Synthesis of novel 5‐aryl‐1H‐tetrazoles

In this study phenylselenocyanate and some of its derivatives (o‐Cl, p‐Cl, p‐Br, o‐NO₂, p‐NO₂, o‐CH₃, p‐CH₃, o‐COOH, p‐COOH, p‐OCH₃ substituted) were synthesized ( 3a–3j ). The synthesized compounds were converted to 5‐aryl‐1H‐tetrazole ( 4a–4j ), by Et₃N ċ HCl‐NaN₃ in toluene, which are a new series of phenylselanyl‐1H‐tetrazoles. The structure of all the presently synthesized compounds were confirmed using spectroscopic methods (FTIR, ¹H NMR, MS). © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:255–258, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20293     

Synthesis,structures, and biological activities of new 1H‐1,2,4‐triazole derivatives containing pyridine unit

Fourteen new 1H‐1,2,4‐triazole derivatives containing pyridine moiety were synthesized by condensation of 1‐(pyridine‐3‐yl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)ethanone with aryl aldehydes, and their reaction conditions were studied. The title compounds were screened for their antibacterial and plant growth regulatory activities. The screening data revealed that most of the compounds showed some antifungal and plant growth regulatory activities. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:376–380, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20308     

Synthesis,structure and characterization of some Schiff bases bearing phenylferrocene

Some novel Schiff bases bearing phenylferrocene were synthesized by condensation reaction of 4‐ferrocenylaniline with different aromatic aldehydes. The compounds prepared were characterized by spectroscopic methods (IR, UV–visible, ¹H and ¹³C NMR) and elemental analysis. The single crystal analysis of compound F1 [monoclinic, space group, P2₁/c (no. 14), a = 19.858(2), b = 7.416(2), c = 12.095(5) Å, β = 106.257(14) ] indicates a trans imine bond with a bond length of 1.270(2) Å, typical of a carbon‐nitrogen double bond. Copyright © 2007 John Wiley & Sons, Ltd.     

Dicoumarol complexes of Cu(II), Fe(II) and Fe(III): preparation,characterization, in‐vitro antibacterial and DNA binding activity

3‐3′‐Benzylidenebis[4‐hydroxycoumarin] or 4‐nitro,3‐3′‐benzylidenebis[4‐hydroxycoumarin] or 4‐methoxy,3‐3′‐benzylidenebis[4‐hydroxycoumarin] and their complexes with Cu(II), Fe(II) and Fe(III) were synthesized and characterized using ¹H‐NMR, ¹³C‐NMR, IR spectra, electronic spectra, magnetic measurements and elemental analyses. The ligands, metal salts, complexes, control and standard drug were tested for their in‐vitro antibacterial activity against Bacillus cereus, Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Salmonella typhi, and Serratia marcescens. The metal complexes exhibit good activity against bacterial strains compared with parental compounds and moderate compared with the standard drug (ciprofloxacin). In‐vitro DNA‐binding activity was carried out using agarose gel electrophoresis. The synthesized compounds show effective DNA‐binding activity. Copyright © 2007 John Wiley & Sons, Ltd.     

Novel antitumor dinuclear platinum (II) complexes with a new chiral tetradentate ligand as the carrier group

Seven dinuclear platinum(II) complexes with a novel chiral tetradentate ligand, (1R,1′R,2R,2′R)‐N¹,N^1′‐(1,4‐phenylenebis(methylene))dicyclohexane‐1,2‐diamine, were designed, synthesized and spectrally characterized. All the complexes were evaluated for their in vitro cytotoxicity against human HepG‐2, A549, HCT‐116 and MCF‐7 cancer cell lines. The results indicated that all compounds showed positive biological activity against HepG‐2, A549 and HCT‐116 cancer cell lines. In particular, compounds D7 and D2 showed better activity than carboplatin against HepG‐2 and A549 and compound D7 also showed an activity close to that of oxaliplatin. Copyright © 2015 John Wiley & Sons, Ltd.     

Synthesis,characterization and catalytic,cytotoxic and antimicrobial activities of two novel cyclotriphosphazene‐based multisite ligands and their Ru(II) complexes

Two novel cyclotriphosphazene ligands ( 2 and 3 ) bearing 3‐oxypyridine groups and their corresponding Ru(II) complexes ( 4 and 5 ) were synthesized and their structures were characterized using Fourier transform infrared, ¹H NMR and ³¹P NMR spectroscopic data and elemental analysis. The Ru(II) complexes were used as catalysts for catalytic transfer hydrogenation of p‐substituted acetophenone derivatives in the presence of KOH. Additionally, the cytotoxic activities of compounds 2 , 3 , 4 , 5 were evaluated against PC3 (human prostate cancer), DLD‐1 (human colorectal cancer), HeLa (human cervical cancer) and PNT1A (normal human prostate) cell lines. Finally the antimicrobial activities of compounds 2 , 3 , 4 , 5 were evaluated against a panel of Gram‐positive and Gram‐negative bacteria and yeast cultures. The complexes showed efficient catalytic activity towards transfer hydrogenation of acetophenone derivatives, especially those bearing electron‐withdrawing substituents on the para‐position of the aryl ring. The compounds were found to have moderate to high cytotoxic and antimicrobial activities, and Ru(II) complexation enhanced both cytotoxic and antimicrobial activities in comparison with the parent compounds. Copyright © 2015 John Wiley & Sons, Ltd.     

Immobilization of aminothiols on poly(oxyethylene H‐phosphonate)s and poly(oxyethylene phosphate)s—An approach to polymeric protective agents for radiotherapy of cancer

This study describes the synthesis and characterization of polymer complexes constructed from the radioprotective agent S‐2(3‐aminopropylamino) ethylphosphorothioic acid dihydrate (amifostine or WR‐2721), applied in the radiation cancer treatment, and biodegradable poly(oxyethylene H‐phosphonate), poly(hydroxyoxyethylene phosphate), or poly(methyloxyethylene phosphate). The immobilization of another radioprotector, used in cancer radiotherapy, 1‐(3‐aminopropyl)aminoethanethiol (WR‐1065) on the same polymers is also achieved through a covalent bond (Atherton‐Todd reaction coupling), ionic bond, and physical complexation, respectively. The structure of the complexes formed is elucidated by ¹H‐ ¹³C‐, ³¹P NMR and FTIR spectroscopy. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 1349–1363, 2007     

Synthesis of phosphonic acid containing thiadiazole

A series of phosphonic acid, 1,3,4‐thiadiazol‐2‐amine‐N‐alkyl have been synthesized by the reaction of 2‐amine thiadiazole, different aldehydes (or ketone), and phosphorous acid via the melting method or the solvent method. These compounds have been characterized by IR, ¹H NMR, ³¹P NMR, and elemental analysis. Results showed that compounds were reacted via the solvent method in better yields. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:140–143, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20395     

Synthesis and characterization of model polybutadiene‐1,4‐b‐polydimethylsiloxane‐b‐polybutadiene‐1,4 copolymers

Model copolymers of poly(butadiene) (PB) and poly(dimethylsiloxane) (PDMS), PB‐b‐PDMS‐b‐PB, were synthesized by sequential anionic polymerization (high vacuum techniques) of 1,3‐butadiene and hexamethylciclotrisiloxane (D₃) on sec‐BuLi followed by chlorosilane‐coupling chemistry. The synthesized copolymers were characterized by nuclear magnetic resonance (¹H NMR), size‐exclusion chromatography (SEC), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). SEC and ¹H NMR results showed low polydispersity indexes (M_w/M_n) and variable siloxane compositions, whereas DSC and TGA experiments indicated that the thermal stability of the triblock copolymers depends on the PDMS composition. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 2726–2733, 2007     

Et3N‐Prompted Efficient Synthesis of Anthracenyl Pyrazolines and Their Cytotoxicity Evaluation against Cancer Cell Lines

A series of anthracenyl pyrazoline derivatives ( 3a – o ) were synthesized with an aim to evaluate their in vitro anticancer activities. Anthracenyl pyrazoline compounds were prepared by the reaction between various anthracenyl chalcones ( 1a – o ) and hydrazine hydrate ( 2 ). The reactions were carried out under reflux in the presence of triethylamine and ethanol for 24 h, and the obtained yields were from good to excellent (90–97%). The structure of each compound is well characterized by IR, ¹H‐NMR, ¹³C‐NMR, elemental analyses, and mass spectroscopic technics, and the molecular structures of compounds 3d and 3e were solved by single‐crystal X‐ray crystallographic methods. The newly synthesized compounds ( 3a – o ) were evaluated for their in vitro cytotoxic studies against four human cancer cell lines MCF‐7 (breast cancer cell lines), SK‐N‐SH (neuroblastoma cancer cell lines), HeLa (cervical cancer cell lines), and HepG2 (liver cancer cell lines), and the screening results show strong cytotoxic effects for most of the synthesized compounds against the three cell lines except SK‐N‐SH cells. Notably, compounds 3a , 3j , 3l , 3m , 3n , and 3o showed a highly potential activity against HeLa cells (IC₅₀: 0.22, 0.3, 0.3, 0.10, 0.25, and 0.25 μM), while compounds 3i , 3k , 3l , and 3m showed a significant cytotoxic activity in HepG2 cells (IC₅₀: 0.22, 0.44, 0.40, and 0.22 μM), whereas compounds 3a , 3b , 3d , and 3e exhibit a promising cytotoxicity against MCF‐7 cells (IC₅₀: 0.73, 0.495, 0.493, and 0.66 μM).     

Synthesis of stannic(IV) complexes: Their structural elucidation in solid and solution state and antimicrobial activity

A series of organotin(IV) thiocarboxylates have been synthesized with the general formula R₂SnL₂ and R₃SnL (R = Ph₂(I), Me₃(II), n‐Bu₃(III), Ph₃(IV), Cy₃(V), Me₂(VI), n‐Bu₂(VII), and L = piperidine‐1‐thiocarboxylic acid) in anhydrous toluene under the reflux conditions. The complexes were characterized by microanalysis, IR, ¹H and ¹³C NMR, mass spectrometry, and XRD. NMR data revealed that thiocarboxylic acid acts as bidentate, and complexes exhibit the four‐coordinated geometry in solution state. In solid state, diorganotin complexes exhibit the hexa‐coordinated geometry whereas the triorganotin(IV) compounds show the five‐coordinated geometry. These complexes were also tested for their antimicrobial activity along with the ligand against different animals, plant pathogens, and Artemia salina. All complexes with few exceptions show high activity as compared to the ligand. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:664–674, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20380     

Synthesis and Inhibitory Activity Evaluation of 2,6‐Disubstituted Purine Derivatives

A series of novel 2,6‐disubstituted purine derivatives were designed and synthesized from 2,6‐dichloropurine. The structures of target compounds were determined by ¹H‐NMR, ¹³C‐NMR, and HRMS. The synthesized compounds were evaluated for their inhibitory activities against lung cancer cell lines of A549 and liver cancer cell lines of Bel‐7402. 2‐(4‐Benzyloxy‐phenylamino)‐6‐(cyclohexylamino)purine( 3 ), 2‐(4‐chloro‐phenylamino)‐6‐(n‐butylamino)purine ( 5 ), 2‐(4‐morpholinoamino)‐6‐(4‐hydroxy‐phenylamino)purine ( 9 ), and 2‐(4‐O‐galactosyl‐phenylamino)‐6‐(cyclohexylamino)purine ( 12 ) exhibited moderate inhibitory activity.     

Synthesis and characterization of oxime‐bearing hexakis(2‐formylphenoxy)‐phosphazene and its derivatives

Hexakis(2‐formylphenoxy)cyclotri‐phosphazene ( 2 ) was obtained from the reaction of hexachlorocylotriphosphazene ( 1 ) with 2‐hydroxy‐benzaldehyde. Hexakis(2‐[(hydroxyimino)methyl]‐phenoxy)cyclotriphosphazene (3) was synthesized from the reaction of 2 with hydroxlaminehydrochloride in pyridine. Hexasubstituted compounds 4, 5, 6, 8, 9 , and 10 were obtained from the reactions of 3 with methyl iodide, ethyl bromide, allyl bromide, propanoyl chloride, benzoyl chloride, and 4‐methoxybenzoyl chloride, respectively. Disubstituted product 7 was obtained from the reaction of 3 with chloroacetyl chloride. Pure and defined products could not be obtained from the reaction of 3 with acetyl chloride, benzyl chloride, and 2‐chlorobenzoyl chloride. The compounds were characterized by elemental analysis and IR, ¹H, ¹³C, and ³¹P NMR spectroscopy. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:791–797, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20350     

N‐substituted bis(tetrazol‐5‐yl)diazenes: Synthesis,spectra, X‐ray molecular and crystal structures,and quantum‐chemical DFT calculations

N‐Substituted bis(tetrazol‐5‐yl)diazenes (substituents are 1‐CH₃ ( 3a ), 1‐Ph ( 3b ), 2‐CH₃ ( 3c ), and 2‐^tBu ( 3d )) were synthesized by oxidative coupling of corresponding 5‐aminotetrazoles. All compounds were characterized with ¹H and ¹³C NMR, IR‐ and UV‐spectroscopy, and thermal analysis. Crystal and molecular structures of bis(1‐phenyltetra‐ zol‐5‐yl)diazene ( 3b ) and bis(2‐tert‐butyltetrazol‐5‐yl)diazene ( 3d ) were determined by single crystal X‐ray diffraction. Molecules of these compounds are trans‐isomers in solid. According to X‐Ray data, 3b molecule is S‐trans‐S‐trans conformer, however 3d is S‐cis‐S‐cis one. Quantum‐chemical investigation of geometry and relative stability of cis‐ and trans‐isomers and stable conformations of compounds 3a–d was carried out. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:24–35, 2010; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20574     

Phenothiazine‐S,S‐dioxide‐ and fluorene‐based light‐emitting polymers: Introduction of e−‐deficient S,S‐dioxide into e−‐rich phenothiazine

A novel series of poly(10‐hexyl‐phenothiazine‐S,S‐dioxide‐3,7‐diyl) and poly(9,9′‐dioctyl‐fluorene‐2,7‐diyl‐alt‐10‐hexyl‐3,7‐phenothiazine‐S,S‐dioxide) (PFPTZ‐SS) compounds were synthesized through Ni(0)‐mediated Yamamoto polymerization and Pd(II)‐catalyzed Suzuki polymerization. The synthesized polymers were characterized by ¹H NMR spectroscopy and elemental analysis and showed higher glass transition temperatures than that of pristine polyfluorene. In terms of photoluminescence (PL), the PFPTZ‐SS compounds were highly fluorescent with bright blue emissions in the solid state. Light‐emitting devices were fabricated with these polymers in an indium tin oxide/poly(3,4‐ethylene dioxythiophene):poly(styrene sulfonate)/polymer/Ca/Al configuration. The electroluminescence (EL) of the copolymers differed from the PL characteristics: the EL device exhibited a redshifted greenish‐blue emission in contrast to the blue emission observed in the PL. Additionally, this unique phenothiazine‐S,S‐dioxide property, triggered by the introduction of an electron‐deficient SO₂ unit into the electron‐rich phenothiazine, gave rise to improvements in the brightness, maximum luminescence intensity, and quantum efficiency of the EL devices fabricated with PFPTZ‐SS. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 1236–1246, 2007     

Synthesis,characterization and in vitro cytotoxicity of palladium(II) complexes with mixed ligands. X‐ray diffraction study of C31H36ClNPPdS2

Pd(II) complexes with organophosphines and dithiocarbamates derivatives of α‐amino acids were synthesized by reacting N,N‐dicyclohexyldithiocarbamate (DCHDTC, compounds 1 – 3 ) and N‐methylcyclohexyldithiocarbamate (MCHDTC, compounds 4 – 6 ) with (R₃P)₂PdCl₂ (R = Ph, o‐tolyl, Ph₂Cl) in a 1:1 molar ratio. The complexes were characterized by elemental analyses, FT‐IR, multinuclear (¹H, ¹³C and ³¹P) NMR and single X‐ray crystallography, showing that the dithiocarbamate acts as a bidentate ligand and binds to Pd(II) via two sulfur atoms, resulting in a square planar geometry around Pd(II). The cytotoxicity of compounds 2, 3 and 4 was determined in vitro against six human tumour cell lines, MCF7, EVSA‐T, WIDR, IGROV, M19 MEL, A498 and H226. Compounds 3 and 4 showed a moderate to low cytotoxicity, whereas compound 2 exhibited a very low cytotoxicity. The results of antifungal assays showed that compounds 1 – 6 possess antifungal activity against Fusarium moniliformes, Fusarium saolani, Mucor sp., Aspergillus niger and Aspergillus fumigatus. The anti‐inflammatory screening results of 1–6 are quite similar to those observed for the standard drug Declofenac at 10 mg kg^?1, which inhibited the odema by 74% after 4 h. Copyright © 2007 John Wiley & Sons, Ltd.     

1,3,2‐Oxazastibinanes: Novel six‐membered heterocycles

The hitherto unreported oxazastibinanes 3 have been synthesized by the sodium borohydride reduction of 3‐phenyl‐1‐arylamino‐3‐oxopropane ( 1 ) and subsequent cyclization of the disodium salt of 3‐phenyl‐1‐arylamino‐3‐hydroxypropane ( 2 ) with R₃SbBr₂ (R = Ph, p‐tolyl, or mesityl). These compounds have been characterized by elemental analyses, molecular weight determination, and by IR, far IR, ¹H, and ¹³C NMR spectral studies. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:417–420, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10155     

2,2,2‐triaryl‐4‐oxo‐1,3,2‐benzoxazastibinines

The hitherto unreported 4‐oxo‐1,3,2‐benzoxazastibinines 2 have been synthesized by the cyclization of disodium salt of salicylanilide ( 1 ) with Ar₃SbBr₂ (Ar = Ph, p‐tolyl, or mesityl). These compounds have been characterized by elemental analyses, molecular weight determination, and by IR, far IR, ¹H, and ¹³C NMR spectral studies. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:622–624, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10202     

Synthesis,structure, and biological activity of novel 4,5‐disubstituted thiazolyl urea derivatives

Novel 1‐(2,4‐dichlorophenyl)‐3‐[4‐aryl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl] urea derivatives were synthesized by the reaction of 2‐amino‐4‐sustituted phentyl‐5‐(1H‐1,2,4‐triazol‐1‐yl) thiazoles with 2,4‐dichloro‐1‐isocyanatobenzene. Structures of the title compounds were confirmed by the elemental analysis, ¹H NMR, and single crystal X‐ray diffraction analysis. Biological evaluation showed that some of them possess promising antitumor activities. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:2–6, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20375     

Synthesis,structural characterization and cytotoxic activity of organotin derivatives of indomethacin

The synthesis, characterization and cytotoxic properties in vitro of tri‐n‐butyltin 1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetate ( 1 ), tri‐phenyltin 1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetate ( 2 ), tetra‐n‐butyltin[bis‐1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetato]distannoxane ( 3 ) and di‐n‐butyltin bis‐1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetate ( 4 ) are described. These compounds have been characterized by ¹H, ¹³C and ¹¹⁹Sn NMR spectroscopy in solution and ¹¹⁹Sn NMR in the solid state, infrared spectroscopy, elemental analysis and X‐ray diffraction for compound 1 . The growth inhibition effects of compounds 1–4 against the lung adenocarcinoma cell line SK‐LU‐1 as well as the cervical cancer cell line HeLa were determined. Compounds 1 and 2 exhibit cytotoxic activity, whereas compounds 3 and 4 are inactive. Copyright © 2008 John Wiley & Sons, Ltd.