cas 934-32-7, 2-Aminobenzimidazole | Articles data

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2-Amino- and 2-hydroxymethylbenzimidazolium bromides as protein tyrosine phosphatase 1В (PTP1В) inhibitors and other targets associated with diabetes mellitus
New 2-amino- and 2-hydroxymethylbenzimidazoles were synthesized and used to prepare the previously unknown 1,2,3-tri- and 1,2,3,5-tetrasubstituted benzimidazolium bromides with a biphenyl-containing substituent at the imidazole nitrogen atom. In some cases, these bromides exhibit activity against targets associated with diabetes mellitus. These compounds are strong protein tyrosine phosphatase 1B (PTP1B) inhibitors, exhibit chelating and antiglycation activity, but have no significant AT1 receptor antagonist activity. Hence, biphenyl-containing benzimidazolium derivatives can be considered as a basis for the development of new promising agents for the treatment of type 2 diabetes mellitus (DM2) and other diseases mediated by high phosphatase PTP1B activity.
Babkov, D. A.,Babkova, V. A.,Brigadirova, A. A.,Litvinov, R. A.,Morkovnik, A. S.,Sokolova, E. V.,Spasov, A. A.,Zhukovskaya, O. N.
p. 774 - 780
(2020)
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Photodecomposition of carbendazim in aqueous solutions
The kinetic of photodecomposition of carbendazim (methyl-2-benzimidazole carbamate) at different pHs (1, 5, 7, 8 and 11) and at two different concentrations of dissolved oxygen has been studied. According to the experimental results, the photodegradation process follows a first-order kinetic and the degradation rate of carbendazim increases with pH and dissolved oxygen concentration. The kinetic of photodecomposition of carbendazim (methyl-2-benzimidazole carbamate) at different pHs (1, 5, 7, 8 and 11) and at two different concentrations of dissolved oxygen has been studied. According to the experimental results, the photodegradation process follows a first-order kinetic and the degradation rate of carbendazim increases with pH and dissolved oxygen concentration. Copyright (C) 2000 Elsevier Science Ltd.
Panadés, Ricard,Ibarz, Albert,Esplugas, Santiago
p. 2951 - 2954
(2000)
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Alternative and efficient method for the preparation of 2-acetamidobenzimidazoles
An alternative method for the synthesis of acetamidobenzimidazoles (3-6) has been developed, including the reacylation of methylbenzimidazol-2-ylcarbamate (carbendazim, MBC, 1) under the action of aliphatic and aromatic carboxylic acids. It was shown that with an increase in the size of the alkyl group and the reaction temperature (in the case of butyric acid), due to the decomposition of the resulting product, the yield of the target acyl products sharply decreases. The obtained compounds are homologues of the anthelmintic drug - N-(1H-benzimidazol-2-yl) acetamide (2-acetylaminobenzimidazole, 3). A possible mechanism of reacylation is presented.
Abdurazakov,Saidov,Okmanov,Kubaev,Elmuradov, Burkhon Zhurayevich
p. 2247 - 2252
(2021/04/22)

Application of sulfonic acid fabricated cobalt ferrite nanoparticles as effective magnetic nanocatalyst for green and facile synthesis of benzimidazoles
This work represents the design and synthesis of efficient sulfonated cobalt ferrite solid acid catalyst. The synthesized solid acid green catalyst was characterized using various techniques viz. FT-IR, powder XRD, SEM, TEM and VSM. The obtained catalyst was used to synthesize biologically significant 2-substituted benzimidazole derivatives by condensation between o-phenylenediamine with various aromatic, aliphatic and heterocyclic aldehydes. High yield (up to 98 %), short reaction time (10?25 min), mild reaction condition, wide functional group tolerance, easy work-up procedure and excellent values of green chemistry metrices such as lower E factor (0.126), high RME value (88.83 %), carbon efficiency (100 %) and high atom economy (AE) value (90.65 %), are some salient features of the present catalytic system. Moreover, the catalyst recovery by simply using an external magnet and catalyst reusability up to 7 times without any significant loss in catalytic efficiency are some additional remarkable features of the current protocol.
Yadav, Priyanka,Kakati, Praachi,Singh, Preeti,Awasthi, Satish K.
(2021/02/06)

Cobalt-Catalyzed Aerobic Oxidative Cyclization of 2-Aminoanilines with Isonitriles: Facile Access to 2-Aminobenzimidazoles
A ligand- and additive-free aerobic cobalt-catalyzed synthesis of 2-aminobenzimidazoles from 2-aminoanilines was developed. A variety of aminoanilines and isonitriles undergo efficient coupling to furnish substituted 2-aminobenzimidazoles in moderate to excellent yields. This protocol enables efficient access to the unsubstituted 2-aminobenzimidazoles.
Liu, Jiaqi,Morgan, Sarah,Hoover, Jessica M.
p. 1297 - 1301
(2020/01/25)

Copper-promoted one-pot approach: Synthesis of benzimidazoles
A facile, one-pot, and proficient method was developed for the production of various 2-arylaminobenzimidazoles. This methodology is based for the first time on a copper catalyst promoted domino C-N cross-coupling reaction for the generation of 2-arylaminobenzimidazoles. Mechanistic investigations revealed that the synthetic pathway involves a copper-based desulphurization/nucleophilic substitution and a subsequent domino intra and intermolecular C-N cross-coupling reactions. Some of the issues typically encountered during the synthesis of 2-arylaminobezimidazoles, including the use of expensive catalytic systems and the low reactivity of bromo precursors, were addressed using this newly developed copper-catalyzed method. The reaction procedure is simple, generally with excellent substrate tolerance, and provides good to high yields of the desired products.
Adil, Syed Farooq,Alduhaish, Osamah,Assal, Mohamed E.,Bollikolla, Hari Babu,Gollapudi, Ravi Kumar,Murthy Boddapati, S. N.,Nurbasha, Sharmila,Siddiqui, Mohammed Rafiq H.,Tamminana, Ramana
(2020/04/24)

Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides
A new class of benzazolyl azolyl sulfamoyl acetamides was prepared from azolyl sulfamoyl acetates and benzazolyl amines in the presence of KOtBu in tetrahydrofuran. Compounds with benzothiazole-thiazole, benzimidazole-thiazole, benzothiazole-imidazole, and benzimidazole-imidazole moieties exhibited excellent antibacterial activity against Bacillus subtilis.
Rajeswari, Tankam,Rekha, Tamatam,Dinneswara Reddy, Guda,Padmaja, Adivireddy,Padmavathi, Venkatapuram
p. 2449 - 2459
(2019/08/07)

Design, synthesis and biological evaluation of 1,2,3-triazole based 2-aminobenzimidazoles as novel inhibitors of LasR dependent quorum sensing in: Pseudomonas aeruginosa
Bacteria regulate their phenotype, growth and population via a signalling pathway known as quorum sensing. In this process, bacteria produce signalling molecules (autoinducers) to recognize their population density. Inhibiting this quorum sensing signalling pathway is one of the potential methods to treat bacterial infection. 2-Aminobenimdazoles are reported to be the strongest inhibitors of quorum sensing against wild-type P. aeruginosa. 1,2,3-Triazole based acyl homoserine lactones are found to be good inhibitors of the quorum sensing LasR receptor. Hence, in our current study, forty 1,2,3-triazole based 2-aminobenzimdazoles were synthesized and characterized using IR, NMR, MS and elemental analysis. A single crystal was developed for N-(1H-benzo[d]imidazol-2-yl)-2-(4-nonyl-1H-1,2,3-triazol-1-yl)acetamide (6d). All final compounds were screened for in vitro quorum sensing inhibitory activity against Pseudomonas aeruginosa. The quorum sensing inhibitory activity was determined in the LasR expressing P. aeruginosa MH602 reporter strain by measuring green fluorescent protein production. Among the title compounds, N-(1H-benzo[d]imidazol-2-yl)-2-(4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl)acetamide (6i) exhibited good quorum sensing inhibitory activity of 64.99% at 250 μM. N-(1H-Benzo[d]imidazol-2-yl)-2-(4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)acetamide (6p) exhibited the most promising quorum sensing inhibitory activity with 68.23, 67.10 and 63.67% inhibition at 250, 125 and 62.5 μM, respectively. N-(1H-Benzo[d]imidazol-2-yl)-2-(4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)acetamide (6o) and N-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-2-(4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)acetamide (7l) also exhibited 64.25% and 65.80% quorum sensing inhibition at 250 μM. Compound 6p, the most active quorum sensing inhibitor, also displayed low cytotoxicity at the tested concentrations (25, 50 and 100 μM) against normal human embryonic kidney cell lines. Finally, a docking study using Schrodinger Glide elucidated the possible putative binding mode of the significantly active compound 6p at the active site of the target LasR receptor (PDB ID: 2UV0).
Srinivasarao, Singireddi,Nandikolla, Adinarayana,Nizalapur, Shashidhar,Yu, Tsz Tin,Pulya, Sravani,Ghosh, Balaram,Murugesan, Sankaranarayanan,Kumar, Naresh,Chandra Sekhar, Kondapalli Venkata Gowri
p. 29273 - 29292
(2019/09/30)

Design, synthesis, and bioactivity of dihydropyrimidine derivatives as kinesin spindle protein inhibitors
A series of twenty-one 3,4-dihydropyrimidine derivatives bearing the heterocyclic 1,3-benzodioxole at position 4 in addition to different substituents at positions 2, 3 and 5 were designed and synthesized as monastrol analogs. The novel synthesized compounds were screened for their cytotoxic activity towards 60 cancer cell lines according to NCI (USA) protocol. Compounds 10b and 15 showed the best antitumor activity against most cell lines. Compound 15 was subsequently tested in 5-doses mode and displayed high selectivity towards CNS, prostate and leukemia subpanel with selectivity ratios of 22.30, 15.38 and 12.56, respectively at GI50 level. The IC50 of compounds 9d, 10b, 12, 15 and 16 against kinesin enzyme were 3.86 ± 0.12, 10.70 ± 0.35, 3.95 ± 0.12, 4.36 ± 0.14, and 14.07 ± 0.45 μM respectively, while the prototype compound, monastrol, reported IC50 value of 20 ± 0.42 μM. The safest compound among test compounds against normal cell line (HEK 293) is 10b with IC50 value of 62.02 ± 2.42 μM/ml in comparison to doxorubicin (IC50 = 11.34 ± 0.44 μM/ml). Cell cycle analysis of SNB-75 cells treated with compound 15 showed cell cycle arrest at G2/M phase. Further, the assay of levels of active caspase-3 and caspase-9 was investigated. Moreover, Molecular docking of compounds, 9d, 10b, 12, 15, 16, monastrol and mon-97 was performed to study the interaction between inhibitors and the kinesin spindle protein allosteric binding site.
Tawfik, Haytham O.,El-Hamamsy, Mervat H.,Sharafeldin, Nabaweya A.,El-Moselhy, Tarek F.
(2019/11/11)

Substituted benzimidazoles as modulators of Ras signaling
Benzimidazole compounds that increase the rate of SOS-mediated nucleotide exchange on Ras by binding to a functionally relevant, chemically tractable pocket on the SOS protein, as part of the Ras:SOS:Ras complex.
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(2019/12/25)

Biomass-based molecular capsule wall material and method for preparing sustained-release algae removal microcapsule by utilizing material
The invention relates to the field of algae removal materials and provides a biomass-based molecular capsule wall material and a method for preparing a sustained-release algae removal microcapsule byutilizing the material to solve the current urgent problems of low utilization rate, short validity period, environmental pollution and the like of the chemical pesticides for treating a green algae disease of Chinese torreya. The biomass-based molecular capsule wall material and the method for preparing the sustained-release algae removal microcapsule by utilizing the material, which are providedby the invention, have the beneficial effects that amphiphilic polysaccharide sodium carboxymethyl cellulose (CMC) is compounded with a non-toxic high-efficiency photosensitive catalytic material toserve as a wall material and a novel green cinnamaldehyde-type algicide serves as a core material to form a sustained-release nano-molecular capsule by self-assembly; and the capsule has the characteristics of high efficiency and low residual, and is of great significance for prolonging the lasting period of the algae removal effect, reducing the application amount of a high-toxic algicide, efficiently utilizing the pesticides and protecting the environment.
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Paragraph 0032; 0057; 0060; 0066; 0069; 0074; 0077

(2019/06/12)

Microwave use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds method
The invention discloses a microwave the use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds, in the aqueous phase under microwave conditions adding benzoic amidine compound under alkaline condition [...] into benzimidazole reaction, invention an environment-friendly, the operation is simple, cheap and safe, efficient process for preparing benzimidazole method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection; .
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Paragraph 0019

(2019/03/28)

Benzimidazole compound and application thereof
The invention relates to a benzimidazole compound and an application thereof. The structure of the benzimidazole compound is shown as a formula I, and the compound is used as a focal adhesion kinase inhibitor and shows relatively good focal adhesion kinase (FAK) inhibition activity. Meanwhile, the benzimidazole compound has stronger medicine effect and better pharmacokinetic property and/or toxicological characteristics, such as good brain/plasma ratio, good bioavailability, good metabolic stability, and reduced inhibition to respiratory action of mitochondria. The benzimidazole compound has agood clinical application prospect.
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Paragraph 0188; 0190; 0191; 0194; 0196; 0197

(2019/01/07)

Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus
Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus.
Giancotti, Gilda,Cancellieri, Michela,Balboni, Andrea,Giustiniano, Mariateresa,Novellino, Ettore,Delang, Leen,Neyts, Johan,Leyssen, Pieter,Brancale, Andrea,Bassetto, Marcella
supporting information
p. 56 - 68
(2018/03/06)

Synthesis and PASS-assisted evaluation of coumarin–benzimidazole derivatives as potential anti-inflammatory and anthelmintic agents
Two series of novel derivatives have been designed by coupling medicinally important coumarin and benzimidazole nuclei through different linkers. These compounds have been predicted to be potent anti-inflammatory and anthelmintic by in silico studies using PASS (prediction of activity spectra for substances) software. The compounds are synthesized and evaluated for the predicted activities as well as for their in vitro antioxidant potential. Compounds of first series (4a–4f) are found good to moderate anti-inflammatory agents. Among these, compounds 4b and 4f exhibited maximum anti-inflammatory activity (45% inhibition), which is equivalent to the activity of indomethacin (48% inhibition) after 3 h (peak inflammatory response time). Compounds of second series (5a–5f) exhibit anthelmintic activity. Amongst these, compound 5f has mortality activity marginally higher than albendazole (10–11 s). Compound 5e is found to be the most potent antioxidant with remarkable EC50 value (0.08 μM/mL), which is though a little less than that of ascorbic acid (0.03 μM/mL). In addition, a comparative analysis of calculated Lipinski’s parameters reveals that all test compounds have the propensity to be orally bioavailable. Based on these findings, compounds 4b, 4f, 5e, and 5f are identified as new leads to develop potent anti-inflammatory, anthelmintic, and antioxidant compounds.
Sethi, Purva,Bansal, Yogita,Bansal, Gulshan
p. 61 - 71
(2018/04/17)

HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
A heterocyclic compound is represented by Formula 1: wherein, in Formula 1, R1 ro R4, R11, ring A1, L1, Ar1, c11, a1, and b1 are as defined in the specification.
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Paragraph 0439-0441

(2018/02/17)

Lewis-acid Promoted Chemoselective Condensation of 2-Aminobenzimidazoles or 3-Aminoindazoles with 3-Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles
A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles or 3-aminoindazoles with 3-ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidine and pyrimido[1,2-b]-indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3+3] annulation reaction of 3-ethoxycyclobutanones. (Figure presented.).
Kong, Weiguang,Zhou, Yao,Song, Qiuling
supporting information
p. 1943 - 1948
(2018/04/02)

Design and synthesis of benzimidazole-based Rho kinase inhibitors for the treatment of glaucoma
Rho kinase inhibitors (ROCK II) play a key role in glaucoma management attributed to their IOP lowering ability and neuroprotective effects. In the present study, a series of novel benzimidazole derivatives (9a–m) has been synthesized and evaluated for their IOP lowering, Rho kinase inhibitory and antioxidant properties. The synthesized compounds were found to be lipophilic and showed a significant IOP lowering effect both in the treated and the contralateral eye comparable to the reference standard fasudil. The nitrophenyl piperazine substituted compound 9j exhibited significant IOP lowering (51.56%) and an inhibition of 57.25 and 77.92% towards ROCK II enzyme at a concentration of 0.5 and 1 mM respectively. It possessed a considerable free radical scavenging activity exhibiting an IC50 value of 95.49 μg/mL in DPPH assay. The molecular docking studies of compound 9j indicated the binding of the compound at the active site of recombinant human ROCK II which makes it a promising antiglaucoma agent.
Abbhi, Vasudha,Saini, Lovneet,Mishra, Srishti,Sethi, Gautam,Prem Kumar, Alan,Piplani, Poonam
p. 6071 - 6085
(2017/10/18)

Cu-Catalyzed Synthesis of 3-Formyl Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources
A highly efficient synthesis of 3-formyl imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine, under Cu-catalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of C-C bond and C-N bond of ethyl group with molecular oxygen as terminal oxidant in this one-pot protocol is reported for the first time. This reaction features broad substrate scope, good functional group tolerance, as well as diversified and valuable products.
Rao, Changqing,Mai, Shaoyu,Song, Qiuling
supporting information
p. 4726 - 4729
(2017/09/22)

Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles
The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.
Mallikarjuna Reddy,Lavanya,Lakshmi Teja,Padmaja,Padmavathi
p. 2755 - 2766
(2017/09/26)

PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS
The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).
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(2017/04/11)

Copper-Catalyzed C NH2Arylation of 2-Aminobenzimidazoles and Related C-Amino-NH-azoles
A copper(II)-catalyzed selective C NH2arylation of 2-aminobenzimidazoles and related C-amino-NH-azoles was achieved in presence of 2,2′-bipyridine and cesium carbonate at 60 °C under open air conditions and this is first method for the copper-catalyzed selective C NH2arylation in the presence of other reactive nucleophilic sites. Previously unexplored heteroaromatics possessing multiple nucleophilic sites that are selectively arylated at the C NH2position are obtained, providing an exceptional tool for rapid delivery of a diverse array of medicinally important C NH(aryl) derivatives of aminoazoles without any protection/deprotection of ring N H bonds. It is first example for the selective C NH2arylation of 5-aminoindazole, 4-aminopyrazole, 5-aminopyrazole, 9H-purine-6-amine, and 1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives. (Figure presented.) .
Rao, Desaboini Nageswar,Rasheed, Sk.,Kumar, Karampoori Anil,Reddy, Annem Siva,Das, Parthasarathi
supporting information
p. 2126 - 2133
(2016/07/16)

The derivatives of imidazo[1,2-a]benzimidazole as 5-HT2A receptor antagonists
We studied in vitro the 5-HT2A antagonistic activity of 16 imidazo[1,2-a]benzimidazole derivatives. Using the radioligand method we showed the binding of 9-(2-diethylaminoethyl)-2-(4-methoxyphenyl)imidazo[1,2-a]benzimidazol dinitrate to the 2A subtype serotonin receptor.
Spasov,Yakovlev,Maltsev,Zhukovskaya,Anisimova,Kovalev,Zimin,Morkovina
p. 397 - 403
(2016/08/03)

Novel prodrugs with a spontaneous cleavable guanidine moiety
Water-soluble prodrug strategy is a practical alternative for improving the drug bioavailability of sparingly-soluble drugs with reduced drug efficacy. Many water-soluble prodrugs of sparingly-soluble drugs, such as the phosphate ester of a drug, have been reported. Recently, we described a novel water-soluble prodrug based on O–N intramolecular acyl migration. However, these prodrug approaches require a hydroxy group in the structure of their drugs, and other prodrug approaches are often restricted by the structure of the parent drugs. To develop prodrugs with no restriction in the structure, we focused on a decomposition reaction of arginine methyl ester. This reaction proceeds at room temperature under neutral conditions, and we applied this reaction to the prodrug strategy for drugs with an amino group. We designed and synthesized novel prodrugs of representative sparingly soluble drugs phenytoin and sulfathiazole. Phenytoin and sulfathiazole were obtained as stable salt that were converted to parent drugs under physiological conditions. Phenytoin prodrug 3 showed a short half-life (t1/2) of 13?min, whereas sulfathiazole prodrug 7 had a moderate t1/2of 40?min. Prodrugs 3 and 7 appear to be suitable for use as an injectable formulation and orally administered drug, respectively.
Hamada, Yoshio
supporting information
p. 1685 - 1689
(2016/07/29)

A new NBS/oxone promoted one pot cascade synthesis of 2-aminobenzimidazoles/2-aminobenzoxazoles: A facile approach
A new strategy for the synthesis of 2-aminobenzimidazoles via a reaction of α-halogenated cyclohexanone with guanidine is reported. It provides a facile N-bromosuccinimide (NBS) mediated transition metal free, sustainable path for the synthesis of 2-substituted azoles. NBS along with the oxone promotes in situ halogenation of cyclohexanone, which in turn, when allowed to react with guanidine, afforded 2-aminobenzimidazoles (2-ABI). This eco-friendly protocol provides a competent laboratory synthesis method associated with significant advantages such as greater selectivity, cost-efficiency, mild reaction conditions, absence of chromatographic purification, clean reaction profile, and a simple work-up procedure to furnish high yields. The structures of all the synthesized compounds were confirmed on the basis of IR, 1H and 13C NMR, mass spectrometry, and elemental analyses data. In addition, we have also extended the scope of this strategy for obtaining 2-amino substituted benzoxazoles.
Daswani, Ujla,Dubey, Nitin,Sharma, Pratibha,Kumar, Ashok
supporting information
p. 8093 - 8099
(2016/09/12)

Benzimidazole Based ‘Turn on’ Fluorescent Chemodosimeter for Zinc Ions in Mixed Aqueous Medium
Benzimidazole based compound 3 is designed and synthesized. The compound 3 is evaluated as fluorogenic sensor for metal ions in mixed aqueous solutions. Among all the metal ions tested, the compound 3 selectively senses Zn2+ ions. The imine bond of 3 gets cleaved by Zn2+ ions. Thus, 3 behave as ‘turn on’ fluorescent chemodosimeter for Zn2+ ions with limit of detction in micromolar range. Furthurmore, we demonstated that 3 can detect Zn2+ ions in cells of Allium cepa. [Figure not available: see fulltext.]
Sharma, Shilpa,Pradeep, Chullikkattil P.,Dhir, Abhimanew
p. 1439 - 1445
(2016/07/30)

TOLL-LIKE RECEPTOR AGONISTS
Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivatives thereof, prodrugs thereof, salts thereof, or stereoisomers thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines, as well as for other therapeutic purposes described herein.
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(2015/02/25)

Design, synthesis and biological evaluation of benzimidazolyl and benzothiazolyl picolinamide derivatives as antimicrobial agents
A series of benzothiazolyl amides and benzimidazolyl amides (6a-f) has been synthesized from the coupling reaction of substituted picolinic acid with benzothiazole and benzimidazoles, respectively. The newly synthesized compounds were evaluated for their efficacy as antimicrobial agents against various Gram-positive and Gram-negative strains of bacteria and fungal strains. Amongst these compounds 6f was found to be the most potent against Bacillus subtilis and Candida albicans. Moreover, other compounds also found to be potential antibacterial agents in comparison to the standard drugs.
Namani, Vasu,Bharath Kumar Goud,Bharathi Kumari,Kumbham, Ramesh,Balakrishna, Kannoju,Bhima, Bhukya
p. 4575 - 4578
(2015/11/27)

Synthesis and antimicrobial activity of amino linked heterocycles
Amino-linked benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines were prepared and their antimicrobial activity studied. The nitro-substituted benzothiazolyl quinazoline (8f) may be a potential antibacterial agent against Staphylococcus aureus and nitro-substituted benzimidazolyl quinazoline (9f) may be a potential antifungal agent against Aspergillus niger.
Mallikarjuna Reddy, Lingaladinne,Dinneswara Reddy, Guda,Padmaja, Adivireddy,Padmavathi, Venkatapuram
p. 75 - 80
(2015/03/04)

Synthesis and in vitro antiproliferative activity of novel 2-arylideneaminobenzimidazole derivatives
A new class of Mannich bases 9-26, derivatives of 2-amino-1H-benzimidazole, were obtained in the condensation of Schiff bases 1-4 or 2-benzylaminobenzimidazoles 5-8 with selected secondary amines: morpholine, piperidine, N-methylpiperazine, N-phenylpiperazine, 1-(2-pyridyl)piperazine, 1(2-methoxyphenyl)piperazine, 1-(2-pyrimidinyl)piperazine and formaldehyde in ethanol. The pyrimido[1,2-a]benzimidazole derivatives 27-29 have been synthesized in the reactions of Schiff base 2 with selected compounds containing active methylene group: acetylacetone, benzoylacetone and malononitrile. The structures 1-29 were confirmed by the results of elementary analysis and their IR, 1H- and 13C-NMR spectra. The products 1-29 are of interest for biological studies and can be substrates for further synthesis. All compounds were screened against the cells of MV4-11 human leukemia and then the most active of them 5, 7, 9-16, 24-26, 28, 29 were tested towards human T47D breast and A549 lung cancer cells as well as normal mouse fibroblasts (BALB/3T3). The most active compound against the cancer cell lines was 4-amino-3-cyano-2-(4-hydroxyphenylene)-1,2-dihydropyrimido[1,2-a]benzimidazole (29) (IC50 0.23 ± 0.05 μg/mL against MV4-11 cells) showing in parallel very low cytotoxicity towards mouse fibroblasts. Cisplatin was the control drug.
Nowicka, Anna,Liszkiewicz, Hanna,Nawrocka, Wanda P.,Wietrzyk, Joanna,Sadowska, Joanna
p. 951 - 963
(2015/10/12)

A facile synthesis of 2-aminobenzoxazoles and 2-aminobenzimidazoles using N -cyano- N -phenyl- P -toluenesulfonamide (NCTS) as an efficient electrophilic cyanating agent
A facile synthesis of 2-aminobenzoxazole and 2-aminobenzimidazole derivatives employing a nonhazardous electrophilic cyanating agent: N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) with various substituted 2-aminophenols and benzene-1,2-diamine derivatives in the presence of lithium hexamethyldisilazide (LiHMDS) is described. This novel protocol boasts operational simplicity, shorter reaction time, and simple workup.
Kasthuri, Mahesh,Babu, H. Sharath,Kumar, K. Shiva,Sudhakar, Ch.,Kumar, P. V. Nagendra
p. 897 - 900
(2015/04/27)

Design, synthesis, and PASS-assisted evaluation of novel 2-substituted benzimidazole derivatives as potent anthelmintics
A series of novel 2-substituted benzimidazole analogs has been designed and synthesized by connecting the benzimidazole nucleus with variedly substituted chalcone moieties through an amino linker. The designed analogs were predicted for their biological activity profile through the computer software PASS. The compounds were predicted to have potent anthelmintic activity. These were synthesized and the activity of each compound was evaluated experimentally at the concentrations of 0.1, 0.2, and 0.5% in terms of mortality time and paralysis time for the helminthes. The experimentally observed activity was found to comply with the PASS predicted activity. All compounds showed dose-dependent activities. The compounds with an electron releasing group at the para position on phenyl ring in the chalcone moiety (8 and 9) were the most active in comparison to those bearing electron withdrawing groups. The corresponding ortho analogs (4 and 5) also revealed good paralytic and lethal activities. The higher activities of 8 and 9 may be attributed to the favorable electronic interactions of the electron releasing groups present at para position of the phenyl ring. Comparative analysis of the Lipinski's parameters and the activities of the compounds revealed all the compounds to comply with the Lipinski's rule of five. Further an optimum hydrophilicity and total polar surface area in the range of 65-80 of the molecule are required for the potent activity, but Molar refractance is not found to have any significant role in determining the anthelmintic activity. Springer Science+Business Media 2013.
Garg, Kamalpriya,Bansal, Yogita,Bansal, Gulshan,Goel
p. 2690 - 2697
(2014/05/06)

Human toll-like receptor 8-selective agonistic activities in 1-alkyl-1 h -benzimidazol-2-amines
Toll-like receptor (TLR)-8 agonists strongly induce the production of T helper 1-polarizing cytokines and may therefore serve as promising candidate vaccine adjuvants, especially for the very young and the elderly. Earlier structure-based ligand design led to the identification of 3-pentyl-quinoline-2-amine as a novel, human TLR8-specific agonist. Comprehensive structure-activity relationships in ring-contracted 1-alkyl-1H-benzimidazol-2-amines were undertaken, and the best-in-class compound, 4-methyl-1-pentyl-1H-benzo[d]imidazol-2-amine, was found to be a pure TLR8 agonist, evoking strong proinflammatory cytokine and Type II interferon responses in human PBMCs, with no attendant CD69 upregulation in natural lymphocytic subsets. The 1-alkyl-1H-benzimidazol-2-amines represent a novel, alternate chemotype with pure TLR8-agonistic activities and will likely prove useful not only in understanding TLR8 signaling but also perhaps as a candidate vaccine adjuvant.
Beesu, Mallesh,Malladi, Subbalakshmi S.,Fox, Lauren M.,Jones, Cassandra D.,Dixit, Anshuman,David, Sunil A.
p. 7325 - 7341
(2014/12/11)

Copper-catalyzed sequential N-arylation of C-amino-NH-azoles
Copper(ii)-catalyzed boronic acid promoted C-N bond cross-coupling reactions have been successfully developed for sequential N-arylation of C-amino-NH-azoles. These general protocols are compatible with a variety of aryl/hetero-aryl boronic acids and provided rapid access to a diverse array of diarylaminoazole derivatives in a two-step sequence or in one-pot. This journal is
Nageswar Rao,Rasheed, Sk.,Vishwakarma, Ram A.,Das, Parthasarathi
supporting information
p. 12911 - 12914
(2014/12/11)

Water compatible photoarylation of amino acids and peptides
A novel photoarylation of amino acids and peptides is described, which tolerates the presence of water. Irradiation of Boc-protected amino acids in the presence of N-protected 2-azidobenzimidazoles leads to selective arylation of carboxy termini or side chains. The new reaction also works for peptides. Irradiation of the nonapeptide H-SPSYVYHQF-OH also resulted in selective arylation of the tyrosine side chains, as indicated by ESI-MS/MS fragmentation. Chemo- and regioselectivity could add the title reaction to the repertoire of photoaffinity labeling methods.
Sudakow, Alex,Papke, Uli,Lindel, Thomas
supporting information
p. 10223 - 10226
(2014/08/18)

Synthesis of some novel phosphorylated and thiophosphorylated benzimidazoles and benzothiazoles and their evaluation for larvicidal potential to Aedes albopictus and Culex quinquefasciatus
Series of benzimidazole and benzothiazole linked phosphoramidates and phosphoramidothioates (5a-j) and benzimidazole linked phenylphosphoramidates and phenylphosphoramidothioates (10a-e) were synthesized. The title compounds were preliminary screened for mosquito larvicidal properties against Aedes albopictus and Culex quinquefasciatus at different concentration from 40 to 5 mg/L. Among the screened compounds three compounds revealed potential larvicidal effects with 100% mortality in the order of 10e > 5j > 5e. Compound 10e was found to be the most toxic compound to Ae. albopictus and Cx. quinquefasciatus. The LC50 of 10e against Ae. albopictus was found to be 6.42 and 5.25 mg/L at 24 and 48 h, respectively, whereas it was 7.01 and 3.88 mg/L, respectively in Cx. quinquefasciatus. Temephos was used as positive control.
Bandyopadhyay, Prabal,Sathe, Manisha,Tikar, Sachin N.,Yadav, Ruchi,Sharma, Pratibha,Kumar, Ashok,Kaushik
supporting information
p. 2934 - 2939
(2014/06/10)

Design, synthesis and PASS assisted evaluation of novel 2-substituted benzimidazole derivatives as potent anthelimintics
Two series of compounds (AB and APB) bearing substituted phenoxy groups at 2-position of benzimidazole nucleus through amino or phenyleneamino were synthesized and evaluated through PASS software for predicting the activity spectrum of each compound. All compounds of both the series were predicted to have potent anthelmintic activity. The activity of each compound was evaluated experimentally at the concentrations of 0.1, 0.2 and 0.5% in terms of mortality time and paralysis time of the helminthes and was found to comply with the PASS predicted activity. In general, all compounds of APB series were more potent than those of AB series probably due to the additional hydrophobic interactions of the spacer phenyl ring in the APB series. The activity of all compounds was found to increase with increasing concentration. The compound with p-chlorophenoxy moiety was the most active from the APB series (mortality time 5.7±0.4 min and paralysis time 3.1±0.3 min) and equipotent to albendazole (mortality time 5.4±0.1 min and paralysis time 2.8±0.2 min) at concentration of 0.2%. The o-chlorophenoxy analogs in both the series were found to be the least active of all. Based on these results, a substituent capable of binding with the receptor through van der Waals and/or electronic interactions at 4-position of the phenoxy ring in the compound is suggested to increase binding interaction leading to potent anthelmintic activity.
Singh, Gurmeet,Bansal, Yogita,Bansal, Gulshan,Goel, Rajesh Kumar
p. 418 - 425
(2014/05/20)

Synthesis and QSAR modeling of novel benzimidazolo thiazolidinones, thiazinones and 5-arylidene-2-imino thiazolidinones as antibacterial agents
A novel series of benzimidazolo thiazolidinones, thiazinones and 5-arylidene-2-imino thiazolidinones were synthesized and evaluated for antibacterial activity. The compounds were synthesized in excellent yield and the structures were characterized on the basis of IR, 1H-NMR and MASS spectral data. Most of the synthesized compounds showed good antibacterial activity against Gram-positive and Gram-negative bacteria. QSAR study was carried out with synthesized compounds using molecular descriptors such as electronic, thermodynamic and steric. Molecular descriptors were used to derive QSAR models between antibacterial activity and structural properties. QSAR study suggested the need of a bulky group to enhance the antibacterial activity in these series of compounds.
Ghate, Manjunath,Devi, Praveena,Parikh, Jignesh,Vyas, Vivek K.
p. 474 - 485
(2013/07/28)

Benzazoles: I. Regioselective arylsulfonylation of benzimidazol-2-amine
Benzimidazol-2-amine reacted with arenesulfonyl chlorides in the presence of triethylamine in regioselective fashion at the endocyclic nitrogen atom, the exocyclic amino group remaining intact. The yields of 1- arylsulfonylbenzimidazol-2-amines depend on the electronic properties of substituents in the benzene ring of arenesulfonyl chlorides.
Kaipnazarov,Abdireimov,Mukhamedov,Okmanov,Tashkhodjaev,Berdimbetova,Shakhidoyatov
p. 108 - 111
(2013/03/28)

A novel route to one-pot three-component synthesis of benzimidazo [2,1-b]-quinazolin-1-one derivatives
One-pot three-component synthesis of benzimidazo[2,1-b]-quinazolin-1-ones was efficiently performed under microwave irradiation and solvent-free condition. The method provides some advantages such as low cost, experimental simplicity, high yields, and short reaction times. The structure of newly synthesized compounds is characterized by IR, 1H-NMR, MS and elemental analysis.
Kahveci, Bahittin,Yilmaz, Fatih,Mentese, Emre,Karaali, Nesrin
p. 490 - 495
(2013/08/23)

Synthesis and exploration of QSAR model of 2-methyl-3-[2-(2-methylprop-1- en-1-yl)-1H-benzimidazol-1-yl]pyrimido[1,2-a]benzimidazol-4(3H)-one as potential antibacterial agents
Present communication deals with the synthesis of novel 2-methyl-3-[2-(2-methylprop-1-en-1-yl)-1H-benzimidazol-1-yl]pyrimido[1,2-a] benzimidazol-4(3H)-one derivatives under phase transfer catalysis (PTC) conditions using benzyl triethyl ammonium chloride (BTEAC) as PTC. It also elicits the studies on in vitro antimicrobial evaluation of synthesized compounds against a representative genera of gram-negative and gram-positive bacteria i.e., Bacillus subtilis, Staphylococcus aureus, Pseudomonas diminuta and Escherichia coli. All the compounds have been found to manifest profound antimicrobial activity. Moreover, extensive quantitative structure-activity relationship (QSAR) studies have been performed to deduce a correlation between molecular descriptors under consideration and the elicited biological activity. A tri-parametric QSAR model has been generated upon rigorous statistical treatment.
Sharma, Pratibha,Kumar, Ashok,Sharma, Manisha,Singh, Jitendra,Bandyopadhyay, Prabal,Sathe, Manisha,Kaushik
experimental part
p. 294 - 301
(2012/07/01)

Synthesis, characterization and cytotoxicity of some novel 1,3-disubstituted-2,3-dihydro-2-iminobenzimidazoles
Some new 1,3-disubstituted-2,3-dihydro-2-iminobenzimidazoles were synthesized using 1-(un)substituted-2-aminobenzimidazoles as precursors in order to determine their cytotoxicity. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. Compounds 4, 7-11 and 13-14 were evaluated for their cytotoxical effect on two cancer cell lines: human colorectal cancer cell line HT-29, breast cancer cells MDA-MB-231 and as well as normal spleen cells. The distinctly marked antiproliferative activity of 1,3-bis(3-phenylpropyl-1)-1,3-dihydro-2H-benzimidazol-2-imine hydro bromide 7, N-(aminopropyl)-2-(3-{2-[(aminopropyl)-amino]-2-oxoethyl}-2-imino-2, 3-dihydro-1H-benzimidazol-1-yl)acetamide 9 and 1,3-bis[2-(4-methylpiperazin-1- yl)-2-oxoethyl]-2,3-dihydro-2H-benzimidazol-2-imine 11 against human colorectal cancer cell line HT-29 was ascertained and the calculated IC50 were 9.26, 0.56 and 0.013 nM respectively. Compounds 4, 9, 10 and 13 exhibited relative high cytotoxic activity against MDA-MB-231 cells. The calculated IC50 values were in the range 0.123-1.65 nM. All tested compounds excluding compound 1,3-bis[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2,3-dihydro- 2H-benzimidazol-2-imine (11) revealed proliferative activities to normal spleen cells. The computed EC50 values varied from 0.05 to 16.91 nM.
Mavrova, Anelia Ts.,Wesselinova, Diana,Vassilev, Nikolay,Tsenov, Jordan A.
body text
p. 3362 - 3367
(2011/07/29)

Synthesis of benzimidazole thiazolinone derivatives under microwave irradiation
Organic compounds containing the thiazolinone ring are of increasing interest due to their bactericidal, pesticidal, anticonvulsant, antiinflammatory, antithyroidal and antimicrobial activities. A rapid microwave-assisted synthesis thiazolinone derivatives is described. The 3-(1H-benzo[d]imidazol-2-yl)-2-substituted phenyl thiazolidin-4-one were identified by IR, 1H NMR, elemental analyses. The target compounds were performed in a shorter reaction time compared to conventional heating methods.
Hu, Jun,Yu, Peng,Zhou, Taoyu,Xu, Yanhua
p. 672 - 673,2
(2020/07/30)

Efficient synthesis of 2-arylamino-2-imidazolines and 2-aminobenzimidazoles with aminoiminomethanesulfonic acid derivatives
A highly efficient synthesis of 2-arylamino-2-imidazolines and 2-aminobenzimidazoles from aminoiminomethanesulfonic acid derivatives is described. The method is simple and practical, generating imidazoline and benzimidazoline derivatives in excellent isolated yields.
Mohanazadeh, Farajollah,Nami, Navabe,Hosseini, Samine Sadat
experimental part
p. 1055 - 1058
(2012/01/04)

The chemical synthesis and antibiotic activity of a diverse library of 2-aminobenzimidazole small molecules against MRSA and multidrug-resistant A. baumannii
Multidrug-resistant bacterial infections continue to be a rising global health concern. Herein is described the development of a class of novel 2-aminobenzimidazoles with antibiotic activity. These active 2-aminobenzimidazoles retain their antibiotic activity against several strains of multidrug-resistant Staphylococcus aureus and Acinetobacter baumannii when compared to susceptible strains.
Huigens III, Robert W.,Reyes, Samuel,Reed, Catherine S.,Bunders, Cynthia,Rogers, Steven A.,Steinhauer, Andrew T.,Melander, Christian
supporting information; experimental part
p. 663 - 674
(2010/05/02)

Gas-phase pyrolysis of benzimidazole derivatives: novel route to condensed heterocycles
Gas-phase pyrolysis of N-(1H-benzimidazol-2-yl)-N′-arylidenehydrazines 1a-e gave the corresponding arylnitriles 2a-e, 2-aminobenzimidazole 3, 2,4,5-triphenylimidazole 4, 1,3-diphenyl-8H-2,3a,8-triazacyclopenta[a]indene 5, and 5,11-diphenyl-6H,12H-dibenzimidazo[1,2-a];1',2'-d]pyrazine 6. The kinetics and analysis of the products of reaction are reported and used to elucidate the mechanism of the elimination process.
Ibrahim, Maher R.,Al-Azemi, Talal F.,Al-Etabi, Alya,El-Dusouqui, Osman M.E.,Al-Awadi, Nouria A.
experimental part
p. 4243 - 4250
(2010/07/05)

Synthesis and antitrichinellosis activity of some bis(benzimidazol-2-yl)amines
Novel bis(benzimidazol-2-yl)amines were synthesized using two methods and studied for antitrichinellosis activity. DFT calculations were performed in order to determine the geometry of molecules. All derivatives of 2-aminobenzimidazole exhibited higher activity in vitro against Trichinella spiralis larvae in regard to the activity of albendazole, moreover compounds 4f-i manifested antitrichinellosis effect, which surpassed five times the activity of albendazole. The in vivo screening of intestinal phase of the T. spiralis revealed 100% effectiveness of compounds 4g-i at oral dosages of 50 and 100 mg/kg mw, while albendazole possesses 100% efficacy only at a dose of 100 mg/kg mw.
Mavrova, Anelia Ts.,Denkova, Pavletta,Tsenov, Yordan A.,Anichina, Kameliya K.,Vutchev, Dimitar I.
p. 6291 - 6297
(2008/04/05)

Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4
High-throughput screening of a small-molecule compound library resulted in the identification of a novel series of N-acyl 2-aminobenzimidazoles that are potent inhibitors of interleukin-1 receptor-associated kinase-4.
Powers, Jay P.,Li, Shyun,Jaen, Juan C.,Liu, Jinqian,Walker, Nigel P.C.,Wang, Zhulun,Wesche, Holger
p. 2842 - 2845
(2007/10/03)

Acyl derivatives of 2-aminobenzimidazole and their fungicide activity
Procedures have been developed for the preparation of methyl 2-benzimidazolylcarbamate, 2-acetylaminobenzimidazole, 2- benzoylaminobenzimidazole, 2-(3,5-dibromo-2-hydroxybenzoylamino)benzimidazole, 1-(3,6-dichloro-2-methoxybenzoyl)-2-aminobenzimidazole, 2-(3,5-dichloro-2- hydroxybenzoylamino)benzimidazole, 2-(3,5-dichloro-2-methoxybenzoylamino) benzimidazole, and 1-(3,5,6-trichloro-2-methoxybenzoyl)-2-aminobenzimidazole. The synthesized compounds have been tested for fungicide activity.
Pilyugin,Sapozhnikov,Sapozhnikova
p. 738 - 743
(2007/10/03)

Formation of nitrogen-containing heterocycles using di(imidazole-1-yl)methanimine
A mild and efficient synthesis of five- and six-membered nitrogen containing heterocyclic compounds, in which di(imidazole-1-yl)methanimine serves as a one-carbon source, is reported.
Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Hamilton, Gregory S.
p. 191 - 193
(2007/10/03)

Synthesis and antiparasitic activity of 1H-benzimidazole derivatives.
Compounds 1-18 have been synthesized and tested in vitro against the protozoa Giardia lamblia, Entamoeba histolytica and the helminth Trichinella spiralis. Inhibition of rat brain tubulin polymerization was also measured and compared for each compound. Results indicate that most of the compounds tested were more active as antiprotozoal agents than Metronidazole and Albendazole. None of the compounds was as active as Albendazole against T. spiralis. Although only compounds 3, 9 and 15 (2-methoxycarbonylamino derivatives) inhibited tubulin polymerization, these were not the most potent antiparasitic compounds.
Valdez, Juan,Cedillo, Roberto,Hernandez-Campos, Alicia,Yepez, Lilian,Hernandez-Luis, Francisco,Navarrete-Vazquez, Gabriel,Tapia, Amparo,Cortes, Rafael,Hernandez, Manuel,Castillo, Rafael
p. 2221 - 2224
(2007/10/03)