Novel asymmetric 3,5-bis(arylidene)piperidin-4-one derivatives: synthesis, crystal structures and cytotoxicity

2018 ◽  
Vol 74 (6) ◽  
pp. 659-665 ◽  
Author(s):  
Binrong Yao ◽  
Ning Li ◽  
Chunhua Wang ◽  
Guige Hou ◽  
Qingguo Meng ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Cell Line ◽  
Antitumour Activity ◽  
Structural Characteristics ◽  
Crystal Structure Analysis ◽  
Unsaturated Ketone ◽  
Dimensional Network ◽  
Ft Ir ◽  
Hepatocellular Carcinoma Cell Line ◽  
Liver Hepatocellular Carcinoma

3,5-Bis(arylidene)piperidin-4-one derivatives (BAPs) display good antitumour activity because of their double α,β-unsaturated ketone structural characteristics. Reported BAPs have generally been symmetric and asymmetric BAPs have been little documented. Three asymmetric BAPs, namely (5E)-3-(4-tert-butylbenzylidene)-5-(4-fluorobenzylidene)-1-methylpiperidin-4-one, C24H26FNO, (5), (5E)-3-(4-tert-butylbenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one, C26H31NO3, (6), and (5E)-3-{3-[(E)-(2,3-dihydroxybenzylidene)amino]benzylidene}-5-(2-fluorobenzylidene)-1-methylpiperidin-4-one, C27H23FN2O3, (12), were generated by Claisen–Schmidt condensation. They are characterized by NMR and FT–IR spectroscopies, and elemental analysis. Single-crystal structure analysis reveals that the two arylidene rings on both sides of the BAP structures adopt an E stereochemistry of the olefinic double bonds and the compounds are E,E isomers. Molecules of (5) and (12) generate one-dimensional chains through intermolecular hydrogen bonds, while compound (6) generates a two-dimensional network through hydrogen bonds. Preliminary cytotoxicities toward human liver hepatocellular carcinoma cell line (HepG2), human acute mononuclear granulocyte leukaemia (THP-1) and human normal hepatical cell line (LO2) were evaluated.

Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

2018 ◽  
Vol 74 (10) ◽  
pp. 1171-1179 ◽  
Author(s):  
Ning Li ◽  
Xianyong Bai ◽  
Lianshuang Zhang ◽  
Yun Hou
Keyword(s):  
Hydrogen Bonds ◽  
High Resolution Mass Spectrometry ◽  
Structural Characteristics ◽  
Crystal Structure Analysis ◽  
Inflammatory Activity ◽  
Unsaturated Ketone ◽  
Activity Data ◽  
Strong Electron ◽  
Phenyl Rings ◽  
Anti Inflammatory

3,5-Bis(arylidene)-4-piperidone (BAP) derivatives display good antitumour and anti-inflammatory activities because of their double α,β-unsaturated ketone structural characteristics. If N-benzenesulfonyl substituents are introduced into BAPs, the configuration of the BAPs would change significantly and their anti-inflammatory activities should improve. Four N-benzenesulfonyl BAPs, namely (3E,5E)-1-(4-methylbenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C28H21F6NO3S·CH2Cl2, (4), (3E,5E)-1-(4-fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C27H18F7NO3S, (5), (3E,5E)-1-(4-nitrobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C27H18F6N2O5S, (6), and (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C28H18F6N2O3S·CH2Cl2, (7), were prepared by Claisen–Schmidt condensation and N-sulfonylation. They were characterized by NMR, FT–IR and HRMS (high resolution mass spectrometry). Single-crystal structure analysis reveals that the two 4-(trifluoromethyl)phenyl rings on both sides of the piperidone ring in (4)–(7) adopt an E stereochemistry of the olefinic double bonds. Molecules of both (4) and (6) are connected by hydrogen bonds into one-dimensional chains. In (5) and (7), pairs of adjacent molecules embrace through intermolecular hydrogen bonds to form a bimolecular combination, which are further extended into a two-dimensional sheet. The anti-inflammatory activity data reveal that (4)–(7) significantly inhibit LPS-induced interleukin (IL-6) and tumour necrosis factor (TNF-α) secretion. Most importantly, (6) and (7), with strong electron-withdrawing substituents, display more potential inhibitory effects than (4) and (5).

Benzyldiethylammonium chloride

2006 ◽  
Vol 62 (5) ◽  
pp. o1735-o1737 ◽  
Author(s):  
Daniel Lorono-Gonzalez
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Ionic Species ◽  
Polar Space ◽  
Crystal Structure Analysis ◽  
Two Dimensional ◽  
Compound C ◽  
Dimensional Network

The title compound, C11H18N+·Cl−, crystallizes in a non-centrosymmetric polar space group and possesess normal geometric parameters. The crystal structure analysis reveals a discrete ionic species, for which the packing is consolidated by an N—H...Cl hydrogen bond and C—H...Cl hydrogen bonds, resulting in a two-dimensional network.

Synthesis, crystal structure and activity evaluation of novel 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives as protein–tyrosine kinase (PTK) inhibitors

2017 ◽  
Vol 73 (11) ◽  
pp. 1003-1009 ◽  
Author(s):  
Ning Li ◽  
Binrong Yao ◽  
Chunhua Wang ◽  
Qingguo Meng ◽  
Guige Hou
Keyword(s):  
Crystal Structure ◽  
Tyrosine Kinases ◽  
Protein Tyrosine Kinase ◽  
Three Dimensional ◽  
Crystal Structure Analysis ◽  
X Ray Diffraction ◽  
Protein Tyrosine ◽  
Dimensional Network ◽  
Ft Ir ◽  
Structure And Activity

Four new 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives, namely (E)-4-(5-bromo-2-hydroxybenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (7), (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (8), (E)-4-(5-bromo-2-hydroxybenzylidene)-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C18H15BrO5, (9), and (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (10), have been synthesized and characterized by FT–IR, NMR and MS. The structure of (9) was confirmed by single-crystal X-ray diffraction. Crystal structure analysis shows that molecules of (9) are connected into a one-dimensional chain in the [010] direction through classical hydrogen bonds and these chains are further extended into a three-dimensional network via C—H...O interactions. The inhibitory activities of these compounds against protein–tyrosine kinases (PTKs) show that 6-hydroxy-substituted compounds (9) and (10) are more effective for inhibiting ErbB1 and ErbB2 than are 6-methoxy-substituted compounds (7) and (8). This may be because (9) and (10) could effectively bind to the active pockets of the protein through intermolecular interactions.

scholarly journals Synthesis, crystal structure and spectroscopic characterization of a new organic bismuthate (III) [C9H28N4][Bi2Cl10].H2O

2014 ◽  
Vol 9 (2) ◽  
pp. 1911-1920 ◽  
Author(s):  
Z. Aloui ◽  
S. Abid ◽  
E. Jeanneau ◽  
M. Rzaigui ◽  
C. Ben Nasr
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Spectroscopic Characterization ◽  
Organic Layer ◽  
Monoclinic System ◽  
Cell Parameters ◽  
Dimensional Network ◽  
Ft Ir

The chemical preparation, crystal structure and spectroscopic characterization of [C9H28N4][Bi2Cl10].H2O have been reported. This compound crystallizes in the monoclinic system in space group P21/c and cell parameters a = 12.2385 (6), b = 17.3062 (7), c = 13.0772 (6) Å, β = 104.475 (5)°, Z = 4 and V = 2681.9 (2) Å3. Its crystal structure has been determined and refined to R = 0.049, using 5848 independent reflections. The atomic arrangement can be described by an alternation of organic and inorganic layers. The inorganic layer built up of [Bi2Cl10]4– bioctahedra arranged in sandwich between the organic layer. The organic groups are interconnected by the water molecules through N-H…O(W) hydrogen bonds to form infinite zig-zag chains spreading along the b-axis. These Chains are themselves interconnected by means of the N–H…Cl hydrogen bonds originating from [Bi2Cl10]4– anions, to form a three-dimensional network. Intermolecular Cl…Cl interactions between adjacent dimeric [Bi2Cl10]4– anions have been observed. The compound was also characterized by FT-IR and Raman spectrscopies.

Calcium tartrate esahydrate, CaC4H4O6·6H2O: a structural and spectroscopic study

2015 ◽  
Vol 71 (1) ◽  
pp. 68-73 ◽  
Author(s):  
Gennaro Ventruti ◽  
Fernando Scordari ◽  
Fabio Bellatreccia ◽  
Giancarlo Della Ventura ◽  
Armida Sodo
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
X Ray Diffraction ◽  
Fourier Synthesis ◽  
Dimensional Network ◽  
Calcium Tartrate ◽  
Network Of Hydrogen Bonds ◽  
Ft Ir ◽  
Difference Fourier ◽  
Ir Spectroscopic

The crystal structure of calcium tartrate esahydrate, CaC4H4O6·6H2O, has been solved by the charge-flipping method from single-crystal X-ray diffraction data and refined toR= 0.021, based on 1700 unique observed diffractions. Salient crystallographic data are:a= 7.7390 (1),b= 12.8030 (2),c= 5.8290 (1) Å,Z= 2, and space groupP21212. During the refinement step it was possible to locate all H atoms by difference Fourier synthesis. The tartrate molecule has a (−)-gaucheconformation and is coordinated to two calcium ions to form infinite chains along theaaxis which alternate Ca polyhedra with tartrate molecules. The chains are interlinked by a three-dimensional network of hydrogen bonds from four water molecules surrounding the Ca ion, reinforced by hydrogen bonds from one interstitial water molecule. Micro-Raman and FT–IR spectroscopic data are provided.

scholarly journals New Series of Substituted Heterocyclics Derived from α , β – Unsaturated Ketone and Their Cytotoxic Activity Tumor Cell Lines

2018 ◽  
Vol 34 (6) ◽  
pp. 2826-2831
Author(s):  
Muna S. AL-Rawi ◽  
Huda A. Hassan ◽  
Dheefaf F. Hassan ◽  
Ismaeel Y. Majeed
Keyword(s):  
Cell Line ◽  
Heterocyclic Compounds ◽  
Carcinoma Cell ◽  
Aldol Condensation ◽  
Chloroacetic Acid ◽  
Cytotoxic Activities ◽  
Moderate Activity ◽  
Unsaturated Ketone ◽  
Rhabdomyosarcoma Cell ◽  
Ft Ir

The aldol condensation of 2-acetylnaphthalene with 9-anthracene carboxaldehyde afforded α, β-unsaturated keton (1) . New heterocyclic compounds containing: cyclohexenone[2], indazole[3], pyrimidinethion [4], thiazolo fused pyrimidine[5], isoxazoline[6], substituted pyrazoline[7]a-d and pyrimidinone[8] rings system were synthesized from α, β-unsaturated keton[1]. Cyclization of [1] with ethylacetoacetate gave the mentioned heterocycle cyclohexanone [2]. The cyclo condensation of [2] with hydrazine gave the new indazole derivative [3]. furthermore, the reation of [1]with thiourea gives thiopyrmidine derivative [4]. The cyclo condensation of [4] with chloroacetic acid gave the fused rings [5]. Then reacted compound[1] with hydroxylamine to produce isoxazoline [6]. Also the reaction of [1]with hydrazine and hydrazide derivatives to produce pyrazole [7]a-d. All the newly synthesized derivatives[2-7a-d] were characterized via the CHN-S, FT- IR, 1H NMR, and13C NMR (of some of theme). The antibacterial and cytotoxic activities were evaluated for these derivatives[2-7a-d] . The study of antibacterial displayed good to moderate activity and the study of anticancer activity showed that were effective for inhibition of L20 B the mice intestines carcinoma cell line and RD human pelvic rhabdomyosarcoma cell line. Treated.

scholarly journals Synthesis, Crystal Structure, and Comparative Study of a New Organic Material 3,4-Diaminobenzophenone Semihydrate

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Tarek Ben Rhaiem ◽  
Habib Boughzala ◽  
Ahmed Driss
Keyword(s):  
Crystal Structure ◽  
Crystal Structure Analysis ◽  
Monoclinic Space Group ◽  
Structural Components ◽  
Dimensional Network ◽  
Cell Dimensions ◽  
Ft Ir ◽  
The Fourier Transform ◽  
Unit Cell Dimensions ◽  
Ft Ir Spectroscopy

The new organic 3,4-diaminobenzophenone semihydrate (34ABPH) is grown by slow evaporation method. The compound crystallizes in the monoclinic space group: C2. The unit cell dimensions are (8) Å, (2) Å, (10) Å, andβ = 99.40 (2)° with . The crystal structure analysis reveals that the C13H12N2O molecules chains are organized into a double ribbon in the (b,c) plane. The structural components interact by N–H⋯O and O–H⋯O hydrogen bonds, building up a two-dimensional network. The presence of functional groups in the molecular structure is confirmed by the Fourier transform infrared (FT-IR) spectroscopy. Thermogravimetric analysis (TGA) confirms the presence of the water molecule.

SYNTHESIS AND CYTOTOXICITY OF POLYHYDROXYLATED CHOLESTEROL DERIVATIVES

2018 ◽  
Vol 56 (4) ◽  
pp. 467
Author(s):  
Thu Thuy Thi Tran ◽  
Ha Thi Dinh ◽  
Phương Lan Doan ◽  
Long Quoc Pham ◽  
Quang Dai Ngo
Keyword(s):  
Hepatocellular Carcinoma ◽  
Cell Line ◽  
Cell Lines ◽  
Carcinoma Cell ◽  
Addition Compound ◽  
Hep G2 ◽  
Physical Methods ◽  
Hepatocellular Carcinoma Cell Line ◽  
Human Hepatocellular Carcinoma Cell ◽  
Hepatocellular Carcinoma Cell

Eight polyhydroxylated cholesterol derivatives (1-8) were prepared from cholesterol, using oxidative reagents as SeO2, OsO4/NMO, HCOOH/H2O2 and BH3/ H2O2. Their structures were elucidated by using physical methods including NMR 1D and 2D. These compounds were evaluated against two cancer cell lines (Hep-G2, T98). Compounds 2, 4 and 8 inhibits human hepatocellular carcinoma cell line (Hep-G2) with IC50 4.69, 4.98 and 2.89 µg/mL, respectively. In addition, compound 8 exhibited strong cytotoxicity against T98 cell line (glioblastoma) with IC50 = 2.28 μM.

Sign in / Sign up

Export Citation Format

Share Document