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Hongbin Zhang - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and antitumor activity of aza-brazilan derivatives containing Imidazolium Salt pharmacophores.
MedChemComm, 2019Co-Authors: Mingqin Huang, Hongbin Zhang, Shengzu Duan, Bicheng Cai, Xiao-dong YangAbstract:The synthesis of a series of novel aza-brazilan derivatives containing Imidazolium Salt pharmacophores is presented. The biological activity of such Imidazolium Salts was further evaluated in vitro against a panel of human tumor cell lines. The results suggest that the electron-withdrawing group on the aza-brazilan moiety, substituted 5,6-dimethyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methylbenzyl group were essential for modulating the cytotoxic activity. Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52–1.30 μM and 0.56–1.51 μM against four human tumor cell lines investigated. Particularly, compound 57 exhibited inhibitory activity against the MCF-7 cell line with an IC50 value of 0.35 μM and was 56-fold more sensitive than DDP. Moreover, compound 55 inhibited cell proliferation through inducing G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
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Synthesis and antitumor activity of novel steroidal Imidazolium Salt derivatives.
European journal of medicinal chemistry, 2019Co-Authors: Guogang Deng, Bei Zhou, Jing Wang, Zhuo Chen, Liang Gong, Gong Yaxiao, Hongbin Zhang, Xiao-dong YangAbstract:Abstract Sixty-one novel steroidal Imidazolium Salt derivatives were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results showed that diosgenin‒Imidazolium Salt derivatives displayed much higher cytotoxic activities than cholesterol‒Imidazolium Salts and dehydroepiandrosterone‒Imidazolium Salts. The SARs results suggested that the existence of substituted 5,6-dimethyl-benzimidazoles or benzimidazole ring and substitution of the imidazolyl-3α-position with a 2-bromobenzyl or 2-naphthylmethyl group could be critical for promoting cytotoxic activity. Diosgenin‒Imidazolium Salt a30 was found to be the most potent compound with IC50 values of 0.44–0.79 μM against five human tumor cell lines. Compound a24 showed inhibitory activity selectively against SMMC-7721 cell lines with IC50 value of 0.21 μM and 54-fold more sensitive to DDP. Moreover, compound a30 inhibited cell proliferation through inducing the G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
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Synthesis and antitumor activity of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives
Organic & biomolecular chemistry, 2016Co-Authors: Bei Zhou, Guogang Deng, Xiao-dong Yang, Li-juan Yang, Wen Chen, Zhengfen Liu, Hongbin ZhangAbstract:The synthesis of a series of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound 41 was observed as a potent derivative with IC50 values of 3.24–8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound 51. Moreover, compound 51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound 51 against human normal lung epithelial cell line BEAS-2B was further evaluated.
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synthesis and antitumor activity of novel n substituted tetrahydro β carboline Imidazolium Salt derivatives
Organic and Biomolecular Chemistry, 2016Co-Authors: Bei Zhou, Guogang Deng, Xiao-dong Yang, Li-juan Yang, Wen Chen, Zhengfen Liu, Hongbin ZhangAbstract:The synthesis of a series of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound 41 was observed as a potent derivative with IC50 values of 3.24–8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound 51. Moreover, compound 51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound 51 against human normal lung epithelial cell line BEAS-2B was further evaluated.
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Synthesis and antitumor activity of novel N-substituted carbazole Imidazolium Salt derivatives
Scientific reports, 2015Co-Authors: Lan-xiang Liu, Bei Zhou, Hongbin Zhang, Xue-quan Wang, Li-juan Yang, Xiao-dong YangAbstract:A series of novel N-substituted carbazole Imidazolium Salt derivatives has been prepared and investigated for their cytotoxic activity against five human tumor cell lines by MTS assay. The results indicated that the existence of 5,6-dimethyl-benzimidazole ring, substitution of the imidazolyl-3-position with a 2-bromobenzyl or naphthylacyl group, as well as alkyl chain length between carbazole and imidazole ring were important for the antitumor activity. Compound 61, bearing a 2-bromobenzyl substituent at position-3 of the 5,6-dimethyl-benzimidazole, showed powerful inhibitory activities and was more selective to HL-60, SMMC-7721, MCF-7 and SW480 cell lines with IC50 values 0.51–2.48 μM. Mechanism of action studies revealed that this new compound could remarkably induce cell cycle arrest and apoptosis in SMMC-7721 cells. This work provides alternative novel way for future drug development based on carbazole and Imidazolium Salt scaffolds.
Xiao-dong Yang - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and antitumor activity of aza-brazilan derivatives containing Imidazolium Salt pharmacophores.
MedChemComm, 2019Co-Authors: Mingqin Huang, Hongbin Zhang, Shengzu Duan, Bicheng Cai, Xiao-dong YangAbstract:The synthesis of a series of novel aza-brazilan derivatives containing Imidazolium Salt pharmacophores is presented. The biological activity of such Imidazolium Salts was further evaluated in vitro against a panel of human tumor cell lines. The results suggest that the electron-withdrawing group on the aza-brazilan moiety, substituted 5,6-dimethyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methylbenzyl group were essential for modulating the cytotoxic activity. Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52–1.30 μM and 0.56–1.51 μM against four human tumor cell lines investigated. Particularly, compound 57 exhibited inhibitory activity against the MCF-7 cell line with an IC50 value of 0.35 μM and was 56-fold more sensitive than DDP. Moreover, compound 55 inhibited cell proliferation through inducing G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
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Synthesis and antitumor activity of novel steroidal Imidazolium Salt derivatives.
European journal of medicinal chemistry, 2019Co-Authors: Guogang Deng, Bei Zhou, Jing Wang, Zhuo Chen, Liang Gong, Gong Yaxiao, Hongbin Zhang, Xiao-dong YangAbstract:Abstract Sixty-one novel steroidal Imidazolium Salt derivatives were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results showed that diosgenin‒Imidazolium Salt derivatives displayed much higher cytotoxic activities than cholesterol‒Imidazolium Salts and dehydroepiandrosterone‒Imidazolium Salts. The SARs results suggested that the existence of substituted 5,6-dimethyl-benzimidazoles or benzimidazole ring and substitution of the imidazolyl-3α-position with a 2-bromobenzyl or 2-naphthylmethyl group could be critical for promoting cytotoxic activity. Diosgenin‒Imidazolium Salt a30 was found to be the most potent compound with IC50 values of 0.44–0.79 μM against five human tumor cell lines. Compound a24 showed inhibitory activity selectively against SMMC-7721 cell lines with IC50 value of 0.21 μM and 54-fold more sensitive to DDP. Moreover, compound a30 inhibited cell proliferation through inducing the G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
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Synthesis and antitumor activity of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives
Organic & biomolecular chemistry, 2016Co-Authors: Bei Zhou, Guogang Deng, Xiao-dong Yang, Li-juan Yang, Wen Chen, Zhengfen Liu, Hongbin ZhangAbstract:The synthesis of a series of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound 41 was observed as a potent derivative with IC50 values of 3.24–8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound 51. Moreover, compound 51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound 51 against human normal lung epithelial cell line BEAS-2B was further evaluated.
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synthesis and antitumor activity of novel n substituted tetrahydro β carboline Imidazolium Salt derivatives
Organic and Biomolecular Chemistry, 2016Co-Authors: Bei Zhou, Guogang Deng, Xiao-dong Yang, Li-juan Yang, Wen Chen, Zhengfen Liu, Hongbin ZhangAbstract:The synthesis of a series of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound 41 was observed as a potent derivative with IC50 values of 3.24–8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound 51. Moreover, compound 51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound 51 against human normal lung epithelial cell line BEAS-2B was further evaluated.
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Synthesis and antitumor activity of novel N-substituted carbazole Imidazolium Salt derivatives
Scientific reports, 2015Co-Authors: Lan-xiang Liu, Bei Zhou, Hongbin Zhang, Xue-quan Wang, Li-juan Yang, Xiao-dong YangAbstract:A series of novel N-substituted carbazole Imidazolium Salt derivatives has been prepared and investigated for their cytotoxic activity against five human tumor cell lines by MTS assay. The results indicated that the existence of 5,6-dimethyl-benzimidazole ring, substitution of the imidazolyl-3-position with a 2-bromobenzyl or naphthylacyl group, as well as alkyl chain length between carbazole and imidazole ring were important for the antitumor activity. Compound 61, bearing a 2-bromobenzyl substituent at position-3 of the 5,6-dimethyl-benzimidazole, showed powerful inhibitory activities and was more selective to HL-60, SMMC-7721, MCF-7 and SW480 cell lines with IC50 values 0.51–2.48 μM. Mechanism of action studies revealed that this new compound could remarkably induce cell cycle arrest and apoptosis in SMMC-7721 cells. This work provides alternative novel way for future drug development based on carbazole and Imidazolium Salt scaffolds.
Steven P. Nolan - One of the best experts on this subject based on the ideXlab platform.
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suzuki miyaura cross coupling reactions mediated by palladium Imidazolium Salt systems
Organometallics, 2002Co-Authors: Gabriela A. Grasa, Mihai S. Viciu, Jinkun Huang, Chunming Zhang, Mark L. Trudell, Steven P. NolanAbstract:Nucleophilic N-heterocyclic carbenes (NHC) have been used as ancillary ligands in palladium-mediated Suzuki−Miyaura cross-coupling reactions involving aryl chlorides or aryl triflates with arylboronic acids. The scope of the coupling process using Pd(0) or Pd(II) sources and an Imidazolium Salt in the presence of a base, Cs2CO3, was tested using various substrates. The Pd(OAc)2 or Pd2(dba)3/IMes·HCl (2, IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) system presents very high activity with respect to electron-neutral and electron-rich aryl chlorides. The ligand IPr·HCl (3, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) is also effective for the Suzuki−Miyaura cross-coupling involving a wide spectrum of aryl chlorides and aryl triflates. The general protocol developed has been applied successfully to the synthesis of an antiinflammatory drug (Fenbufen) and to a key intermediate in the synthesis of sartans. Mechanistically, palladium-to-ligand ratio studies support an active palladium spec...
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Suzuki—miyaura cross-coupling reactions mediated by palladium/Imidazolium Salt systems.
Organometallics, 2002Co-Authors: Gabriela A. Grasa, Mihai S. Viciu, Jinkun Huang, Chunming Zhang, Mark L. Trudell, Steven P. NolanAbstract:Nucleophilic N-heterocyclic carbenes (NHC) have been used as ancillary ligands in palladium-mediated Suzuki−Miyaura cross-coupling reactions involving aryl chlorides or aryl triflates with arylboronic acids. The scope of the coupling process using Pd(0) or Pd(II) sources and an Imidazolium Salt in the presence of a base, Cs2CO3, was tested using various substrates. The Pd(OAc)2 or Pd2(dba)3/IMes·HCl (2, IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) system presents very high activity with respect to electron-neutral and electron-rich aryl chlorides. The ligand IPr·HCl (3, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) is also effective for the Suzuki−Miyaura cross-coupling involving a wide spectrum of aryl chlorides and aryl triflates. The general protocol developed has been applied successfully to the synthesis of an antiinflammatory drug (Fenbufen) and to a key intermediate in the synthesis of sartans. Mechanistically, palladium-to-ligand ratio studies support an active palladium spec...
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Amination Reactions of Aryl Halides with Nitrogen-Containing Reagents Mediated by Palladium/Imidazolium Salt Systems
The Journal of organic chemistry, 2001Co-Authors: Gabriela A. Grasa, Mihai S. Viciu, Jinkun Huang, Steven P. NolanAbstract:Nucleophilic N-heterocyclic carbenes have been conveniently used as catalyst modifiers in amination reactions involving aryl chlorides, aryl bromides, and aryl iodides with various nitrogen-containing substrates. The scope of a coupling process using a Pd(0) or Pd(II) source and an Imidazolium Salt in the presence of a base, KO(t)Bu or NaOH, was tested using various substrates. The Pd(2)(dba)(3)/IPr.HCl (1, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) system presents the highest activity with respect to electron-neutral and electron-rich aryl chlorides. The ligand is also effective for the synthesis of benzophenone imines, which can be easily converted to the corresponding primary amines by acid hydrolysis. Less reactive indoles were converted to N-aryl-substituted indoles using as supporting ligand the more donating SIPr.HCl (5, SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene). The Pd(OAc)(2)/SIPr.HCl/NaOH system is efficient for the N-arylation of diverse indoles with aryl bromides. The general protocol developed has been applied successfully to the synthesis of a key intermediate in the synthesis of an important new antibiotic. Mechanistically, palladium-to-ligand ratio studies strongly support an active species bearing one nucleophilic carbene ligand.
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amination reactions of aryl halides with nitrogen containing reagents mediated by palladium Imidazolium Salt systems
Journal of Organic Chemistry, 2001Co-Authors: Gabriela A. Grasa, Mihai S. Viciu, Jinkun Huang, Steven P. NolanAbstract:Nucleophilic N-heterocyclic carbenes have been conveniently used as catalyst modifiers in amination reactions involving aryl chlorides, aryl bromides, and aryl iodides with various nitrogen-containing substrates. The scope of a coupling process using a Pd(0) or Pd(II) source and an Imidazolium Salt in the presence of a base, KO(t)Bu or NaOH, was tested using various substrates. The Pd(2)(dba)(3)/IPr.HCl (1, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) system presents the highest activity with respect to electron-neutral and electron-rich aryl chlorides. The ligand is also effective for the synthesis of benzophenone imines, which can be easily converted to the corresponding primary amines by acid hydrolysis. Less reactive indoles were converted to N-aryl-substituted indoles using as supporting ligand the more donating SIPr.HCl (5, SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene). The Pd(OAc)(2)/SIPr.HCl/NaOH system is efficient for the N-arylation of diverse indoles with aryl bromides. The general protocol developed has been applied successfully to the synthesis of a key intermediate in the synthesis of an important new antibiotic. Mechanistically, palladium-to-ligand ratio studies strongly support an active species bearing one nucleophilic carbene ligand.
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catalytic dehalogenation of aryl halides mediated by a palladium Imidazolium Salt system
Organometallics, 2001Co-Authors: Mihai S. Viciu, And Gabriela A. Grasa, Steven P. NolanAbstract:A convenient and efficient catalytic aryl halide dehalogenation protocol has been developed using an Imidazolium Salt/palladium/base system. The use of the ligand precursor SIMes·HCl ((2,4,6-trimethylphenyl)dihydroImidazolium chloride) in conjunction with Pd(dba)2 was found to be most effective for the dehalogenation of aryl chlorides, bromides, and polyhalogenated aromatic hydrocarbons. Strong bases having β-hydrogens both perform deprotonation of the Imidazolium Salt and are hydrogen sources for the dehalogenation process. The oxidative addition of the Imidazolium Salt to the palladium(0) precursor generating a carbene palladium hydride species may also be involved in the dehalogenation process. This oxidative-addition reaction may have fundamental implications in low-valent metal carbene mediated transformations.
Shogo Tomita - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of Imidazolium Salt-terminated poly(amidoamine)-typed POSS-core dendrimers and their solution and bulk properties
Polymer Journal, 2014Co-Authors: Kensuke Naka, Ryusuke Shinke, Maki Yamada, Yoko Aijo, Yasuyuki Irie, Noriyoshi Matsumi, Fadila Djouadi Belkada, Sonu Ram Shankar, Kumar Sai Smaran, Shogo TomitaAbstract:Imidazolium bromide-terminated first and second generation poly(amidoamine) (PAMAM)-typed polyhedral oligomeric silsesquioxane (POSS)-core dendrimers, denoted as POSS-PIm16Br and POSS-PIm32Br, respectively, were prepared by the reaction of the corresponding imidazole-terminated PAMAM-typed POSS-core dendrimers with 1-bromopropane. The structures of POSS-PIm16Br and POSS-PIm32Br were identified using multinuclear nuclear magnetic resonance data, MALDI-TOF-MS spectra, and elemental analysis. Wide-angle X-ray scattering (WAXS) data for cast films of the Imidazolium hexafluorophosphate (PF_6)-terminated first and second generation POSS-core dendrimers, denoted as POSS-PIm16PF_6 and POSS-PIm32PF_6, respectively, which were prepared by anion exchange reactions of POSS-PIm16Br and POSS-PIm32Br, were characterized by the occurrence of two amorphous halos, with a strong peak at q =15 nm^−1 and another weak peak around q =10 nm^−1. Our present X-ray diffraction data for the cast films of POSS-PIm16PF_6 and POSS-PIm32PF_6 reflect the same features that were described for 1-butyl-3-methylImidazolium hexafluorophosphate. Ionic conductivities for the Imidazolium bis(trifluoromethanesulfonyl)imide (TFSI)-terminated POSS-core dendrimers, which were prepared by anion exchange reactions of POSS-PIm16Br and POSS-PIm32Br, were estimated by the ac impedance method after the addition of LiTFSI. Maximum ionic conductivity of 4.03 × 10^−5 S cm^−1 at 51 °C was observed for the POSS-core dendrimer of lower generation and less lithium Salt addition. Imidazolium Salt-terminated first and second generation poly(amidoamine)-typed polyhedral oligomeric silsesquioxane (POSS)-core dendrimers were prepared. Wide-angle X-ray scattering (WAXS) data for cast films of the Imidazolium hexafluorophosphate (PF_6)-terminated first and second generation POSS-core dendrimers reflect the same features that were described for 1-butyl-3-methylImidazolium hexafluorophosphate. Ionic conductivities for the Imidazolium bis(trifluoromethanesulfonyl)imide (TFSI)-terminated POSS-core dendrimers were estimated by the ac impedance method after the addition of LiTFSI. Maximum ionic conductivity of 4.03 × 10^−5 S cm^−1 at 51 °C was observed for the POSS-core dendrimer of lower generation and less lithium Salt addition.
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Synthesis of Imidazolium Salt-terminated poly(amidoamine)-typed POSS-core dendrimers and their solution and bulk properties
Polymer Journal, 2013Co-Authors: Kensuke Naka, Ryusuke Shinke, Maki Yamada, Fadila Djouadi Belkada, Yoko Aijo, Yasuyuki Irie, Sonu Ram Shankar, Kumar Sai Smaran, Noriyoshi Matsumi, Shogo TomitaAbstract:Imidazolium Salt-terminated first and second generation poly(amidoamine)-typed polyhedral oligomeric silsesquioxane (POSS)-core dendrimers were prepared. Wide-angle X-ray scattering (WAXS) data for cast films of the Imidazolium hexafluorophosphate (PF6)-terminated first and second generation POSS-core dendrimers reflect the same features that were described for 1-butyl-3-methylImidazolium hexafluorophosphate. Ionic conductivities for the Imidazolium bis(trifluoromethanesulfonyl)imide (TFSI)-terminated POSS-core dendrimers were estimated by the ac impedance method after the addition of LiTFSI. Maximum ionic conductivity of 4.03 × 10−5 S cm−1 at 51 °C was observed for the POSS-core dendrimer of lower generation and less lithium Salt addition.
Bei Zhou - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and antitumor activity of novel steroidal Imidazolium Salt derivatives.
European journal of medicinal chemistry, 2019Co-Authors: Guogang Deng, Bei Zhou, Jing Wang, Zhuo Chen, Liang Gong, Gong Yaxiao, Hongbin Zhang, Xiao-dong YangAbstract:Abstract Sixty-one novel steroidal Imidazolium Salt derivatives were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results showed that diosgenin‒Imidazolium Salt derivatives displayed much higher cytotoxic activities than cholesterol‒Imidazolium Salts and dehydroepiandrosterone‒Imidazolium Salts. The SARs results suggested that the existence of substituted 5,6-dimethyl-benzimidazoles or benzimidazole ring and substitution of the imidazolyl-3α-position with a 2-bromobenzyl or 2-naphthylmethyl group could be critical for promoting cytotoxic activity. Diosgenin‒Imidazolium Salt a30 was found to be the most potent compound with IC50 values of 0.44–0.79 μM against five human tumor cell lines. Compound a24 showed inhibitory activity selectively against SMMC-7721 cell lines with IC50 value of 0.21 μM and 54-fold more sensitive to DDP. Moreover, compound a30 inhibited cell proliferation through inducing the G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.
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Novel 3-substituted N-methylcarbazole-Imidazolium Salt derivatives: Synthesis and cytotoxic activity.
Chemical biology & drug design, 2018Co-Authors: Li Yanhua, Bei Zhou, Yi-min Shi, Yu-peng Xun, Yun-han Yang, Li-juan YangAbstract:A series of novel 3-substituted N-methylcarbazole-Imidazolium Salt derivatives has been prepared and evaluated in vitro against a panel of tumor cell lines (Hep G-2, Hela and PC12). The results suggest that the presence of substituted 2-methyl-imidazole or imidazole ring and substitution of the imidazolyl-3-position with a naphthylacyl or 4-bromophenacyl group were important for improving cytotoxic activity. Compounds 17, 18, 27, and 28 with 4-bromophenacyl and naphthylacyl groups displayed good activities with IC50 values of 0.09-7.20 μm against three tumor cell lines investigated and more active than DDP. Compound 35 exhibited cytotoxic activity selectively against Hela cell.
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Synthesis and antitumor activity of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives
Organic & biomolecular chemistry, 2016Co-Authors: Bei Zhou, Guogang Deng, Xiao-dong Yang, Li-juan Yang, Wen Chen, Zhengfen Liu, Hongbin ZhangAbstract:The synthesis of a series of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound 41 was observed as a potent derivative with IC50 values of 3.24–8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound 51. Moreover, compound 51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound 51 against human normal lung epithelial cell line BEAS-2B was further evaluated.
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synthesis and antitumor activity of novel n substituted tetrahydro β carboline Imidazolium Salt derivatives
Organic and Biomolecular Chemistry, 2016Co-Authors: Bei Zhou, Guogang Deng, Xiao-dong Yang, Li-juan Yang, Wen Chen, Zhengfen Liu, Hongbin ZhangAbstract:The synthesis of a series of novel N-substituted tetrahydro-β-carboline–Imidazolium Salt derivatives is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. The results suggest that the benzimidazole ring and 1-(naphthalen-2-yl)ethan-1-one or 2-naphthylmethyl substituent at the imidazolyl-3-position were vital for modulating cytotoxic activity. Compound 41 was observed as a potent derivative with IC50 values of 3.24–8.78 μM and exhibited cytotoxic activity selectively against HL-60, A-549 and MCF-7 cell lines. Meanwhile, high inhibitory activities selectively against HL-60 and MCF-7 cell lines were observed for compound 51. Moreover, compound 51 was able to induce G1 phase cell cycle arrest and apoptosis in MCF-7 cells. The cytotoxicity of compound 51 against human normal lung epithelial cell line BEAS-2B was further evaluated.
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Synthesis and antitumor activity of novel N-substituted carbazole Imidazolium Salt derivatives
Scientific reports, 2015Co-Authors: Lan-xiang Liu, Bei Zhou, Hongbin Zhang, Xue-quan Wang, Li-juan Yang, Xiao-dong YangAbstract:A series of novel N-substituted carbazole Imidazolium Salt derivatives has been prepared and investigated for their cytotoxic activity against five human tumor cell lines by MTS assay. The results indicated that the existence of 5,6-dimethyl-benzimidazole ring, substitution of the imidazolyl-3-position with a 2-bromobenzyl or naphthylacyl group, as well as alkyl chain length between carbazole and imidazole ring were important for the antitumor activity. Compound 61, bearing a 2-bromobenzyl substituent at position-3 of the 5,6-dimethyl-benzimidazole, showed powerful inhibitory activities and was more selective to HL-60, SMMC-7721, MCF-7 and SW480 cell lines with IC50 values 0.51–2.48 μM. Mechanism of action studies revealed that this new compound could remarkably induce cell cycle arrest and apoptosis in SMMC-7721 cells. This work provides alternative novel way for future drug development based on carbazole and Imidazolium Salt scaffolds.
