Synthesis,characterization, and biological activity of a Cu(I) complex with 2-(9H-carbazol-9-yl) acetic acid

A new dicopper(I) complex with 2-(9H-carbazol-9-yl) acetic acid (HL) of the formula [Cu₂(dppm)₂L(NO₃)(CH₃OH)] [dppm = bis(diphenylphosphino)methane] was prepared. The complex was structurally characterized by IR, ¹H NMR spectra, and elemental analysis. Single crystal X-ray crystallography revealed that this complex is monoclinic, space group P2₁/c, with a = 13.6552(17) Å, b = 23.123(2) Å, c = 19.257(2) Å, α = γ = 90.00°, β = 106.860(2)°, V = 5818.8(11) ų, Z = 4, D _Calcd = 1.386 mg m^?3, F(000) = 2512, goodness-of-fit = 1.015. The complex was also tested in vitro for its cytotoxic activity using human hepatocellular carcinoma cell line (BEL-7402) and human hepatocellular liver carcinoma cell line (Hep-G2); 5-Fluorouracil was used as a positive control substance. The results indicated that the complex exhibited good cytotoxic activity against both human tumor cell lines.     

Synthesis, crystal structure and in vitro antitumor activity of a novel organotin(IV) complex with 9-hexyl-9H-carbazole-3-carboxylic acid

9-Hexyl-9H-carbazole-3-carboxylic acid (LCOOH) and its complex with Ph₃Sn(OH), [Ph₃SnO₂CL] (I), were synthesized. The structure of complex I was solved by single-crystal X-ray diffraction determination, indicating that I shows the discrete framework. Furthermore, this complex was tested in vitro for its cytotoxic activity, using human hepatocellular carcinoma cell line (BEL-7402) and human hepatocellular liver carcinoma cell line (HepG2); 5-fluorouracil was used as a positive control substance. This complex showed cytotoxicity greater than that of 5-fluorouracil.     

Efficient and mild one-pot synthesis of (E)-8′-arylidene-5′,6′,7′,8′-tetrahydrospiro[oxindole-3,4′-pyrano[3,2-c]pyridin] derivatives with potential antitumor activity

A mild and efficient cyclization procedure for the synthesis of (E)-8′-arylidene-5′,6′,7′,8′-tetrahydrospiro[oxindole-3,4′-pyrano[3,2-c]pyridin] derivatives was achieved via one-pot three-component condensation of isatins, malononitrile and (E)-3-arylidene-1-methylpiperidin-4-ones using piperidine as an efficient catalyst and ethanol as an environmentally benign solvent. The in vitro antitumor activity of these compounds was evaluated in human cervical carcinoma cell line (Hela), human liver hepatocellular carcinoma cell line (HepG2), and human breast carcinoma cell line (MDA-MB-231).     

In Vitro Evaluation of Antiproliferative Properties of Novel Organotin(IV) Carboxylate Compounds with Propanoic Acid Derivatives on a Panel of Human Cancer Cell Lines

The synthesis of novel triphenyltin(IV) compounds, Ph₃SnLn (n = 1–3), with oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid), HL1, and the new propanoic acid derivatives 3-(4,5-bis(4-methoxylphenyl)oxazol-2-yl)propanoic acid, HL2, and 3-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)propanoic acid, HL3, has been performed. The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC₅₀ values ranging from 0.100 to 0.758 µM. According to the CV assay (IC₅₀ = 0.218 ± 0.025 µM), complex Ph₃SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph₃SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph₃SnL1 induces caspase-independent apoptosis in MCF-7 cells.     

有机锡9-芴酮-4-甲酸酯的合成、结构及抗癌活性

合成了3个有机锡9-芴酮-4-甲酸酯:三苯基锡9-芴酮-4-甲酸酯[(C₆H₅)₃Sn(C₁₄H₇O₃)](1)、三环己基锡9-芴酮-4-甲酸酯[(C₆H₁₁)₃Sn(C₁₄H₇O₃)](2)和三(2-甲基-2-苯基丙基)锡9-芴酮-4-甲酸酯[(C₆H₅C(CH₃)₂CH₂)₃Sn(C₁₄H₇O₃)](3)。通过元素分析、红外光谱、核磁共振谱(¹H、¹³C和¹¹⁹Sn)、热重分析进行了表征;用单晶X射线衍射方法测定了化合物的晶体结构,并对其进行了量子化学计算和体外抗...     

1,3,4-Oxadiazole N-Mannich Bases: Synthesis,Antimicrobial, and Anti-Proliferative Activities

The reaction of 5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thione 3 with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding N-Mannich bases 3-arylaminomethyl-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thiones 4a–l or 3-[(4-substituted piperazin-1-yl)methyl]-5-(3,4-dimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thiones 5a–d, respectively. The in vitro inhibitory activity of compounds 4a–l and 5a–d was assessed against pathogenic Gram-positive, Gram-negative bacteria, and the yeast-like pathogenic fungus Candida albicans. The piperazinomethyl derivatives 5c and 5d displayed broad-spectrum antibacterial activities the minimal inhibitory concentration (MIC) 0.5–8 μg/mL) and compounds 4j, 4l, 5a, and 5b showed potent activity against the tested Gram-positive bacteria. In addition, the anti-proliferative activity of the compounds was evaluated against prostate cancer (PC3), human colorectal cancer (HCT-116), human hepatocellular carcinoma (HePG-2), human epithelioid carcinoma (HeLa), and human breast cancer (MCF7) cell lines. The optimum anti-proliferative activity was attained by compounds 4l, 5a, 5c, and 5d.     

Antitumor,cytotoxic, and antioxidant evaluation of six heterocyclic compounds containing different heterocycle moieties

Heterocyclic compounds with different heterocycle moieties, namely benzoxazinone, benzimidazole, quinazolinone, and benzofuranone heterocyclic rings, were synthesized, characterized, and evaluated for their anticancer activity against human hepatocellular carcinoma cell line (HepG2) using sulforhodamine B (SRB) and dimethylthiazol-diphenyltetrazolium bromide (MTT) assays. Also, their cytotoxic activities were tested against human epithelioid carcinoma (Hela) cell line in comparison with normal cell, amniotic epithelial (WISH) cell line, as an in vitro toxicity estimation model. The results showed clearly that 2-(2-benzyl-4-oxoquinazolin-3(4H)-yl)acetohydrazide 4 is the most potent antioxidant and anticancer agents. Although, 3-amino-2-benzylquinazolin-4(3H)-one 5 is less potent anticancer agent against Hela but it is more safe against normal cell (WISH).     

Cytotoxic properties of platinum(IV) and dinuclear platinum(II) complexes and their ligand substitution reactions with guanosine-5′-monophosphate

The substitution reaction of the Pt(IV) complex [PtCl₄(bipy)] with guanosine-5??-monophosphate (5??-GMP) was studied by UV?CVis spectrophotometry. This reaction was investigated under pseudo-first-order conditions at 37?°C in 25?mM Hepes buffer (pH?=?7.2) in the presence of 10?mM NaCl to prevent the hydrolysis of the complex. The substitution of chlorides in [{trans-Pt(NH₃)₂Cl}₂(??-1,2-bis(4-pyridyl)ethane)](ClO₄)₂ (Pt3) complex by 5??-GMP was followed by ¹H NMR spectroscopy under second-order conditions. Very similar values for the rate constants of both substitution steps were obtained. The Pt(IV) complexes, [PtCl₄(bipy)] and [PtCl₄(dach)], as well as dinuclaer Pt(II) [{trans-Pt(NH₃)₂Cl}₂(??-pyrazine)](ClO₄)₂ (Pt1), [{trans-Pt(NH₃)₂Cl}₂(??-4,4??-bipyridyl)](ClO₄)₂?·?DMF (Pt2) and [{trans-Pt(NH₃)₂Cl}₂(??-1,2-bis(4-pyridyl)ethane)](ClO₄)₂ (Pt3) complexes, displayed potent cytotoxic activity against human ovarium carcinoma cell line TOV21G and lower activity toward human colon carcinoma HCT116 cell line at the same concentrations. Our data indicate that these platinum complexes could be explored further, as potential therapeutic agents for ovarian cancer.     

End-to-End Thiocyanato-Bridged Helical Chain Polymer and Dichlorido-Bridged Copper(II) Complexes with a Hydrazone Ligand: Synthesis,Characterisation by Electron Paramagnetic Resonance and Variable-Temperature Magnetic Studies,and Inhibitory Effects on Human Colorectal Carcinoma Cells

The reactions of the tridentate hydrazone ligand, N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide (HL), obtained by condensation of 2-acetylpyridine with acetic hyadrazide, with copper nitrate trihydrate in the presence of thiocyanate, or with CuCl₂ produce two distinct coordination compounds, namely a one-dimensional helical coordination chain of [CuL(NCS)]_n (1) units, and a doubly chlorido-bridged dinuclear complex [Cu₂L₂Cl₂] (2) (where L=CH₃C(O)=N–N=CCH₃C₅H₄N). Single-crystal X-ray structural determination studies reveal that in complex 1, a deprotonated hydrazone ligand L⁻ coordinates a copper(II) ion that is bridged to two neighbouring metal centres by SCN⁻ anions, generating a one-dimensional helical coordination chain. In complex 2, two symmetry-related, adjacent copper(II) coordination entities are doubly chlorido-bridged, producing a dicopper entity with a Cu⋅⋅⋅Cu distance of 3.402 (1) Å. The two coordination compounds have been fully characterised by elemental analysis, spectroscopic techniques including IR, UV–vis and electron paramagnetic resonance, and variable-temperature magnetic studies. The biological effects of 1 and 2 on the viability of human colorectal carcinoma cells (COLO-205 and HT-29) were evaluated using an MTT assay, and the results indicate that these complexes induce a decrease in cell-population growth of human colorectal carcinoma cells with apoptosis.     

Synthesis, characterization, crystal structure and antitumor activities of a novel demethylcantharidato bridged copper(II) phenanthroline complex

A new polymeric demethylcantharidato (DCA) bridged copper(Ⅱ) phenanthroline (phen) complex ([Cu(DCA)(phen)] n ·nH2O) has been synthesized and characterized by elemental analysis, IR and electronic spectra studies, molar conductivity measurement, and single crystal X-ray diffraction. The complex crystallizes in the orthorhombic space group Pbca with crystallographic data: a = 12.4537(4), b = 9.3897(5), c = 30.1264(10), and Z = 8. In the crystal structure, the octahedral coordinated copper(Ⅱ) ions are bridged by demethylcantharidate ligands into a one-dimensional zigzag-like structure with the Cu···Cu separation of 6.1719, along with phen ligands attached to both sides of the chain alternatively. Interdigitation of the chelating phen ligands of two neighboring chains via hydrophobic interaction and van der Waals forces along ac plane forms two-dimensional polymeric bilayers with discrete water sandwich layer between the adjacent polymeric bilayers. The evaluation of the cytotoxic activity of the copper(Ⅱ) complex against HCT-8 (colorectal carcinoma), A549 (pulmonary carcinoma), HeLa (cervical cancer), HepG2 (hepatocarcinoma), BGC-823 (gastric carcinoma), and MCF-7 (breast adenocarcinoma) cell lines revealed that it is a potent cytotoxic agent, superior to Na2DCA and phen against HeLa, HepG2 and BGC-823 cells.     

Synthesis of Novel Methyl 7-[(Hetero)arylamino]thieno[2,3-b]pyrazine-6-carboxylates and Antitumor Activity Evaluation: Effects in Human Tumor Cells Growth,Cell Cycle Analysis,Apoptosis and Toxicity in Non-Tumor Cells

Several novel methyl 7-[(hetero)arylamino]thieno[2,3-b]pyrazine-6-carboxylates were synthesized by Pd-catalyzed C–N Buchwald–Hartwig cross-coupling of either methyl 7-aminothieno[3,2-b]pyrazine-6-carboxylate with (hetero)arylhalides or 7-bromothieno[2,3-b]pyrazine-6-carboxylate with (hetero)arylamines in good-to-excellent yields (50% quantitative yield), using different reaction conditions, namely ligands and solvents, due to the different electronic character of the substrates. The antitumoral potential of these compounds was evaluated in four human tumor cell lines: gastric adenocarcinoma (AGS), colorectal adenocarcinoma (CaCo-2), breast carcinoma (MCF7), and non-small-cell lung carcinoma (NCI-H460) using the SRB assay, and it was possible to establish some structure–activity relationships. Furthermore, they did not show relevant toxicity against a non-tumor cell line culture from the African green monkey kidney (Vero). The most promising compounds (GI₅₀ ≤ 11 µM), showed some selectivity either against AGS or CaCo-2 cell lines without toxicity at their GI₅₀ values. The effects of the methoxylated compounds 2b (2-OMeC₆H₄), 2f and 2g (3,4- or 3,5-diOMeC₆H₃, respectively) on the cell cycle profile and induction of apoptosis were further studied in the AGS cell line. Nevertheless, even for the most active (GI₅₀ = 7.8 µM) and selective compound (2g) against this cell line, it was observed that a huge number of dead cells gave rise to an atypical distribution on the cell cycle profile and that these cells were not apoptotic, which points to a different mechanism of action for the AGS cell growth inhibition.     

Synthesis,crystallographic and spectroscopic studies,evaluation as antimicrobial and cytotoxic agents of a novel mixed-ligand nickel(II) complex

A new mononuclear mixed-ligand complex of Ni(II) has been synthesized and structurally characterized by single-crystal X-ray diffraction as [Ni(4-Cl-pydc)(apym)(H₂O)₂], where 4-Cl-pydc and apym are 4-chloropyridine-26-dicarboxylate and 2-aminopyrimidine, respectively. Spectroscopic studies such as FT-IR, UV-vis, ¹H-NMR, and thermal analysis (TGA/DTA) were carried out. The fluorescence properties were studied in solvents with different dipole moments. Antimicrobial activities of 4-chloropyridine-26-dicarboxylic acid (1), 2-aminopyrimidine (2), complex (3), and nickel(II) nitrate hexahydrate (4) were investigated by disk diffusion and broth microdilution methods against three Gram-positive bacteria, Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis and three Gram-negative bacteria, Escherichia coli, Pseudomonas aeruginosa, S. marcescens; also antifungal effect was evaluated on Aspergillus niger and Saccharomyces cerevisiae in vitro. The highest antibacterial activity of complex was observed nearly equal to gentamicin as a standard drug toward S. epidermids with IZD of 18 mm. The in vitro antiproliferative activity of 1–4 on H1299 (a human non-small cell lung carcinoma), HepG2 (a human liver hepatocellular carcinoma), and β-TC3 (a mouse beta pancreatic) cell lines was evaluated by MTT (3-(45-dimethylthiazol-2-yl)-25-diphenyl-2H-tetrazolium bromide) assay and, effect of complex on depolarization of mitochondrial membrane (MMP) of all three cell lines was measured by rhodamine 123. The highest cytotoxic effect of complex was exhibited toward H1299 cell line with IC₅₀ value equal to 10 μM.     

Synthesis and Antiproliferative Activity of Phosphorus Substituted 4-Cyanooxazolines, 2-Aminocyanooxazolines, 2-Iminocyanooxazolidines and 2-Aminocyanothiazolines by Rearrangement of Cyanoaziridines

Several phosphorus-substituted N-acylated cyanoaziridines 2 and N-carbamoylated cyanoziridines 5 were prepared in good to high yields. N-Acylated cyanoaziridines 2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative 3a and in a completely regio-controlled reaction in the presence of NaI. Conversely, N-carbamoyl cyanoaziridines 5 reacted with NaI to obtain a regioisomeric mixture of 2-aminocyanooxazolines 7. Mild acidic conditions can be used for the isomerization of N-thiocarbamoyl cyanoaziridine 6a into a 2-aminocyanothiazoline derivative 8a by using BF₃·OEt₂ as a Lewis acid. Likewise, a one pot reaction of NH-cyanoaziridines 1 with isocyanates obtained 2-iminocyanooxazolidines 9 regioselectively. This synthetic methodology involves the addition of isocyanates to starting cyanoaziridines to obtain N-carbamoyl cyanoaziridines 5, which after the ring opening, reacts with a second equivalent of isocyanate to give the final 2-imino cyanooxazolidines 9. In addition, the cytotoxic effect on the cell lines derived from human lung adenocarcinoma (A549) was also screened. 2-Iminooxazolidines 9 exhibited moderate activity against the A549 cell line in vitro. Furthermore, a selectivity towards cancer cells (A549) over non-malignant cells (MCR-5) was detected.     

Synthesis,characterization, X-ray diffraction,antimicrobial and in vitro cytotoxicity studies of 7a-Aza-B-homostigmast-5-eno [7a,7-d] tetrazole

The synthesis, spectral characterization, crystal structure and antimicrobial activity of the novel synthetic molecule 7a-Aza-B-homostigmast-5-eno [7a,7-d] tetrazole, C₂₉H₄₈N₄ has been reported. The structure has also been determined by X-ray diffraction technique using direct method and was refined on F² by the full-matrix least-squares. Crystals are orthorhombic and their space group is P212121, with a = 7.230(3), b = 31.451(13), c = 11.974(5) (Å), α = β = γ = 90°. It can be conveniently obtained by the reaction of 7-Oxostigmast-5-ene with hydrazoic acid. The molecule has also been screened for its possible in vitro antimicrobial activity against Staphylococcus aureus, Streptococcus mutans, Streptococcus pyogenes, Staphylococcus epidermidis, Bacillus cereus, Corynebacterium xerosis, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris and Pseudomonas aeruginosa (MTCC 424). Minimum inhibitory concentration (MIC) of the synthesized compound has also been evaluated. The highest activity is observed against C. xerosi and P. vulgaris. Moreover, the compound has also been screened for its in vitro cytotoxicity against human colon carcinoma cell line, HCT116 and human liver hepatocellular carcinoma cell line, HepG2, using doxorubicin as standard. On the basis of its IC₅₀ values, 7a-Aza-B-homostigmast-5-eno [7a,7-d] tetrazole was found to inhibit the cancer cells effectively.     

Synthesis,characterization, antiproliferative,and antimicrobial activity of osmium(II) half-sandwich complexes

New osmium(II)-arene complexes [(η⁶-C₆H₆)OsCl(C₅H₄N-2-CH=N-C₆H₅X)](PF₆) (X = p-flouro (1), p-chloro (2), p-methyl (3)) were synthesized by reaction of the corresponding bidentate N,N′-ligands with the osmium-arene precursor [(η⁶-C₆H₆)Os(μ-Cl)Cl]₂ in a 2:1 ratio. These complexes were characterized by UV–Vis, IR, ¹H, ¹³C NMR spectroscopy, and elemental analysis and, for compound 1, a single crystal X-ray structure was also obtained. The complexes were investigated for antiproliferative activity in vitro against MCF-7 (human breast adenocarcinoma), Caco-2 (human epithelial colorectal adenocarcinoma), and HepG2 (human hepatocellular carcinoma) tumor cell lines. To test their selectivity, the non-tumor HEK293 (human embryonic kidney) cell line was used. The compounds were selective toward the tumor cell lines when compared to the known anticancer drug 5-fluorouracil which displayed low selectivity. The compounds were substantially more active against Caco-2 than 5-fluorouracil. They also showed moderate activity against the other two tumor cell lines. In addition, the antimicrobial activity of complex 2 was explored against a panel of antimicrobial-susceptible and -resistant Gram-negative and Gram-positive bacteria. Complex 2 showed anti-mycobacterial activity against Mycobacterium smegmatis and bactericidal activity against drug-resistant Enterococcus faecalis and methicillin-resistant Staphylococcus aureus ATCC 43300.     

Organotin complexes of pyruvic acid thiosemicarbazone: Synthesis,crystal structures and antiproliferative activity of neutral and cationic diorganotin complexes

The synthesis and spectral characterization of novel neutral and cationic organotin complexes with pyruvic acid thiosemicarbazone, H₂pt (1), [SnPh₂(pt)] (2), [SnMe₂(Hpt)(H₂O)]Cl (3) and [SnPh₂(Hpt)(H₂O)]Cl (4) are reported. The crystal structure of the complexes [SnPh₂(pt)] (2) and [SnMe₂(Hpt)(H₂O)]Cl (3) have been solved by single-crystal X-ray diffraction. The crystal structure of complex 2 showed that the ligand is doubly deprotonated at the oxygen and amide nitrogen atoms and is coordinated to the SnPh₂ fragment via two five-membered chelate rings. The monomers of 2 are linked through intermolecular hydrogen bonds of C−H–O type and through π−π intermolecular interactions. The crystal structure of [SnMe₂(Hpt)(H₂O)]Cl (3) showed that the ligand is mono-deprotonated at the oxygen atom and is coordinated to the SnMe₂ fragment via two five-membered chelate rings. The counter ion chloride is participated in intermolecular hydrogen bonds. An extended network of intermolecular hydrogen bonds leads to aggregation and a supramolecular assembly. The IR and NMR spectroscopic data of the complexes are reported. The in vitro cytotoxic activity has been evaluated against the cells of three human cancer cell lines: MCF-7 (human breast cancer cell line), T-24 (bladder cancer cell line), A-549(non-small cell lung carcinoma) and a mouse L-929 (a fibroblast-like cell line cloned from strain L). The most active of all was found the diorganotin complex 2. The cytotoxic activity shown by these compounds against all these cancer cell lines indicates that coupling of 1 with R₂Sn(IV) metal center result in metallic complexes with important biological properties and remarkable cytotoxic activity, since they are display IC₅₀ values in a μM range the same or better to that of the antitumor drug cisplatin. Compound 2 is considered as agent with potential antitumor activity, and can therefore be candidate for further stages of screening in vitro and/or in vivo.     

有机锡9-芴酮-4-甲酸酯的合成、结构及抗癌活性

合成了 3 个有机锡 9-芴酮-4-甲酸酯:三苯基锡 9-芴酮-4-甲酸酯[(C₆H₅)₃Sn(C₁₄H₇O₃)] (1)、三环己基锡 9-芴酮-4-甲酸酯[(C₆H₁₁)₃Sn(C₁₄H₇O₃)] (2)和三(2-甲基-2-苯基丙基)锡 9-芴酮-4-甲酸酯[(C₆H₅C(CH₃)₂CH₂)₃Sn(C₁₄H₇O₃)] (3)。通过元素分析、红外光谱、核磁共振谱(¹H、¹³C和 ¹¹⁹Sn)、热重分析进行了表征;用单晶X射线衍射方法测定了化合物的晶体结构,并对其进行了量子化学计算和体外抗癌活性研究。结果显示:化合物1为一维链状结构,中心锡原子为五配位的畸变三角双锥构型;化合物2和3均为单核分子,锡原子均为四配位的畸变四面体构型。化合物对人宫颈癌细(HeLa)、人肝癌细胞(HUH-7)、人非小细胞肺癌细胞(A549)、人肺腺癌细胞(H1975)和人乳腺癌细胞(MCF-7)都有较好的抑制活性。     

Synthesis,structural characterization and in vitro cytotoxicity of diorganotin complexes with Schiff base ligands derived from 3‐hydroxy‐2‐naphthoylhydrazide

A series of diorganotin complexes with Schiff base ligands, (E)‐N′‐(5‐bromo‐2‐hydroxybenzylidene)‐3‐hydroxy‐2‐naphthohydrazide, H₂L1, and (E)‐N′‐(5‐chloro‐2‐hydroxybenzylidene)‐3‐hydroxy‐2‐naphthohydrazide, H₂L2, were synthesized and characterized by elemental analysis, IR, ¹H, ¹³C and ¹¹⁹Sn NMR spectroscopy. The molecular structures of the complexes, [(5‐bromo‐2‐oxidobenzylidene)‐3‐hydroxy‐2‐naphthohydrazidato]di(o‐chlorobenzyl)tin(IV) 6 and [(5‐chloro‐2‐oxidobenzylidene)‐3‐hydroxy‐2‐naphthohydrazidato]dibutyltin(IV) 9, were determined through single‐crystal X‐ray diffraction and revealed a distorted trigonal‐bipyramidal configuration. The in vitro cytotoxic activity of the Schiff bases and their diorganotin complexes was also evaluated against several human carcinoma cell lines, namely HT29 (human colon carcinoma cell line), SKOV‐3 (human ovarian cancer cell line), MCF7 (hormone‐dependent breast carcinoma cell line) and MRC5 (non‐cancer human fibroblast cell line). [(5‐Bromo‐2‐oxidobenzylidene)‐3‐hydroxy‐2‐naphthohydrazidato]dibutyltin(IV) 2 and [(5‐bromo‐2‐oxidobenzylidene)‐3‐hydroxy‐2‐naphthohydrazidato]dibenzyltin(IV) 5 were the most active diorganotin complexes of H₂L1 ligand. Among the diorganotin complexes of H₂L2 ligand, [(5‐chloro‐2‐oxidobenzylidene)‐3‐hydroxy‐2‐naphthohydrazidato]dicyclohexyltin(IV) 11 showed good cytotoxic activity against all the tested cell lines. As such, the above compounds can be considered agents with potential anticancer activities, and can therefore be investigated further in in vitro or in vivo anticancer studies. Copyright © 2012 John Wiley & Sons, Ltd.     

NHC-gold(I)-alkyne complexes induced hepatocellular carcinoma cell death through bioorthogonal activation by palladium complex in living system

Bioorthogonal reactions can take place in biological environments without interfering with biochemical processes. In this study, Pd(PPh₃)₂Cl₂ was used as a bioorthogonal catalyst to in situ transform the stable N-heterocyclic carbene (NHC)-gold(I)-alkyne complex 5 to its active species which can effectively inhibit thioredoxin reductase (TrxR) and exhibit significant anticancer bioactivity in hepatocellular carcinoma (HCC).     

Phytochemical Characterization,In Vitro Anti-Inflammatory,Anti-Diabetic,and Cytotoxic Activities of the Edible Aromatic Plant; Pulicaria jaubertii

Pulicaria jaubertii is a medicinal herb that alleviates inflammations and fever. Chromatographic separation, phytochemical characterization, and in vitro biological activities of the plant n-hexane extract were conducted for the first time in this study. Six compounds were isolated for the first time from the n-hexane fraction of Pulicaria jaubertii aerial parts and were identified on the bases of NMR and MS analyses as pseudo-taraxaterol (1), pseudo-taraxasterol acetate (2), 3β-acetoxytaraxaster-20-en-30-aldehyde (3), calenduladiol-3-O-palmitate (4), stigmasterol (5), and α-tocospiro B (6). Compound (6) was a rare tocopherol-related compound and was isolated for the first time from family Asteraceae, while compound (3) was isolated for the first time from genus Pulicaria. The total alcoholic extract and n-hexane fraction were tested for their anti-inflammatory, antidiabetic, and cytotoxic activities. The n-hexane fraction has dose dependent red blood cells (RBCs) membrane stabilization and inhibition of histamine release activities with IC₅₀: 60.8 and 72.9 µg/mL, respectively. As antidiabetic activity, the alcoholic extract exerted the most inhibition on the activity of yeast α-glucosidase, with an IC₅₀: 76.8 µg/mL. The n-hexane fraction showed cytotoxic activity against hepatocarcinoma (HepG-2), breast carcinoma (MCF-7), and prostate carcinoma (PC-3) cell lines with IC₅₀: 51.8, 90.8 and 62.2 µg/mL, respectively. In conclusion, the anti-inflammatory effect of Pulicaria jaubertii might be attributed to the triterpenoid constituents of the n-hexane extract of the plant.