615-21-4Relevant articles and documents
Six-membered spirocycle triggered probe for visualizing Hg2+ in living cells and bacteria-EPS-mineral aggregates
Yang, Zheng,Hao, Likai,Yin, Bing,She, Mengyao,Obst, Martin,Kappler, Andreas,Li, Jianli
, p. 4334 - 4337 (2013)
A novel rhodamine based probe with a unique six-membered spirocycle was rationally designed for detection of Hg2+ with greatly improved selectivity, sensitivity, and photostability. The probe has been shown to be suitable for Hg2+ imaging in living cells and mapping Hg2+ distribution in living cell-EPS-mineral aggregates under anoxic conditions.
Selective “off-on” detection of magnesium (II) ions using a naphthalimide-derived fluorescent probe
zhang, Huifang,Yin, Caixia,Liu, Tao,Chao, Jianbin,Zhang, Yongbin,Huo, Fangjun
, p. 344 - 351 (2017)
A novel “off-on” fluorescent probe based on 1, 8-naphthalimide derivative for the detection of Mg2+ in ethanol solution was designed and synthesized. The probe displayed responses to Mg2+ with a fluorescence enhancement at 523 nm, accompanying with a distinct fluorescence change from nearly colorless to bright yellow-green. Besides, the probe showed a rapid detection process (45 s), high fluorescence enhancement (up to 15-fold), a good binding constant (6.17 × 105 M?1) and a low detection limit of Mg2+ (5.01 × 10?8 M). Moreover, density functional theory (DFT) calculations were also performed to support the responding mechanism between the probe and the coordination complex. In addition, the cell cytotoxicity experiments suggested that the probe is nearly non-toxic and the fluorescence scanning microscopic experiments demonstrated that the probe was capable of monitoring at the intracellular Mg2+ level successfully.
In situ oxidation triggered heteroleptically deprotonated cobalt(III) and homoleptic nickel(II) complexes of diacetyl monoxime derived tri-nitrogen chelators; Synthesis, molecular structures and biological assay
Kamat, Vinayak,Kotian, Avinash,Nevrekar, Anupama,Naik, Krishna,Kokare, Dhoolesh,Revankar, Vidyanand K.
, p. 625 - 631 (2017)
Two tri-nitrogen chelating unsymmetrical Schiff base ligands, 3-(hydroxyimino)-2-butanone-2-(1H-benzothiazol-2-yl)hydrazone and 3-(hydroxyimino)-2-butanone-2-(1H-benzimidazol-2-yl)hydrazone are synthesized by the condensation reaction of diacetyl monoxime with 2-hydrazino-benzothiazole/benzimidazole. Ligands have shown ML2 type octahedral coordination towards Ni(II) and in situ generated Co(III) ions. Ligands and complexes are characterized by various spectro-analytical techniques. Both the ligands have shown a similar mode of ligation, but a different mode of deprotonation towards the cobalt and nickel ions. Ligands are left neutral in the case of nickel complexes while anionic in the case of cobalt complexes. Further, in situ oxidation of Co(II) to Co(III) has triggered a different mode of deprotonation between the two ligands of the same cobalt complex. Out of the four complexes synthesized, three complexes are characterized by single crystal X-ray diffraction technique, to evidence the structural facts. A comparative account of bond lengths of two complexes of the benzothiazole based ligand is presented. Structures of all the four complexes have been checked preliminarily for their NCI-60 Human Cancer Cell Line anticancer screening. Further, one among the four, the nickel complex of benzothiazole core is used for one dose growth inhibition screening against 60 different human cancer cell lines. The tested complex has shown highest growth inhibition over a Non-Small Cell Lung Cancer cell line EKVX. In addition, compounds are screened for their antibacterial and antifungal potencies against few microorganisms. The complexes have shown promising antimicrobial potencies.
Functionalized 2-hydrazinobenzothiazole with isatin and some carbohydrates under conventional and ultrasound methods and their biological activities
Badahdah, Khadija O.,Hamid, Hamida M. Abdel,Noureddin, Sawsan A.
, p. 67 - 74 (2015)
Several chemical reactions were carried out on 3-(benzothiazol-2-yl-hydrazono)-1,3-dihydro-indol-2-one (2). 3-(Benzothiazol-2-yl-hydrazono)-1-alkyl-1,3-dihydro-indol-2-one 3a-c have been achieved. Reaction of compound 2 with ethyl bromoacetate in the presence of K2CO3 resulted the uncyclized product 4. Reaction of compound 2 with benzoyl chloride afforded dibenzoyl derivative 5. Compound 2 was smoothly acetylated by acetic anhydride in pyridine to give diacetyl derivative 6b. Moreover, when compound 4 reacted with methyl hydrazine, it yielded dihydrazide derivative 7, whereas the hydrazinolysis of this compound with hydrazine hydrate gave the monohydrazide derivative 8. {N-(Benzothiazol-2-yl-N'-(3-oxo-3,4-dihydro-2H- 1,2,4-triaza-fluoren-9-ylidene)hydrazino]-acetic acid ethyl ester (9) was prepared by ring closure of compound 8 by the action of glacial acetic acid. In addition, the reaction of 2-hydrazinobenzothiazole (1) with D-glucose and D-arabinose in the presence of acetic acid yielded the hydrazones 10a,b, respectively. Acetylation of compound 10b gave compound 11b. On the other hand, compound 13 was obtained by the reaction of compound 1 with gama-D-galactolactone (12). Acetylation of compound 13 with acetic anhydride in pyridin gave the corresponding N1-acetyl-N2-(benzothiazolyl)-2-yl)-2,3,4,5,6-penta-O-acetyl-D-galactohydrazide (14). Better yields and shorter reaction times were achieved using ultrasound irradiation. The structural investigation of the new compounds is based on chemical and spectroscopic evidence. Some selected derivatives were studied for their antimicrobial and antiviral activities.
Novel benzo[4,5]thiazolo[2,3-C][1,2,4]triazoles: Design, synthesis, anticancer evaluation, kinase profiling and molecular docking study
Abdelazeem, Ahmed H.,Alqahtani, Alaa M.,Arab, Hany H.,Gouda, Ahmed M.,Safi El-Din, Asmaa G.
, (2021)
In the current study, we report the synthesis and cytotoxic evaluation of a new series of S-benzo[4,5]thiazolo[2,3-c][1,2,4]triazole-based derivatives 8-12. Cytotoxicity of the new compounds was investigated in A549, MCF-7, and Hep3B cancer cell lines. Among these derivatives, compound 12 bearing an isatin moiety was the most active derivative (IC50 = 2.40-3.53 μM). A mechanistic study of compound 12 was performed using the kinase profiling test to explore its inhibitory activity against 10 types of the oncogenic kinases and the potential activation of caspase 3/7 enzymes. The results revealed that compound 12 showed moderate inhibition of the EGFR and LCK kinases. Moreover, compound 12 also activated caspase-3/7 in A549 cells. The docking study of compound 12 into EGFR ATP-active site revealed that it fits nicely with good binding affinity. Together, the results indicated that compound 12 could serve as a good lead for developing new potential anticancer agents.
Multi-Step Synthesis, Physicochemical investigation and optical properties of pyrazoline derivative: A Donor-π-Acceptor chromophore
Alfaifi, S. Y.,Alimuddin,Almalki, Abdulraheem S. A.,Alsharif, Meshari A.,Khan, Salman A.,Kumar, Sanjay,Obaid, Rami J.,Syed, Salauddin,Ullah, Qasim
, (2020/12/17)
The new extended π-bond pyrazoline derivative (ENTD) was prepared from heterocyclic chalcone with 2-hydrazinylbenzo[d] thiazole. The spectroscopic methods established the structure of the ENTD, and the elemental analysis established the purity of the ENTD. In ten different solvents, physicochemical ENTD parameters such as the molar absorption coefficient, transition dipole moments, Stokes shift, oscillator intensity and fluorescence quantum yield were determined to see the effect of the solvent with pyrazoline derivative (ENTD) on the basis of different polarity. In addition, the interaction of ENTD chromophore with the cationic and anionic surfactants have been studied. The intensity of fluorescence spectrum of the ENTD was found to increase with an increase in the surfactant concentration. This indicates that there is a strong interaction between ENTD and surfactants. The ENTD chromophore can therefore be used as a probe to define the surfactants' CMC.
Design, Synthesis, Antibacterial Evaluation and Molecular Docking Studies of Some Newer Baenzothiazole Containing Aryl and Alkaryl Hydrazides
Afzal Azam, Mohammed,Gurram, Swarupa Rani
, (2021/06/27)
The alarming rise of bacterial resistance is occurring worldwide and endangering the efficacy of antibiotics. Therefore, development of new and efficient antibacterial agents remains paramount. In the present work, we designed and synthesized a series of N′-(1,3-benzothiazol-2-yl)-substituted aryl/aralkyl hydrazides C1–C27 and evaluated them in vitro for their antibacterial activity. Among all tested compounds, C10, C15, and C24 showed potent activity against Staphylococcus aureus ATCC 43300 (MRSA). Minimum bactericidal concentration studies of synthesized compounds are performed against selected bacterial strains. Time kill kinetics showed that the compounds C10 and C15 possess bactericidal activity against MRSA ATCC 43300, while compound C24 possess bactericidal activity against S. aureus NCIM 5022. In the extra-precision docking, compounds C1–C27 exhibited interactions mainly with the N-terminal and central domains of S. aureus GyrB catalytic pocket. Binding free energy (ΔGbind) of compounds C1–C27/3U2K complexes were computed by MM-GBSA approach. Free energy components indicated Coulomb energy term as favorable for binding, while van der Waals and electrostatic solvation energy terms strongly disfavored the binding. ADMET properties of synthesized compounds C1–C27 are also computed.
