Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives as novel anticancer agents

Qian, Yanlong; Zhang, Hongjia; Zhang, Hao; Xu, Chen; Zhao, Jing; Zhu, Hai‐Liang

doi:10.1016/j.bmc.2010.06.003

Cited by 109 publications

(23 citation statements)

References 20 publications

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“…In this small series the anticonvulsant activity was observed both for compounds with low (6,8) as well as high (3,9,10) values of logP so actually the values do not correspond with the anticonvulsant activity of the tested compounds. One conclusion could be made that increased lipophilicity may be partially responsible for neurotoxicity of 9 and 10 (but not in case of compound 3).…”

Section: Structure-anticonvulsant Activity Relationshipmentioning

confidence: 59%

“…Cinnamic acid derivatives are known to exhibit a variety of pharmacological activities, such as antimalarial [4], antifungal [5], antimycobacterial [6], anticancer [7,8], myorelaxant [9], local anesthetic [10] or tyrosinase inhibition [11]. Moreover, anticonvulsant activity was also reported among others by Balsamo et al [12,13] and more recently by Guan et al [14].…”

Section: Introductionmentioning

confidence: 85%

“…The products were obtained as white solids and they were purified by recrystallization from toluene and n-hexane (5:1 v/v) (1, 9, 10), toluene, n-hexane and acetone (5:1:0.5 v/v/v) (2, 3, 4) or acetone (5,6,7,8). Structure of the tested compounds is shown in Table 1.…”

Section: Synthesis Of the Tested Compoundsmentioning

confidence: 99%

See 2 more Smart Citations

Preliminary Evaluation of Anticonvulsant Activity of Some Aminoalkanol and Amino Acid Cinnamic Acid Derivatives

Gunia¹,

Waszkielewicz²,

Cegła³

et al. 2012

LDDD

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A series of aminoalkanol and amino acid derivatives of trans-cinnamic acid as well as aminoalkanol derivatives of -phenylcinnamic acid was synthesized and evaluated for anticonvulsant activity. All compounds were verified in mice after intraperitoneal (i.p.) administration in maximal electroshock (MES) and subcutaneous pentetrazole (ScMet) induced seizures as well as neurotoxicity assessment. Six of them showed protection in MES at 100 mg/kg b.w. and one at 300 mg/kg b.w. For selected derivatives evaluation in ScMet test in rats after per os (p.o.) administration, 6-Hz test in mice and pilocarpine-induced status in rats were performed. The results are quite encouraging and further modification of the structures might lead to discovering new potential anticonvulsants.

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Section: Structure-anticonvulsant Activity Relationshipmentioning

confidence: 59%

Section: Introductionmentioning

confidence: 85%

See 1 more Smart Citation

Preliminary Evaluation of Anticonvulsant Activity of Some Aminoalkanol and Amino Acid Cinnamic Acid Derivatives

Gunia¹,

Waszkielewicz²,

Cegła³

et al. 2012

LDDD

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“…Similarly, SSG also contains an ester group attached to one of the tetrahydrofuran rings and showed a promising cytotoxicity against HL-60 (IC 50 = 15.7 µM). A number of studies have shown that compounds containing ester groups induce anticancer activity against cancer cells [35], [36], [37], [38] especially against HL-60 cell line [39].…”

Section: Resultsmentioning

confidence: 99%

Crystal Structure Elucidation and Anticancer Studies of (-)-Pseudosemiglabrin: A Flavanone Isolated from the Aerial Parts of Tephrosia apollinea

et al. 2014

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Tephrosia apollinea is a perennial shrublet widely distributed in Africa and is known to have medicinal properties. The current study describes the bio-assay (cytotoxicity) guided isolation of (-)-pseudosemiglabrin from the aerial parts of T. apollinea. The structural and stereochemical features have been described using spectral and x-ray crystallographic techniques. The cytotoxicity of isolated compound was evaluated against nine cancer cell lines. In addition, human fibroblast was used as a model cell line for normal cells. The results showed that (-)-pseudosemiglabrin exhibited dose-dependent antiproliferative effect on most of the tested cancer cell lines. Selectively, the compound showed significant inhibitory effect on the proliferation of leukemia, prostate and breast cancer cell lines. Further studies revealed that, the compound exhibited proapoptotic phenomenon of cytotoxicity. Interestingly, the compound did not display toxicity against the normal human fibroblast. It can be concluded that (-)-pseudosemiglabrin is worthy for further investigation as a potential chemotherapeutic agent.

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“…α-4-Hydroxy benzoyl β-4 ' -petyloxy phenyl ethylene (C) was prepared by usual established method. Final product (D) was prepared by the esterification of (B) and (C) [23]. Alkyl halides, EtOH, KOH, Acetone, 4-Hydroxy acetophenone, 4-Hydroxy benzaldehyde, Pentyl Bromide, Malonic acid etc., required for synthesis were used as received except solvents which were dried and remove by rota evaporator.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Liquid Crystals with Substituents in Terminal Benzene Cores and their Mesomorphic Behaviour

Sharma

Patel

Jarodwala³

2015

ILCPA

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Abstract.A new homologous series consisting of thirteen homologues central ester and chalcone linkage with Pentyloxy side chain at terminal benzene ring is synthesized and their mesomorphic properties are studied, with the exception of the methyl, ethyl and propyl homologues. However, the rest of homologues show mesomorphism enantiotropically manner with exhibition of nematic phase. The texture image of the nematic mesophases is observed by optical polarizing microscope equipped with heating stage (POM) is threaded or Schlieren type. An odd-even effect is observed in the nematic-isotropic curve with alternation in transition temperatures. The mesomorphic properties of the novel series are compared with other structurally similar homologous series. Analytical and spectral data confirm the molecular structure of the compounds.

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Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives as novel anticancer agents

Cited by 109 publications

References 20 publications

Preliminary Evaluation of Anticonvulsant Activity of Some Aminoalkanol and Amino Acid Cinnamic Acid Derivatives

Preliminary Evaluation of Anticonvulsant Activity of Some Aminoalkanol and Amino Acid Cinnamic Acid Derivatives

Crystal Structure Elucidation and Anticancer Studies of (-)-Pseudosemiglabrin: A Flavanone Isolated from the Aerial Parts of Tephrosia apollinea

Synthesis of Liquid Crystals with Substituents in Terminal Benzene Cores and their Mesomorphic Behaviour

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