- Synthesis and fungicidal activity of 2-benzoylaminobenzimidazole complex compounds with copper
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Special features of the formation of 2-benzoylaminobenzimidazole complexes with copper(II) chloride, sulfate, and acetate were studied. Optimal conditions of obtaining the complexes were found, and chemical compositions, some physicochemical properties, a
- Chikisheva,Sapozhnikov,Mudarisova,Buslaeva,Galieva,Davletov
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- Synthesis, Fungicidal Activity, and Molecular Docking of 2-Acylamino and 2-Thioacylamino Derivatives of 1 H-benzo[ d]imidazoles as Anti-Tubulin Agents
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This work deals with the synthesis and evaluation of fungicidal activity of benzimidazole derivatives, which are structural analogues of commercial anti-tubulin fungicides. A number of N-acyl and N-thioacyl derivatives of 2-amino-1H-benzo[d]imidazole were prepared, and their fungicidal activity against 13 strains of phytopathogenic fungi was studied. The most active compounds against the majority of the studied strains were 3a, 4l, and 4o, and the EC50 values of these compounds were in the range 2.5-20 μg/mL. Compound 3a showed the highest activity against the P. infestans strain, the growth of which is not suppressed by carbendazim. The formation of ligand-receptor complexes of various tautomeric forms of the studied benzimidazoles with homologous models of β-tubulins of B. cinerea, F. oxysporum, and P. infestans was modeled. Induced fit docking has been used for the simulation. The obtained data suggest the possibility of binding of benzimidazole fungicides to β-tubulin in the nocodazole cavity in the tautomeric form bearing a double exocyclic C=N bond. The importance of the formation of hydrogen bonds of benzimidazoles with the amino acid residue Val236 along with the Glu198 residue is also revealed in the present study.
- Bakulev, Vasiliy A.,Beryozkina, Tetyana V.,Fan, Zhijin,Galieva, Nadezhda A.,Glukhareva, Tatiana V.,Kalinina, Tatiana A.,Obydennov, Konstantin L.,Zhang, Yue
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p. 12048 - 12062
(2021/10/26)
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- Alternative and efficient method for the preparation of 2-acetamidobenzimidazoles
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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
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p. 2247 - 2252
(2021/04/22)
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- 2-Aminobenzimidazole and -benzoxazole as N-nucleophile in palladium-catalysed aminocarbonylation
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Palladium-catalysed aminocarbonylation of aryl iodides in the presence of 2-aminobenzimidazole and 2-aminobenzoxazole as N-nucleophile was carried out. Single CO insertion took place, however, instead of the expected carboxamides (C(O)NH) the correspondin
- Bényei, Attila,Gergely, Máté,Kollár, László
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supporting information
(2020/03/13)
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- Copper promoted C-S and C-N cross-coupling Reactions:The synthesis of 2-(N-Aryolamino)benzothiazoles and 2-(N-Aryolamino)benzimidazoles
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The synthesis of 2-(N-aryolamino)benzothiazoles and 2-(N-aryolamino)benzimidazoles has been accomplished in the presence of copper catalyst. These reactions involve C-S and C-N cross-coupling reaction. All electron donating and withdrawing substituent's readily underwent the reaction to give target products in good to excellent yield. In addition, the reaction also gave target product in high yield with bulk scale.
- Shaik, Baji vali,Seelam, Mohan,Tamminana, Ramana,Kammela, Prasad Rao
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p. 3865 - 3874
(2019/06/20)
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- PTSA catalyzed straightforward protocol for the synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles in PEG
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An efficient PTSA catalyzed synthesis of 2-(N-acyl)aminobenzimidazoles and 2-(N-acyl)aminobenzothiazoles has been described using S-ethylated-N- acylthioureas as substrates and polyethylene glycol as solvent.
- Vidavalur, Siddaiah,Gajula, Mahaboob Basha,Tadikonda, Ramu,Nakka, Mangarao,Dega, Sudhakar,Yadav, Santosh Kumar,Voosala, Christopher
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supporting information
p. 2691 - 2694
(2014/05/06)
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- Practical preparation of challenging amides from non-nucleophilic amines and esters under flow conditions
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A fast and efficient protocol for the formation of amides from low nucleophilic amines and esters in flow is described. Products were obtained in good to excellent yields and with the advantage of simultaneous mixing of all reagents at once, avoiding steps for intermediate formation. The protocol is also suitable to be combined with ester synthesis, resulting in the preparation of amides in-line from haloarenes. This journal is
- Vrijdag, Johannes L.,Delgado, Francisca,Alonso, Nerea,De Borggraeve, Wim M.,Prez-Macias, Natalia,Alczar, Jesus
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supporting information
p. 15094 - 15097
(2014/12/11)
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- Phosphonium-mediated cyclization of N-(2-aminophenyl)thioureas: Efficient synthesis of 2-aminobenzimidazoles
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BOP efficiently promoted the phosphonium-mediated cyclization of thioureas, leading to a convenient synthesis of 2-aminobenzimidazoles. Compared to conventional methods, the reactions were complete at room temperature with times ranging from a few minutes
- Wan, Zhao-Kui,Ousman, Erena Farah,Papaioannou, Nikolaos,Saiah, Eddine
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supporting information; experimental part
p. 4149 - 4152
(2011/09/19)
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- 13C NMR spectra and biological activity of N-(1H-benzimidazol-2- yl)benzamides
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Derivatives of 1H-benzimidazol-2-amine and halo-, nitro-, methoxy-, and hydroxy-substituted benzoic acids were synthesized, and their fungicide activity against pure Fusarium culmorum and Helminthosporium sativum cultures and pathogenic microflora of wheat and barley seeds in laboratory and field tests was studied. Some compounds were found to exhibit a strong fungicide activity. Nauka/Interperiodica 2006.
- Pilyugin,Sapozhnikov,Davydov,Chikisheva,Vorob'eva,Klimakova,Kiseleva,Kuznetsova,Davletov,Sapozhnikova,Yumadilov
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p. 1653 - 1659
(2008/02/09)
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- Discovery and initial SAR of inhibitors of interleukin-1 receptor-associated kinase-4
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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
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p. 2842 - 2845
(2007/10/03)
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- A one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles
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A rapid and efficient one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles is described. The reaction is mediated by a polymer-supported carbodiimide, which simplifies product isolation. The scope and limitations of this method are described.
- Cee, Victor J.,Downing, Nicholas S.
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p. 3747 - 3750
(2007/10/03)
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- A facile synthesis of 2-acyl and 2-alkylaminobenzimidazoles for 5-lipoxygenase inhibitors
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2-Acylaminobenzimidazoles (2a-r) have been synthesized from o-phenylenediamines (4) with benzoylcarbonimidodithioic acid dimethyl ester (5a) or isobutyrylcarbonimidodithioic acid dimethyl ester (5b) in good yield. 2-Alkylaminobenzimidazoles could be prepa
- Lee, An Ha,An, Mi Hyun,Choi, Eun Hyun,Choo, Hea-Young Park,Han, Gyoonhee
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p. 571 - 580
(2008/02/02)
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- Acyl derivatives of 2-aminobenzimidazole and their fungicide activity
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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
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p. 738 - 743
(2007/10/03)
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- Photoinduced molecular rearrangements. The photochemistry of some 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles. Formation of 1,2,4-triazoles, indazoles, and benzimidazoles
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The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O-N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.
- Buscemi, Silvestre,Vivona, Nicolo,Caronna, Tullio
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p. 8397 - 8401
(2007/10/03)
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- SYNTHESIS OF 4-ARYL BENZIMIDAZOLO-s-TRIAZIN-2-ONES AND 2-AROYLAMINOBENZIMIDAZOLO-1,2,4-THIADIAZOLINES
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Reaction of 2-aminobenzimidazole with aroylisothiocyanates gave 2-aroylaminobenzimidazoles (3) and N-aroyl-N'-(benzimidazol-2-yl)-thioureas (4).The products obtained on reaction of 4 with PCl5 in POCl3 , and with oxidising agents have been identified as 4
- Sridevi, G.,Rao, P. Jayaprasad,Reddy, K. Kondal
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p. 965 - 972
(2007/10/02)
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- SYNTHESIS OF 2-ARYL-1H-s-TRIAZOLOBENZIMIDAZOLES
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2-Aroylaminobenzimidazoles (2) have been converted into 1(2-benzimidazolyl)-5-aryl-1H-tetrazoles (4) by treatment with PCl5 followed by azidation with NaN3 in aqueous acetone solution.Pyrolysis of 4 in diphenylether yielded 2-aryl-1H-s-triazolobenzimidazoles (6).The product of benzylation of 6a has been characterised.A reasonable pathway for the formation of 6 from 4 has been suggested.
- Rao, P. Jayaprasad,Reddy, K. Kondal
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p. 1995 - 2002
(2007/10/02)
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- Heterocyclic Photorearrangements. Photochemical Behaviour of Some 3,5-Disubstituted 1,2,4-Oxadiazoles in Methanol at 254 nm
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Photochemical behaviour of some 3,5-disubstituted 1,2,4-oxadiazoles in methanol at 254 nm has been investigated.Ring photoisomerization to the 1,3,4-oxadiazole heterocycle or formation of open chain compounds involving the nucleophilic solvent was shown to depend on the nature and the position of the substituent.Photoinduced ring closure into the benzimidazole system, involving a 3-N-phenylamino side chain sequence and a photolytic intermediate of the oxadiazole heterocycle, is also reported.
- Buscemi, Silvestre,Cicero, Maria G.,Vivona, Nicolo,Caronna, Tullio
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p. 931 - 935
(2007/10/02)
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- REACTIONS OF CARBONYL ISOTHIOCYANATES WITH NUCLEOPHILIC BIFUNCTIONAL REAGENTS
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Reactions of benzoyl-, 2-furoyl-, acetyl-, and trichloroacetyl isothiocyanates with 1,2-diaminobenzene, 2-aminophenol, 5,6-diamino-1,3-uracil and 2,3-diaminopyridine were investigated.Formation of the individual products and their IR, UV and electron impa
- Uher, Michal,Berkes, Dusan,Lesko, Jan,Floch, Lubomir
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p. 1651 - 1658
(2007/10/02)
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- Reactions with N-Acylimino-dithiocarbonic-acid-diesters
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Reactions of N-acylimino-dithiocarbonic-acid-S,S-diesters 1 with nucleophilic compounds present new possibilities to synthesize heterocycles.With amines 1a reacts by mono- and disubstitution, respectively, of methylthio-groups to isothioureas 2 and guanidines 3, with 1,2-binucleophilic arenes to benzoheterocycles 4, with aliphatic diamines to imidazolines 5, pyrimidines 6, diazepines 7 and the hexamethylene-diamine-derivatives 8. 1a reacts also with hydrazines to 1,2,4-triazoles 9 and with hydrazides to the thiosemicarbazones 10 or 1,3,4-oxadiazoles 11.Heterocyclisations of 1 with guanidines, thiourea, salts of thiourea and amidines give the 1,3,5-triazines 12, 14, 15 and 16.N-benzoyl-dithiocarbonic-acid-methylester -amid reacts with CH-acidic compounds to thiazoles 17.The structures of the final products are determined by i.r.-, 1H-n.m.r.-, u.v.- and mass-spectras.
- Augustin, M.,Richter, M.,Salas, S.
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