative character of the S1 state, which reaches a conical intersection point between S1/S0 states, and through this point, goes back to the ground state by a nonradioactive decay. In addition, the DNA binding assays by UV–Vis absorption and fluorescence emission methodologies indicated that the benzazoles presented strong interaction with CT-DNA, which could be attributed to π-stacking and/or intermolecular hydrogen-bonding. Docking was also performed to better understand the observed interaction.
- Gil, Eduarda S.,da Silva, Cláudia B.,Nogara, Pablo A.,da Silveira, Carolina H.,da Rocha, Jo?o B.T.,Iglesias, Bernardo A.,Lüdtke, Diogo S.,Gon?alves, Paulo F.B.,Rodembusch, Fabiano S.
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- Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
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The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.
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Page/Page column 89-90
(2020/01/09)
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- Design, Synthesis, and Biological Evaluation of 2-(4-Aminophenyl)benzothiazole Analogues as Antiproliferative Agents
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A series of 28 novel 2-(4-aminophenyl)benzothiazole analogues have been synthesized and characterized using various analytical techniques like 1H NMR, 13C NMR, electrospray ionization mass spectrometry, and IR and bioevaluated for their antiproliferative activity over a group of three human cancer cell lines, namely, lung cancer (A549), cervical cancer (HeLa), and breast cancer (MDA-MB-231), using sulforhodamine B assay method. Few synthesized molecules (5a, 5c, 5d, 5f, 7b, and 7j) displayed effective growth inhibition (GI50) activity against the tested human cancer cell lines at lower micromolar concentration (GI50) values in the range 0.2–1.7?μM. Noticeably, compound 7b exhibited reasonable activity in all three cancer cell lines in the GI50 range 0.55–1.2?μM. Further, when 7b was screened for tubulin polymerization inhibition, it exhibited more than 55% inhibition at concentration of 5.0?μM. The molecular docking simulations supported the molecular interactions of the derivatives with the targeted receptor. These derivatives may serve as lead structures for development of potential anticancer drug candidates, and 7b might act as a potential microtubule polymerization inhibitor.
- Narva, Suresh,Chitti, Surendar,Amaroju, Suresh,Goud, Sridhar,Alvala, Mallika,Bhattacharjee, Debanjan,Jain, Nishant,Kondapalli Venkata Gowri, Chandra Sekhar
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p. 520 - 532
(2018/12/11)
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- Design and synthesis of new benzoxazole/benzothiazole-phthalimide hybrids as antitumor-apoptotic agents
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Herein, we synthesized a series of twelve benzoxazole and benzothiazole derivatives incorporated with phthalimide core as anticancer agents. The most active compounds were 5a and 5g against HepG2 and MCF7 cell lines with IC50 = 0.011 and 0.006 μM, respectively. They evaluated against EGFR and HER2 enzymes. From cell cycle analysis, it was observed that test compounds exerted pre G1 apoptosis and cell cycle arrest at G2/M phase. The achieved results suggested that apoptosis was due to activation of caspase-7 and caspase-9. EGFR was chosen as a biological target for carrying molecular modeling study for the newly synthesized compounds.
- Philoppes, John N.,Lamie, Phoebe F.
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- Small molecule inhibition of microRNA-21 expression reduces cell viability and microtumor formation
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MicroRNAs (miRNAs) are short, non-coding RNA molecules estimated to regulate expression of a large number of protein-coding genes and are implicated in a variety of biological processes such as development, differentiation, proliferation, and cell surviva
- Ankenbruck, Nicholas,Kumbhare, Rohan,Naro, Yuta,Thomas, Meryl,Gardner, Laura,Emanuelson, Cole,Deiters, Alexander
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supporting information
p. 3735 - 3743
(2019/07/03)
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- Tertiary amine derivatives and organic electroluminescent device including the same
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Provided is a tertiary amine derivative which contributes to a substantial increase in service life of an organic electroluminescent device by minimizing damages to organic matter inside the organic electroluminescent device via effective absorption of a high-energy external light source in the UV region. According to the present invention, the organic electroluminescent device comprises: a first electrode and a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the organic material layers comprise a tertiary amine derivative represented by chemical formula 1. In the chemical formula 1, Z_1, Z_2, and Z_3 are each independently O or S.COPYRIGHT KIPO 2020
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- Tribenzazole amine derivatives and organic electroluminescent device including the same
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The present invention provides a tribenzazole amine derivative which contributes to substantial life improvement of an organic electroluminescent device by effectively absorbing a high energy external light source of an UV area and minimizing the damage of organic materials in the organic electroluminescent device. The organic electroluminescent device according to the present invention includes: a first electrode; a second electrode; an organic material layer disposed between the first electrode and the second electrode; and a capping layer disposed on the second electrode. The capping layer includes a tribenzazole amine derivative represented by chemical formula 1. In chemical formula 1, R^1, R^2 and R^3 are the same as or different from each other and are respectively and independently hydrogen and an alkyl group having 1 to 10 carbon atoms. l, n, and m are integers of 0 to 4.COPYRIGHT KIPO 2020
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- Virtual screening identification and chemical optimization of substituted 2-arylbenzimidazoles as new non-zinc-binding MMP-2 inhibitors
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Matrix metalloproteinases (MMPs) are a large family of zinc-dependent endoproteases known to exert multiple regulatory roles in tumor progression and invasiveness. This encouraged over the years the approach of MMP, and particularly MMP-2, targeting for anticancer treatment. Early generations of MMP inhibitors, based on aspecific zinc binding groups (ZBGs) assembled on (pseudo)peptide scaffolds, have been discontinued due to the clinical emergence of toxicity and further drawbacks, giving the way to inhibitors with alternative zinc-chelator moieties or not binding the catalytic zinc ion. In the present paper, we continue the search for new non-zinc binding MMP-2 inhibitors: exploiting previously identified compounds, a virtual screening (VS) campaign was carried out and led to the identification of a new class of ligands. The structure-activity relationship (SAR) of the benzimidazole scaffold was explored by synthesis of several analogues whose inhibition activity was tested with enzyme inhibition assays. By performing the molecular simplification approach, we disclosed different sets of single-digit micromolar inhibitors of MMP-2, with up to a ten-fold increase in inhibitory activity and ameliorated selectivity towards off-target MMP-8, compared to selected lead compound. Molecular dynamics calculations conducted on complexes of MMP-2 with docked privileged structures confirmed that analyzed inhibitors avoid targeting the zinc ion and dip inside the S1′ pocket. Present results provide a further enrichment of our insights for the design of novel MMP-2 selective inhibitors.
- Agamennone, Mariangela,Caradonna, Alessia,Di Pizio, Antonella,Laghezza, Antonio,Loiodice, Fulvio,Luisi, Grazia,Piemontese, Luca,Tortorella, Paolo
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- A Multi-step Virtual Screening Protocol for the Identification of Novel Non-acidic Microsomal Prostaglandin E2 Synthase-1 (mPGES-1) Inhibitors
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Microsomal prostaglandin E2 synthase-1 (mPGES-1) is a potential therapeutic target for the treatment of inflammatory diseases and certain types of cancer. To identify novel scaffolds for mPGES-1 inhibition, we applied a virtual screening (VS) p
- Shekfeh, Suhaib,?al??kan, Burcu,Fischer, Katrin,Yal??n, Tansu,Garscha, Ulrike,Werz, Oliver,Banoglu, Erden
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p. 273 - 281
(2019/01/04)
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- Luminescent properties of benzothiazole derivatives and their application in white light emission
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Three benzothiazole derivatives, N-[4-(benzothiazol-2-yl)-3-hydroxyphenyl]-octanamide (BHPO1), N-[3-(benzothiazol-2-yl)-4-hydroxyphenyl]-octanamide (BHPO2), N-[4-(benzothiazol-2-yl)phenyl]-octanamide (BPO) were prepared and their luminescence properties w
- Lu, Fengxian,Hu, Rui,Wang, Shuangqing,Guo, Xudong,Yang, Guoqiang
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p. 4196 - 4202
(2017/02/05)
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- New benzothiazole/benzoxazole-pyrazole hybrids with potential as COX inhibitors: design, synthesis and anticancer activity evaluation
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Ten new hybrids were designed and synthesized, their chemical structures were confirmed through spectral and elemental analysis. The new hybrids were screened against lung, breast and liver cancer cell lines (A549, MCF7 and Hep3B), in addition to normal f
- Belal, Amany,Abdelgawad, Mohamed A.
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p. 3859 - 3872
(2017/06/20)
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- Enhanced cytotoxicity by a benzothiazole-containing cisplatin derivative in breast cancer cells
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In recent years, the concept of nanoparticles being used as an intelligent drug carrier has gained great attention. In this paper, the formulation of a liposome delivery system loaded with a novel benzothiazole-containing cisplatin derivative (CJM-Pt) was carried out. The particle size distributions were determined using dynamic light scattering, and the prepared liposomes showed a suitable size of around 98 nm. Stability studies showed that the CJM-Pt loaded liposomes were stable at 4 °C for more than four weeks. Investigation of triggered release indicated that the release performance of the prepared liposomes was controllable and the releasing effect was remarkable under low pH (42 °C). To test the suitability of the chosen formulation, CJM-Pt loaded liposomes were investigated against several tumor cell lines: MGC-803, SGC-7901, MCF-7 and MDA-MB-231. Furthermore, the cell cycle arrest was examined. The CJM-Pt loaded liposomes have the potential to be applied in drug delivery systems (DDS) for breast cancer therapy.
- You, Chaoqun,Yu, Jia,Sun, Yu,Luo, Yanghui,Zhang, Xiangyang,Zhu, Jin,Sun, Baiwang
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supporting information
p. 773 - 785
(2017/02/05)
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- Synthesis of 2-arylbenzothiazoles via direct condensation between in situ generated 2-aminothiophenol from disulfide cleavage and carboxylic acids
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In this work we describe a simple and efficient general methodology for 2-arylbenzothiazole preparation employing disulfides and carboxylic acids. The reaction is promoted by tributylphosphine that acts both in disulfide bond cleavage and as activating agent for coupling with carboxylic acids. The reaction scope was studied using bis(2-aminophenyl)disulfide and different carboxylic acids with donor/withdrawing substituents, which resulted in the desired 2-arylbenzothiazole with moderate to good yields. The method was tested with success in preparation of the amyloid probe 2-(4-aminophenyl)-6-methoxybenzothiazole that employed a substituted bis(2-aminophenyl)disulfide.
- Coelho, Felipe L.,Campo, Leandra F.
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supporting information
p. 2330 - 2333
(2017/05/29)
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- Design, synthesis and antimetastatic evaluation of 1-benzothiazolylphenylbenzotriazoles for photodynamic therapy in oral cancer cells
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We have designed and synthesized a new series of 1-benzothiazolylphenylbenzotriazoles 9a-p and studied their antimetastatic mechanism involved in photosensitive effects induced by UVA in oral cancer cell Ca9-22. Our results revealed that the compounds plus UVA significantly suppressed migration and invasion, as detected by wound healing assay and Boyden chamber assay. Quantitative RT-PCR assay indicated that compound 9i plus UVA induced an antimetastatic effect through up-regulation of syndecan-1 and TIMP-3 and down-regulation of heparanase, MMP-2 and MMP-9 mRNA expressions. Western blot analysis showed that Ca9-22 treated with 9i plus UVA resulted in decreased levels of p-EGFR and p-ERK, MMP-2 and MMP-9, and an increased level of TIMP-3. These results are the first to report the function of UVA-activated 1-benzothiazolylphenylbenzotriazoles in tumor metastasis and their underlying molecular mechanism, and thus suggest that compound 9i plus PDT may serve as a potential ancillary modality for the treatment of oral cancer.
- Senadi, Gopal Chandru,Liao, Chieh-Ming,Kuo, Kung-Kai,Lin, Jian-Cheng,Chang, Long-Sen,Wang, Jeh Jeng,Hu, Wan-Ping
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p. 1151 - 1158
(2016/07/06)
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- Design, synthesis and mode of action of novel 2-(4-aminophenyl)benzothiazole derivatives bearing semicarbazone and thiosemicarbazone moiety as potent antimicrobial agents
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A novel series of substituted benzothiazoles, bearing semicarbazone and thiosemicarbazone moieties, was designed, synthesized and evaluated for their antimicrobial activity and possible mode of action. Structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, IR and Mass spectral data. The results revealed that compounds SC06, SC09, TS05 and TS07 have potent antibacterial activity against both Gram-positive and Gram-negative strains. Compound TS05 displayed most potent activity with MIC values of 3.91, 7.81 and 1.56 μg/ml against S. aureus, E. coli and P. aeruginosa, respectively. The results from cytoplasmic membrane permeabilization assay, FACS study as well as DNA-binding assays, evaluated against clinically relevant pathogens S. aureus and E. coli, suggest membrane perturbing as well as intracellular mode of action of this class of compounds. In addition, hemolytic activity of the compounds was measured which indicated their low cytotoxicity.
- Singh, Meenakshi,Singh, Sudhir Kumar,Gangwar, Mayank,Nath, Gopal,Singh, Sushil K.
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p. 263 - 282
(2016/01/25)
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- Design, synthesis and mode of action of some new 2-(4'-aminophenyl) benzothiazole derivatives as potent antimicrobial agents
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Background: The rapid evolution of antibiotic resistance poses a serious threat to public health. The development of heterocyclic benzothiazole derivatives, as efficient and potential agents, has been the focus of antibacterial drug discovery. Objective: Present study attempts to evaluate the antibacterial activity and mechanism of action of novel 2-(4'- aminophenyl) benzothiazole derivatives. Methods: Antibacterial activity of novel benzothiazole derivatives was evaluated by agar disc diffusion method against a panel of susceptible Gram-positive and Gram-negative strains. The mechanism of action was explored by bactericidal kinetics, membrane depolarization, fluorescent assisted cell cytometry and DNA cleavage studies. Results: Our findings revealed that compounds A07a and A07b turned out to be the most potent analogues having minimum inhibitory concentration values in the range of 3.91-31.2 g/ml against Staphylococcus aureus, Salmonella typhi, Pseudomonas aeruginosa and Escherichia coli. The new benzothiazole derivatives displayed different modes of action as elucidated by the studies on intact bacterial cells and plasmid DNA. The structure activity relationship studies showed prominent activity of compound A07a containing oxime moiety on carbonyl carbon along with less bulky electron releasing and lipophillic group (methoxy and chloro) in phenyl ring at C2 position of 2-(4'-aminophenyl) benzothiazole ring system. Conclusion: The potent antibacterial activity of compounds (A07a and A07b) was mediated by membrane perturbing and intracellular mode of actions. These results further validate the use of these derivatives in the treatment of microbial diseases and provide scope for further research.
- Singh, Meenakshi,Kumar Singh, Sudhir,Gangwar, Mayank,Sellamuthu, Satheeshkumar,Nath, Gopal,Singh, Sushil K.
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p. 429 - 437
(2016/05/24)
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- Oxo carbon-based compounds, a resin composition comprising the same and a filter containing the resin composition
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The invention relates to oxo carbon-based compounds, a resin composition comprising the same and a filter containing the resin composition. A novel oxo carbon-based compound is provided, the absorption spectrum in a visible-near infrared region does not h
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Paragraph 0497; 0498
(2016/10/10)
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- Synthesis and antitumor activity evaluation of NEW 2-(4-aminophenyl) benzothiazole/oxazole/imidazole derivatives
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A NEW series of 2-(4-aminophenyl)benzothiazole and related structure compounds, bearing thiocyanate, thiol in the 3'postion as well as new condensed benzothiazoles and related structure compounds having thiazolones,tetrazole, oxadiazole have been synthesized. All the newly synthesized compounds were screened for their anti-tumor activities. The results revealed promising effects against most of the cancer cell lines.
- El-Arab, Elham Ezz,El-Said,Amine,Moharram
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p. 967 - 984
(2017/04/17)
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- Synthesis and Antitumor Activity Evaluation of New 2-(4-aminophenyl) benzothiazole/oxazole/imidazole Derivatives
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A NEW series of 2-(4-aminophenyl)benzothiazole and related structure compounds, bearing thiocyanate, thiol in the 3′postion as well as new condensed benzothiazoles and related structure compounds having thiazolones, tetrazole, oxadiazole have been synthesized. All the newly synthesized compounds were screened for their anti-tumor activities. The results revealed promising effects against most of the cancer cell lines.
- El-Arab, Elham Ezz,El-Said,Amine,Moharram
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p. 967 - 984
(2017/04/17)
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- Containing 2 - (4-aminophenyl) benzocarbazoles [...] imide compound and use thereof
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The invention relates to an anti-tumor naphthalimide compound containing 2-(4-aminophenyl) benzothiazole and an application thereof in the field of organisms. The compound is characterized in that 2-(4-aminophenyl)-benzothiazole is introduced to a naphthalimide matrix structure in a side chain form through reactions such as amino condensation and amino substitution. The compound has wide anti-tumor activity, and has a better inhibition effect on normal growth of tumor cells with various different tissue origins such as cervical cancer, liver cancer and breast cancer.
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Paragraph 0034-0036
(2017/04/08)
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- Photocatalytic Generation of 2-Azolyl Radicals: Intermediates for the Azolylation of Arenes and Heteroarenes via C-H Functionalization
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The 2-azolyl radical, generated from 2-bromoazoles via photocatalysis, is a powerful intermediate for the intermolecular arylation of unmodified (hetero)arenes. The reaction is characterized by mild conditions, operational simplicity, tolerance toward functional and sterically demanding groups, broad scope, and anti-Minisci selectivity. A working mechanism is provided, and a low-solubility amine is essential for successful coupling. The utility of the reaction is demonstrated via late-stage functionalization of methyl estrone and application toward other bromoarenes.
- Arora, Amandeep,Weaver, Jimmie D.
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supporting information
p. 3996 - 3999
(2016/08/30)
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- Hit to lead optimization of a series of N-[4-(1,3-benzothiazol-2-yl)phenyl]acetamides as monoacylglycerol lipase inhibitors with potential anticancer activity
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A total of thirty five new N-[4-(1,3-benzothiazol-2-yl)phenyl]acetamide derivatives were synthesized and structures of all the compounds were confirmed on the basis of elemental analysis and collective use of IR, 1H NMR, 13C NMR and
- Afzal, Obaid,Akhtar, Md Sayeed,Kumar, Suresh,Ali, Md Rahmat,Jaggi, Manu,Bawa, Sandhya
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p. 318 - 330
(2016/07/06)
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- Green, efficient and large-scale synthesis of benzimidazoles, benzoxazoles and benzothiazoles derivatives using ligand-free cobalt-nanoparticles: As potential anti-estrogen breast cancer agents, and study of their interactions with estrogen receptor by mo
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A facile and high yielding method for the synthesis of 2-aryl benzoxazoles, benzimidazole and benzothiazoles is reported employing cobalt oxide nanoparticles. The cobalt oxide nanoparticles were used as a convenient, green, easy available and highly effic
- Hajipour, Abdol R.,Khorsandi, Zahra,Mortazavi, Maryam,Farrokhpour, Hossein
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p. 107822 - 107828
(2016/01/09)
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- Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions
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Abstract A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental analysis. The resin could be easily recovered and reused for subsequent reactions.
- Lei, Yingjie,Wu, Xinshi,Zhang, Guochun,Ai, Cuiling
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p. 679 - 682
(2015/05/05)
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- Synthesis and antitumor activity evaluation of new 2-(4-aminophenyl)benzothiazole derivatives bearing different heterocyclic rings
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Twenty-five new N-[4-(benzothiazole-2-yl)phenyl]acetamide derivatives bearing different heterocyclic ring systems were synthesized using 2-(4-aminophenyl)benzothiazole structure as a pharmacophoric group. Final compounds were screened for their potential
- Yurtta?, Leyla,Tay, Funda,Demirayak, ?eref
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p. 458 - 465
(2015/07/23)
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- Synthesis and characterization of new s-triazine bearing benzimidazole and benzothiazole derivatives as anticancer agents
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Two new series of s-triazine derivatives appended with benzimidazole (15a-h) and benzothiazole derivatives (16a-h) are synthesized, and structure-activity relationships on anticancer activity of these 15a-h and 16a-h were probed. In vitro inhibitory activity against the growth of six cancer cell lines, viz., MCF-7, MDAMB-231, PC-3, DU-145, HT-29 and HGC-27 was evaluated for synthesized analogues. Among the two series of compounds, derivatives containing benzimidazole scaffold were found to be relatively potent over benzothiazole analogues. In accordance with our previous observation, within benzimidazole derivatives, tri-substituted s-triazine derivatives were found to be more potent over di-substituted derivatives irrespective of cell lines. Structure-activity relationships provided useful insights into these classes of compounds and paved the way to design novel analogues with more potency.
- Kumar, G. Jagadeesh,Kumar, S. Naveen,Thummuri, Dinesh,Adari, Lavanya Bindu Sree,Naidu,Srinivas, Kolupula,Rao, V. Jayathirtha
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p. 3991 - 4001
(2015/11/02)
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- Discovery of novel N-(5-(tert-butyl)isoxazol-3-yl)-N′-phenylurea analogs as potent FLT3 inhibitors and evaluation of their activity against acute myeloid leukemia in vitro and in vivo
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FLT3 inhibitors have been explored as a viable therapy for acute myeloid leukemia (AML). However, the clinical outcomes of these FLT3 inhibitors were underwhelming except AC220. Therefore, the development of novel FLT3 inhibitors with high potency against
- Xu, Ying,Wang, Ning-Yu,Song, Xue-Jiao,Lei, Qian,Ye, Ting-Hong,You, Xin-Yu,Zuo, Wei-Qiong,Xia, Yong,Zhang, Li-Dan,Yu, Luo-Ting
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p. 4333 - 4343
(2015/08/03)
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- Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia
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A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.
- Fan, Mengyang,Zhou, Wei,Jiang, Yongwen,Ma, Dawei
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supporting information
p. 5934 - 5937
(2015/12/11)
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- Elemental sulfur disproportionation in the redox condensation reaction between o-halonitrobenzenes and benzylamines
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The disproportionation of elemental sulfur at moderate temperatures is investigated in the redox condensation involving o-halonitrobenzenes 1 and benzylamines 2. As a redox moderator, elemental sulfur plays the dual role of both electron donor and acceptor, generating its lowest and highest oxidation states: S-2 (sulfide equivalent) in benzothiazole 3 and S+6 (sulfate equivalent) in sulfamate 4, and filling the electron gap of the global redox condensation process. Along with this process, a cascade of reactions of reduction of the nitro group of 1, oxidation of the aminomethyl group of 2, metal-free aromatic halogen substitution, and condensation finally led to 2-arylbenzothiazoles 3.
- Nguyen, Thanh Binh,Ermolenko, Ludmila,Retailleau, Pascal,Al-Mourabit, Ali
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supporting information
p. 13808 - 13812
(2015/02/19)
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- Direct arylation of heterocycles through C-H bond cleavage using metal-organic-framework Cu2(OBA)2(BPY) as an efficient heterogeneous catalyst
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A crystalline porous metal-organic-framework Cu2(OBA)2(BPY) was synthesized and characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. The Cu-MOF was shown to be an efficient heterogeneous catalyst for direct C-arylation of a variety of heterocycles by iodoarenes. The optimal conditions employed tBuOLi in dioxane at elevated temperature. In addition, a leaching test was also conducted to investigate the heterogeneity. Gratifyingly, the MOF catalyst can be facilely recycled several times under identical conditions without remarkable loss in catalytic reactivity. This journal is
- Truong, Thanh,Nguyen, Vu T.,Le, Hue T. X.,Phan, Nam T. S.
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p. 52307 - 52315
(2014/12/10)
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- Synthesis, characterization and 11C-radiolabeling of aminophenyl benzothiazoles: Structural effects on the alkylation of amino group
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Several aminophenyl benzothiazoles were prepared with a view to using them as amyloid binding agents for imaging β-amyloid in Alzheimer's disease. These precursors were radiolabeled with 11C-positron-emitting radioisotope using an automated synthesizer and selected radiolabeled compounds were further purified by HPLC. Our results demonstrate that changes in structure have a major influence on the radioactive yield and the ease with which the radiolabel can be introduced. Aminophenyl benzothiazoles with an attached isopropyl group resisted dialkylation perhaps due to steric hindrance caused by this group. Straight chain attachment of methyl, ethyl, butyl, and crotyl groups in the structure decreased the radiochemical yield. Notably, the o-aminophenyl benzothiazole derivatives were difficult to alkylate despite stringent experimental conditions. This reactivity difference is attributed to the hydrogen bonding characteristics of the o-amino group with the nitrogen atom of the thiazole ring. Copyright
- Venkatachalam,Stimson,Bhalla,Pierens,Reutens
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p. 566 - 573
(2014/11/07)
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- Design, synthesis and mode of action of some benzothiazole derivatives bearing an amide moiety as antibacterial agents
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In this study ten benzothiazole derivatives bearing the amide moiety were designed, synthesized and evaluated for their antibacterial activity and possible mode of action. Structures of the synthesized compounds were elucidated by spectral data. Four different Gram-negative and two different Gram-positive bacterial strains were used in antibacterial activity tests. Among all the synthesised compounds, compound A07 displayed the most potent inhibitory activity with minimum inhibitory concentration (MIC) values of 15.6, 7.81, 15.6, 3.91 μg ml-1 against S. aureus, E. coli, S. typhi and K. pneumoniae respectively. Structure-activity relationship (SAR) studies revealed that electronic and lipophillic factors of the phenyl ring had a significant effect on the antimicrobial activity of the designed compounds. The benzothiazole bearing amide (A01-A10) series exhibited different modes of action based on aryl group substitution as revealed by studies on intact bacterial cells and plasmid DNA. The present study provides us two active compounds (A07 and A10) with a membrane perturbing mode of action, and an intracellular mode of action due to binding with DNA along with potent activity against clinically relevant pathogens E. coli and S. aureus.
- Singh, Sushil K.,Singh, Meenakshi,Singh, Sudhir K.,Gangwar, Mayank,Nath, Gopal
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p. 19013 - 19023
(2014/05/20)
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- A comparative study between para-aminophenyl and ortho-aminophenyl benzothiazoles using NMR and DFT calculations
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Ortho-substituted and para-substituted aminophenyl benzothiazoles were synthesised and characterised using NMR spectroscopy. A comparison of the proton chemical shift values reveals significant differences in the observed chemical shift values for the NH
- Pierens,Venkatachalam,Reutens
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p. 453 - 459
(2014/08/05)
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- Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells
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By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 μM as well as 4 μM concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers.
- Kamal, Ahmed,Faazil, Shaikh,Ramaiah, M. Janaki,Ashraf, Md.,Balakrishna,Pushpavalli,Patel, Nibedita,Pal-Bhadra, Manika
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p. 5733 - 5739
(2013/10/01)
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- Synthesis of 2-(4-aminophenyl) benzothiazole derivatives and use thereof
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The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R1 of formulae 1-6 is H, C1-10 alkyl, C1-10 alkoxy or C1-10 haloalkyl, and R2 of formulae 1-6 is H or C1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R1 and R2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.
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- Design, synthesis and neuroprotective evaluation of novel tacrine-benzothiazole hybrids as multi-targeted compounds against Alzheimer's disease
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Alzheimer's disease (AD) is a multifactorial disorder with several target proteins contributing to its etiology. In search for multifunctional anti-AD drug candidates, taking into account that the acetylcholinesterase (AChE) and beta-amyloid (Aβ) aggregat
- Keri, Rangappa S.,Quintanova, Catarina,Marques, Sérgio M.,Esteves, A. Raquel,Cardoso, Sandra M.,Santos, M. Amélia
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p. 4559 - 4569
(2013/07/26)
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- Synthesis, characterization and coordination chemistry of aminophenylbenzothiazole substituted 1,4,7-triazacyclononane macrocycles
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The synthesis and spectroscopic characterization of four new 2-(4-aminophenyl)benzothiazole substituted 1,4,7-triazacyclononane derivatives with and without appended pyridyl groups on the macrocycle is reported: 1-(2-(4-aminophenyl)benzothiazolyl)-2-oxoethyl)-1,4,7-triazacyclononane (L1), 1-(2-(4-aminophenyl)benzothiazolyl)-2-oxoethyl)-4-(2-pyridylmethyl)-1,4, 7-triazacyclononane (L2), 1-(2-(4-N-methylaminophenyl)benzothiazolyl)-2- oxoethyl)-4-(2-pyridylmethyl)-1,4,7-triazacyclononane (L3), 1,4-bis(2- pyridylmethyl)-7-(2-(4-aminophenyl)benzothiazolyl)-2-oxoethyl)-1,4, 7-triazacyclononane (L4). The ligands have been applied in the synthesis of a series of copper (II) complexes, [Cu(L1)(OH2)](ClO4) 2·0.5ACN (C1), [Cu(L3)](ClO4)2· ACN (C2) and [Cu(L4)(OH2)](ClO4)2·0.5THF (C4) whose structures have been determined by X-ray crystallography. As commonly observed for Cu(II) complexes of 1,4,7-triazacyclononane derivatives, the geometry of the metal centre ranges from distorted square pyramidal to pseudo-octahedral. Notably, the amide carbonyl coordinates to the copper(II) centre in C1 and C2 but not in C4 where the presence of an additional pyridyl group results in an N5 coordination sphere.
- Barreto, José,Venkatachalam, Taracad K.,Joshi, Tanmaya,Kreher, Ute,Forsyth, Craig M.,Reutens, David,Spiccia, Leone
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p. 128 - 138
(2013/06/05)
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- Synthesis, anti-breast cancer activity, and molecular modeling of some benzothiazole and benzoxazole derivatives
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A new series of benzothiazoles and benzoxazoles was synthesized using 4-benzothiazol-2-yl-phenylamine and 4-benzoxazol-2-yl-phenylamine as starting materials. All the prepared compounds were evaluated for their antitumor activities against human breast ca
- Abdelgawad, Mohamed A.,Belal, Amany,Omar, Hany A.,Hegazy, Lamees,Rateb, Mostafa E.
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p. 534 - 541
(2013/07/26)
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- Synthesis and in vitro antimicrobial activity of novel 2-(4-(substituted- carboxamido)benzyl/phenyl)benzothiazoles
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A new series of 2-[4-(4-substitutedbenzamido/phenylacetamido/ phenylpropionamido) benzyl/phenyl]benzothiazole derivatives (6a-6w) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis,
- Yilmaz, Serap,Yalcin, Ismail,Kaynak-Onurdag, Fatma,Ozgen, Selda,Yildiz, Ilkay,Aki, Esin
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p. 223 - 231
(2013/11/06)
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- Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts
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A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.
- Cheung, Chi Wai,Surry, David S.,Buchwald, Stephen L.
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supporting information
p. 3734 - 3737
(2013/08/23)
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