Synthesis and studying the antitumor activity of novel 5-(2-methylbenzimidazol-5-yl)-1,3,4-oxadiazole-2(3H)-thiones

Synthesis and Characterization of Some New Benzimidazole Derivatives

“…This paper reports a simple and an effective method for the synthesis of some new benzimidazole derivatives which were obtained in good to excellent yield . 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) :…”

Synthesis and Characterization of Some New Benzimidazole Derivatives

“…This paper reports a simple and an effective method for the synthesis of some new benzimidazole derivatives which were obtained in good to excellent yield . 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) :…”

Synthesis and Biological Evaluation of Some 1,2‐Disubstituted Benzimidazole Derivatives as New Potential Anticancer Agents

“…Chemistry Target molecules (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) were synthesized in three steps as shown in Scheme 1. In the first step, 2-(chloromethyl)benzimidazole (1) benzimidazole (2) was obtained from 2-(chloromethyl)benzimidazole (1) via Willgerodt-Kindler reaction.…”

“…In this study, unlike classical procedures, we used benzylic structure (1) as a starting material instead of aryl, alkyl ketone to obtain the thioamide structure [29]. Finally, 1H-2-[(morpholine-4yl)thioxomethyl]benzimidazole (2) was reacted with appropriate a-bromoacetophenone derivatives via bimolecular nucleophilic substitution (S N 2) reaction to give the intended 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Finally, 1H-2-[(morpholine-4yl)thioxomethyl]benzimidazole (2) was reacted with appropriate a-bromoacetophenone derivatives via bimolecular nucleophilic substitution (S N 2) reaction to give the intended 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18).…”

“…The DNA % synthesis inhibitory activity of the compounds 3, 5, 8,9,10,11,14,18, and standard drugs on C6 cells is seen in This increase can be clearly appreciated in particular for the compound 18. Measurement of the inhibition for the compound 18 at lower dose (IC 50 /2) after 48 h incubation was seven times higher than at 24 h of measurement and there was a twofold increase at the other two doses (IC 50 , and IC 50 Â 2).…”

Synthesis and Characterization Platinum (II), Palladium (II) and Nickel (II) Complexes with some Heterocyclic Ligand of 1,3,4-Oxadazole Derivative

“…The infrared spectrum of APOD showed bands in the range (3396-3269) cm -1 , which are corresponding to ν(NH) of amine group (Galal et al, 2010;Tomi, 2012). A shifted with change in shape were observed from these bands, while increasing in intensity were noticed.…”

Synthesis and Characterization of Some New Benzimidazole Derivatives

“…This paper reports a simple and an effective method for the synthesis of some new benzimidazole derivatives which were obtained in good to excellent yield . 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) :…”

Synthesis and Biological Evaluation of Some 1,2‐Disubstituted Benzimidazole Derivatives as New Potential Anticancer Agents

“…Chemistry Target molecules (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) were synthesized in three steps as shown in Scheme 1. In the first step, 2-(chloromethyl)benzimidazole (1) benzimidazole (2) was obtained from 2-(chloromethyl)benzimidazole (1) via Willgerodt-Kindler reaction.…”

“…In this study, unlike classical procedures, we used benzylic structure (1) as a starting material instead of aryl, alkyl ketone to obtain the thioamide structure [29]. Finally, 1H-2-[(morpholine-4yl)thioxomethyl]benzimidazole (2) was reacted with appropriate a-bromoacetophenone derivatives via bimolecular nucleophilic substitution (S N 2) reaction to give the intended 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Finally, 1H-2-[(morpholine-4yl)thioxomethyl]benzimidazole (2) was reacted with appropriate a-bromoacetophenone derivatives via bimolecular nucleophilic substitution (S N 2) reaction to give the intended 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18).…”

“…The DNA % synthesis inhibitory activity of the compounds 3, 5, 8,9,10,11,14,18, and standard drugs on C6 cells is seen in This increase can be clearly appreciated in particular for the compound 18. Measurement of the inhibition for the compound 18 at lower dose (IC 50 /2) after 48 h incubation was seven times higher than at 24 h of measurement and there was a twofold increase at the other two doses (IC 50 , and IC 50 Â 2).…”

Synthesis and Characterization Platinum (II), Palladium (II) and Nickel (II) Complexes with some Heterocyclic Ligand of 1,3,4-Oxadazole Derivative

“…The infrared spectrum of APOD showed bands in the range (3396-3269) cm -1 , which are corresponding to ν(NH) of amine group (Galal et al, 2010;Tomi, 2012). A shifted with change in shape were observed from these bands, while increasing in intensity were noticed.…”

Synthesis and Characterization of Some New Benzimidazole Derivatives

“…This paper reports a simple and an effective method for the synthesis of some new benzimidazole derivatives which were obtained in good to excellent yield . 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) :…”

Synthesis and Biological Evaluation of Some 1,2‐Disubstituted Benzimidazole Derivatives as New Potential Anticancer Agents

“…Chemistry Target molecules (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) were synthesized in three steps as shown in Scheme 1. In the first step, 2-(chloromethyl)benzimidazole (1) benzimidazole (2) was obtained from 2-(chloromethyl)benzimidazole (1) via Willgerodt-Kindler reaction.…”

“…In this study, unlike classical procedures, we used benzylic structure (1) as a starting material instead of aryl, alkyl ketone to obtain the thioamide structure [29]. Finally, 1H-2-[(morpholine-4yl)thioxomethyl]benzimidazole (2) was reacted with appropriate a-bromoacetophenone derivatives via bimolecular nucleophilic substitution (S N 2) reaction to give the intended 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Finally, 1H-2-[(morpholine-4yl)thioxomethyl]benzimidazole (2) was reacted with appropriate a-bromoacetophenone derivatives via bimolecular nucleophilic substitution (S N 2) reaction to give the intended 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18).…”

“…The DNA % synthesis inhibitory activity of the compounds 3, 5, 8,9,10,11,14,18, and standard drugs on C6 cells is seen in This increase can be clearly appreciated in particular for the compound 18. Measurement of the inhibition for the compound 18 at lower dose (IC 50 /2) after 48 h incubation was seven times higher than at 24 h of measurement and there was a twofold increase at the other two doses (IC 50 , and IC 50 Â 2).…”

Synthesis and Characterization Platinum (II), Palladium (II) and Nickel (II) Complexes with some Heterocyclic Ligand of 1,3,4-Oxadazole Derivative

“…The infrared spectrum of APOD showed bands in the range (3396-3269) cm -1 , which are corresponding to ν(NH) of amine group (Galal et al, 2010;Tomi, 2012). A shifted with change in shape were observed from these bands, while increasing in intensity were noticed.…”