- One-pot enantioselective aziridination of olefins catalyzed by a copper(I) complex of a novel diimine ligand by using PhI(OAc)2 and sulfonamide as nitrene precursors
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A novel chiral C2-symmetric 1,4-diamine with multistereogenic centers at the backbone of the ligand has been synthesized from cheap natural product D-mannitol through multistep transformations. Its diimine derivative (3a) was found to be highly
- Wang, Xisheng,Ding, Kuiling
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Read Online
- Radiosensitization of human pancreatic cancer by piperlongumine analogues
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Radiotherapy is commonly used to treat advanced pancreatic cancers and can improve survival by 2 months in combination with gemcitabine. However, prognosis and survival improvement remain unsatisfactory, and effective therapies are urgently needed. Piperlongumine has been demonstrated to have therapeutic potentials against various cancers. In this study, we synthesized a series of piperlongumine derivatives and provided evidence that piperlongumine derivatives could be used as effective radiosensitizers in pancreatic cancer. Two compounds enhanced the radiosensitivity of Panc-1 and SW1990 cells. In a pancreatic bi-flank xenograft tumor model, they significantly inhibited tumor growth. Piperlongumine derivatives could induce reactive oxygen species (ROS) expression and regulate the Keap1-Nrf2 protective pathway with enhancement of radiation-induced DNA damage, G2/M-phase cell cycle arrest, and apoptosis. Collectively, our data offer a proof of concept for the use of piperlongumine derivatives as a novel class of radiosensitizers for the treatment of pancreatic cancer.
- Ma, Hao,Wu, Yuelin,Zhang, Wannian,Zhang, Huojun,Miao, Zhenyuan,Zhuang, Chunlin
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supporting information
p. 1197 - 1201
(2020/10/02)
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- Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
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Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.
- Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio
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supporting information
p. 4876 - 4894
(2021/09/20)
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- Pyridazinone derivative, and preparation method and medical application thereof
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The invention provides a pyridazinone derivative, and a preparation method and a medical application thereof. O-formylbenzoic acid used as a raw material reacts with dimethyl phosphite to obtain dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate, the dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate reacts with 3-cyano-4-fluorobenzaldehyde in the presence of triethylamine to prepare (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile, and the (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile is reduced by hydrazine hydrate to prepare 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid; and benzaldehyde or substituted aromatic formaldehyde or furfural used as a raw material and malonic acid undergo a Knoevenagel reaction to obtain cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid, the cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid and 1-tert-butoxycarbonylpiperazine undergo an amidation reaction, a tert-butoxycarbonyl group is removed from the obtained amidation product in the presence of trifluoroacetic acid, and the obtained product and the 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid undergo the amidation reaction to obtain a series of (E)-4-{3-[4-[(3-substituted aryl)acryloyl]piperazin-1-carbonyl]-4-fluorobenzyl}-2H-pyridazin-1-one derivatives. Results of preliminary pharmacological activity screening show that the compound represented by a general formula shown in the present invention has a certain in-vitro PARP-1 inhibition ability and a certain in-vitro tumor cell proliferation resisting activity. The structural general formula of compound is shown in the description; and in the general formula, Ar is selected from two formulas also shown in the description, and R1, R2, R3, R3, R4 and R5 can be the hydrogen atom, the fluorine atom, the chlorine atom, the bromine atom, a methyl group, a methoxy group, a tetrafluoromethyl group and a nitro group.
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- Design, synthesis, bioactivity, and computational studies of some morpholine-clubbed coumarinyl acetamide and cinnamide derivatives
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Abstract: The novel derivatives of morpholine-clubbed 3-substituted coumarinyl acetamide and cinnamide derivatives 5a–5j and 6a–6j have been synthesized via various 2-chloro-N-phenyl acetamide and cinnamoyl chloride derivatives, respectively. The required motif has been generated through Vilsmeier–Haack reaction on 4-hydroxycoumarin annelation of morpholine followed by imine formation and subsequently condensation with various 2-chloro-N-phenylacetamide and cinnamoyl chloride to furnish the desired molecule. The synthesized molecules were characterized by various spectroscopic methods viz IR, 1H NMR, 13C NMR. Their antimicrobial activities against various strains of bacteria and fungi have been evaluated, and computational studies have also been performed for all the newly synthesized analogs. Graphical Abstract: [Figure not available: see fulltext.].
- Chauhan, Prakashsingh M.,Thummar, Sandeep N.,Chikhalia, Kishor H.
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p. 1261 - 1277
(2018/05/22)
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- Design, synthesis, and docking studies of afatinib analogs bearing cinnamamide moiety as potent EGFR inhibitors
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Two series of afatinib derivatives bearing cinnamamide moiety (10a-n and 11a-h) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, PC-3, MCF-7 and Hela). Two selected compounds (10e, 10k) were further evaluated for the inhibitory activity against EGFR and VEGFR2/KDR kinases. Seven of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Three of them are equal to more active than positive control afatinib against one or more cell lines. The most promising compound 10k showed the best activity against A549, PC-3, MCF-7 and Hela cancer cell lines and EGFR kinase, with the IC50 values of 0.07 ± 0.02 μM, 7.67 ± 0.97 μM, 4.65 ± 0.90 μM and 4.83 ± 1.28 μM, which were equal to more active than afatinib (0.05 ± 0.01 μM, 4.1 ± 2.47 μM, 5.83 ± 1.89 μM and 6.81 ± 1.77 μM), respectively. Activity of compounds 10e (IC50 9.1 nM) and 10k (IC50 3.6 nM) against EGFR kinase were equal to the reference compound afatinib (IC50 1.6 nM). Structure-activity relationships (SARs) and docking studies indicated that replacement of the aqueous solubility 4-(dimethylamino)but-2-enamide group by cinnamamide moiety didn't decrease the antitumor activity. The results suggested that methoxy substitution had a significant impact on the activity and methoxy substituted on C-4 or C-2,3,4 position was benefit for the activity.
- Tu, Yuanbiao,Ouyang, Yiqiang,Xu, Shan,Zhu, Yan,Li, Gen,Sun, Chao,Zheng, Pengwu,Zhu, Wufu
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p. 1495 - 1503
(2016/03/15)
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- Investigation of cationic Claisen-type electrophilic rearrangements of amides
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Abstract Herein we report an extension of the electrophilic rearrangement of amides to the preparation of α-prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-
- Padmanaban, Mohan,Carvalho, Luísa C.R.,Petkova, Desislava,Lee, Ji-Woong,Santos, A. Sofia,Marques, M. Manuel B.,Maulide, Nuno
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supporting information
p. 5994 - 6005
(2015/08/03)
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- Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives
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A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.
- Singh, Manjeet,Kumar, Sunil,Kumar, Ashwani,Kumar, Pradeep,Narasimhan, Balasubramanian
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experimental part
p. 511 - 522
(2012/08/07)
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- Syntheses and structure-activity relationship studies of N-substituted-β-d-glucosaminides as selective cytotoxic agents
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Twenty-four diosgenyl saponins bearing cinnamoyl, carbamido and thiosemicarbazone groups were synthesized concisely. The cytotoxicities of the synthetic compounds on six human caner cell lines were evaluated employing MTT method. Structure-activity relationship could be observed, and two of the synthesized compounds (5c and 5f) exhibited selective inhibition on HeLa and MCF-7 cells, while three of them (5d, 5f and 5h) showed strong inhibition against HT1080.
- Wang, Bo,Liu, Yang,Wang, Yanshi,Liu, Xin,Cheng, Mao-Sheng
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supporting information
p. 7110 - 7113
(2013/01/15)
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- Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
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Tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N-N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building b
- Armstrong, Alan,Ferguson, Alexandra
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supporting information
p. 1747 - 1752,6
(2020/09/16)
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- The combination of 4-anilinoquinazoline and cinnamic acid: A novel mode of binding to the epidermal growth factor receptor tyrosine kinase
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A novel type of cinnamic acid quinazoline amide derivatives (20-42), which designed the combination between quinazoline as the backbone and various substituted cinnamic acid as the side chain, have been synthesized and their biological activities were evaluated within cytotoxicity assay firstly and then potent EGFR inhibitory activity. Compound 42 demonstrated the most potent inhibitory activity (IC50 = 0.94 μM for EGFR), which could be optimized as a potential EGFR inhibitor in the further study. Docking simulation was performed to position compound 42 into the EGFR active site to determine the probable binding model. Analysis of the binding conformation of 42 in active site displayed compound 42 was stabilized by hydrogen bonding interactions with Lys822, which was different from other derivatives. In the further study, Compounds 43 and 44 had been synthesized and their biological activities were also evaluated, which were the same as that we expected. Compound 43 has demonstrated significant EGFR (IC50 = 0.12 μM) and tumor growth inhibitory activity as a potential anticancer agent.
- Li, Dong-Dong,Lv, Peng-Cheng,Zhang, Hui,Zhang, Hong-Jia,Hou, Ya-Ping,Liu, Kai,Ye, Yong-Hao,Zhu, Hai-Liang
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p. 5012 - 5022
(2011/10/04)
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- Synthesis of polyhydroxylated aromatics having amidation of piperazine nitrogen as HIV-1 integrase inhibitor
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(E)-N-[3-(4-Cinnamoylpiperazin-1-yl)propyl]-3,4-dihydroxybenzamide and (E)-N-[3-(4-cinnamoylpiperazin-1-yl)propyl]-3,4,5-trihydroxybenzamide were designed and synthesized as potential HIV-1 integrase inhibitors and evaluated their inhibition to the strand
- Yang, Leifu,Xu, Xuemei,Huang, Yali,Zhang, Bin,Zeng, Chengchu,He, Hongqiu,Wang, Cunxin,Hu, Liming
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supporting information; experimental part
p. 5469 - 5471
(2010/12/24)
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- Use of the curtius rearrangement of acryloyl azides in the synthesis of 3,5-disubstituted pyridines: Mechanistic studies
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A series of disubstituted pyridine derivatives was synthesized from the corresponding acryloyl azides by acetic acid-promoted cycloaddition. This represents a novel and convenient synthetic approach to the symmetric 3,5-disubstituted pyridines. The nature of the substituent on the double bond and the utilized solvent were found to be crucial to the yield of pyridines. The reactivity of the acid-promoted cycloaddition increases with the presence of aryl groups, such as phenyl and pyridinyl. We also explored the comprehensive mechanism by the acid-promoted cycloaddition of 13C-labeled cinnamoyl azide. The symmetric 3,5-disubstituted pyridines were synthesized from acryloyl azides by acetic acid-promoted trimolecular condensation.
- Chuang, Ta-Hsien,Chen, Yu-Chi,Pola, Someshwar
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supporting information; experimental part
p. 6625 - 6630
(2010/11/18)
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- Mixed k/μ opioid receptor agonists: The 6β-naltrexamines
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Ligands from the naltrexamine series have consistently demonstrated agonist activity at κ opioid receptors (KOR), with varying activity at the μ opioid receptor (MOR). Various 6β-cinnamoylamino derivatives were made with the aim of generating ligands with
- Cami-Kobeci, Gerta,Neal, Adrian P.,Bradbury, Faye A.,Purington, Lauren C.,Aceto, Mario D.,Harris, Louis S.,Lewis, John W.,Traynor, John R.,Husbands, Stephen M.
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supporting information; experimental part
p. 1546 - 1552
(2010/01/07)
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- Discovery of novel protease activated receptors 1 antagonists with potent antithrombotic activity in vivo
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Protease activated receptors (PARs) or thrombin receptors constitute a class of G-protein-coupled receptors (GPCRs) implicated in the activation of many physiological mechanisms. Thus, thrombin activates many cell types such as vascular smooth muscle cells, leukocytes, endothelial cells, and platelets via activation of these receptors. In humans, thrombin-induced platelet aggregation is mediated by one subtype of these receptors, termed PAR1. This article describes the discovery of new antagonists of these receptors and more specifically two compounds: 2-[5-oxo-5-(4-pyridin-2-ylpiperazin-1-yl)penta-1,3- dienyl]benzonitrile 36 (F 16618) and 3-(2-chlorophenyl)-1-[4-(4-fluorobenzyl) piperazin-1-yl]propenone 39 (F 16357), obtained after optimization. Both compounds are able to inhibit SFLLR-induced human platelet aggregation and display antithrombotic activity in an arteriovenous shunt model in the rat after iv or oral administration. Furthermore, these compounds are devoid of bleeding side effects often observed with other types of antiplatelet drugs, which constitutes a promising advantage for this new class of antithrombotic agents. 2009 American Chemical Society.
- Perez, Michel,Lamothe, Marie,Maraval, Catherine,Mirabel, Etienne,Loubat, Chantal,Planty, Bruno,Horn, Clemens,Michaux, Julien,Marrot, Sebastien,Letienne, Robert,Pignier, Christophe,Bocquet, Arnaud,Nadal-Wollbold, Florence,Cussac, Didier,De Vries, Luc,Le Grand, Bruno
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experimental part
p. 5826 - 5836
(2010/03/24)
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- Design and synthesis of novel 2-phenylaminopyrimidine (PAP) derivatives and their antiproliferative effects in human chronic myeloid leukemia cells
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A series of novel 2-phenylaminopyrimidine (PAP) derivatives structurally related to STI-571 were designed and synthesized. The abilities of these compounds to inhibit proliferation were tested in human chronic myeloid leukemia K562 cells. (E)-3-(2-bromophenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2- ylamino)phenyl]acrylamide( 12d) was the most effective cell growth inhibitor and was 3-fold more potent than STI-571.
- Chang, Sheng,Yin, Shi-Liang,Wang, Jian,Jing, Yong-Kui,Dong, Jin-Hua
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experimental part
p. 4166 - 4179
(2009/12/28)
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- Synthesis of quaternary salts of ammonia from cinnamic acids and their plant growth retardant activity
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A series of N,N-dimethyl-N-benzyl ammonium chloride cinnamides (1a-e) were prepared from the reaction between cinnamyl chlorides (4a-e) and N,N-dimethylphenylmethanamines (6a-e). These salts were tested for their biological activity on germination, seedling growth and adventitious root formation on hypocotyl cuttings of Vigina radiata (SML-668) and were found to be markedly inhibit germination and seedling growth of mungbean seeds under laboratory conditions.
- Sharma,Kaur, Sukhvir
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p. 612 - 614
(2008/12/20)
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- Structural determinants of opioid activity in derivatives of 14-aminomorphinones: Effect of substitution in the aromatic ring of cinnamoylaminomorphinones and codeinones
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In recent years there has been substantial interest in the 14-aminodihydromorphinone derivatives methoclocinnamox (MC-CAM) and clocinnamox (C-CAM). To investigate the importance of the cinnamoyl ring substituent, a series of analogues have been prepared w
- Nieland, Nick P. R.,Moynihan, Humphrey A.,Carrington, Simon,Broadbear, Jillian,Woods, James H.,Traynor, John R.,Husbands, Stephen M.,Lewis, John W.
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p. 5333 - 5338
(2007/10/03)
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- Molecular structure and pretilt control of photodimerized-monolayers (PDML)
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We have studied the alignment of nematic liquid crystals on photo-sensitive chemisorbed monolayers. Surface modification and a single UV exposure at normal incidence resulted in photo-dimerized monolayers. A uniform, planar alignment of liquid crystals is realized on these surfaces. Chemical modification of the photo-sensitive chromophores of the monolayer allow fine-tuning of the pretilt. For a given alignment layer, there is a good correlation between the value of the pretilt and the polar properties of the liquid crystal used. Furthermore, the value of the pretilt depends on the chemical functionality at the outermost portion of the photo-alignment layer.
- Naciri, Jawad,Shenoy, Devanand K.,Grueeneberg, Kirsten,Shashidhar, Ranganathan
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p. 3468 - 3473
(2007/10/03)
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- Anthranilic acid based CCK1 antagonists: The 2-indole moiety may represent a "needle" according to the recent homonymous concept
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Recently we described an innovative class of non-peptide CCK1 antagonists keeping appropriate pharmacophoric groups on the anthranilic acid employed as a molecular scaffold. The lead compound obtained, VL-0395, characterized by the presence of Phe and the 2-indole moiety at the C- and N-termini of anthranilic acid, respectively, is endowed with submicromolar affinity towards CCK1 receptors. Thus, we have prepared and tested on CCK receptors a library of VL-0395 analogues in order to investigate the precise topological and essential key interactions of the 2-indole group of the lead with the CCK1 receptor. The obtained results confirm that this group establishes very specific interactions with this receptor sub-site and may be viewed as a "needle" group.
- Varnavas, Antonio,Lassiani, Lucia,Valenta, Valentina,Berti, Federico,Tontini, Andrea,Mennuni, Laura,Makovec, Francesco
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- Non-thiol farnesyltransferase inhibitors: Utilization of the far aryl binding site by 5-cinnamoylaminobenzophenones
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We recently described two novel aryl binding sites of farnesyltransferase. In this study, the cinnamoyl residue was designed as an appropriate substituent for our benzophenone-based AAX-peptidomimetic compound capable of occupying the far aryl binding site.
- Mitsch, Andreas,Wissner, Pia,Boehm, Markus,Silber, Katrin,Klebe, Gerhard,Sattler, Isabel,Schlitzer, Martin
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p. 493 - 501
(2007/10/03)
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- Photocyclization reactions. Part 8 [1]. Synthesis of 2-quinolone, quinoline and coumarin derivatives using trans-cis isomerization by photoreaction
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2-Quinolone 2, quinoline 3, coumarin (2H-1-benzopyran-2-one) 5, and 2H-1-benzopyran hemiacetal 6 were synthesized by photocyclization reaction of trans-o-aminocinnamoyl derivatives trans-1 and trans-o-hydroxycinnamoyl derivatives trans-4. The reaction proceeds through trans-cis isomerization followed by intramolecular cyclization.
- Horaguchi, Takaaki,Hosokawa, Nobuyuki,Tanemura, Kiyoshi,Suzuki, Tsuneo
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- Flash Vacuum Pyrolysis of Stabilised Phosphorous Ylides. Part 6. Pyrolysis of Substituted Cinnamoyl Ylides as a Route to Conjugated Enynes
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The substituted cinnamoyl ylides 6 and 7, readily prepared in one step from the quaternary phosphonium salts 8 and cinnamoyl chlorides 9, undergo extrusion of Ph3PO upon FVP to give the 1,3-enynes 12 and 13 in moderate yield.At 500 deg C there is little double bond isomerisation, but at 700 deg C this does occur to give almost 1:1 mixtures of E and Z isomers.In a few cases, including those with a nitrophenyl group present, the yields are poor or the reactions fail stabilised ylide was only partly successful since the severe conditions required for loss of the ester group resulted in significant isomerisation to naphthalene.The fully assigned 13C NMR spectra for 20 enynes are reported.One examples of the isomeric β,γ-unsaturated-δ-oxo ylides, 14 has been prepared and is found to undergo loss of Ph3P on FVP at 700 deg C to give indene and benzene in low yield.
- Aitken, R. Alan,Boeters, Christine,Morrison, John J.
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p. 2473 - 2480
(2007/10/02)
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- Hypoxic radiosensitizers: Substituted styryl derivatives
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A number of novel styryl epoxides, N-substituted-styryl-ethanolamines, N-mono and N,N'-bis-(2-hydroxyethyl)-cinnamamides - analogues to the known radiosensitizers RSU- 1069, pimonidazole and etanidazole - display selective hypoxic radiosensitizing activity. The styryl group, especially when substituted by electron withdrawing groups, was found to be bioisosteric to the nitroimidazolyl functionality. The most active derivative 2-(2'-nitrophenyl)ethen-1-yl-oxirane 8a displayed a sensitizer enhancement ratio (SER) of 5 relative to misonidazole.
- Nudelman,Falb,Odesa,Shmueli-Broide
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p. 619 - 625
(2007/10/02)
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- Anthelmintic activity of some 3-substituted phenyl-1-alkyl or phenyl propenones and propenamides
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In a search for new anthelmintic compounds, α,β-unsaturated ketones and amides were synthetized. Their anthelmintic activity was tested against two gastrointestinal worms, a nematode Syphacia obvelata and a cestode Hymenolepis nana. Structure-activity rel
- Walchshofer,Minjat,Petavy Paris
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p. 1068 - 1071
(2007/10/02)
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- MECHANISM OF ESTER AMINOLYSIS IN APROTIC MEDIA AND SPECIFIC SOLVENT EFFECTS
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The n-butylaminolysis of nitro-substituted 4'-nitrophenyl benzoates and cinnamates as well as of phenylacetates in aprotic solvents is governed by a kinetic law implying higher order terms in nucleophile.It is shown that the attacking nucleophile forms a n-? type molecular complex with the substrate before reaching the transition state in the subsequent kinetic step.This molecular complex is a true reaction intermediate as evidenced by the observed negative activation enthalpy.Other nucleophile molecules intervene as general base catalysts.Tertiary amines also catalyse the reaction.Their catalytic activity is linearly related to their hydrogen bond forming ability and it is not a direct function of their proton basicity.By varying the nucleophile structure, an excellent Broensted relationship could be obtained for the first time in aprotic media, the β of which confirms that the catalytic collapse of tetrahedral intermediate is the rate determining step.The reaction of cinnamates turns out to be less sensitive to structural changes of the substrate than is the reaction of benzoates as shown by the corresponding Hammet ? values.The electronic effects of 2-nitro groups are strongly solvent dependent.Once more, it is established that whenever specific solvent effects (?-donor or n-donor ability) are present, they dominate the overall effect.A general reaction mechanism is proposed which not only explains the various roles played by the nucleophile but also accounts successfully for the great variety of kinetic schemes observed in aprotic media.
- Nagy, Otto B.,Reuliaux, Victor,Bertrand, Nicole,Mensbrugghe, Anne Van Der,Leseul, Jean,Nagy, Janos B.
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p. 1055 - 1074
(2007/10/02)
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