4760-35-4Relevant academic research and scientific papers
Half-sandwich Iridium(III) Benzimidazole-Appended Imidazolium-Based N-heterocyclic Carbene Complexes and Antitumor Application
Han, Yali,Liu, Xicheng,Tian, Zhenzhen,Ge, Xingxing,Li, Juanjuan,Gao, Min,Li, Yanru,Liu, Yi,Liu, Zhe
, p. 3697 - 3705 (2018)
A series of half-sandwich iridium(III) benzimidazole-appended imidazolium-based N-heterocyclic carbene (NHC) antitumor complexes [(η5-Cpx)Ir(C^N)Cl]Cl, where Cpx is pentamethylcyclopentadienyl (Cp*) or its biphenyl derivative (Cpxbiph) and C^N is a NHC chelating ligand, were successfully synthesized and characterized. The IrIII complexes showed potential antitumor activity against A549 cells, at most three times more potent than cis-platin under the same conditions. Complexes could bind to BSA by a static quenching mode, catalyzing the change of NADH to NAD+ and inducing the production of reactive oxygen species (maximum turnover number, 9.8), which play an important role in regulating cell apoptosis. Confocal microscopy showed that the complexes could specifically target lysosomes in cells with a Pearson's co-localization coefficient 0.76 and 0.72 after 1 h and 6 h, respectively, followed an energy-dependent cellular uptake mechanism and damaged the integrity of lysosomes. At the same time, complexes caused a marked loss of mitochondrial membrane potential.
Synthesis of 1-alkyl-2-chloromethylbenzimidazole under green conditions
Rao, S. Srinivas,Reddy, Ch. Venkata Ramana,Dubey
, p. 98 - 100 (2015)
A green approach for the synthesis of 1-alkyl-2-chloromethylbenzimidazoles (3) (R1 = CH3, C2H5, CH2Ph) under, different conditions has been developed from 2-chloromethylbenzimidazole (2) by reaction with an alkylating agent (i.e. DMS, DES, PhCH2Cl) by physical grinding or by using green solvent like PEG-600 or by using micro-wave irradiation technique.
Dicopper(II) complexes of chiral C2-symmetric diamino-bis(2-methylpyridyl) and diamino-bis(2-methylbenzimidazolyl) ligands
Pérez, Viridiana,Monsalvo, Iván,Demare, Patricia,Gómez-Vidales, Virginia,Regla, Ignacio,Castillo, Ivan
, p. 389 - 391 (2011)
Reaction of the chiral ligands (1S,4S)-2,5-bis(6-methylpyridyl)- diazabicyclo[2.2.1]heptane (L1), and (1S,4S)-2,5-bis(2- methylbenzimidazolyl)-diazabicyclo[2.2.1]heptane (L2) with copper(II) acetate results in the hydroxo-bridged dic
Structure, magnetism and reactivity of a {MnIII(μ-O)2MnIV}3+ core towards oxidation of phenols
Kumar, Akhilesh,Sengupta, Arunava,Demeshko, Serhiy,Mukherjee, Rabindranath
, p. 226 - 235 (2019)
Two complexes [(L)2MnII(OClO3)(CH3CN)](ClO4)·CH3CN (1) and [(L)4MnIII/IV 2(μ-O)2](ClO4)3·2CH3CN·Et2O (2), where L is 2-((1H-pyrazol-1-yl)methyl)-1-methyl-1H-benzimidazole, have been synthesized, structurally characterized, UV–Vis and EPR spectral properties, variable-temperature (2–300 K) magnetic susceptibility and redox behavior investigated. Structural analysis reveals that the {MnIII(μ-O)2MnIV}3+ core in 2 is an example of delocalized class III system. Complex 1 has S = 5/2 ground-state. The MnIII and MnIV centres in 2 are antiferromagnetically coupled (J = ?192 cm?1) and has S = 1/2 ground-state. Complex 2 exhibits characteristic 16-line EPR spectrum (120 K) centered at g ≈ 2. Reactivity of 2 towards p-X-2-tert-butylphenols (X = H, Me, OMe, tBu) has been investigated. The oxidation of phenols generate phenoxyl radical (2,4,6-tri-tert-butylphenol exhibits EPR signal due to radical)/radical-coupled bis-phenol product (in the case of 2,4-di-tert-butylphenol, DTBP). Kinetic experiments have allowed us to evaluate second-order rate constant values for the faster initial step (k2 × 10?2 M?1 s?1) for p-X-2-tert-butylphenols: 0.6 (X = H), 1.95 (Me), 3.0 (OMe), 1.85 (tBu) and for the slower second step (k2 × 10?3 M?1 s?1) for p-X-2-tert-butylphenols: 0.9 (X = H), 2.5 (Me), 4.0 (OMe). Reaction between {MnIII(μ-O)2MnIV}3+ of 2 and phenols proceeds via hydrogen atom transfer mechanism to produce oxidation products. Initial reaction supposedly generates {MnIII(O)(OH)MnIII}3+ species, which finally ends up as (L)-coordinated MnII species (ESI-MS spectrum for the reaction between 2 and DTBP).
Design, synthesis, and antitumor activity of novel benzoheterocycle derivatives as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase
Ding, Yangyang,Liu, Kai,Zhao, Xinyu,Lv, Yingtao,Yu, Rilei,Kang, Congmin
, p. 286 - 294 (2020/01/28)
The vascular endothelial growth factor receptor-2 signaling pathway promotes the formation of new blood vessels, and vascular endothelial growth factor receptor-2 tyrosine kinase exists in both active and inactive conformations. Novel indole–benzimidazole and indole–benzothiazole derivatives joined by different linkers are designed and synthesized as inhibitors of vascular endothelial growth factor receptor-2 tyrosine kinase. All the synthesized compounds were evaluated for their cytotoxicity against four human cancer cell lines (HeLa, HT29, A549, and MDA-MB-435) and human umbilical vein endothelial cell. Meanwhile, the inhibitory activities against vascular endothelial growth factor receptor-2 are estimated in vitro and the binding interactions with dual conformations of vascular endothelial growth factor receptor-2 tyrosine kinase are evaluated by molecular docking. Compounds 5a–c and 14 show inhibitory activity against vascular endothelial growth factor receptor-2 tyrosine kinase and promising cytotoxicity, specifically with IC50 values ranging between 0.1 and 1 μM, which imply broad-spectrum antitumor activity. These results provide a deep insight into potential structural modifications for developing potent vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors.
Antitubercular and Antiparasitic 2-Nitroimidazopyrazinones with Improved Potency and Solubility
Ang, Chee Wei,Tan, Lendl,Sykes, Melissa L.,Abugharbiyeh, Neda,Debnath, Anjan,Reid, Janet C.,West, Nicholas P.,Avery, Vicky M.,Cooper, Matthew A.,Blaskovich, Mark A. T.
, p. 15726 - 15751 (2020/12/02)
Following the approval of delamanid and pretomanid as new drugs to treat drug-resistant tuberculosis, there is now a renewed interest in bicyclic nitroimidazole scaffolds as a source of therapeutics against infectious diseases. We recently described a nitroimidazopyrazinone bicyclic subclass with promising antitubercular and antiparasitic activity, prompting additional efforts to generate analogs with improved solubility and enhanced potency. The key pendant aryl substituent was modified by (i) introducing polar functionality to the methylene linker, (ii) replacing the terminal phenyl group with less lipophilic heterocycles, or (iii) generating extended biaryl side chains. Improved antitubercular and antitrypanosomal activity was observed with the biaryl side chains, with most analogs achieved 2- to 175-fold higher activity than the monoaryl parent compounds, with encouraging improvements in solubility when pyridyl groups were incorporated. This study has contributed to understanding the existing structure-activity relationship (SAR) of the nitroimidazopyrazinone scaffold against a panel of disease-causing organisms to support future lead optimization.
Synthesis, molecular docking, α-glucosidase inhibition, and antioxidant activity studies of novel benzimidazole derivatives
Singh, Gagandeep,Singh, Amanjot,Singh, Varinder,Verma, Raman K.,Tomar, Jyoti,Mall, Rajiv
, p. 1846 - 1866 (2020/08/03)
A novel series of N-methyl/benzyl-substituted benzimidazolyl-linked para-substituted benzyl-based compounds containing 2,4-thiazolidinediones, dimethyl malonate (DMM), and diethyl malonate (DEM) 17–27 were designed, docked, synthesized, and evaluated for their antidiabetic activity studies. Structures of all the synthesized compounds were confirmed through 1H NMR, 13C NMR, FTIR, and mass spectrometry. Four targeted compounds (17–18 and 22–23) showed good inhibitory potential in the range of 4.10 ± 0.01 to 9.12 ± 0.06 μM. Furthermore, synthesized compounds 17–27 were evaluated for their antioxidant potential and compared with standard ascorbic acid and results showed that compound 18 (EC50 = 0.176 ± 0.002 mM) being the most active. Compounds 17–18 and 22–23 exhibited prominent antidiabetic as well as antioxidant activity. Compound 18 was considered a promising candidate for this series. The designed molecules were docked into α-glucosidase protein (PDB Code. 3TOP) to develop a correlation with the α-glucosidase inhibition studies and were also additionally docked into PPARγ proteins (PDB ID: 2PRG) with rosiglitazone (standard drug) to study their PPARγ binding affinity in comparison with rosiglitazone and to classify these compounds for their PPARγ agonistic behavior.
Synthesis of Carbophosphinocarbene and Their Donating Ability: Expansion of the Carbone Class
Liu, Shu-Kai,Chen, Wen-Ching,Yap, Glenn P. A.,Ong, Tiow-Gan
supporting information, p. 4395 - 4401 (2020/12/23)
In recent years, carbones (CL2) have established themselves to be reliable ligands in organometallic and catalytic reactions. With its superb donating ability as well as a second lone pair for extra coordination, it distinguishes itself from the widely used carbenes and phosphines. However, a lack of modular structural diversity in carbones has limited its use. A carbophosphinocarbene (CPC), a subclass of carbones containing a carbene and phosphine as flanking groups, offers an easy structural modification. In this work, we report a new modular synthetic procedure for CPCs by using readily available starting materials. In addition, the phosphine moiety can be easily exchanged and directly used out of the bottle. The resulting CPCs offer a strong donating ability. Their electronic properties have been determined using Ga and Au complexes.
High performance benzoimidazolyl-based aminophenolate zinc complexes for isoselective polymerization of: Rac -lactide
Gong, Yanmei,Ma, Haiyan
, p. 10112 - 10115 (2019/08/30)
Zinc complexes supported by achiral benzoimidazolyl-based aminophenolate ligands exhibit high catalytic activities and excellent isoselectivities toward the ring-opening polymerization of rac-lactide under mild conditions.
Anti-oligomerization sheet molecules: Design, synthesis and evaluation of inhibitory activities against α-synuclein aggregation
Liu, Hao,Chen, Li,Zhou, Fei,Zhang, Yun-Xiao,Xu, Ji,Xu, Meng,Bai, Su-Ping
supporting information, p. 3089 - 3096 (2019/06/14)
Aggregation of α-synuclein (α-Syn) play a key role in the development of Parkinson Disease (PD). One of the effective approaches is to stabilize the native, monomeric protein with suitable molecule ligands. We have designed and synthesized a series of sheet-like conjugated compounds which possess different skeletons and various heteroatoms in the two blocks located at both ends of linker, which have good π-electron delocalization and high ability of hydrogen-bond formation. They have shown anti-aggregation activities in vitro towards α-Syn with IC50 down to 1.09 μM. The molecule is found binding in parallel to the NACore within NAC domain of α-Syn, interfering aggregation of NAC region within different α-Syn monomer, and further inhibiting or slowing down the formation of α-Syn oligomer nuclei at lag phase. The potential inhibitor obtained by our strategy is considered to be highly efficient to inhibit α-Syn aggregation.
