- Structure-based design of novel benzimidazole derivatives as PIN1 inhibitors
-
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
-
-
Read Online
- Environmental Effects on the Absorption and Fluorescence Spectral Characteristics of Benzimidazole-2-carboxylic Acid and Its Esters
-
The absorption and fluorescence spectra of benzimidazole-2-carboxylic acid (BIA) and 5-chlorobenzimidazole-2-carboxylic acid (CBIA) have clearly indicated that benzimidazole (BI) ring and -COOH group are coplanar to each other and are held together in a rigid frame by intramolecular hydrogen-bonding.Dual fluorescence is observed in polar and hydrogen bonding solvents.The short wavelength fluorescence band is assigned to a structure where the -COOH group is perpendicular to the BI moiety and the long wavelength fluorescence band to the planar configuration.This is further manifested from the spectral characteristics of the ester of 5-chlorobenzimidazole-2-carboxylic acid (CBIM).Various prototropic reactions taking place in S0 ans S1 states for all the three molecules are studied in the H0/pH/H- range of -10 to 16.All the dissociation constants are determined, both in the S0 and S1 states and are discussed.
- Sinha, Hermant K.,Dogra, Sneh K.
-
-
Read Online
- Green synthesis of 1,1-Carbonyldiimidazole using copper oxide nanofiber as a heterogeneous catalyst
-
Poly(vinyl pyrrolidone) (PVP)/copper oxide composite nanofibers were prepared by electrospinning technique using PVP and copper acetate as precursors and calcinated at high temperature to yield polymer free, phase pure copper oxide nanofibers (CuO NFs). T
- Sukumar, Thenmozhi,Nallasamy, Dharmaraj
-
-
Read Online
- Fragment-Based Optimization of Dihydropyrazino-Benzimidazolones as Metabotropic Glutamate Receptor-2 Positive Allosteric Modulators against Migraine
-
Our previous scaffold-hopping attempts resulted in dihydropyrazino-benzimidazoles as metabotropic glutamate receptor-2 (mGluR2) positive allosteric modulators (PAMs) with suboptimal drug-like profiles. Here, we report an alternative fragment-based optimization strategy applied on the new dihydropyrazino-benzimidazolone scaffold. Analyzing published high-affinity mGluR2 PAMs, we used a pharmacophore-guided approach to identify suitable growing vectors and optimize the scaffold in these directions. This strategy resulted in a new fragment like lead (34) with improved druglike properties that were translated to sufficient pharmacokinetics and validated proof-of-concept studies in migraine. Gratifyingly, compound34showed reasonable activity in the partial infraorbital nerve ligation, a migraine disease model that might open this indication for mGluR2 PAMs.
- Szabó, Gy?rgy,Erdélyi, Péter,Kolok, Sándor,Vastag, Mónika,Halász, Attila S.,Kis-Varga, Istvánné,Lévay, Gy?rgy I.,Béni, Zoltán,Kóti, János,Greiner, István,Keser?, Gy?rgy M.
-
p. 8607 - 8620
(2021/06/28)
-
- Discovery of heterocyclic carbohydrazide derivatives as novel selective fatty acid amide hydrolase inhibitors: design, synthesis and anti-neuroinflammatory evaluation
-
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
-
-
- benzimidazole chiral heterocyclic compound as well as preparation method and application thereof
-
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.
- -
-
-
- Substituted heterocyclic compound containing urea skeleton and preparation method and application of substituted heterocyclic compound
-
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.
- -
-
-
- Substituted heterocyclic compound containing acylhydrazone skeleton as well as preparation method and application thereof (by machine translation)
-
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)
- -
-
Paragraph 0056-0057; 0061-0063
(2019/09/14)
-
- Syntheses, Crystal Structures, and Spectral Characterization of Six Novel Benzimidazolyl Substituted Triaryltriazoles
-
Six new benzimidazolyl substituted triaryltriazoles, 3-(2-pyridyl)-4-(p-R-phenyl)-5-(2-benzimidazolyl)-1,2,4-triazoles (L1: R?=?OCH3; L2: R?=?CH3; L3: R?=?H; L4: R?=?Br; L5: R?=?Cl; L6: R?=?F) were successfully synthesized. Yield of L1–6 is in the range from 61 to 76%. The compounds L1–6 were characterized by UV–vis, FTIR, 1H-NMR, ESI-MS spectra, and elemental analysis. Additionally, the absolute configurations of L1–5 were determined by single crystal X-ray crystallography.
- Zhou, Yong-Fei,Zhang, Shi-Pei,Feng, Zhe,Shen, Xuan,Zhu, Dun-Ru
-
p. 2773 - 2780
(2017/09/26)
-
- 1,2-dis-substituted benzimidazole derivative and application thereof
-
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).
- -
-
-
- 18 beta-glycyrrhetinic acid derivative and application thereof
-
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.
- -
-
-
- Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents
-
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
-
p. 15206 - 15223
(2015/09/21)
-
- Lanthanide coordination compounds with 1H-benzimidazole-2-carboxylic acid: Syntheses, structures and spectroscopic properties
-
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
-
-
- Synthesis and characterization of nitrogen heterocyclic derivatives containing sulfur-ether and schiff base
-
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
-
p. 1564 - 1575
(2013/10/21)
-
- NITROGEN HETEROCYCLIC COMPOUNDS USEFUL AS PDE10 INHIBITORS
-
Unsaturated nitrogen heterocyclic compounds of formula (I): (I), as defined in the specification, compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, Huntington's Disease, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.
- -
-
Page/Page column 138
(2011/12/02)
-
- Synthesis, in-vitro microbial and cytotoxic studies of new benzimidazole derivatives
-
Several new classes of benzimidazole derivatives were synthesized and evaluated for in-vitro antimicrobial and cytotoxic activities. The results showed that all synthesized compounds exhibited moderate antimicrobial activity, and compounds 2, 4, and 13 displayed cytotoxic activity (as LD50) at the concentration 1 × 10-3 M against Artemia salina.
- Harisha, Reddy S.,Hosamani, Kallappa M.,Keri, Rangappa S.
-
experimental part
p. 412 - 419
(2009/12/01)
-
- NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT
-
Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT2c receptors, act selectively on the 5-HT2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT2c receptors.
- -
-
-
- NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT
-
Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT2c receptors, act selectively on the 5-HT2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT2c receptors.
- -
-
Page/Page column 9
(2009/10/21)
-
- Novel indol carboxylic acid bispyridyl carboxamide derivatives as 5-HT2c receptor antagonists
-
Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT2c receptors, act selectively on the 5-HT2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT2c receptors.
- -
-
Page/Page column 14
(2009/10/21)
-
- Benzimidazole-2-carboxamides as novel NR2B selective NMDA receptor antagonists
-
A novel series of benzimidazole-2-carboxamide derivatives was prepared and identified as NR2B selective NMDA receptor antagonists. The influence of some structural elements, like H-bond donor groups placed on the benzimidazole skeleton and the substitution pattern of the piperidine ring, on the biological activity was studied. Compound 6a showed excellent analgetic activity in the mouse formalin test following po administration.
- Borza, Istvan,Kolok, Sandor,Gere, Aniko,Nagy, Jozsef,Fodor, Laszlo,Galgoczy, Kornel,Fetter, Jozsef,Bertha, Ferenc,Agai, Bela,Horvath, Csilla,Farkas, Sandor,Domany, Gyoergy
-
p. 4638 - 4640
(2007/10/03)
-
- BENZIMIDAZOLE CARBOXAMIDES AS RAF KINASE INHIBITORS
-
The present invention relates to benzimidazole carboxamides of formula (I), the use of the compounds of formula (I) as inhibitors of as inhibitors of one or more kinases, the use of the compounds of formula (I) for the manufacture of a pharmaceutical composition and a method of treatment, comprising administering said pharmaceutical composition to a patient. Accordingly, the compound of Formula (I) or a pharmaceutically acceptable salt thereof is administered for the treatment of diseases mediated by one or more kinase phathways, preferably by the raf kinase pathway, especially cancers.
- -
-
Page/Page column 136
(2008/06/13)
-
- HETEROCYCLIC COMPOUNDS
-
Certain thienopyrrolyl and furanopyrrolyl compounds are disclosed as useful to treat or prevent disorders and conditions mediated by the histamine H4 receptor, including allergic rhinitis.
- -
-
Page/Page column 21
(2008/06/13)
-
- Synthesis and spectral properties of a variety of 2-styrylbenzimidazoles
-
Studies on the synthesis of various 2-styrylbenzimidazoles 3, 7 and N-methylated 2-styrylbenzimidazoles 5, 9 from 2-methyl/ethyl benzimidazoles 2, 6 and 1,2-dimethyl/1-methyl-2-ethylbenzimidazoles 4, 8 respectively by condensation with different aromatic aldehydes are described. The spectral characteristics of 2-styrylbenzimidazoles and N-methylated-2-styrylbenzimidazoles are discussed. An efficient and convenient phase-transfer catalysed methylation procedure for the synthesis of N-methylated-2-styrylbenzimidazoles from 2-styrylbenzimidazoles is reported.
- Ramaiah,Dubey,Eswara Rao,Ramanatham,Kumar,Grossert,Hooper
-
p. 904 - 914
(2007/10/03)
-
- Studies on synthesis of 2-acetylbenzimidazole and related benzimidazole derivatives
-
Condensation of o-phenylenediamine (1) with propanoic acid under Phillips' conditions gives 2-ethylbenzimidazole (2). Attempts to oxidise 2 to 2-acetylbenzimidazole (3) using H2O2, SeO2, KMnO4/acetone were unsuccessful. Condensation of 2 with benzaldehyde yields 2-(α-methylstyryl)benzimidazole (4) which on oxidation with KMnO4 gives benzimidazole-2-carboxylic acid (5) as the sole product. Reaction of 1 with pyruvic acid results in 3-methylbenzo-1H-dihydropyrazine-2-one (7) rather than 3 as the major product. Treatment of 1 with formic acid gives the known compound benzimidazole (9) which with acetic anhydride in the presence of NaOAc does not yield 3. Reaction of 1 with lactic acid under Phillips' conditions gives 2-(α-hydroxyethyl)benzimidazole (10) which on oxidation with acid dichromate, however, yields 3. Studies on syntheses and spectral properties of related benzimidazoles are reported.
- Ramaiah,Grossert,Hooper,Dubey,Ramanatham
-
p. 140 - 144
(2007/10/03)
-
- Preparation of imidazole-2-carboxylic acids
-
4,5-Disubstituted imidazole-2-carboxylic acids are prepared by reacting 4,5-disubstituted imidazoles with carbon dioxide under superatmospheric pressure at from 150° to 300° C. in the presence of a base.
- -
-
-
- Photochemistry of 2-(2-Furyl)-benzimidazole (Fuberidazole)
-
The photodegradation of 2-(2-furyl)-benzimidazole (Fuberidazole 1) has been reinvestigated employing advanced HPLC-UV/VIS techniques and fluorescence emission and excitation spectroscopy in methanol at natural pH, in acidic medium and in aqueous solutions at pH 7 and 3, and four main products benzimidazole-2-carboxyclic acid 3, its methyl ester 2, 1-methoxy benzimidazole 5, methyl 4-oxo-2-benzimidazole crotonate 7 (cis and trans isomers) besides benzimidazole 4 and 2,2'-bibenzimidazole 6 and other side products have been isolated and characterized.The kinetics of the photodegradation process was followed independently be HPLC-UV and fluorescence emission showing a significant similarity of the curve habit; this allows to monitor a photodegradation at very low concentrations (5*10-5 - 5*10-6 M).The quantum yield of disappearance of Fuberidazole has been determined. Key Words: 2-(2-Furyl)-benzimidazole, Fuberidazole, Photodegradation, HPLC Separation, Fluorescence Emission
- Herrmann, Christiane,Foerster, Rolf,Koch, Helmut,Wamhoff, Heinrich
-
p. 1431 - 1437
(2007/10/02)
-
- TRANSFORMATIONS OF PYRIDOBENZIMIDAZOLE
-
The electrophilic bromination and nitration of pyridobenzimidazole take place at position 8.The alkylation of pyridobenzimidazole by halogenoalkanes takes place at the N5 atom.During the oxidation of pyridobenzimidazole the six-membered nitrogen-containing ring is broken, and benzimidazole-2-carboxylic acid is formed.Dipyridobenzimidazoles isomeric with respect to the fusion of the rings were obtained from 8-aminopyridobenzimidazole by the Skraup reaction.
- Prostakov, N. S.,Varlamov, A. V.,N'ende, D. L. S.,Krapivko, A. P.,Fomichev, A. A.,et al.
-
p. 1166 - 1170
(2007/10/02)
-
- About the Reactions of Benzimidazole-2-carbohydrazide with Electrophilic Compounds
-
Benzimidazole-2-carbohydrazide (1) reacts with aldehydes and ketones to form N-alkylidene-benzimidazole-2-carbohydrazides (2a-j).With carbon disulfide, diphenyl carbonate and cyanates, ring closure takes plase to afford 1,2,4-triazines and 1,3,4-oxadiazoles.Attempts to synthesize 2-isocyanato-benzimidazole failed. 1H-n.m.r. and 13C-n.m.r. spectroscopic data of the compounds are given.
- Graubaum, Heinz,Martin, Dieter
-
p. 515 - 521
(2007/10/02)
-
- Practicable Syntheses of 2-Hydroxymethyl-substituted Benzimidazoles and 2-Formylbenzimidazole
-
N-Protection of benzimidazole by a diethoxymethyl group, as in , allows exclusive lithiation at the 2-position.This protected anion can be made to react with various electrophiles (e. g. ketones, aldehydes) to yield the corresponding 2-hydroxymethylbenzimidazoles (1).Facile deprotection occurs with acid.Two practicable syntheses of 2-formylbenzimidazole are also described and an indirect route to benzimidazole-2-alcohols is discussed.
- Ooi, Hong Chin,Suschitzky, Hans
-
p. 2871 - 2876
(2007/10/02)
-