Syntheses, characterizations and biological activities of two Cu(II) complexes with acylhydrazone ligand bearing pyrrole unit

Ye, Xingpei; Zhu, Tao; Wu, Wei-Na; Ma, Tieliang; Xu, Jun; Zhang, Zhao-Po; Wang, Yuan; Jia, Lei

doi:10.1016/j.inoche.2014.07.022

Cited by 22 publications

(9 citation statements)

References 18 publications

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“…Our previous work shows that acylhydrazone ligands bearing pyrrole units and their Cu(II) complexes exhibit considerable antibacterial and antitumor activity [3,5,6]. The structure of N′- (5-ethoxycarbonyl-3,4dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide DMF adduct has been reported [3], while its monohydrate was characterized by X-ray diffraction in this work.…”

Section: Commentmentioning

confidence: 66%

“…The structure of N′- (5-ethoxycarbonyl-3,4dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide DMF adduct has been reported [3], while its monohydrate was characterized by X-ray diffraction in this work. In the title crystal structure, the acylhydrazone molecule is in a ketone form and adopts an E configuration at the C = N double bond, in which all the bond lengths are comparable with those observed in the DMF adduct [6] …”

Section: Commentmentioning

confidence: 79%

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N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C₁₇H₂₁N₃O₅

Mao

Yan

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 17 H 21 N 3 O 5 , monoclinic, P2 1 /n (no. 14), a = 9.2278(16) Å, b = 15.093(3) Å, c = 12.698(2) Å, CCDC no.: 1569105The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. -(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide was prepared according to the Source of materials N′

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Section: Commentmentioning

confidence: 66%

Section: Commentmentioning

confidence: 79%

N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C₁₇H₂₁N₃O₅

Mao

Yan

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Our previous work shows that acylhydrazone ligands bearing pyrrole units and their complexes exhibit considerable antibacterial and antitumor activity [1,5,6]. In fact, the structure of DMF solvate of ethyl (E)-5-((2-(4-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate has been reported [1]. As its isomer, the title compound was synthesized and characterized by X-ray diffraction.…”

Section: Discussionmentioning

confidence: 99%

“…The title compound was prepared according to the literature method [1]. Crystals of the title crystals were obtained by the recrystallization of the compound from ethanol solution.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C₁₉H₂₇N₃O₆

Hao

Lin

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 19 H 27 N 3 O 6 , monoclinic, P2 1 /c (no. 14), a = 8.132(7) Å, CCDC no.: 1587584The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was prepared according to the literature method [1]. Crystals of the title crystals were obtained by the recrystallization of the compound from ethanol solution.

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“…It is well known that a large amount of pyrrole constitutes, such as sunitinib, are a class of promising anticancer agents (16). Our previous work has also shown that certain acylhydrazones bearing a pyrrole unit have antitumor activity towards hepatocellular carcinoma HepG2 cells (17). In addition, certain pyrrole imines can bind to DNA effectively (18).…”

Section: Introductionmentioning

confidence: 96%

Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents

et al. 2017

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Abstract.A series of N(4)-substituted thiosemicarbazones (TSCs) bearing pyrrole unit (1a-1e) were synthesized and fully characterized by elemental analyses, infrared spectra, 1 H nuclear magnetic resonance and single crystal X-ray diffraction. The compounds were assessed as potential chemotherapeutic agents. All newly synthesized compounds were screened for their anticancer activity against lung cancer PC-9, esophageal cancer Eca-109 and gastric cancer SGC-7901 cell lines. The results of MTT, Terminal deoxynucleotidyl transferase dUTP nick end labeling and fluorescence-activated cell sorting assays indicated that all the prepared compounds exhibited cytotoxicity against PC-9, Eca-109 and SGC-7901 cells in vitro. All the compounds significantly induced cancer cell apoptosis accompanied by increasing the Bax/Bcl-2 ratio and activation of caspase-3. The structure-activity association was discussed and the potential pre-clinical trials may be conducted. The present findings have a great potential in biomedical applications of novel N(4)-substituted TSCs.

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Syntheses, characterizations and biological activities of two Cu(II) complexes with acylhydrazone ligand bearing pyrrole unit

Cited by 22 publications

References 18 publications

N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C₁₇H₂₁N₃O₅

N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C₁₇H₂₁N₃O₅

Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C₁₉H₂₇N₃O₆

Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents

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Syntheses, characterizations and biological activities of two Cu(II) complexes with acylhydrazone ligand bearing pyrrole unit

Cited by 22 publications

References 18 publications

N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C17H21N3O5

N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C17H21N3O5

Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C19H27N3O6

Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents

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N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C₁₇H₂₁N₃O₅

N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-4-hydroxybenzohydrazide monohydrate, C₁₇H₂₁N₃O₅

Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C₁₉H₂₇N₃O₆