- Design, synthesis and in vitro evaluation of 6-amide-2-aryl benzoxazole/benzimidazole derivatives against tumor cells by inhibiting VEGFR-2 kinase
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Herein, we have carried out a structural optimization campaign to discover the novel anti-tumor agents with our previously screened YQY-26 as the hit compound. A library of thirty-seven 6-amide-2-aryl benzoxazole/benzimidazole derivatives has been designe
- Yuan, Xu,Yang, Qingyi,Liu, Tongyan,Li, Ke,Liu, Yuwen,Zhu, Changcheng,Zhang, Zhiyun,Li, Linghua,Zhang, Conghai,Xie, Mingjin,Lin, Jun,Zhang, Jihong,Jin, Yi
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Read Online
- Discovery of 6-Arylurea-2-arylbenzoxazole and 6-Arylurea-2-arylbenzimidazole Derivatives as Angiogenesis Inhibitors: Design, Synthesis and in vitro Biological Evaluation
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We embarked on a structural optimization campaign aimed at the discovery of novel anti-angiogenesis agents with previously reported imidazole kinase inhibitors as a lead compound. A library of 29 compounds was synthesized. Several title compounds exhibite
- Zi, Mengli,Liu, Feifei,Wu, Di,Li, Ke,Zhang, Da,Zhu, Changcheng,Zhang, Zhiyun,Li, Linghua,Zhang, Conghai,Xie, Mingjin,Lin, Jun,Zhang, Jihong,Jin, Yi
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Read Online
- COMPOUNDS FOR TREATING TUBERCULOSIS
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The invention concerns a compound of formula (Ia) or (Ib) wherein R1 is hydrogen or a methyl group; R2 is an unsubstituted or substituted alkyl group; R3 is an aryl group or a heteroaryl group, optionally substituted by on
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Paragraph 95-96
(2021/06/04)
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- Synthesis, bioevaluation and docking studies of some 2-phenyl-1H-benzimidazole derivatives as anthelminthic agents against the nematode Teladorsagia circumcincta
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Gastrointestinal nematode infections are the main diseases in herds of small ruminants. Resistance to the main established drugs has become a worldwide problem. The purpose of this study is to obtain and evaluate the in vitro ovicidal and larvicidal activity of some 2-phenylbenzimidazole derivatives on susceptible and resistant strains of Teladorsagia circumcincta. Compounds were prepared by known procedures from substituted o-phenylenediamines and arylaldehydes or intermediate sodium 1-hydroxyphenylmethanesulfonate derivatives. Egg Hatch Test (EHT), Larval Mortality Test (LMT) and Larval Migration Inhibition Test (LMIT) were used in the initial screening of compounds at 50 μM concentration, and EC50 values were determined for the most potent compounds. Cytotoxicity evaluation of compounds was conducted on human Caco-2 and HepG2 cell lines to calculate their Selectivity Indexes (SI). At 50 μM concentration, nine out of twenty-four compounds displayed more than 98% ovicidal activity on a susceptible strain, and four of them showed more than 86% on one resistant strain. The most potent ovicidal benzimidazole (BZ) 3 showed EC50 = 6.30 μM, for the susceptible strain, while BZ 2 showed the lowest EC50 value of 14.5 μM for the resistant strain. Docking studies of most potent compounds in a modelled Teladorsagia tubulin indicated an inverted orientation for BZ 1 in the colchicine binding site, probably due to its fair interaction with glutamic acid at codon 198, which could justify its inactivity against the resistant strain of T. circumcincta.
- Escala, Nerea,Valderas-García, Elora,Bardón, María álvarez,Gómez de Agüero, Verónica Castilla,Escarcena, Ricardo,López-Pérez, José Luis,Rojo-Vázquez, Francisco A.,San Feliciano, Arturo,Bala?a-Fouce, Rafael,Martínez-Valladares, María,Olmo, Esther del
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- Novel imidazole derivatives having FLT3-inhibitory activity and use thereof
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The present invention relates to a novel benzoimidazole derivative having fms-like tyrosine kinase 3 (FLT3) inhibitory activity, and a use thereof. The novel benzoimidazole derivative or a pharmaceutically acceptable salt thereof according to the present invention exhibits excellent inhibitory activity on FLT3, thereby being expected for target treatment through further fundamental approach in preventing or treating acute myeloid leukemia (AML).COPYRIGHT KIPO 2020
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Paragraph 0235-0238; 0276-0278
(2020/04/22)
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- Fragment-based lead discovery of a novel class of small molecule antagonists of neuropeptide B/W receptor subtype 1 (GPR7)
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Here, we report the discovery of a new class of NPBWR1 antagonists identified from a fragment-based screen. Compound 1 (cAMP IC50 = 250 μM; LE = 0.29) emerged as an initial hit. Further optimization of 1 by SAR-by-catalogue and chemical modification produced 21a (cAMP IC50 = 30 nM; LE = 0.39) with a 6700-fold increase in potency from fragment 1. Somewhat surprisingly, Schild analysis of compound 21a suggested that in vitro inhibition of NPW-mediated effects on upon cAMP accumulation were saturable, and that compound 21a dose-dependently increased [125I]-hNPW23 dissociation rate constants from NPBWR1 in kinetic binding studies. Collectively, these data are inconsistent with a classic surmountable, orthosteric mechanism of inhibition. The benzimidazole inhibitors reported herein may therefore represent a mechanistically differentiated class of compounds with which to form a better appreciation of the pharmacology and physiological roles of this central neuropeptide system.
- Moningka, Remond,Romero, F. Anthony,Hastings, Nicholas B.,Guo, Zhiqiang,Wang, Ming,Di Salvo, Jerry,Li, Ying,Trusca, Dorina,Deng, Qiaoling,Tong, Vincent,Terebetski, Jenna L.,Ball, Richard G.,Ujjainwalla, Feroze
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- Aerobic {Mo72V30} nanocluster-catalysed heterogeneous one-pot tandem synthesis of benzimidazoles
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A novel heterogeneous one-pot protocol is developed for tandem aerobic synthesis of benzimidazoles through dehydrogenative coupling of primary benzylic alcohols and aromatic diamines co-catalysed by Keplerate-type {Mo72V30} polyoxometalate and N-hydroxyphthalimide (NHPI). The catalytic system also works well for the synthesis of benzimidazoles using benzaldehydes, as commonly used starting materials, in the absence of NHPI. The high activity of the solid nanocluster provides standard conditions avoiding current limitations of oxidation methods including high catalyst loadings. The spectral results and leaching experiments revealed that the nanocapsule preserved its structural integrity after being reused in consecutive runs.
- Khoshyan, Ashkan,Pourtahmasb, Mehrdad,Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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- Synthetic method of benzimidazole compounds
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The invention discloses a synthetic method of benzimidazole compounds. The synthetic route of the synthetic method is shown in the description. The method comprises the following steps: 1) substitutedo-phenylenediamine (I), aromatic aldehyde (II) and L-ca
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Paragraph 0042-0047
(2019/01/14)
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- Inexpensive weight-reducing aid (L-carnitine) as an efficient catalyst for synthesis of benzimidazoles
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Aim and Objective: The benzimidazole derivatives have been obtained via weight-reducing aid (L-Carnitine) as a cheap catalyst. A wide range of aromatic aldehydes easily undergo condensations with substituted o-phenylendiamine under mild condition to affor
- Zhang, Min,Huang, Guoling,Zhang, Xuefang,Lin, Zhenyuan,Li, Yibiao,Li, Bin,Chen, Lu
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p. 567 - 570
(2019/01/14)
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- Synthesis of benzimidazole and quinoxaline derivatives using reusable sulfonated rice husk ash (RHA-SO3H) as a green and efficient solid acid catalyst
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In this work, a simple, rapid and efficient method for the preparation of benzimidazoles and quinoxalines from the condensation of o-phenylene diamines with aldehydes and/or 1,2-dicarbonyl compounds in the presence of sulfonated rice husk ash (RHA-SO3H) as an efficient green catalyst is reported. RHA-SO3H can be easily prepared using a readily available organic compound by simple modification of rice husk ash. All reactions are performed under mild reaction conditions with high to excellent yields. The method is applicable to aromatic, unsaturated and hetero aromatic aldehydes. The advantages of this method are short reaction times, milder conditions, easy work-up, solvent-free conditions and catalyst reusability.
- Shamsi-Sani, Mahnaz,Shirini, Farhad,Abedini, Masoumeh,Seddighi, Mohadeseh
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p. 1091 - 1099
(2016/04/26)
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- Preparation, characterization, and application of 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride ionic liquid as an efficient catalyst for the synthesis of benzimidazole derivatives
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In this study, 2,2′-bipyridine was treated with chlorosulfonic acid and 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride, [BiPy](SO3H)2Cl2, as a new ionic liquid catalyst was obtained and characterized with a variety of techniques including IR, 1H, and 13C NMR, Hammett acidity function as well as mass spectra method. After preparation and characterization, this ionic liquid was used as an efficient catalyst for the green and mild synthesis of benzimidazole derivatives. In addition, this reagent is efficiently able to catalyze the preparation of benzimidazole derivatives from the protected derivatives of aldehydes including oximes and semicarbazones. All reactions are performed under mild conditions in excellent yields.
- Shirini, Farhad,Abedini, Masoumeh,Seddighi, Mohadeseh,Arbosara, Fatemeh Shaabani
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p. 7683 - 7693
(2015/02/19)
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- Highly chemoselective synthesis of benzimidazoles in Sc(OTf)3-catalyzed system
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The present researches elicit a simple, green and efficient method for the synthesis of substituted benzimidazoles through the coupling of o-phenylenediames with aldehydes catalyzed by Sc(OTf)3 in ethanol, which obtains high chemoselectivity and excellent yield of many biologically active 1,2-disubstitued and 2-substituted benzimidazoles respectively and are also environment friendly.
- Fan, Liyan,Kong, Lulu,Chen, Wen
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p. 2306 - 2314
(2016/03/01)
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- Discovery of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinolin-4-amine derivatives as novel VEGFR-2 kinase inhibitors
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Inhibition of the VEGF signaling pathway has become a valuable approach in the treatment of cancers. In this work, a series of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinolin-4-amine derivatives were designed and identified as potent inhibitors of VEGFR-2 (
- Shi, Lei,Wu, Ting-Ting,Wang, Zhi,Xue, Jia-Yu,Xu, Yun-Gen
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p. 698 - 707
(2014/08/18)
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- Discovery of quinazolin-4-amines bearing benzimidazole fragments as dual inhibitors of c-Met and VEGFR-2
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Both c-Met and VEGFR-2 are important targets for the treatment of cancers. In this study, a series of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinazolin-4- amine derivatives were designed and identified as dual c-Met and VEGFR-2 inhibitors. Among these compounds bearing quinazoline and benzimidazole fragments, compound 7j exhibited the most potent inhibitory activity against c-Met and VEGFR-2 with IC50 of 0.05 μM and 0.02 μM, respectively. It also showed the highest anticancer activity against the tested cancer cell lines with IC50 of 1.5 μM against MCF-7 and 8.7 μM against Hep-G2. Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of c-Met and VEGFR-2, which demonstrates that compound 7j is a potential agent for cancer therapy deserving further researching.
- Shi, Lei,Wu, Ting-Ting,Wang, Zhi,Xue, Jia-Yu,Xu, Yun-Gen
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p. 4735 - 4744
(2014/10/15)
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- Synthesis of 2-substituted benzimidazoles using 25 % Co/Ce-ZrO2 as a heterogeneous and nanocatalyst
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25 % Co/Ce-ZrO2 nano fine particles are reported as a new catalyst for the efficient synthesis of 2-arylbenzimidazoles. A simple and convenient procedure, reusable catalyst, easy purification and shorter reaction times are the advantageous features of this method. Also prepared catalyst according to the coprecipitation method was characterized by common techniques such as SEM, XRD, FTIR and so on analysis. The catalyst is reusable and, reusable catalyst was characterized by XRD and FTIR techniques. Graphical Abstract: [Figure not available: see fulltext.]
- Behbahani, Farahnaz K.,Rezaee, Elham,Fakhroueian, Zahra
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p. 2184 - 2190
(2015/02/19)
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- Benzimidazole derivatives: Synthesis, leishmanicidal effectiveness, and molecular docking studies
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Leishmanolysin GP63 is a zinc metalloprotease, expressed at the surface of Leishmania promastigotes. Studies on this protein are hindered as only a limited number of effective non-toxic inhibitors of this drug target are known. Present study describes the identification of a variety of 2-aryl- and 5-nitro-2-arylbenzimidazoles as new GP63 inhibitors. All the compounds were tested for in vitro activity against the promastigote form of Leishmania major and showed very good activity. 2-(Thiophen-2-yl)-1H-benzimidazole (19) and 2-(1H-indol-3-yl)-5-nitro-1H-benzimidazole (34) with IC50 value of 0.62 μg/mL were identified as lead of this library. Molecular docking studies were performed on binding site of GP63 to study the binding mode of compounds. The results of both in vitro and in silico studies clearly indicated that benzimidazoles may serve as new drug candidates in the combat against leishmaniasis.
- Shaukat, Awais,Mirza, Hira M.,Ansari, Amna H.,Yasinzai, Masoom,Zaidi, Sohail Z.,Dilshad, Sana,Ansari, Farzana L.
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p. 3606 - 3620
(2013/07/26)
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- New benzimidazole derivatives as topoisomerase i inhibitors - Synthesis and fluorometric analysis
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A series of new benzimidazole derivatives with potential anticancer activity were tested as a new topoisomerase I inhibitors. The fluorometric method was used to determine in vitro the quantitative level of plasmid DNA relaxation by these compounds. Optim
- B?aszczak-Swiatkiewicz, Katarzyna,Mikiciuk-Olasik, Elzbieta
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p. 451 - 458
(2013/07/28)
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- Reusable α-MoO3 nanobelts catalyzes the green and heterogeneous condensation of 1,2-diamines with carbonyl compounds
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Crystalline nanobelts of α-MoO3 have been obtained successfully using novel and safe agents through a simple and safe sol-gel method (polymerizing-complexing) and characterized by XRD, FT-IR, Raman spectroscopies, high resolution transmission electron microscopy (HRTEM), scanning electron microscopy (SEM) and the temperature programmed desorption (TPD) of ammonia. An orthorhombic lattice system for nano-MoO3 was established. The HRTEM images showed that the nanobelt morphology of α-MoO3 mostly ranged from 20-70 nm in width and 200-400 nm in length. The ammonia TPD profile demonstrated strong acidic sites. The spectral and analysis data confirmed the effectiveness of the method for the preparation of α-MoO3 nanobelts by prevention of grain growth or agglomeration of the particles. The nanostructured MoO3 exhibited a high efficiency in catalyzing the condensation reaction of various 1,2-diamine and carbonyl compounds for synthesis of heterocyclic compounds. The recovery of the title heterogenous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk material.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Ghahramaninezhad, Mahboube,Tabibi, Tooba
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p. 2087 - 2095
(2013/10/08)
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- Fast and efficient method for the synthesis of 2-arylbenzimidazoles using MCM-41-SO3H
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Nanosized MCM-41-SO3H material based on ordered mesoporous silica gel with covalently attached sulfonic acid groups was synthesized and used as acid catalyst for green synthesis of 2-substituted benzimidazole derivatives. Echofriendly protocol, short reaction times, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure. Copyright by Walter de Gruyter.
- Mahdavinia, Gholam Hossein,Rostamizadeh, Shahnaz,Amani, Ali Mohammad,Sepehrian, Hamid
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experimental part
p. 33 - 37
(2012/07/28)
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- One-pot synthesis of 2-substituted benzimidazoles catalyzed by anhydrous FePO4
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Anhydrous FePO4 has been employed as a catalyst for efficient synthesis of 2-substituted benzimidazoles. Simple and convenient procedure, easy purification and shorter reaction time are the advantages of this method, resulting in several known and three new compounds.
- Behbahani, Farahnaz K.,Ziaei, Parisa
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p. 1011 - 1017
(2013/03/13)
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- Discovery of 2-arylbenzoxazoles as upregulators of utrophin production for the treatment of duchenne muscular dystrophy
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Figure Presented. A series of novel 2-arylbenzoxazoles that upregulate the production of utrophin in murine H2K cells, as assessed using a luciferase reporter linked assay, have been identified. This compound class appears to hold considerable promise as a potential treatment for Duchenne muscular dystrophy. Following the delineation of structure-activity relationships in the series, a number of potent upregulators were identified, and preliminary ADME evaluation is described. These studies have resulted in the identification of 1, a compound that has been progressed to clinical trials.
- Chancellor, Daniel R.,Davies, Kay E.,De Moor, Olivier,Dorgan, Colin R.,Johnson, Peter D.,Lambert, Adam G.,Lawrence, Daniel,Lecci, Cristina,Maillol, Carole,Middleton, Penny J.,Nugent, Gary,Poignant, Séverine D.,Potter, Allyson C.,Price, Paul D.,Pye, Richard J.,Storer, Richard,Tinsley, Jonathon M.,Van Well, Renate,Vickers, Richard,Vile, Julia,Wilkes, Fraser J.,Wilson, Francis X.,Wren, Stephen P.,Wynne, Graham M.
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supporting information; experimental part
p. 3241 - 3250
(2011/07/06)
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- An efficient synthesis of 2-arylbenzimidazoles from o-phenylenediamines and arylaldehydes catalyzed by Fe/CeO2-ZrO2 nano fine particles
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75% Fe/CeO2-ZrO2 nano fine particles (0.005 mol%) are reported as a new catalyst for the efficient synthesis of 2-arylbenzimidazoles. A simple and convenient procedure, easy purification and shorter reaction times are the advantageous features of this method. Springer-Verlag 2011.
- Behbahani, Farahnaz K.,Ziaei, Parisa,Fakhroueian, Zahra,Doragi, Neda
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experimental part
p. 901 - 906
(2012/01/06)
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- Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles
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A practical and convenient synthetic method has been developed for the facile synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles. The method described has the benefits of operational simplicity, excellent yields, and high chemoselectivity. The Royal Society of Chemistry 2010.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Nejati, Akbar
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experimental part
p. 1237 - 1241
(2010/10/03)
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- Rapid and cheap synthesis of benzimidazoles via intermittent microwave promotion: A simple and potential industrial application of air as oxidant
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Using inexpensive KI as the catalyst in the presence of ambient air, benzimidazoles were synthesized from aromatic aldehydes and o-phenylenediamine with excellent yields via intermittent microwave irradiation without reflux equipment. The synthesis process was mild and only needed only a short reaction time (7-10min). As a simple example of the utilization of molecular oxygen under mild conditions, this method provides a novel way to synthesize benzimidazoles. The industrial synthesis of benzimidazoles may be realized by a cycle of microwave irradiation. Copyright
- Mao, Zhengzhou,Wang, Zhaoyang,Li, Jingning,Song, Xiumei,Luo, Yufen
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experimental part
p. 1963 - 1977
(2010/09/07)
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- Design, synthesis and biological evaluation of some novel benzimidazole derivatives for their potential anticonvulsant activity
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Selective GABAA receptor ligands are widely used clinically to reduce the occurrence of convulsions. Hence there is an intense interest in developing new benzimidazole derivatives demonstrating high selectivity and high affinity for GABAA
- Jain, Priyal,Sharma, Prakash Kumar,Rajak, Harish,Pawar, Rajesh Singh,Patil, Umesh Kumar,Singour, Pradeep Kumar
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experimental part
p. 971 - 980
(2011/12/02)
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- Solvent-free chemoselective synthesis of some novel substituted 2-arylbenzimidazoles using amino acid-based prolinium nitrate ionic liquid as catalyst
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A simple and eco-friendly protocol for the synthesis of substituted 2-arylbenzimidazoles is described. In this process, 2-arylbenzimidazoles were prepared in the presence of a newly introduced ionic liquid prolinium nitrate [Pro]NO3 as catalyst, under solvent-free condition. This process was performed under mild condition without using any oxidant with good to excellent yields and remarkable chemoselectivity in the absence of any byproduct. The ionic liquid can be recovered easily and reused.
- Rostamizadeh, Shahnaz,Aryan, Reza,Ghaieni, Hamid Reza,Amani, Ali Mohammad
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scheme or table
p. 74 - 78
(2009/05/07)
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- Very fast and efficient synthesis of some novel substituted 2-arylbenzimidazoles in water using ZrOCl2?nH2O on montmorillonite K10 as catalyst
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A simple and eco-friendly protocol for the synthesis of some novel substituted 2-arylbenzimidazoles was developed. In this process, these compounds were prepared in water as the solvent using ZrOCl2?nH 2O supported on montmorillonite K10 as an efficient water tolerating Lewis acid. The reaction was performed under mild conditions with good to excellent yields and remarkable chemoselectivity in the absence of any byproduct.
- Rostamizadeh, Shahnaz,Amani, Ali Mohammad,Aryan, Reza,Ghaieni, Hamid Reza,Norouzi, Leila
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experimental part
p. 547 - 552
(2010/06/16)
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- H2O2/HCI as a new and efficient system for synthesis of 2-substituted benzimidazoles
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The system, H2O2/HCI, oxidises carbon-nitrogen bonds for the synthesis of benzimidazoles from aldehydes and diamines in water at 100°C. Both aryl aldehydes bearing electron-donating and electron-withdrawing substituents afforded desired benzimidazoles in excellent yields. This procedure is also applicable to substituted o-phenylenediamines, which produced 2-phenylbenzimidazoles smoothly in excellent yields. The simplicity of the system, the use of water as the solvent, large-scale synthesis and easy work-up are main advantages of this procedure.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Kavianinia, Iman
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p. 783 - 784
(2007/10/03)
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- Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production
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Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which:G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; andZ is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.
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Page/Page column 27
(2010/02/13)
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- Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production
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Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which: G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; and Z is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.
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Page/Page column 19
(2010/02/13)
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- Studies on analgesic and anti-inflammatory activities of 1- dialkylaminomethyl-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives
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In this study the analgesic and anti-inflammatory activity of 1,2,5- trisubstituted benzimidazole derivatives have been examined. Analgesic activities of these compounds were investigated by using the modified Koster test. Among the compounds synthesized especially compound 1g (1- diethylaminomethyl)-2-(p-chlorophenyl)-5-nitro benzimidazole hydrochloride) has shown higher activity than acetylsalicylic acid (ASA) and indometacin. Compound 1e (1-(diethylaminomethyl)-2-(p-methoxyphenyl)-5-nitro benzimidazole hydrochloride, 1f (1-(diethylaminomethyl)-2-(p-tolyl)-5-nitro henzimidazole hydrochloride and 1i (1-(pipenridinomethyl)-2-(p-methoxyphenyl)-5-nitro benzimidazole hydrochloride) proved as potent as the standard ASA. Therefore the compounds 1e, 1f, 1g and 1i were screened for their anti-inflammatory activities using the carrageenan-induced hind paw edema test. Except 1g all compounds were almost inactive against this model of inflammation compared to indometacin.
- Ersan, Seyhan,Nacak, Sultan,Noyanalpan, Ningur,Yesilada, Erdem
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p. 834 - 836
(2007/10/03)
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- Synthesis and antimicrobial activity of 1-dialkylaminomethyl-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives
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1-(Dialkylaminomethyl)-2-(p-substituted phenyl)-5-substituted benzimidazole derivatives 1 have been synthesized by reacting 2-phenylbenzimidazole derivatives with formaldehyde and a secondary amine. The derivatives of 2-phenylbenzimidazole were obtained by reacting the bisulfide addition product of substituted benzaldehydes with 4-substituted-o-phenylenediamines. Their structures were confirmed by microanalysis, IB and NMB spectral analysis. Antimicrobial activity of the compounds was investigated by the microdilution susceptibility test in Mueller-Hinton Broth and Sabouraud Dextrose Broth was used for the determination of antibacterial and antifungal activities. Test organisms: Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 as Gram-positive bacteria, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853 as Gram-negative bacteria, and Candida albicans, C. parapsilosis, C. stellatoidea as yeast-like fungi. Compounds 1a, 1b, 1c, 1e and 1i showed slight to moderate activity against all microorganisms. Compound 1g showed the highest activity. It was found more potent than streptomycin against Enterococcus faecalis and Pseudomonas aeruginosa.
- Ersan, Seyhan,Nacak, Sultan,Acar, Nilguen,Noyanalpan, Ningur
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p. 410 - 412
(2007/10/03)
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- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, a Mild Catalyst for the Formation of Carbon-Nitrogen Bonds
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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) catalyzes the preparation of N-tetrahydropyranylbenzazoles, 2-substituted 1,3-diphenylimidazolidines, and N-(arylmethylene)benzene-1,2-diamines.In the latter case, use of one equivalent of DDQ provides a novel one-pot method for the synthesis of 1H-benzimidazoles.
- Eynde, Jean Jacques Vanden,Delfosse, Florence,Lor, Pascal,Haverbeke, Yves Van
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p. 5813 - 5818
(2007/10/02)
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- AN EXPEDIENT ROUTE TO 1H-BENZIMIDAZOLES AND 1H-IMIDAZOPYRIDINES
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1H-Benzimidazoles, 1H-imidazopyridines, and 1H-imidazopyridines can be synthesized readily by reaction of unisolated N-(1-chloroalkyl)pyridinium chlorides with 1,2-benzenediamines, 2,3-pyridinediamine, and 3,4-pyridinediamine, respectively.
- Eynde, Jean-Jacques Vanden,Mayence, Annie,Maquestiau, Andre,Anders, Ernst
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p. 357 - 364
(2007/10/02)
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