- The construction of coordination networks based on imidazole-based dicarboxylate ligand containing hydroxymethyl group
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Reaction of Cd(ii), Fe(ii), and Cu(ii) with a new ligand 2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylic acid (H4hmIDC) and 4,4′-bipyridine (bpy) affords three coordination polymers of {[Cd(H 2hmIDC)(bpy)]·0.5bpy·H2O}n (1), [Fe2(HhmIDC)2]n (2), and {[Cu 2(ITC)(bpy)(H2O)3]·2.5H 2O}n (3) (ITC = imidazole-2,4,5-tricarboxylic acid), respectively. Complex 1 and complex 3 are (4,4) nets in topological view and display in different packing mode, while hydroxymethyl group in complex 3 is oxidized to carboxylic group in situ. Complex 2 is a rare example of a cdl-e network containing both tetrahedral and square nodes. The hydroxymethyl groups act as a precursor and undergo different reactions directed by metal ions.
- Zheng, Sheng-Run,Cai, Song-Liang,Pan, Mei,Fan, Jun,Xiao, Tian-Tian,Zhang, Wei-Guang
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- Synthesis, in-vitro cytotoxic activity and DNA interactions of new dicarboxylatoplatinum(II) complexes with 2-hydroxymethylbenzimidazole as carrier ligands
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Objectives The aim of this study was to investigate the in-vitro cytotoxic activity of new platinum(II) complexes on the human HeLa (ER-), MCF-7 (ER+) and MDA-MB 231 (ER-) cell lines. Furthermore, we investigated plasmid DNA interactions and inhibition of BamHI and HindIII restriction enzyme activity of the complex 1-4,7. Methods Platinum(II) complexes were synthesised from precursor complexes of [PtL2Cl2] and [PtL2I2]. Their cytotoxic activity was tested by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Their plasmid DNA interactions and restriction enzyme activities were also investigated using the agarose gel electrophoresis method. Key findings The growth inhibitory effect results showed that the cytotoxicity of complex 2 was found to be the most active complex among the synthesised complexes. Conclusions The MTT results showed that complex 2 was found to be cytotoxic equal to cisplatin and higher than carboplatin against the MCF-7 and MDA-MB-231 cell lines. Furthermore, the estrogen or progesterone co-treatment slightly increased the cytotoxicity of complex 2, the cisplatin and carboplatin compared with the complex 2 tested alone in 50μm concentration. According to plasmid DNA interaction and the restriction studies, complexes 1-4,7 modified the tertiary structure of pBR322 plasmid DNA, and complexes 2-4 prevented enzyme digestion at high concentrations.
- Utku, Semra,?zelik, Azime Berna,Gümü, Fatma,Aik, Leyla,Yilmaz, ükran,Arsoy, Taibe,elebi Keskin, Ayten
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- Cobalt(II) complexes based on (1-methyl-1H-benzo[d]imidazol-2-yl) methanol derivative: synthesis, crystal structure, spectroscopy, DFT calculations, and antioxidant activity
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In this paper, we present a combined experimental and computational study of two new cobalt(II) complexes as [Co(Hmbm)2(OAc)2] and [Co(Hmbm)2(H2O)2]Cl2 (Hmbm = (1-methyl-1H-benzo[d]imidazol-2-yl)methanol). Both complexes were characterized by FT-IR and UV–vis spectroscopy, elemental analysis, and single-crystal X-ray crystallography. The molecular geometries, electronic transitions, and vibrational frequencies of the two complexes and the ligand (Hmbm) in the ground state have been calculated using global hybrid (B3LYP) and range-separated hybrid (CAM-B3LYP) density functional. Qualitative description of excited states and charge transfer character of electronic transitions states were carried out by plotting the Natural Transition Orbitals (NTOs) for main states, and were assigned to LMCT. The ligand and its Co(II) complexes have been evaluated for their potential as DPPH radical scavengers.
- Benhassine, Anfel,Boulebd, Houssem,Anak, Barkahem,Bouraiou, Abdelmalek,Bouacida, Sofiane,Bencharif, Mustapha,Belfaitah, Ali
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- A novel Trans-Pt(II) complex bearing 2-acetoxymethylbenzimidazole as a non-leaving ligand (trans-[Pt(AMBi)2Cl2]): Synthesis, antiproliferative activity, DNA interaction and molecular docking studies compared with its cis isomer (cis-[Pt(AMBi)2Cl2])
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Trans-[Pt(AMBi)2Cl2 (1) in which AMBi is 2-acetoxymethylbenzimidazole, was synthesized and characterized by spectroscopic methods. Novel complex 1 was evaluated for its potential antiproliferative effect against three human cancer cell lines, including HeLa (human cervix cancer), MCF-7 (human breast cancer) and A549 (human non-small-cell lung cancer) in comparison with those of cis-[Pt(AMBi)2Cl2 (2) and cisplatin by means of the MTT assay. Interaction of complexes 1, 2 and cisplatin with pBR322 plasmid DNA and their restriction endonuclease reactions by BamHI and HindIII enzymes were studied by agarose gel electrophoresis. Cytotoxicity tests showed that complex 1 exhibited similar in vitro cytotoxicity profile as compared with cisplatin whereas better than corresponding cis isomer against MCF-7 and A549 human cancer cell lines. The electrophoretic mobility shift assay showed that although no comigration of the Form I and II bands of plasmid DNA was observed for complex 1 at the concentrations tested, the binding of complex 1 was able to prevent partially BamHI digestion for concentrations ranging from 40 to 160 μM while having no inhibitory effect on HindIII activity in the digestion studies with restriction enzymes. Molecular docking studies on DNA were carried out to explore the binding mode and the best orientation of the complexes 1 and 2 to DNA.
- Eren, Gokcen,Emerce, Esra,Acik, Leyla,Aydin, Betul,Gumus, Fatma
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- One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles
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It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.
- Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao
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supporting information
(2022/02/07)
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- Discovery of benzimidazole derivatives as potent and selective aldehyde dehydrogenase 1A1 (ALDH1A1) inhibitors with glucose consumption improving activity
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Aldehyde dehydrogenase 1A1 (ALDH1A1) plays vital physiological and toxicological functions in many areas, such as CNS, inflammation, metabolic disorders, and cancers. Overexpression of ALDH1A1 has been disclosed to play an important role in obesity, diabetes and other diseases, indicating the potential need for the identification and development of small molecule ALDH1A1 inhibitors. Herein, a series of benzimidazole derivatives was designed, synthesized and evaluated. Among them, compounds 21, 27, 29, 61 and 65 exhibited excellent inhibitory activity against ALDH1A1 with IC50 values in the low micromolar range and high selectivity over ALDH1A2, ALDH1A3, ALDH2 and ALDH3A1. Moreover, an in vitro study demonstrated that all five compounds effectively improved glucose consumption in HepG2 cells, of which, 61 and 65 at 10 μM produced nearly equal glucose consumption with positive control Metformin (Met) at 1 mM. Furthermore, 61 and 65 showed desirable metabolic stability in human liver microsomes. All these results suggest that 61 and 65 are suitable for further studies.
- Feng, Yu,Jiang, Cheng,Jiang, Ling,Li, Bingyan,Liang, Dailin,Liu, Li,Ma, Zonghui
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- Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2
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Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.
- Maciejewska, Agnieszka Monika,Paprocki, Daniel,Poznański, Jaros?aw,Speina, El?bieta,Winiewska‐szajewska, Maria
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supporting information
(2021/06/09)
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- Polyheterocyclic substituted pyrimidines or pyridylamine derivatives Composition and medical application thereof
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The invention discloses a polycyclic substituted pyrimidine or pyridine amine derivative, and the structure is shown in a formula (I). The invention further discloses a pharmaceutically acceptable salt of the derivative, a solvate, a stereoisomer, a prodrug, a pharmaceutical composition and and an application thereof in medicine. The compounds of the present invention have significant adenosine A. 2A Receptor and/or adenosine A2B The receptor antagonism activity is very practical.
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Paragraph 0344-0346
(2021/09/26)
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- Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon
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D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.
- Raja, Dineshkumar,Philips, Abigail,Sundaramurthy, Devikala,Chandru Senadi, Gopal
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p. 3754 - 3759
(2021/10/14)
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- Design, synthesis and anti-tumor activity of novel benzimidazole-chalcone hybrids as non-intercalative topoisomerase II catalytic inhibitors
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Chemical diversification of type II topoisomerase (Topo II) inhibitors remains indispensable to extend their anti-tumor therapeutic values which are limited by their side effects. Herein, we designed and synthesized a novel series of benzimidazole-chalcone hybrids (BCHs). These BCHs showed good inhibitory effect in the Topo II mediated DNA relaxation assay and anti-proliferative effect in 4 tumor cell lines. 4d and 4n were the most potent, with IC50values less than 5 μM, superior to etoposide. Mechanistic studies indicated that the BCHs functioned as non-intercalative Topo II catalytic inhibitors. Moreover, 4d and 4n demonstrated versatile properties against tumors, including inhibition on the colony formation and cell migration, and promotion of apoptosis of A549 cells. The structure-activity relationship and molecular docking analysis suggested possible contribution of the chalcone motif to the Topo II inhibitory and anti-proliferative potency. These results indicated that 4d and 4n could be promising lead compounds for further anti-tumor drug research.
- Du, Zhiyun,Jiang, Zhi-Hong,Peng, Yi,Zhang, Lanyue,Zhang, Wenjin,Zhou, Wei
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- Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of d -Glucose with o-Phenylenediamines in Water
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d-Glucose has been identified as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. Isotopic studies with 13C6-d-glucose and D2O unambiguously confirmed the source of methine. The notable features of this method include the following: broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a short reaction time, water as an environmentally benign solvent, and the synthesis of vitamin B12 component on the gram scale.
- Raja, Dineshkumar,Philips, Abigail,Palani, Pushbaraj,Lin, Wei-Yu,Devikala, Sundaramurthy,Senadi, Gopal Chandru
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p. 11531 - 11540
(2020/10/12)
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- ADENOSINE RECEPTOR BINDING COMPOUNDS
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The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.
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Paragraph 00642-00643
(2020/02/06)
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- Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
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We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
- Aleku, Godwin A.,Leys, David,Roberts, George W.
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p. 3927 - 3939
(2020/07/09)
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- Discovery of heterocyclic carbohydrazide derivatives as novel selective fatty acid amide hydrolase inhibitors: design, synthesis and anti-neuroinflammatory evaluation
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Fatty acid amide hydrolase (FAAH) is a promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound 26 showed strong inhibition against human FAAH with IC50 of 2.8 μM. Corresponding docking studies revealed that the acyl hydrazide group of compound 26 well-occupied the acyl-chain binding pocket. It also exhibited high selectivity towards FAAH when comparing with CES2 and MAGL. Additionally, compound 26 effectively suppressed the LPS-induced neuroinflammation of microglial cells (BV2) via the reduction of interleukin-1β and tumor necrosis factor-α. Our results provided significative lead compounds for the further discovery of novel selective and safe FAAH inhibitors with potent anti-neuroinflammation activity.
- Hao, Qingjing,He, Mengting,Jiang, Kaixuan,Shang, Yanguo,Wang, Jinxin
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supporting information
(2020/04/08)
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- Benzimidazole chalcone derivative, and preparation method and application thereof
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The invention belongs to the technical field of drug synthesis, and especially relates to a benzimidazole chalcone derivative, and a preparation method and an application thereof. The structural formula of the benzimidazole chalcone derivative is represented by formula (I); and in the formula (I), R1 is fluorine or a methyl group, and R2 is selected from a nitro group, a cyano group, fluorine, chlorine, bromine, a methyl group, a methoxy group, a dimethoxy group, a trimethoxy group, an ethyl group and an isopropyl group. Results of studies show that the benzimidazole chalcone derivative of thepresent invention can target DNA topoisomerase II, can effectively inhibit the activity of human DNA topoisomerase II (TopoII), and can be used for preparing antitumor drugs with topoisomerase II asa target. The benzimidazole chalcone derivative of the present invention has a strong inhibitory effect on the proliferation of a plurality of tumor cells, and can be used for preparing anticancer drugs.
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Paragraph 0051-0053
(2019/08/30)
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- Structure-based design of novel benzimidazole derivatives as PIN1 inhibitors
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Peptidyl-prolyl cis/trans isomerase Pin1 plays a key role in amplifying and translating multiple oncogenic signaling pathways during oncogenesis. The blockade of Pin1 provided a unique way of disrupting multiple oncogenic pathways and inducing apoptosis. Aiming to develop potent Pin1 inhibitors, a series of benzimidazole derivatives were designed and synthesized. Among the derivatives, compounds 6h and 13g showed the most potent Pin1 inhibitory activity with IC50 values of 0.64 and 0.37 μM, respectively. In vitro antiproliferative assay demonstrated that compounds 6d, 6g, 6h, 6n, 6o and 7c exhibited moderate antiproliferative activity against human prostate cancer PC-3 cells. Taken together, these unique benzimidazole derivatives exhibited great potential to be further explored as potent Pin1 inhibitors with improved potency.
- Wang, Shuxiang,Guan, Lihong,Zang, Jie,Xing, Kun,Zhang, Jian,Liu, Dan,Zhao, Linxiang
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- Substituted heterocyclic compound containing acylhydrazone skeleton as well as preparation method and application thereof (by machine translation)
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The invention discloses a substituted heterocyclic compound containing an acylhydrazone skeleton as well as a preparation method and application, of the substituted heterocyclic compound. The invention relates to the field, in particular to a substituted heterocyclic compound containing an acylhydrazone skeleton or a pharmaceutically acceptable salt, a pharmaceutical composition containing the compounds and medical application, in particular to an FAAH inhibitor, and application, in preparation of drugs for preventing or treating diseases related to FAAH, including depression, analgesia, cannabinoid use disorders and other related diseases. (by machine translation)
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Paragraph 0056-0060
(2019/09/14)
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- Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species
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Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkylbenzimidazoles with arenes in the Br?nsted superacid TfOH resulted in the formation of the corresponding Friedel-Crafts reaction products, 2-diarylmethyl and 2-arylmethyl-substituted benzimidazoles, in yields up to 90%. The reaction intermediates, protonated species derived from starting benzimidazoles in TfOH, were thoroughly studied by means of NMR and DFT calculations and plausible reaction mechanisms are discussed.
- Ryabukhin, Dmitry S.,Turdakov, Alexey N.,Soldatova, Natalia S.,Kompanets, Mikhail O.,Ivanov, Alexander Yu.,Boyarskaya, Irina A.,Vasilyev, Aleksander V.
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supporting information
p. 1962 - 1973
(2019/09/03)
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- benzimidazole chiral heterocyclic compound as well as preparation method and application thereof
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The invention discloses a benzimidazole chiral heterocyclic compound as well as a preparation method and application thereof. The structure formula of the benzimidazole chiral heterocyclic compound isshown in formula I, formula II or formula III in the description. The benzimidazole chiral heterocyclic compound is prepared by treating an iridium complex which is prepared through a metal iridium compound and a phosphoramidite ligand as a catalyst, performing intra-molecular allyl amination on allyl substrate, and then synthesizing with high efficiency and high enantioselectivity. The method has the advantages of being high in catalytic reaction activity, mild in reaction conditions, high in enantioselectivity, wide in substrate applicable scope, and environmentally friendly; the primary in-vitro enzyme inhibition activity test shows that the compound is high in alpha-glucosidase inhibiting activity and can be used as an alpha-glucosidase inhibiting agent, and the compound can also be used as a further modified drug intermediate; the compound has a potential application value in preventing or treating II-diabetes, obesity and complication medicines thereof and pilot compounds thereof.
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Paragraph 0161; 0162; 0163
(2019/02/27)
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- Substituted heterocyclic compound containing urea skeleton and preparation method and application of substituted heterocyclic compound
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The invention discloses a substituted heterocyclic compound containing a urea skeleton and a preparation method and application of the substituted heterocyclic compound, and relates to the field of pharmaceutical chemistry, in particular to the substituted heterocyclic compound containing the urea skeleton or pharmaceutically acceptable salt of the substituted heterocyclic compound, a pharmaceutical composition containing the compounds and medical application of the compounds. Particularly, the invention relates to application of the substituted heterocyclic compound as an FAAH inhibitor in preparing drugs for preventing or treating diseases associated with FAAH, such as depression, analgesia, cannabinoid using disorders and other related diseases.
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Paragraph 0116; 0118-0121
(2019/10/01)
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- Efficient Aliphatic C?H Bond Oxidation Catalyzed by Manganese Complexes with Hydrogen Peroxide
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A tetradentate nitrogen ligand containing a benzimidazole ring and an electron-rich pyridine ring was developed, the resulting manganese complex exhibited good activity in the C?H oxidation of simple alkanes. In particular, cyclic aliphatic alkanes were transformed into ketones in very good yields (up to 89 %) by using environmentally benign H2O2 as the terminal oxidant. This protocol was also applied successfully in benzylic C?H oxidation, giving the corresponding ketones with very good selectivities. In addition, tertiary C?H bond oxidation of complex molecules by the manganese complex showed potential utility for assembling alcohols with good selectivity in late-stage chemical synthesis.
- Wang, Wenfang,Xu, Daqian,Sun, Qiangsheng,Sun, Wei
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supporting information
p. 2458 - 2464
(2018/04/02)
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- Benzimidazole derivative, preparation method thereof and application of benzimidazole derivative to tumor resistance
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The invention provides a benzimidazole derivative which is provided with a structure as shown in a formula (I). R1 and R2 are independently selected from one of hydrogen, halogen, alkyl, alkoxy, halogenated alkyl, nitryl and a nitrile group, R3 is carboxyl, alkyl, phenyl or a cyano group, the value range of m is 0-3, the value range of n is 0-3, X is CH or nitrogen, and Y is CH2 or carbonyl. The benzimidazole derivative has a strong inhibiting effect on activity of topoisomerase II, so that the benzimidazole derivative can serve as a topoisomerase II inhibitor. Research finds that the compoundis the catalytic inhibitor of Topo II, so that the compound can be used for preparing an anti-tumor drug taking the topoisomerase II as a target spot. Besides, the benzimidazole derivative has good anti-proliferative activity for a plurality of tumor cells, so that the benzimidazole derivative can be used for preparing the anti-tumor drug.
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Paragraph 0111; 0112; 0113; 0114
(2018/04/02)
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- Design, synthesis and biological evaluation of benzimidazole-rhodanine conjugates as potent topoisomerase II inhibitors
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In this study, a series of benzimidazole-rhodanine conjugates were designed, synthesized and investigated for their topoisomerase II (Topo II) inhibitory and cytotoxic activities. The results from Topo II-mediated pBR322 DNA relaxation and cleavage assays showed that the synthesized compounds might act as Topo II catalytic inhibitors. Certain compounds displayed potent Topo II inhibition at 10 μM. The cytotoxic activities of these compounds against HeLa, A549, Raji, PC-3, MDA-MB-201, and HL-60 cancer cell lines were evaluated. The results indicated that these compounds exhibited strong antiproliferative activity. A good relationship was observed between the Topo II inhibitory potency and the cytotoxicity of these compounds. The structure-activity relationship revealed that the electronic effects, the phenyl group, and the rhodanine moiety were particularly important for the Topo II inhibitory potency and cytotoxicity.
- Li, Penghui,Zhang, Wenjin,Jiang, Hong,Li, Yongliang,Dong, Changzhi,Chen, Huixiong,Zhang, Kun,Du, Zhiyun
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supporting information
p. 1194 - 1205
(2018/08/01)
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- 1,2-dis-substituted benzimidazole derivative and application thereof
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The invention belongs to the technical field of medicines, and particularly relates to a 1,2-dis-substituted benzimidazole derivative and pharmaceutically acceptable salt thereof, a preparation method of the derivative, a medicine composition with the derivative serving as an active component, and application of the derivative in preparation of a Pin1 inhibitor and preparation of a medicine for treating and/or preventing various cancers. The 1,2-dis-substituted benzimidazole derivative and the pharmaceutically acceptable salt thereof are as shown in the general formula I, and definitions of all substituents are described in claims and the specification. (Refer to Specification).
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Paragraph 0127-0129
(2017/07/19)
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- 18 beta-glycyrrhetinic acid derivative and application thereof
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The invention relates to the technical field of medicines, in particular to an 18 beta-glycyrrhetinic acid derivative with Pin1 inhibitory activity and pharmacologically-acceptable salt thereof, a preparation method of the derivative, a pharmaceutical composition taking the derivative as an active ingredient and application of the derivative to the preparation of a Pin1 inhibitor and the preparation of a drug for treating and/or preventing various cancers. The derivative shown in a general formula I or the pharmacologically-acceptable salt thereof has the following structure, wherein R, X, Y and n are stated in the claims and the descriptions.
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Paragraph 0117; 0118; 0119
(2017/09/18)
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- Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors
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A series of novel indole derivatives were synthesized as potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase. Among those, compound 10b demonstrated the highest growth inhibition rate of 66.7% against the VEGFR-2 tyrosine kinase at 10 μM which indicates that indole-benzothiazole might be the favorable structure. The binding mode of compound 10b with VEGFR-2 tyrosine kinase was evaluated by molecular docking.
- Zhang,Xu,Wang,Kang
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p. 3006 - 3016
(2018/02/21)
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- β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction
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Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.
- Llabres-Campaner, Pedro J.,Ballesteros-Garrido, Rafael,Ballesteros, Rafael,Abarca, Belén
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supporting information
p. 5552 - 5561
(2017/08/22)
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- Synthesis and biological evaluation of heterocyclic privileged medicinal structures containing (benz)imidazole unit
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Abstract: New heterocyclic privileged medicinal scaffolds involving 4H-pyran, 1,4-dihydropyridine, quinazoline, and 2-aminochromene bearing a (benz)imidazole unit were prepared in good to excellent yields, and evaluated for their in vitro hepatotoxicity on HepG2 cells and antioxidant activity using DPPH radical-scavenging assay. From these results, 2-amino-4-(1-methyl-1H-imidazol-2-yl)-4H-benzo[h]chromene-3-carbonitrile has been identified as a racemic, readily available imidazole derivative, significantly less hepatotoxic than tacrine at 100?μM concentration. One compound was found to be a potent antioxidant agent. The catalytic effect of the 1-methylimidazole unit, in the synthesis of some heterocycle, was also demonstrated. Crystal X-ray structures are reported for six compounds. Graphical abstract: [Figure not available: see fulltext.]
- Boulebd, Houssem,Zama, Sana,Insaf, Bataiche,Bouraiou, Abdelmalek,Bouacida, Sofiane,Merazig, Hocine,Romero, Alejandro,Chioua, Mourad,Marco-Contelles, José,Belfaitah, Ali
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p. 2209 - 2220
(2016/11/17)
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- Design, synthesis, and biological evaluation of novel thiazolidinediones as PPAR3/FFAR1 dual agonists
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Diabetes mellitus is a chronic metabolic disorder that affects more than 180 million people worldwide. Peroxisome proliferator activated receptors (PPARs) are a group of nuclear receptors that have been targeted by the thiazolidinedione (TZD) class of compounds for the management of type II diabetes. PPAR3 is known to regulate adipogenesis and glucose metabolism. Another emerging target for the design of antidiabetic agents is the free fatty acid receptor 1 (FFAR1), previously known as GPR40. Agonists of this receptor were found to enhance insulin secretion in diabetic patients. It has been reported that some thiazolidinediones (TZDs) activate FFAR1 with micromolar potency. In this study, based on docking studies into the crystal structure of PPAR3 and a homology model of FFAR1, nineteen compounds were designed, synthesized, and biologically tested for agonistic activity on both receptors. Nine compounds showed promising dual activity, with two compounds, 11a and 5b, having affinities in the low micromolar range on both targets. These molecules represent the first antidiabetic agents that could act as insulin sensitizers as well as insulin secretagogues.
- Darwish, Khaled M.,Salama, Ismail,Mostafa, Samia,Gomaa, Mohamed S.,Helal, Mohamed A.
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p. 157 - 172
(2016/01/16)
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- Synthesis and antinociceptive activity of meperidine-like benzimidazole derivatives
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(Graph presented) A series of novel benzimidazole derivatives have been prepared and characterized by IR, 1H-NMR spectroscopic data and elemental analysis. All the final compounds were screened for their antinociceptive activities with tail flick test. Among the synthesized compounds 3a, 4a, 4c, 8a, 9a exhibited significant antinociceptive activity. Compound 9a was found to have the highest antinociceptive activity at both 60 minutes and 120 minutes. Additionally, compounds 3a, 4a, 8a and 9a showed naloxone-reversible antinociceptive activity.
- Ercanli, Taner,Bal, Nur Banu,?zdemir, Elif Derya,Dündar, Yasemin,Uluda?, M. Orhan,?akir, Bilge,?zden, Tuncel,?nkol, Tijen
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- New (E)-1-alkyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies
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A new series of (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 8l showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC50values of 3.26 ± 0.24 μM and 5.96 ± 0.67 μM respectively. The compounds 8f, 8i, 8l and 8o were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 8l led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry analysis reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 8l induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 8l treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells.
- Sharma, Pankaj,Thummuri, Dinesh,Reddy, T. Srinivasa,Senwar, Kishna Ram,Naidu,Srinivasulu, Gannoju,Bharghava, Suresh K.,Shankaraiah, Nagula
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p. 584 - 600
(2016/07/22)
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- Synthesis and biological evaluation of new benzimidazole-thiazolidinedione hybrids as potential cytotoxic and apoptosis inducing agents
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A series of new benzimidazole-thiazolidinedione hybrids has been synthesized and evaluated for their cytotoxic potential against a selected human cancer cell lines of prostate (PC-3 and DU-145), breast (MDA-MB-231), lung (A549) and a normal breast epithelial cells (MCF10A). Among the tested compounds, 11p exhibited promising cytotoxicity with IC50value of 11.46?±?1.46?μM on A549 lung cancer cell line and did not show significant toxicity on normal MCF10A cells. Lung cancer cells (A549) have been used to know the mechanism of cell growth inhibition and apoptosis inducing effect with compound 11p. The treatment of A549?cells with 11p showed typical apoptotic morphology like cell shrinkage, chromatin condensation and horseshoe shaped nuclei formation. Flow-cytometry analysis revealed the G2/M phase of cell cycle arrest in a dose dependent manner. Preliminary mechanistic studies suggested that the cell migration was inhibited through the disruption of F-actin protein. Acridine orange-ethidium bromide (AO-EB), DAPI, annexin V-FITC/propidium iodide, rhodamine-123 and MitoSOX assays suggested the induction of apoptosis in A549 cells by compound 11p.
- Sharma, Pankaj,Srinivasa Reddy,Thummuri, Dinesh,Senwar, Kishna Ram,Praveen Kumar, Niggula,Naidu,Bhargava, Suresh K.,Shankaraiah, Nagula
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p. 608 - 621
(2016/09/14)
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- Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi
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A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.
- Wang, Xing,Chen, Yong-Fei,Yan, Wei,Cao, Ling-Ling,Ye, Yong-Hao
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- Photoredox-Catalyzed Hydroxymethylation of Heteroaromatic Bases
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We report the development of a method for room-temperature C-H hydroxymethylation of heteroarenes. A key enabling advance in this work was achieved by implementing visible light photoredox catalysis that proved to be applicable to many classes of heteroarenes and tolerant of diverse functional groups found in druglike molecules.
- Huff, Chelsea A.,Cohen, Ryan D.,Dykstra, Kevin D.,Streckfuss, Eric,DiRocco, Daniel A.,Krska, Shane W.
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p. 6980 - 6987
(2016/08/30)
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- BOIMPYs: Rapid Access to a Family of Red-Emissive Fluorophores and NIR Dyes
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A fundamental, highly fluorescent, and easily accessible scaffold derived from the BODIPY core is reported. The use of benzimidazole as a bridging ligand at the meso position enables the binding of two BF2units to provide sufficient rigidity and enhanced electron-withdrawing strength. Absorption and emission events thus take place in the red (λ≈600 nm); the fluorescence quantum yields can reach unity (0.96) and show little dependence on solvent polarity. The synthetic route was shortened to two steps starting from commercially available precursors while the preparation is modular and tolerates various pyrrole and benzimidazole moieties. Fluoride replacement by propynyl groups, various halogenations, as well as Knoevenagel-type condensations were applied to extend the versatility of these new photostable fluorophores, which we termed BOIMPYs.
- Patalag, Lukas J.,Jones, Peter G.,Werz, Daniel B.
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supporting information
p. 13340 - 13344
(2016/10/30)
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- Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents
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A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1Hbenzo[ d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.
- Alasmary, Fatmah A.S.,Snelling, Anna M.,Zain, Mohammed E.,Alafeefy, Ahmed M.,Awaad, Amani S.,Karodia, Nazira
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supporting information
p. 15206 - 15223
(2015/09/21)
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- TNF -Alpha Modulating Benzimidazoles
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A series of benzimidazole derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.
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Paragraph 0483
(2015/06/10)
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- Structure-Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents
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Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-dihereroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clinical treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles. (Chemical Equation Presented).
- Wang, Rubing,Chen, Chengsheng,Zhang, Xiaojie,Zhang, Changde,Zhong, Qiu,Chen, Guanglin,Zhang, Qiang,Zheng, Shilong,Wang, Guangdi,Chen, Qiao-Hong
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p. 4713 - 4726
(2015/06/25)
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- One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives
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A new one-pot protocol has been developed for the facile and efficient synthesis of aza-fused polycyclic quinolines (e.g., pyrrolo[1,2-a]quinolines) by the base-catalyzed reaction of 2-formylpyrroles and 2-halophenylacetonitriles. This reaction proceeded under transition metal-free conditions and showed high functional group tolerance, with the desired products being formed in good yields.
- Jiang, Zeng-Qiang,Miao, Da-Zhuang,Tong, Yao,Pan, Qiang,Li, Xiao-Tong,Hu, Ren-He,Han, Shi-Qing
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supporting information
p. 1913 - 1921
(2015/06/30)
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- SUBSTITUTED TRIAZINE BMI-1 INHIBITORS
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Amine substituted triazine compounds and forms thereof that inhibit the function and reduce the level of B-cell specific Moloney murine leukemia virus integration site 1 (Bmi-1) protein and methods for their use to inhibit Bmi- 1 function and reduce the level of Bmi- 1 to treat a cancer mediated by Bmi-1 are described herein.
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Page/Page column 140
(2015/06/08)
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- Synthesis, characterization and antibacterial evaluation of some novel derivatives of 2-bromomethyl-benzimidazole
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In the present study, synthesis, and biological evaluation of some novel derivatives of 2-bromomethyl-benzimidazole were investigated. The structures of the new synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR, mass spectrometry and elemental analysis and screened for antimicrobial activity against two Gram-positive strains (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative strains (Escherichia coli and Pseudomonas aeruginosa). Results indicate that new compounds showed moderate to good activity when compared with standard antibiotic Ciprofloxacin and Streptomycin.
- Ahmadi, Abbas
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p. 451 - 456
(2015/01/09)
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- QUINAZOLINES AND AZAQUINAZOLINES AS DUAL INHIBITORS OF RAS/RAF/MEK/ERK AND PI3K/AKT/PTEN/MTOR PATHWAYS
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The present application provides novel quinazolines and azaquinazolines and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in for co-regulating RAS/RAF/MEK/ERK and PI3K/AKT/PTEN/mTOR pathways by administering a therapeutically effective amount of one or more of the compounds of formula (I), wherein X, Y, T and R4, and R6 to R8' are defined herein, to a patient. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the RAS/RAF/MEK/ERK and PI3K/AKT/PTEN/mTOR pathways. A variety of conditions can be treated using these compounds and include diseases which are characterized by abnormal cellular proliferation. In one embodiment/ the disease is cancer.
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Page/Page column 60
(2014/10/29)
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- Synthesis and characterization of nitrogen heterocyclic derivatives containing sulfur-ether and schiff base
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A series of new nitrogen heterocyclic compounds containing sulfur-ether (8a-8f) and Schiff-base (9a-9q) functionalities were synthesized by the reaction of the pharmaceutical lead compound containing both benzimidazole and 1,2,4-triazole rings. The compounds were characterized by 1H NMR, 13C NMR, FT-IR, HR-MS, and ESI-MS.
- Zheng, Jinyun,Yu, Yujian,Zhen, Xiaomin,Yang, Erbing,Zhao, Yufen
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p. 1564 - 1575
(2013/10/21)
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- Gold catalysis opens up a new route for the synthesis of benzimidazoylquinoxaline derivatives from biomass-derived products (glycerol)
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Process intensification by using well-defined solid catalysts able to perform one-pot multistep reactions is one of the open fronts in heterogeneous catalysis. This is even more relevant if new, more efficient synthesis routes are open. Herein, a gold catalyst was used to synthesize benzimidazoylquinoxalines compounds by two efficient and selective novel methods in a multistep one-pot methodology. The first method involved the synthesis of benzimidazoylquinoxaline compounds with the same substituents in both heterocycles through oxidation-cyclization of glycerol with o-phenylenediamine derivatives, whereas the second one allowed the synthesis of benzimidazoylquinoxalines compounds with different substituents in each aromatic ring through coupling of o-phenylenediamine derivatives with glyceraldehyde in a first stage to produce the benzimidazol compound as an intermediate, followed by an oxidation-cyclization with another o-phenylenediamine compound in a second stage. Both stages were performed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) as the catalyst and air as the oxidant, in absence of any homogeneous reagent. A reaction mechanism has been proposed. A smooth route: Benzimidazoylquinoxaline derivatives can be obtained in good yields through one-pot oxidative coupling of glycerol or glyceraldehydes with 1,2-phenylenediamines in a two-step reaction, using Au/CeO2 as the catalyst, base-free conditions, mild temperature, and air as the oxidant. Copyright
- Climent, Maria J.,Corma, Avelino,Iborra, Sara,Martinez-Silvestre, Sergio
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p. 3866 - 3874
(2014/01/06)
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- Lanthanide coordination compounds with 1H-benzimidazole-2-carboxylic acid: Syntheses, structures and spectroscopic properties
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A flexible multidentate ligand, 1H-benzimidazole-2-carboxylic acid, was synthesized to construct a series of lanthanide coordination polymers [Ln(HBIC)3]n (Ln = Eu (1), Tb (2), Gd (3), Pr (4), Nd (5); H2BIC = 1H-benzimidazole-2-carboxylic acid) under hydrothermal conditions. All the compounds were fully characterized by elemental analysis, IR spectroscopy, single-crystal X-ray diffraction, thermal analysis and various spectroscopic techniques. Structural analyses reveal that they are isostructural and feature a 2D wave-like layer structure with distorted grids, in which the adjacent Ln3+ centers are bridged by the HBIC- ligands with two kinds of new coordination modes and the adjacent HBIC- ligands are tightly bound by two types of distinct intra-layer hydrogen bonds. The adjacent 2D layers are further interconnected by strong inter-layer hydrogen bond ring motifs R22(10) to generate a 3D supramolecular architecture. Optical studies indicate that the compounds 1, 2, 4 and 5 exhibit characteristic luminescence emission bands of the corresponding lanthanide ions in the visible or near-infrared regions at room temperature. In particular, compound 2 displays bright green luminescence in the solid state with a satisfactory 5D4 lifetime of 1.2 ms and a high overall quantum yield of 31%, due to an ideal energy gap between the lowest triplet state energy level of H2BIC ligand and the 5D4 state energy level of Tb3+. The energy transfer mechanisms in compounds 1 and 2 were also described and discussed. The Royal Society of Chemistry.
- Xia, Zhengqiang,Wei, Qing,Yang, Qi,Qiao, Chengfang,Chen, Sanping,Xie, Gang,Zhang, Guochun,Zhou, Chunsheng,Gao, Shengli
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- Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity
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A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4- methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (12a-12h). The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound 14c with IC50 of 1.0 and 1.9 μM has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, respectively, and that compound 15h with IC50 of 1.9 μM has a strong inhibitory effect on the growth of MCF-7 cancer cells.
- Woo, Ho Bum,Eom, Young Woo,Park, Kyu-Sang,Ham, Jungyeob,Ahn, Chan Mug,Lee, Seokjoon
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scheme or table
p. 933 - 936
(2012/03/11)
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- Iridium-catalyzed condensation of amines and vicinal diols to substituted piperazines
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A straightforward procedure is described for the synthesis of piperazines from amines and 1,2-diols. The heterocyclization is catalyzed by [Cp*IrCl2]2 and sodium hydrogen carbonate and can be achieved with either toluene or water as solvent. The transformation does not require any stoichiometric additives and only produces water as the byproduct. The reaction can be performed between a 1,2-diamine and a 1,2-diol or by a double condensation between a primary alkylamine and a 1,2-diol. At least one substituent is required on the piperazine ring to achieve the cyclization in good yield. The mechanism is believed to involve dehydrogenation of the 1,2-diol to the α-hydroxy aldehyde, which condenses with the amine to form the α-hydroxy imine. The latter rearranges to the corresponding α-amino carbonyl compound, which then reacts with another amine followed by reduction of the resulting imine. Piperazines are prepared by [Cp*IrCl 2]2-catalyzed heterocyclization of 1,2-diols with either 1,2-diamines or primary alkylamines. The reaction is performed in toluene or water and requires no stoichiometric additive. The key step in the mechanism is believed to be the isomerization of an α-hydroxy imine to the corresponding α-amino carbonyl compound. Copyright
- Lorentz-Petersen, Linda L. R.,Nordstrom, Lars Ulrik,Madsen, Robert
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p. 6752 - 6759
(2013/01/15)
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- A novel rhodamine-benzimidazole conjugate as a highly selective turn-on fluorescent probe for Fe3+
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In this manuscript, a novel probe RHBI based on the rhodamine-benzimidazole conjugate was designed and synthesized. RHBI showed an extreme selectivity for Fe3+ over other metal ions such as Pb2+, Ni2+, Co2+, Mn2+, Zn2+, Hg2+, Cd 2+, Ag+, Mg2+, Ca2+, Ba 2+, Na+ and K+ in acetonitrile. Upon the addition of 10 equiv. of Fe3+, a 1098-fold fluorescence intensity enhancement was observed at the maximum emission wavelength of 582 nm. Both the Job's plot and ESI-MS showed that RHBI coordinated with Fe3+ in a 1:1 stoichomitry and the calculated binding constant was 1. 01∈×∈104 M-1. The competition experiment for Fe3+ ions mixed with other metal ions exhibited no obvious change except Cu2+ that could induce a mild fluorescence quenching. Moreover, the fluorescence emission increased linearly with the Fe3+ concentration in the range of 6∈×∈10-6- 4∈×∈10-5 M and the detection limit was 1.5∈×∈10-8 M.
- Li, Junbo,Hu, Qihui,Yu, Xianglin,Zeng, Yang,Cao, Cancan,Liu, Xiwen,Guo, Jia,Pan, Zhiquan
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scheme or table
p. 2005 - 2013
(2012/04/10)
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- Lithium bromide catalyzed solvent free method for synthesis of 2-substituted benzimidazoles and imidazopyridines
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The first successful lithium bromide mediated solvent free condensation of arylenediamine and esters to obtain 2-substituted benzimidazole and imidazopyridine in good to excellent yields is described.
- Dekhane, Deepak V.,Pawar, Shivaji S.,Gupta, Sunil V.,Shingare, Murlidhar S.,Thore, Shivaji N.
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experimental part
p. 519 - 523
(2011/01/13)
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