10041-06-2Relevant academic research and scientific papers
Synthesis and crystal structures of coordination complexes containing Cu2I2 units and their application in luminescence and catalysis
Zhao, Huaixia,Li, Xinxiong,Wang, Jinyun,Li, Liuyi,Wang, Ruihu
, p. 1491 - 1502 (2013)
The reaction of bis- or tris-chelating nitrogen-containing ligands (L1-L5) with CuI gave rise to five coordination complexes consisting of Cu 2I2 dimeric units. L1 in complex 1 adopts a cis conformation and links Cu2I2 into a dinuclear structure. L2 and L3 in complexes 2 and 3 exhibit a trans conformation, and the alternative linkage of L2 or L3 and Cu2I2 results in the formation of a 1D chain. In complex 4, two pyrazolyl-pyridine units of L4 at the same side of the central phenyl ring are connected to Cu2I2 forming a tetranuclear macrocycle, and the third pyrazolyl-pyridine unit at the other side of the central phenyl ring further links the macrocycle into a 1D chain. L5 bridges Cu2I2 in a cis conformation forming a tetranuclear complex, which is very different from 1 owing to the difference of the electronic property between pyrazolyl and triazolyl rings. The coordination nitrogen atoms in two pairs of ortho-positioned nitrogen-containing chelating rings in L1 and L5 are directed toward opposite and the same directions, respectively. Complexes 1-4 containing pyrazolyl-pyridine units showed luminescence whereas no clear emission was observed in complex 5 containing triazolyl-pyridine units, despite the fact that they were investigated under the same conditions. The application of complexes 1-5 in the copper(I)-catalyzed Ullmann cross-coupling reaction and azide-alkyne cycloaddition reaction was preliminarily evaluated. Making a difference: Five copper(I) complexes consisting of Cu2I2 units (see figure for example) have been prepared by using readily available bis- or tris-chelating nitrogen-containing ligands. These complexes possess different crystal structures, luminescence properties, and catalytic performances owing to the difference in steric and electronic properties of the organic ligands. Copyright
Co/NHPI-mediated aerobic oxygenation of benzylic C-H bonds in pharmaceutically relevant molecules
Hruszkewycz, Damian P.,Miles, Kelsey C.,Thiel,Stahl, Shannon S.
, p. 1282 - 1287 (2017)
A simple cobalt(ii)/N-hydroxyphthalimide catalyst system has been identified for selective conversion of benzylic methylene groups in pharmaceutically relevant (hetero)arenes to the corresponding (hetero)aryl ketones. The radical reaction pathway tolerates electronically diverse benzylic C-H bonds, contrasting recent oxygenation reactions that are initiated by deprotonation of a benzylic C-H bond. The reactions proceed under practical reaction conditions (1 M substrate in BuOAc or EtOAc solvent, 12 h, 90-100 °C), and they tolerate common heterocycles, such as pyridines and imidazoles. A cobalt-free, electrochemical, NHPI-catalyzed oxygenation method overcomes challenges encountered with chelating substrates that inhibit the chemical reaction. The utility of the aerobic oxidation method is showcased in the multigram synthesis of a key intermediate towards a drug candidate (AMG 579) under process-relevant reaction conditions.
Copper nanoparticles incorporated on a mesoporous carbon nitride, an excellent catalyst in the Huisgen 1,3-dipolar cycloaddition and N-arylation of N-heterocycles
Kazemi Movahed, Siyavash,Salari, Parinaz,Kasmaei, Melika,Armaghan, Mahsa,Dabiri, Minoo,Amini, Mostafa M.
, (2018)
Cu nanoparticles with average particles size around 10?nm were incorporated on the surface of a mesoporous carbon nitride support. The XRD and N2 adsorption isotherms show that it maintains a hexagonal mesoporous structure with a high surface a
Synthesis and biological evaluation of some novel thiobenzimidazole derivatives as anti-renal cancer agents through inhibition of c-MET kinase
Ibrahim, Hany S.,Albakri, Mohamed E.,Mahmoud, Walaa R.,Allam, Heba Abdelrasheed,Reda, Ahmed M.,Abdel-Aziz, Hatem A.
, p. 337 - 348 (2019)
Benzimidazole is an interesting scaffold constituting a main core in many anticancer agents against variable cell lines as Carbendazim (I) and Nocodazole (II). Accordingly, eighteen compounds of 2-((1H-benzoimidazol-2-yl)thio)-1-(aryl/heteroaryl)ethan-1-ones, in their sulfate salt and free forms, were designed and investigated as anticancer agents. In vitro preliminary screening of selected compounds by the National Cancer Institute (NCI) on a panel of 60 cell lines revealed renal cancer cell line (A498) as the most vulnerable cell line; accordingly, IC50 values against A498 cell line were determined for compounds with the best results. The best inhibitory activity was for compound 4a with (IC50 = 6.97 μM) compared to sunitinib as a reference drug (IC50 = 6.99 μM). Compound 4a was further subjected to cell cycle analysis that indicated the decrease in cell population in the G2/M phase when compared to the untreated control cells. In addition, it showed significant increase in the late apoptosis in Annexin-V FTIC study compared to the control cells. An enzymatic inhibitory study on compound 4a against c-Met and MAP kinases revealed its better activity against c-Met kinase with (IC50 = 0.27 μM) compared to sunitinib (IC50 = 0.18 μM). Molecular docking study was conducted to reveal the interactions of compound 4a in the active site of c-Met kinase. Computational ADME study was performed to insure that compound 4a has proper pharmacokinetic and drug-likeness properties.
1-[4 - (1H-imidazol-1-yl)phenyl]-3-phenylprop-2-en-1-ones - A potential pharmacophore bearing anti-leishmanial activity
Hussain, Tanvir,Zia-Ur-Rehman, Muhammad,Zaheer, Muhammad,Ashraf, Chouhdary Muhammad,Bolte, Michael
, p. 199 - 204 (2016)
A series of new potentially anti-microbial 1-[4-(1H-imidazol-1-yl)phenyl]-3-phenylprop-2-en-1-ones was synthesised by condensation of various substituted benzaldehydes with 1-[4-(1H-imidazol-1-yl)phenyl]ethanone, which was itself prepared by N-arylation o
Ligand-free N-arylation of heterocycles using metal-organic framework [Cu(INA)2] as an efficient heterogeneous catalyst
Truong, Thanh,Nguyen, Chi V.,Truong, Ngoc T.,Phan, Nam T. S.
, p. 107547 - 107556 (2015)
A metal-organic framework [Cu(INA)2] was synthesized and used as a heterogeneous catalyst for arylation of a wide range of N-H heterocycles and aryl halides under ligand-free conditions. The N-arylation reaction involved the use of 5 mol% Cu-MOF catalyst with K3PO4 or tBuOLi as the base in dimethylacetamide (DMA) solvent at 100 °C in 6 h. [Cu(INA)2] exhibited higher catalytic activity for the N-arylation transformation than that of common homogeneous copper catalysts and other Cu-MOFs with unsaturated open metal sites such as Cu2(BDC)2(BPY), Cu3(BTC)2, and Cu2(BDC)2(DABCO). Interestingly, reaction conditions are compatible with a wide range of N-H heterocycles, functional groups, and aryl chlorides. A leaching test indicated no contribution of leached active species in the reaction filtrate. Furthermore, the [Cu(INA)2] catalyst could be facilely separated from the reaction mixture and recovered and reused several times without a significant degradation in catalytic activity.
Synthesis and anticandidal activity of new imidazole-chalcones
Osmaniye, Derya,Avu?o Glu, Bet l Kaya,Sa gl?k, Beg m Nurpelin,Levent, Serkan,Acar evik, Ulviye,Atl?, Zlem,Zkay, Yusuf,Kaplanc?kl?, Zafer As?m
, (2018)
In the present work, 15 new 1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-substituedphenyl)prop-2-en-1-one derivatives (3a–3o) were synthesized to evaluate their antifungal activity. Structures of newly synthesized imidazole derivatives (3a–3o) were characterized by IR,1H-NMR,13C-NMR, and LCMSMS spectroscopic methods. The anticandidal activity of compounds (3a–3o) against C. albicans (ATCC 24433), C. krusei (ATCC 6258), C. parapsilosis (ATCC 22019), and C. glabrata (ATCC 90030) was elucidated according to the EUCAST definitive (EDef 7.1) method. Consistent with the activity studies, 3a–3d were found to be more potent derivatives with their MIC50 values (0.78 μg/mL–3.125 μg/mL) against Candida strains. Compound 3c indicated similar antifungal activity to ketoconazole against all Candida species and was evaluated as the most active derivative in the series. Effects of the most potent derivatives 3a–3d on ergosterol biosynthesis were observed by LC-MS-MS method, which is based on quantification of the ergosterol level in C. krusei. Moreover, these compounds were subjected to a cytotoxicity test for the preliminary toxicological profiles and were found as non-cytotoxic. Furthermore, docking studies for the most active derivative 3c were performed to evaluate its binding modes on lanosterol 14-α-demethylase. In addition to in vitro tests, docking studies also revealed that Compound 3c is a potential ergosterol biosynthesis inhibitor.
A simple and efficient 2N2O-Cu(II) complex as a catalyst for N-arylation of imidazoles in water
Liu, Yashuai,Gu, Ningning,Liu, Ping,Xie, Jianwei,Dai, Bin,Liu, Yan
, p. 468 - 470 (2015)
Four inexpensive and air- and moisture-stable 2N2O-Cu complexes were synthesized, one of which proved to exhibit good catalytic activity for the N-arylation of imidazoles in water. A variety of aryl iodides and aryl bromides underwent coupling with imidazoles promoted by the catalytic system with moderate to excellent yields.
A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib
Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.
supporting information, p. 5222 - 5229 (2021/07/29)
Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.
Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water
Venkateswarlu, Katta,Rao, Kanusu Umamaheswara
, (2021/03/03)
The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.
