Applied Organometallic Chemistry

Cover image for Vol. 30 Issue 5

Early View (Online Version of Record published before inclusion in an issue)

Editor-in-Chief Cornelis J. Elsevier

Impact Factor: 2.248

ISI Journal Citation Reports © Ranking: 2014: 11/45 (Chemistry Inorganic & Nuclear); 19/72 (Chemistry Applied)

Online ISSN: 1099-0739

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  1. 1 - 40
  1. Full papers

    1. Synthesis of the first nanomagnetic particles with semicarbazide-based acidic ionic liquid tag: an efficient catalyst for the synthesis of 3,3′-(arylmethylene)bis(4-hydroxycoumarin) and 1-carbamato-alkyl-2-naphthol derivatives under mild and green conditions

      Mohammad Ali Zolfigol, Roya Ayazi-Nasrabadi and Saeed Baghery

      Article first published online: 26 APR 2016 | DOI: 10.1002/aoc.3461

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      The synthesis is reported of the first semicarbazide-based ionic liquid stabilized on silica-coated Fe3O4 Brønsted acid magnetic nanoparticles – {Fe3O4@SiO2@(CH2)3Semicarbazide-SO3H/HCl} – as a full-fledged efficient catalyst for the synthesis of 3,3′-(arylmethylene)bis(4-hydroxycoumarins) and 1-carbamato-alkyl-2-naphthol derivatives.

    2. Synthesis and bio-evaluation of Tc-99 m-labeled fatty acid derivatives for myocardial metabolism imaging

      Jianping Liu, Qianqian Xue, Huan Wang, Hang Wang, Dawei Wang, Yu Fang and Huabei Zhang

      Article first published online: 26 APR 2016 | DOI: 10.1002/aoc.3476

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      We report the synthesis of a series of cyclopentadienyl tricarbonyl 99mTc complexes for myocardial imaging. Biodistribution and evaluation of 99mTc complexes in vitro have been studied.

    3. Cu–S-(propyl)-2-aminobenzothioate on magnetic nanoparticles: highly efficient and reusable catalyst for synthesis of polyhydroquinoline derivatives and oxidation of sulfides

      Arash Ghorbani-Choghamarani, Bahman Tahmasbi, Parisa Moradi and Nasrin Havasi

      Article first published online: 25 APR 2016 | DOI: 10.1002/aoc.3478

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      An efficient heterogenized copper catalyst was synthesized on Fe3O4 magnetic nanoparticles and was characterized. The activity of this organometallic catalyst was studied in the synthesis of polyhydroquinolines and also for selective oxidation of sulfides to sulfoxides in environmentally friendly solvent or under solvent-free conditions. The catalyst was separated using an external magnet and reused for several runs without significant loss of catalytic efficiency.

    4. Synthesis of a new iron–sulfur cluster compound and its photocatalytic H2 evolution activity through visible light irradiation

      Xiao-Bo Wang, Hui-Qin Zheng, Heng Rao, Hong-Chang Yao, Yao-Ting Fan and Hong-Wei Hou

      Article first published online: 21 APR 2016 | DOI: 10.1002/aoc.3481

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      A new iron–sulfur cluster compound was designed, synthesized and characterized. Photocatalytic hydrogen evolution using the target bioinspired complex was evaluated though a noble-metal-free homogeneous system. The total hydrogen production reached a turnover number of 404 (versus catalyst) under optimal conditions

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    5. Oxidation of ethylbenzene to styrene oxide in the presence of cellulose-supported Pd magnetic nanoparticles

      Sajjad Keshipour and Nastaran Kalam Khalteh

      Article first published online: 14 APR 2016 | DOI: 10.1002/aoc.3485

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      Pd and Fe3O4 nanoparticles were deposited on the N-(2-aminoethyl)acetamide functionalized cellulose for application in the catalytic oxidation reaction of ethylbenzene. Styrene oxide was obtained as the sole product of the oxidation reaction during 24h. This reaction has some advantages such as one-pot transformation of ethylbenzene to styrene oxide, high yield, excellent selectivity and magnetically recoverable catalyst. Also, the recovered catalyst is applicable in the oxidation reaction for 4 times without decrease in yield.

    6. Synthesis and characterization of a novel magnetic nano-palladium Schiff base complex: application in cross-coupling reactions

      Millad Aghayee, Mohammad Ali Zolfigol, Hassan Keypour, Meysam Yarie and Leila Mohammadi

      Article first published online: 13 APR 2016 | DOI: 10.1002/aoc.3477

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      A novel and task-specific nano-magnetic Schiff base ligand with phosphate spacer using 2-aminoethyl dihydrogen phosphate for coating of nano-magnetic Fe3O4 is introduced and successfully employed as catalyst for Sonogashira and Mizoroki–Heck C–C coupling reactions.

  2. Full Papers

    1. A highly efficient layered double hydroxide catalyst for direct ethoxylation of butyl acetate to oligo-ethylene glycol butyl ether acetates

      Jinchang Zhang, Lei Shi, Yan Meng, Yang Fu, Zhaobin Liu and Jianmin Zhu

      Article first published online: 13 APR 2016 | DOI: 10.1002/aoc.3454

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      A novel synthetic route that directly inserts ethylene oxide (EO) into butyl acetate (BAC) without any labile hydrogen to produce oligo-ethylene glycol butyl ether acetates (oligo-EBACs) is developed using an efficient acid–base bifunctional catalyst. After modification by organic acid, the as-prepared catalysts exhibit higher BAC conversion and EO catalytic activity with narrow EBAC adduct distribution. The molar ratio of BAC to EO is an important variable, significantly affecting the conversion and selectivity.

  3. Full papers

    1. Another application of (NH4)42[MoVI72MoV60O372(CH3COO)30(H2O)72] as a highly efficient recyclable catalyst for the synthesis of dihydropyrano[3,2-c]chromenes

      Marziyeh Rohaniyan, Abolghasem Davoodnia and Ahmad Nakhaei

      Article first published online: 12 APR 2016 | DOI: 10.1002/aoc.3479

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      We report another application of (NH4)42[MoVI72MoV60O372(CH3COO)30(H2O)72], a Keplerate-type giant-ball nanoporous isopolyoxomolybdate, as catalyst in the synthesis of 2-amino-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carbonitriles. The reactions occur in ethanol–water at room temperature and the process is operative with various aldehydes, giving the corresponding products in high yields. Other beneficial features include short reaction times, simple work-up and the recyclability and reusability of the catalyst for up to five consecutive runs.

    2. Synthesis, structure and cytotoxic activity of diethyltin N-[(2-oxyphenyl)methylene]phenylalaninates

      Qingtao Liu, Hao Zhang, Xiaoliang Zheng, Wenqiang Wang and Laijin Tian

      Article first published online: 12 APR 2016 | DOI: 10.1002/aoc.3480

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      Four new diethyltin N-[(2-oxyphenyl)methylene]phenylalaninates have been synthesized and characterized. Their trimeric macrocyclic and dimeric binuclear structures are discussed. Their in vitro cytotoxic activities against two human tumor cell lines have been tested.

    3. Synthesis of homoallylic amines and acylhydrazides by tin powder-promoted multicomponent one-pot allylation reactions

      Junyan Ma, Danfeng Huang, Ke-Hu Wang, Yanli Xu, Siying Chong, Yingpeng Su, Ying Fu and Yulai Hu

      Article first published online: 6 APR 2016 | DOI: 10.1002/aoc.3472

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      A convenient and efficient method for the synthesis of homoallylic amines and N′-homoallylic hydrazides is developed from one-pot reaction of carbonyl compounds, amines or N-acylhydrazines and allyllic bromide promoted by tin powder using water as solvent. N-Acylhydrazines, which are found to be more reactive than amines in these processes, can react not only with aldehydes but also with ketones to give the corresponding N′-homoallylic hydrazides.

  4. Full Papers

    1. Magnetic iron oxide nanoparticles–N-heterocyclic carbene–palladium(II): a new, efficient and robust recyclable catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions

      Abdol R. Hajipour, Nayereh S. Tadayoni and Zahra Khorsandi

      Article first published online: 6 APR 2016 | DOI: 10.1002/aoc.3475

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      We have synthesized a stable and powerful nano magnetic NHCs–palladium catalyst. It was characterized by different methods and used as an easy recyclable phosphine-free Pd catalyst for Mizoroki–Heck and Suzuki–Miyaura cross-coupling reaction.

  5. Book reviews

  6. Full papers

    1. Synthesis, spectral characterization and inhibitory potency of ferrocene-containing mannosides towards type 1 fimbriated Escherichia coli

      Veronika Kovač, Rosana Ribić, Vesna Petrović Peroković, Srđanka Tomić and Lidija Barišić

      Article first published online: 5 APR 2016 | DOI: 10.1002/aoc.3465

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      Mannose-based bioorganometallics containing an extended alkyl chain between sugar and ferrocene moieties were synthesized and tested as inhibitors of hemagglutination of guinea pig erythrocytes by type 1 fimbriated E. coli.

  7. Full Papers

    1. N-Heterocyclic carbenes derived from imidazo-[1,5-a]pyridines related to natural products: synthesis, structure and potential biological activity of some corresponding gold(I) and silver(I) complexes

      Monica Mihorianu, M Heiko Franz, Peter G Jones, Matthias Freytag, Gerhard Kelter, Heinz-Herbert Fiebig, Matthias Tamm and Ion Neda

      Article first published online: 28 MAR 2016 | DOI: 10.1002/aoc.3474

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      A series of Au(I) NHC complexes and Ag(I) NHC complexes derived from imidazo[1,5-a]pyridin-3-ylidenes were synthesized. Two of them were characterized by singlecrystal X-ray diffraction. All complexes were evaluated for their in vitro antitumor activity against 12 cell lines by using a monolayer cell survival and proliferation assay with a best IC50 value of 10.09 μM.

  8. Full papers

    1. Highly selective copper-catalyzed oxidation of benzyl alcohols to aromatic aldehydes in water at room temperature

      Jianglong Wu, Yan Liu, Xiaowei Ma, Ping Liu, Chengzhi Gu and Bin Dai

      Article first published online: 28 MAR 2016 | DOI: 10.1002/aoc.3473

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      Water-soluble 2N2O–Cu(II) complexes have been synthesized and used for the selective catalytic oxidation of benzylic alcohols to aromatic aldehydes in pure water resulting in high yields of up to 94% at room temperature.

    2. Ruthenium(II) complexes containing 4-methoxybenzhydrazone ligands: synthesis, characterization, DNA binding, DNA cleavage, radical scavenging and in vitro cytotoxic activity

      Maruthachalam Mohanraj, Ganesan Ayyannan, Gunasekaran Raja and Chinnasamy Jayabalakrishnan

      Article first published online: 28 MAR 2016 | DOI: 10.1002/aoc.3468

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      Ruthenium(II) complexes containing 4-methoxybenzhydrazone ligands were synthesized and characterized using various spectroscopic techniques. The DNA interaction of the ligands and complexes examined by absorption and cyclic voltammetry methods. The results indicated that, the compounds could interact with CT-DNA through intercalation. Further, in vitro free radical scavenging and cytotoxic potential of the synthesized complexes were also evaluated.

    3. Excellent Suzuki–Miyaura catalytic activity of a new Pd(II) complex with sulfonamide–Schiff base ligand

      Biplab Banik, Archana Tairai, Pradip K. Bhattacharyya and Pankaj Das

      Article first published online: 28 MAR 2016 | DOI: 10.1002/aoc.3464

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      A new Pd(II) complex derived from a sulfonamide–Schiff base ligand has been found to be an excellent catalyst for the Suzuki–Miyaura reactions of aryl bromides in water at room temperature and aryl chlorides in isopropanol at 60°C.

    4. Lanthanum immobilized on chitosan: a highly efficient heterogeneous catalyst for facile synthesis of novel (α,β-unsaturated) β-aminoketones

      Saima Tarannum and Zeba N. Siddiqui

      Article first published online: 28 MAR 2016 | DOI: 10.1002/aoc.3457

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      Lanthanum immobilized on chitosan was used as an efficient, recyclable and heterogeneous catalyst for aza-Michael reaction of β-enaminone.

  9. Full Papers

    1. Synthesis of 2,4,5-trisubstituted imidazoles over reusable CoFe2O4 nanoparticles: an efficient and green sonochemical process

      Esmaiel Eidi, M. Z. Kassaee and Zahra Nasresfahani

      Article first published online: 21 MAR 2016 | DOI: 10.1002/aoc.3470

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      Green sonochemical synthesis of trisubstituted imidazoles is achieved, in high yields through condensation of an aldehyde, benzyl and ammonium acetate, over reusable superparamagnetic CoFe2O4 nanoparticles.

  10. Full papers

    1. Eco-friendly synthesis of benzoxazepine and malonamide derivatives in aqueous media

      Mirzaagha Babazadeh, Rahim Hosseinzadeh-Khanmiri and Solmaz Zakhireh

      Article first published online: 17 MAR 2016 | DOI: 10.1002/aoc.3463

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      A series of malonamide and 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine derivatives was synthesized and characterized in the presence of a special, efficient and reusable heterogeneous catalyst of MCM-48/H5PW10V2O40 in aqueous media at room temperature. This method requires no toxic organic solvent or inert atmosphere and is according to green chemistry protocol.

    2. Amide (A)–thioamide (T) interconversions using Ph3SiSH (A to T) and Ph3SnOH (T to A) reagents

      Renzo N Arias-Ugarte, Hemant K Sharma and Keith H Pannell

      Article first published online: 17 MAR 2016 | DOI: 10.1002/aoc.3462

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      Oxophilicity of Si contrasts the thiophlicity of Sn in the conversions of amides to thioamides by Ph3SiSH, and the reverse process using Ph3SnOH.

  11. Full Papers

    1. Cobalt(II) acetylacetonate complex immobilized on aminosilane-modified SBA-15 as an efficient catalyst for epoxidation of trans-stilbene with molecular oxygen

      Qinghu Tang, Yanyan Wang, Jian Zhang, Ran Qiao, Xiaopei Xie, Yi Wang and Yanhui Yang

      Article first published online: 17 MAR 2016 | DOI: 10.1002/aoc.3451

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      Co(acac)2APTS@SBA-15 synthesized by a post-synthetic method using APTS (3-aminopropytrimethoxysilane) as a linking agent were attempted in the epoxidation of trans-stilbene (TS) with molecular oxygen. Compared to the sample prepared by the impregnation method as well as Co(acac)2 solutions, the Co(acac)2 immobilized catalysts exhibited remarkably higher TS conversion and TSO selectivity. The superior catalytic performance of this particular catalyst is attributed to high activity of the immobilized Co(acac)2 species on SBA-15.

    2. Immobilization of copper ions onto α-amidotriazole-functionalized magnetic nanoparticles and their application in the synthesis of triazole derivatives in water

      Firouz Matloubi Moghaddam, Seyed Ebrahim Ayati, Hamid Reza Firouzi and Fereshte Ghorbani

      Article first published online: 17 MAR 2016 | DOI: 10.1002/aoc.3460

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      Various types of triazoles were synthesized using magnetic nanoparticles functionalized with a new ligand based on triazole. Reactions were carried out in water and gave very good yields.

  12. Full papers

    1. Biological screening and DNA nuclease activity of transition metal complexes of N2O2 type of Knoevenagel condensate Schiff base

      Rajakkani Paul Pandiyan and Natarajan Raman

      Article first published online: 17 MAR 2016 | DOI: 10.1002/aoc.3466

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      Research Highlights

      • Developed novel DNA targeting metal chelates
      • Synthesis and characterization of new metallointercalators of N2O2 type
      • These complexes display better chemical nuclease activity
      • All the complexes are having better antimicrobial efficacy
    2. Synthesis and characterization of Mannich base monophenolate lanthanide complexes and their application in ring-opening polymerization of ε-caprolactone

      Ling Peng, Jing Zhao, Li-Jun Wang, Xian Tao, Yu-Long Wang and Ying-Zhong Shen

      Article first published online: 11 MAR 2016 | DOI: 10.1002/aoc.3455

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      A series of homoleptic lanthanide complexes [LaA3 (1), GdA3 (2), LaB3 (3), GdB3 (4), LaC3 (5), GdC3 (6), LaD3 (7), GdD3 (8), LaE3 (9), GdE3 (10)] were prepared by the amine elimination reactions of ligands reacting with Ln[N(SiMe3)2]3 (Ln = La, Gd). Complexes 1, 3, 5, 7 and 9 were all characterized. Complexes 3 and 5 were determined using single-crystal X-ray diffraction. The catalytic properties of complexes 1-10 in the ring-opening polymerization of ε-caprolactone were studied.

    3. A magnetic nanoparticle-catalyzed regioselective ring opening of epoxides by aromatic amines

      Najmedin Azizi, Parisa Kamrani and Mostafa Saadat

      Article first published online: 11 MAR 2016 | DOI: 10.1002/aoc.3450

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      Sulfonic acid-functionalized silica-coated magnetic Fe3O4 nanoparticles (Fe3O4@SiO2/SO3H) were synthesized and applied as a green catalyst for ring opening of epoxides with aromatic amines in good to excellent yields.

    4. New anticancer zinc(II) complexes comprising thiosemicarbazones of saturated ring: structure, DNA/protein binding, DNA cleavage, topoisomerase-1 inhibition and anti-proliferation studies

      Vikneswaran Rajamuthy, Naser Eltaher Eltayeb, Ramesh Subramaniam and Yahya Rosiyah

      Article first published online: 11 MAR 2016 | DOI: 10.1002/aoc.3458

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      Two zinc(II) complexes are identified as having excellent DNA/protein binding, nuclease and topoisomerase inhibition and antitumor activity.

    5. Green synthesis and characterization of monodispersed silver nanoparticles obtained using oak fruit bark extract and their antibacterial activity

      Hamed Veisi, Saba Hemmati, Hooman Shirvani and Hojat Veisi

      Article first published online: 10 MAR 2016 | DOI: 10.1002/aoc.3444

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      The Green synthesis of silver nanoparticles (Ag NPs) has been achieved using oak fruit bark extract as a reducing, capping and stabilizing agent. The antimicrobial activity of Ag NPs was greater towards Gram-positive bacteria compared to Gram-negative bacteria as determined using standard Kirby–Bauer disc diffusion assay and serial dilution.

  13. Book reviews

  14. Full Papers

    1. A structural investigation of heteroleptic pentavalent antimonials and their leishmanicidal activity

      Rabia Mushtaq, Muhammad Khawar Rauf, Marcus Bond, Amin Badshah, Muhammad Irshad Ali, Akhtar Nadhman, Masoom Yasinzai and Muhammad Nawaz Tahir

      Article first published online: 10 MAR 2016 | DOI: 10.1002/aoc.3456

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      Leishmanicidal activity and biocompatibility were assessed against Leishmania tropica KWH23 and human fibroblast blood cells, respectively. On the basis of significant (p < 0.01) IC50 values, the compounds were found to be most potent in comparison with the standard Glucantime (4.4 ± 0.77μg ml−1).

  15. Full papers

    1. Design, preparation and characterization of Cu/GA/Fe3O4@SiO2 nanoparticles as a catalyst for the synthesis of benzodiazepines and imidazoles

      Ahmad Shaabani, Heshmatollah Sepahvand, Seyyed Emad Hooshmand and Mahmoud Borjian Boroujeni

      Article first published online: 10 MAR 2016 | DOI: 10.1002/aoc.3448

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      The Cu supported on amino acid functionalized magnetic silica nanoparticles was prepared and characterized, which showed an excellent activity in the synthesis of the benzodiazepines and benzoimidazoles. This catalytic system could be magnetically separated and reused for five times without significant loss of its activity.

    2. Palladium–S-propyl-2-aminobenzothioate immobilized on Fe3O4 magnetic nanoparticles as catalyst for Suzuki and Heck reactions in water or poly(ethylene glycol)

      Arash Ghorbani-Choghamarani, Bahman Tahmasbi and Parisa Moradi

      Article first published online: 10 MAR 2016 | DOI: 10.1002/aoc.3449

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      A moisture- and air-stable heterogenized palladium catalyst was immobilized on Fe3O4 magnetic nanoparticles and characterized using various techniques. The catalytic activity of this organometal catalyst was studied in the Suzuki and Heck C–C coupling reactions in environmentally friendly solvents under phosphine-free conditions.

    3. A practical synthesis of 2-aminobenzothiazoles via copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in ionic liquids

      Ling Chen, Bin Huang, Quan Nie and Mingzhong Cai

      Article first published online: 10 MAR 2016 | DOI: 10.1002/aoc.3453

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      A highly efficient and reusable CuI/1,10-phenanthroline/[bmim][PF6] system for the tandem reaction of 2-iodoanilines with isothiocyanates has been developed. The reactions generated a variety of 2-aminobenzothiazoles in good to excellent yields and the CuI/1,10-phenanthroline/[bmim][PF6] system could be easily recycled and reused eight times without any loss of catalytic activity.

    4. Ferrocene-substituted 3,3′-diindolylmethanes with improved anticancer activity

      Julienne K. Muenzner, Aamir Ahmad, Matthias Rothemund, Sebastian Schrüfer, Subhash Padhye, Fazlul H. Sarkar, Rainer Schobert and Bernhard Biersack

      Article first published online: 6 MAR 2016 | DOI: 10.1002/aoc.3452

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      The ‘nutraceutical’ di(indol-3-yl)methane (DIM) was modified for improved antiproliferative effects in cancer cells by attachment of a ferrocene moiety at the methine bridge. The derivatives 2a, 2b and 2f were more active than DIM against breast, pancreas and prostate carcinoma cell lines, and also overcame the resistance to DIM of melanoma, cervix and colon cancer cell lines.

  16. Book reviews

  17. Full papers

    1. Design, synthesis, characterization and catalytic performance of a new cellulose-based magnetic nanocomposite in the one-pot three-component synthesis of α-aminonitriles

      Ali Maleki, Elnaz Akhlaghi and Reza Paydar

      Article first published online: 18 FEB 2016 | DOI: 10.1002/aoc.3443

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      A new biopolymer-based magnetic nanocomposite was prepared, characterized and applied as an efficient heterogeneous nanocatalyst in an important organic reaction.

    2. Synthesis, characterization and application of sulfonic acid supported on ferrite–silica superparamagnetic nanoparticles

      H. Hassani, M. A. Nasseri, B. Zakerinasab and F. Rafiee

      Article first published online: 18 FEB 2016 | DOI: 10.1002/aoc.3447

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      The synthesis of sulfuric acid supported on ferrite–silica superparamagnetic nanoparticles (Fe3O4@SiO2@SO3H) as a nanocatalyst with large density of acidic groups is suggested. The applicability of the synthesized magnetic nanoparticles was tested for the synthesis of diindolyloxindoles.

    3. New heteroleptic palladium(II) dithiocarbamates: synthesis, characterization, packing and anticancer activity against five different cancer cell lines

      Shahan Zeb Khan, Muhammad Kashif Amir, Imdad Ullah, Asma Aamir, John M. Pezzuto, Tamara Kondratyuk, Francine Bélanger-Gariepy, Akbar Ali, Sajid Khan and Zia-ur-Rehman

      Article first published online: 18 FEB 2016 | DOI: 10.1002/aoc.3445

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      We report two new heteroleptic palladium(II) dithiocarbamates and their anticancer activity against five cancer cell lines. The DNA binding ability may be the reason for their anticancer action. Furthermore, the anticancer activity depends on the stability of the complexes as confirmed by density functional theory studies.

    4. Polysiloxane microspheres functionalized with imidazole groups as a palladium catalyst support

      Piotr Pospiech, Julian Chojnowski, Urszula Mizerska, Tomasz Makowski, Krzysztof Strzelec and Natalia Sienkiewicz

      Article first published online: 11 FEB 2016 | DOI: 10.1002/aoc.3446

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      Palladium on polysiloxane microspheres is an efficient, recyclable catalyst of the hydrogenation of cinnamaldehyde. The reduction of olefin bond competes with direct hydrogenation of both aldehyde and olefinic functions without intermediate product.

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