24613-99-8Relevant academic research and scientific papers
Synthesis, characterization, crystal structures and biological activity of set of Cu(II) benzothiazole complexes: Artificial nucleases with cytotoxic activities
Steiner, Ramsey A.,Foreman, David,Lin, Han X.,Carney, Bruce K.,Fox, Kristin M.,Cassimeris, Lynne,Tanski, Joseph M.,Tyler, Laurie A.
, p. 1 - 11 (2014)
A series of Cu(II) complexes with ligand frames based on quinoline derivatives appended with a benzothiazole substituent has been isolated. The complexes, Cu(Q(oBt))(NO3)2(H2O)CH 3OH (1 CH3OH), Cu(8OHQ(oBt))Cl2 CH 3OH (2 CH3OH), Cu(8OQ(oBt))Cl(CH3OH) CH 3OH (3 CH3OH) and [Cu(8OH1/2Q(oBt))(CH 3OH)(NO3)]2(NO3) (4) have been characterized by single crystal X-ray diffraction, IR and UV-visible spectroscopies, and elemental analysis. The ligand frame within the set of complexes differs in the substituent on the quinoline ring: complex 1 remains unsubstituted at this position while complexes 2-4 have a substituted OH group. In complex 2, the bound phenol remains protonated while in 3 it is a phenolato group. Complex 4 contains two complexes within the unit cell and one NO 3- giving rise to an overall 'half-protonation'. The interaction between complexes 1-3 with CT-DNA was investigated using fluorescence emission spectroscopy and revealed 2 and 3 strongly intercalate DNA with Kapp values of 1.47 × 107 M- 1 and 3.09 × 107 M- 1, respectively. The ability of complexes 1-3 to cleave SC-DNA was monitored using gel electrophoresis. Each complex exhibits potent, concentration dependent nuclease activity forming single and double-nicked DNA as low as 10 μM. The nuclease activity of complexes 1-3 is primarily dependent on 1O2 species while ·OH radicals play a secondary role in the cleavage by complexes 2 and 3. The cytotoxic effects of 1-3 were examined using HeLa cells and show cell death in the micromolar range. The distribution of cell cycle stages remains unchanged when complexes are present indicating DNA damage may be occurring throughout the cell cycle.
TD-DFT study on the fluorescent chemosensor for Hg2+, 2-(Benzo-d-thiazol-2-yl)quinoline
Miyamoto, Ryo,Kawakami, Jun,Ohtake, Rie,Nagaki, Masahiko,Ito, Shunji
, p. 73 - 78 (2011)
2-(Benzo-d-thiazol-2-yl)quinoline (BTQ) was synthesized and tested for its use as a fluorescent chemosensor for Hg2+. The metal-ion recognition of BTQ was investigated by adding several metal ions (M2+) to a solution of BTQ in acetonitrile. The shape and intensity of the fluorescence spectra did not change upon addition of several metal ions, except for Hg 2+ and Cu2+. The time-dependent density functional calculations were carried out on BTQ and BTQ-M2+ complexes (M = Zn, Cd, and Hg) to clarify their spectroscopic properties. The results of the calculation showed that the energy levels of the excited singlet and triplet states are similar in Zn2+ and Cd2+ complexes, whereas the Hg2+ complex has lower transition energy. The character of their excited states was also different between zinc and cadmium complexes with the mercury complex.
Quinoline functionalized schiff base silver (I) complexes: Interactions with biomolecules and in vitro cytotoxicity, antioxidant and antimicrobial activities
Adeleke, Adesola A.,Islam, Md. Shahidul,Mocktar, Chunderika,Olofinsan, Kolawole,Omondi, Bernard,Salau, Veronica F.,Zamisa, Sizwe J.
, (2021)
A series of fifteen silver (I) quinoline complexes Q1-Q15 have been synthesized and studied for their biological activities. Q1-Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1-L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline derivatives) with AgNO3, AgClO4 and AgCF3SO3. Q1-Q15 were characterized by various spectroscopic techniques and the structures of [Ag(L1)2]NO3 Q1, [Ag(L1)2]ClO4 Q6, [Ag(L2)2]ClO4 Q7, [Ag(L2)2]CF3SO3 Q12 and [Ag(L4)2]CF3SO3 Q14 were unequivocally determined by single crystal X-ray diffraction analysis. In vitro antimicrobial tests against Gram-positive and Gramnegative bacteria revealed the influence of structure and anion on the complexes’ moderate to excellent antibacterial activity. In vitro antioxidant activities of the complexes showed their good radical scavenging activity in ferric reducing antioxidant power (FRAP). Complexes with the fluorine substituent or the thiophene or benzothiazole moieties are more potent with IC50 between 0.95 and 2.22 mg/mL than the standard used, ascorbic acid (2.68 mg/mL). The compounds showed a strong binding affinity with calf thymus-DNA via an intercalation mode and protein through a static quenching mechanism. Cytotoxicity activity was examined against three carcinoma cell lines (HELA, MDA-MB231, and SHSY5Y). [Ag(L2)2]ClO4 Q7 with a benzothiazole moiety and [Ag(L4)2]ClO4 Q9 with a methyl substituent had excellent cytotoxicity against HELA cells.
Synthesis, characterization and X-ray crystal structure of copper(I) complexes of the 2-(2-quinolyl)benzothiazole ligand. Electrochemical and antibacterial studies
Meghdadi, Soraia,Amirnasr, Mehdi,Mirhashemi, Afsaneh,Amiri, Ahmad
, p. 234 - 239 (2015)
Two new copper(I) complexes of the general formula [Cu(qbtz)(PPh3)(X)] {qbtz = 2-(2-quinolyl)benzothiazole and X = Br (1), I (2)} have been synthesized and characterized by elemental analyses, IR, UV-Vis and 1H NMR spectroscopy. The crystal and molecular structures of these complexes have been determined by single-crystal X-ray diffraction. The coordination geometry around the central metal ion is a distorted tetrahedron. The electrochemical behavior of the ligand and its copper(I) complexes has been investigated by cyclic voltammetry in DMF solution. The redox potential of the copper center is influenced by the nature (the σ-donor ability) of the coordinated halide X-, and it shifts to more anodic potentials for complex 2 as compared to that of 1. The in vitro antibacterial activities of the ligand and its copper complexes were tested against Staphylococcus aureus, Bacillus cereus and Salmonella typhi.
Synthesis, characterization, and X-ray crystal structures of copper(I) halide and pseudohalide complexes with 2-(2-quinolyl)benzothiazole. Diverse coordination geometries and electrochemical properties
Meghdadi, Soraia,Amirnasr, Mehdi,Yavari, Elaheh,Mereiter, Kurt,Bagheri, Maryam
, p. 730 - 737 (2017)
Three new copper(I) complexes with the ligand 2-(2-quinolyl)benzothiazole (qbtz) have been synthesized and characterized by elemental analyses, infrared, and ultraviolet–visible spectroscopy, and their crystal structures have been determined by X-ray diffraction. The coordination geometry around copper in [Cu(qbtz)(μ-I)]2, complex (1), a centrosymmetric dimer, is a distorted CuI2N2 tetrahedron supplemented by a short Cu?Cu interaction of 2.5855 ?. The copper(I) cyanide–bridged complex [Cu3(qbtz)2(μ-CN)3] (2) exhibits a one-dimensional chain structure with three crystallographically independent Cu atoms. Two of the copper atoms feature tetrahedral four coordination each by a chelating qbtz ligand and two CN groups, and the third features a quasi-linear two-coordination geometry by two CN. In [Cu(qbtz)(μ-SCN)] (3), copper is in a distorted tetrahedral coordination by two N atoms of a chelating qbtz ligand and by one N atom and one S atom of a bridging SCN group. The complex exhibits a one-dimensional zigzag chain structure with two crystallographically inequivalent Cu atoms in the chain. The spectroscopic and electrochemical properties of compounds 1–3 are in accord with the variation in copper(I) coordination environments.
Three-component synthesis of 2-heteroaryl-benzothiazoles under metal-free conditions
Li, Guozheng,Xie, Hao,Chen, Jinjin,Guo, Yanjun,Deng, Guo-Jun
, p. 4043 - 4047 (2017)
A three-component procedure for the preparation of 2-heteroaryl-benzothiazoles from anilines, 2-methylquinolines and sulfur powder is described. This reaction was promoted using NH4I to give the corresponding biheteroaryl products in moderate to good yields in the absence of metals.
Transition-Metal-Free Synthesis of 2-Substituted Benzothiazoles from Nitrobenzenes, Methylheteroaryl Compounds, and Elemental Sulfur, Based on Nitro-Methyl Redox-Neutral Cyclization
Teramoto, Masahiro,Imoto, Mitsutaka,Takeda, Motonori,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya
, p. 15213 - 15220 (2020/12/02)
Greener and more sustainable chemical processes are required to address increasing environmental pollution and depletion of natural resources. This paper aims to develop greener and more sustainable modern synthetic chemical processes using redox-neutral cyclization. Redox-neutral cyclization has been shown to promote the efficient synthesis of 2-substituted benzothiazoles from easily available nitrobenzenes, methyl-heteroaryl compounds, and elemental sulfur in the absence of transition-metal catalysts. The 2-substituted benzothiazoles were obtained in reasonable yields through the sulfuration of electron-deficient C-H bonds with elemental sulfur. This synthetic methodology also affords a high atom economy without the use of any external oxidizing and/or reducing reagents.
Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline
Rahim, Abdul,Shaik, Siddiq Pasha,Baig, Mirza Feroz,Alarifi, Abdullah,Kamal, Ahmed
, p. 635 - 644 (2018/02/07)
Iodine-promoted oxidative C-H/C-H cross-coupling of unprotected anilines and 2-methylquinoline to furnish C4-carbonylated aniline (4-aminophenyl)(quinoline-2-yl) methanones in moderate to good yields has been demonstrated. This work provides the first site-selective approach for the synthesis of free amino groups containing methanones including unprecedented C-H functionalization rather than the N-H functionalization of unprotected anilines via the Kornblum oxidation of 2-methylquinoline. Furthermore, we noticed that the incorporation of KOH under standard conditions provides 2-heteroarylbenzothiazoles from benzothiazoles and 2-methylquinoline in good to excellent yields. These transformations do not require any transition metals or peroxides and tolerate various functional groups such as methoxy, hydroxy, bromo, chloro and nitro groups. Moreover, a plausible mechanistic pathway is proposed.
Oxidative Csp3-H functionalization of 2-methylazaarenes: A practical synthesis of 2-azaarenyl-benzimidazoles and benzothiazoles
Yaragorla, Srinivasarao,Vijaya Babu
, p. 1879 - 1882 (2017/04/21)
Oxidative Csp3-H functionalization of 2-methylazaarenes using I2-DMSO in open flask has been described first time for the synthesis of 2-azaarenyl benzimidazoles and 2-azaarenyl benzothiazoles. Generally, methyl group of 2-methylazaa
N-Iodosuccinimide involved one-pot metal-free synthesis of 2-heteroaromatic benzothiazole compounds
Chu, Xianglong,Duan, Tiantian,Liu, Xuan,Feng, Lei,Jia, Jiong,Ma, Chen
, p. 1606 - 1611 (2017/02/23)
A one-pot protocol for the synthesis of structurally diverse 2-hetarylbenzothiazoles via oxidative condensation of the sp3 C-H bond with benzothiazoles has been described. This process is metal free and operationally simple. A series of 2-hetarylbenzothiazoles were prepared in moderate to good yield under mild conditions.
