Synthesis of some 1- and 2-carboxyalkyl substituted benzimidazoles and their derivatives

Mickevičienė, Kristina; Voskienė, Aušra; Mickevičius, Vytautas

doi:10.1007/s11164-013-1067-6

Cited by 10 publications

(6 citation statements)

References 15 publications

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“…[ 34 ] Similarly, hydrazino acetate 8 was obtained by the reaction of hydrazide derivative 6 with ethyl chloroacetate in ethanol with a few drops of TEA under reflux. [ 35 ] Spectral and elemental analyses of synthesized compounds were compatible with their proposed structures.…”

Section: Resultsmentioning

confidence: 55%

“…To a solution of compound 6 (0.01 mol) in absolute ethanol (10 ml), ethyl chloroacetate (0.01 mol) was added with a few drops of TEA. [ 35 ] The reaction mixture was refluxed for 4 h. The precipitate was filtered and crystallized from ethanol to yield a white powder (70%), m.p. 110–114°C.…”

Section: Methodsmentioning

confidence: 99%

“…To a solution of compound 6 (0.01 mol) in absolute ethanol (10 ml), ethyl chloroacetate (0.01 mol) was added with a few drops of TEA. [35] The reaction mixture was refluxed for 4 h.…”

Section: Synthesis Of Ethyl 4-{[(4-oxothiazolidin-2-ylidene)amino]ben...mentioning

confidence: 99%

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Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Elzahabi

Nossier

Mousa

et al. 2022

Archiv der Pharmazie

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The need for new chemotherapeutics to overcome development of resistance merits research to discover new agents. Benzocaine derivatives are essential compounds in medicinal chemistry due to their various biological activities including antibacterial and anticancer activities. Therefore, this study focuses on the synthesis of new benzocaine derivatives 3a–e, 6, 7a and 7b, 8, 10–14, and 16a–d and their in vitro evaluation as antibacterial agents against gram +ve and –ve strains and as anticancer agents against HepG‐2, HCT‐116, and MCF‐7 human cancer cell lines. The obtained results demonstrated that thiazolidines 6 and 7b showed higher antibacterial and anticancer activity in comparison with the reference drugs. In addition, 6 and 7b showed high potency as inhibitors toward their biological targets, that is DNA gyrase and human topoisomerase IIα, as compared to the reference standard drugs novobiocin and etoposide, respectively. Molecular docking demonstrated that both compounds could identify the active site of their target enzymes and develop effective binding interactions. Absorption, distribution, metabolism and elimination (ADME) and drug‐likeness predictions of both compounds showed that they both have good ADME profiles and no structural alerts that might cause toxicity. Based on this, 6 and 7b could serve as lead compounds for the design of more potent antibacterial and anticancer agents.

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Section: Resultsmentioning

confidence: 55%

Section: Methodsmentioning

confidence: 99%

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Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Elzahabi

Nossier

Mousa

et al. 2022

Archiv der Pharmazie

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“…In the present work 2-(5-chloro-1H-benzo[d] imidazole-2yl)aniline (1)which was synthesized from the condensation reaction of 4chloro-o-phenylenediamine with anthranilic acid was used as the key intermediate for further synthesis Thus, the compound (1)was allowed to undergo the Mannich reaction with different secondary amines namely indole, isatine, 4-chloro acetanilide, and benzanilide using formaldehyde in absolute methanol to give compounds (2)(3)(4)(5) respectively. Also, the condensation reaction of the compound (1) with different aromatic aldehydes ,namely, benzaldehye,4-hydroxybenzaldehyde, 4-bromo benzaldehyde, 4-chloro Benzaldehyde, and N,Ndimethyl benzaldehyde in absolute ethanol afforded the corresponding Schiff's bases (6)(7)(8)(9)(10).On the other hand, the cyclo condensation of some substituted Schiff's bases (9,10) with thioglygolic acid afforded the corresponding thiazolidine (11,12) respectively [12] .The reactions sequence was illustrated in the scheme (1) :…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Some New Benzimidazole Derivatives

Journal¹

2016

Baghdad Sci.J

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In this paper the new starting material 2-(5-chloro-1H-benzo[d]imidazole-2-yl) aniline (1) was synthesized by the condensation reaction of 4-chloro-o-phenylenediamine and anthranilic acid .The new Mannich base derivatives were synthesized using formaldehyde and different secondary amines to synthesize a new set of benzimidazole derivatives(2-5). Also, the new Schiff-base derivatives (6-10) were synthesized from the reaction of compound (1) with various aromatic aldehydes and the closure-ring was done successfully using mercapto acetic acid to get the new thiazolidine derivatives(11-12).These new compounds were characterized using some physical techniques like:FT-IR Spectra and 1HNMR Spectra.

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“…Also, the compounds whose molecules possess an azole ring, such as pyrrole [11][12][13], 1,3,4-oxadiazole [14][15][16][17][18][19] and 1,2,4-triazole [19][20][21][22][23], are often characterized as good antimicrobial agents. In our previous works [24][25][26][27], we have reported that the heating under reflux of 4-(1H-benzimidazol-2-yl)-1-(substituted phenyl)pyrrolidin-2-ones in a 20% aqueous sodium hydroxide solution leads to the opening of the 2-pyrrolidinone cycle, followed by the formation of sodium salts of the corresponding N-substituted γ-amino acids. These acids are obtained by acidifying the corresponding salt solutions with acetic acid and can be easily cyclized to the initial pyrrolidin-2-ones under the influence of heat or mineral acids.…”

Section: Introductionmentioning

confidence: 99%

Nucleophilic ring opening of 1,4-disubstituted 2-pyrrolidones with hydrazine. Synthesis of azoles with a high antibacterial activity

Peleckis¹,

Anusevičius²,

Šiugždaitė³

et al. 2018

chemija

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3-(1H-Benzimidazol-2-yl)-4-[(phenyl and 4-substituted phenyl)amino]butanohydrazides were synthesized in good yields by treating the corresponding 4-(1H-benzimidazol-2-yl)-1-phenyl(substituted phenyl)-2-pyrrolidinones with the excess of hydrazine monohydrate. The utility of the newly synthesized hydrazides in the preparation of pyrroles, pyrazoles, oxadiazoles and triazoles has been demonstrated. All compounds were screened for their antibacterial activity. A significant antibacterial activity was found.

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Synthesis of some 1- and 2-carboxyalkyl substituted benzimidazoles and their derivatives

Cited by 10 publications

References 15 publications

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Synthesis and Characterization of Some New Benzimidazole Derivatives

Nucleophilic ring opening of 1,4-disubstituted 2-pyrrolidones with hydrazine. Synthesis of azoles with a high antibacterial activity

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