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2010 Vol. 21, No. 05
Published: 2010-05-20

507 Synthesis and antibacterial activity of C-2(S)-substituted pleuromutilin derivatives
Li Qiang Fu, Xing Sheng Guo, Xin Liu, Hui Li He, Yu Ling Wang, Yu She Yang

In order to probe the effect of C-2(S)-substituted groups in the antibacterial activity, a series of novel C-2(S) substituted pleuromutilin analogs of SB-225586 were synthesized and evaluated for their in vitro antibacterial activity. The results of antibacterial acticities indicated that C-2(S)-substituted pleuromutilin derivatives retained appreciable antibacterial activity, and the 2-fluorination compounds 6a and 6b are more potent than the corresponding 2-hydroxylation analogues7a and 7b.

2010 Vol. 21 (05): 507-510 [Abstract] ( 1648 ) HTML (1 KB)  PDF  (0 KB)  ( 530 )
511 Synthesis of 2, 5-disubstiututed tetrahedrofurans from organozinc halides and lactones
Dan Feng Huang, Hai Feng Wang, Chang Ming Xu, Teng Niu, Yu Lai Hu

2,5-Disubstituted tetrahydrofurans were obtained from lactones and organozinc halides in moderate to high yield in the presence of Lewis acids.

2010 Vol. 21 (05): 511-514 [Abstract] ( 1037 ) HTML (1 KB)  PDF  (0 KB)  ( 529 )
515 A novel thermoregulated phosphine ligand used for the Rh-catalyzed hydroformylation of mixed C11~12 olefins in aqueous/organic biphasic system
Zhi Jiang Ji, Jing Yang Jiang, Yan Hua Wang

A novel thermoregulated phosphine ligand Ph2P(CH2CH2O)nCH3 ( n = 22 ) was synthesized and used for the Rh-catalyzed hydroformylation of mixed C11~12 olefins in aqueous/organic biphasic system. Under the optimized conditions, pressure = 5 MPa (H2:CO = 1:1 ), phosphine / Rh = 13 ( molar ratio ), reaction time = 6 h and temperature =130 oC, the conversion of C11~12 olefins and the yield of aldehyde are 99 % and 94%, respectively. The catalyst retained in aqueous phase can be easily separated from the product-containing organic phase by simple phase separation and the catalytic activity remains almost constant after four consecutive cycles.

2010 Vol. 21 (05): 515-518 [Abstract] ( 1072 ) HTML (1 KB)  PDF  (0 KB)  ( 662 )
519 Lithium bromide catalyzed solvent free method for synthesis of 2-substituted benzimidazoles and imidazopyridines
Deepak V. Dekhane, Shivaji S. Pawar, Sunil V. Gupta, Murlidhar S. Shingare, Shivaji N. Thore

The first successful lithium bromide mediated solvent free condensation of arylenediamine and esters to obtain 2-substituted benzimidazole and imidazopyridine in good to excellent yields is described.

2010 Vol. 21 (05): 519-523 [Abstract] ( 1118 ) HTML (1 KB)  PDF  (0 KB)  ( 567 )
524 A new approach to the synthesis of diacetals (diketals) pentaerythritol catalyzed by SO3H-functionalized ionic liquids
Yuan Yuan Wang, Yan Nan Xu, Zhi Zhong Wang, Li Yi Dai

In this article, an efficient, simple and environmentally friendly approach to the synthesis of diacetals (diketals) pentaerythritol using SO3H-functionalized ionic liquids (ILs) as catalysts was reported. The ILs show high catalytic activity and reusability with good to excellent yields of the desired products. Hammett method has been used to determine the acidity order of these ionic liquids and the results are consistent with the catalytic activities observed in acetalization reaction. Maximum product yield 93% were observed on using [PSPy]OTf as catalyst and it can be reused at least 8 times without obvious activity loss.

2010 Vol. 21 (05): 524-528 [Abstract] ( 1297 ) HTML (1 KB)  PDF  (0 KB)  ( 600 )
529 Synthesis of 3-hydroxyflavone fluorescent probes and study of their fluorescence properties
Xiao Dong Zhao, Chang Jun Sun, Qing Qiang Yao, Wen Bao Li

Direct measurement of dipole potential in biological membranes has been impossible and 3-hydroxyflavones (3HFs) have allowed detection of changes in dipole potential in biological systems. In the present study, sixteen derivatives of 3HF with aliphatic hydrocarbon chains of different lengths at 4′-position and 6-position were synthesized. The basic fluorescence properties of 3HFs are maintained in all the probes in terms of strong blue shift in maximum fluorescence emission wavelength and >100 fold increase in quantum yield in organic solvents and in dioleoylphosphatidylcholine (DOPC) small unilamellar vesicles (SUV) in comparison to in aqueous Hepes buffer (15 mmol/L, pH 7.4). More importantly, the ability of the new compounds to report dipole potential changes in biological systems are also maintained, since all the new probes showed spectrum properties that are similar to yet different from that of F4N1, which potentially may allow more sensitive measurement of the dipole potential change in membranes.

2010 Vol. 21 (05): 529-532 [Abstract] ( 1306 ) HTML (1 KB)  PDF  (0 KB)  ( 740 )
533 Preparation and characterization of hexadecane microcapsule with polyurea--melamine formaldehyde resin shell materials
Gui Bo Gao, Chun Xiang Qian, Min Jie Gao

This paper gives a brief report of the preparation of hexadecane microcapsule with polyurea-melamine formaldehyde resin shell materials (HMPM). The sealing performance and thermal stability of HMPM was enhanced much more effectively than that of microcapsule with polyurea shell material (HPM). The results of microscopical imaging analysis system, DSC, TG, and laser particle analyzer were briefly introduced.

2010 Vol. 21 (05): 533-537 [Abstract] ( 1083 ) HTML (1 KB)  PDF  (0 KB)  ( 532 )
538 An efficient chemo- and regioselective three component synthesis of pyridazinones and phthalazinones using activated KSF
L. Zare, N. O. Mahmoodi, A. Yahyazadeh, M. Mamaghani, K. Tabatabaeian

The first three component and regioselective synthesis of pyridazinones and phthalazinones from arenes, anhydrides and ArNHNH2 in the presence of efficient recyclable heterogeneous catalyst, montmorillonite-KSF, in high yield and short reaction time is reported.

2010 Vol. 21 (05): 538-541 [Abstract] ( 1054 ) HTML (1 KB)  PDF  (0 KB)  ( 564 )
542 Synthesis of 6-chloro and 6-fluoro-4-hydroxyl-2-quinolone and their azo disperse dyes
Enayat O’llah Moradi-e-Rufchahi

In this study, 6-chloro-4-hydroxy-2-quinolone and 6-flouro-4-hydroxy-2-quinolone were synthesized from corresponding dianilides. These compounds were coupled with some diazotized aromatic amines to give the corresponding azo disperse dyes. The structures of the quinolone derivatives and new azo dyes were confirmed by UV-vis, FT-IR, 1H NMR and elemental analysis.

2010 Vol. 21 (05): 542-546 [Abstract] ( 1172 ) HTML (1 KB)  PDF  (0 KB)  ( 509 )
547 Efficient one-pot synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes using boric acid under solvent-free conditions
Zahed Karimi-Jaberi, Mohsen Keshavarzi

Boric acid efficiently catalysed the one-pot reaction of alkyl or aryl aldehydes with 2-naphthol to afford the corresponding 14-alkyl- or aryl-14H-dibenzo[a,j]xanthenes in good yields under solvent-free conditions.

2010 Vol. 21 (05): 547-549 [Abstract] ( 1534 ) HTML (1 KB)  PDF  (0 KB)  ( 528 )
550 Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst
A. Davoodnia, S. Allameh, A.R. Fakhari, N. Tavakoli-Hoseini

A simple and efficient procedure for the synthesis of 2-arylquinazolin-4(3H)-ones has been developed through cyclocondensation of 2-aminobenzamide with aromatic aldehydes using tetrabutylammonium bromide (TBAB) as novel neutral ionic liquid catalyst in the presence of copper (II) chloride (CuCl2) as oxidizing agent under solvent-free conditions at 100 oC. In the absence of CuCl2 and under a nitrogen atmosphere, the unoxidized intermediates, 2-aryl-2,3-dihydroquinazolin-4(1H)-ones, were isolated. Treatment of these intermediates with CuCl2 in TBAB media gave the oxidized products 2-arylquinazolin-4(3H)-ones. On the other hand, cyclocondensation of 2-aminobenzamide with aromatic aldehydes in TBAB under microwave irradiation directly gave 2-arylquinazolin-4(3H)-ones.

2010 Vol. 21 (05): 550-553 [Abstract] ( 1540 ) HTML (1 KB)  PDF  (0 KB)  ( 615 )
554 Design, synthesis and antitumor activity of 6,7-disubstituted-4-(heteroarylamino)quinoline-3-carbonitrile derivatives
Bao Liu, Qi Dong You, Zhi Yu Li

A series of new 6,7-disubstituted-4-(benzothiazol-6-ylamino)quinoline-3-carbonitrile derivatives (12a-l) were synthesized. The cytotoxicity of 12 new compounds was evaluated in AGS, HepG2 and HT-29 cell lines. The results showed that compounds 12g, 12h, 12i, 12k and 12l displayed more potent cytotoxic activities than Bosutinib, compound 12l exhibited the most potent antitumor activity among the tested compounds.

2010 Vol. 21 (05): 554-557 [Abstract] ( 1495 ) HTML (1 KB)  PDF  (0 KB)  ( 571 )
558 Synthesis of a novel benzoxazine containing benzoxazole structure
Po Yang, Yi Gu

A high-purity benzoxazine (Boz-BOA) containing benzoxazole structure was successfully synthesized by three-step synthetic method using 2-(4-aminophenyl)-1H-benzoxazole-5-amine (BOA) and ortho-hydroxybenzaldehyde. The structure of Boz-BOA was confirmed by FTIR and 1H NMR spectra. The DSC was utilized to probe the curing behavior of Boz-BOA and exhibited a narrow melting peak and curing exothermic peak.

2010 Vol. 21 (05): 558-562 [Abstract] ( 1431 ) HTML (1 KB)  PDF  (0 KB)  ( 555 )
563 One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives using new organocatalyst
Seyed Meysam Baghbanian, Samad Khaksar, Seyed Mohammad Vahdat, Maryam Farhang

Herein we report an efficient organocatalyst for the multicomponent Hantzsch reaction at mild condition. The product easily isolated by simple filtration and catalyst can be recovered.

2010 Vol. 21 (05): 563-567 [Abstract] ( 1181 ) HTML (1 KB)  PDF  (0 KB)  ( 549 )
568 A contribution to the study of the modified Marschalk reaction: Hydroxymethylation of 6,8-O-dimethyl emodin
Hai Shan Jin, Li Ming Zhao

Hydroxymethylation of 6,8-O-dimethyl emodin was easily achieved in good yields by the modified Marschalk reaction. The influence of the amount of solvent, base and formaldehyde toward the hydroxymethylation was discussed. The results showed that a relatively dilute reaction solution facilitated the generation of the desired 2-hydromethyl product, while the thick reaction solution benefited the generation of the methylated quinizarins.

2010 Vol. 21 (05): 568-571 [Abstract] ( 1239 ) HTML (1 KB)  PDF  (0 KB)  ( 558 )
572 Synthesis of two new cage molecules containing trinitromethyl group
Cheng Hui Sun, Xin Qi Zhao, Yu Chuan Li, Si Ping Pang

Two new cage compounds, 4-trinitroethyl-10-nitro-2,6,8,12-tetraacetylhexaazaisowurtzitane (3) and 4-trinitroethyl-2,6,8,10,12-pentanitrohexaazaisowurtzitane (4), containing trinitromethyl group were synthesized by a novel method, and their structures were confirmed by IR, 1H NMR, MS and single crystal X-ray. DSC result shows that compound 4 has surprising thermal stability and could be a potential energetic compound.

2010 Vol. 21 (05): 572-575 [Abstract] ( 1927 ) HTML (1 KB)  PDF  (0 KB)  ( 505 )
576 Alkoxy substituted MeO-BIPHEP-type diphosphines ligands for asymmetric hydrogenation of aryl ketones
Meng Lin Ma, Zong Hai Peng, Yu Guo, Li Chen, Hua Chen, Xian Jun Li

In this paper, a series of optically active MeO-BIPHEP-type ligands, (S)-6,6´-dimethoxy-2,2´-bis(di-p- alkoxyphenylphosphine)-1,1´-biphenyl were synthesized and used to prepare the ruthenium complex. The effects of para-substituted were observed, the results showed that the ruthenium catalysts [diphosphine RuCl2 diamine] containing both t-Bu- and i-Pr substitutions have better activities and enantioselectivities than the non-substituted ruthenium catalysts in the asymmetric hydrogenation of acetophenone.

2010 Vol. 21 (05): 576-579 [Abstract] ( 1178 ) HTML (1 KB)  PDF  (0 KB)  ( 542 )
580 Two new furostanol saponins from Tribulus terrestris L.
Ya Juan Xu, Tun Hai Xu, Jun Ying Yang, Sheng Xu Xie, Yue Liu, Yun Shan Si, Dong Ming Xu

Two new furostanol glycoside, 26-O-β-D-glucopyranosyl-(25S)-5α-furost-3β,22α,26-triol-3-O-β-D- rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside (1) and 26-O-β-D-glucopyranosyl- (25S)-5α-furost-20(22)-en-2α,3β,26–triol-3-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2) were isolated from the fruits of Tribulus terrestris L.. The structures of two new furostanol saponins were elucidated by spectroscopic methods.

2010 Vol. 21 (05): 580-583 [Abstract] ( 982 ) HTML (1 KB)  PDF  (0 KB)  ( 532 )
584 A new benzophenone C-glycoside from Polygala telephioides Willd
Ting Jun Ma, Xi Cheng Shi, Chang Xi Jia

A new benzophenone C-glucoside, 3'-C-[4-O-(5-hydroxyferuloyl)-β-D-glucopyranosyl]-2',4',6'-trihydroxy-3,4-dimethoxy benzophenone, named telephenone D, was isolated from the whole plants of Polygala telephioides, and its structure was determined by analysis of spectroscopic data.

2010 Vol. 21 (05): 584-586 [Abstract] ( 935 ) HTML (1 KB)  PDF  (0 KB)  ( 567 )
587 A new ent-labdane diterpenoid lactone from Andrographis paniculata
Xiao Chi Ma, Zhan Ping Gou, Chang Yuan Wang, Ji Hong Yao, Xiu Lan Xin, Yuan Lin, Ke Xin Liu

A new ent-labdane diterpenoid lactone was isolated from Andrographis paniculata. Its structure was identified on the basis of spectral data including 2D NMR.

2010 Vol. 21 (05): 587-589 [Abstract] ( 952 ) HTML (1 KB)  PDF  (0 KB)  ( 536 )
590 A new sesquiterpene from hairy root culture of Artemisia annua
Dan Dan Zhai, Hui Zi Jin, Jian Jiang Zhong

A new sesquiterpene, (Z)-7-acetoxy-methyl-11-methyl-3-methylenedodeca-1,6,10-triene (AMDT) was isolated and identified from the methanol extract of the hairy root culture of Artemisia annua. The structure of AMDT was determined based on the analysis of spectroscopic data, notably of the 2D NMR spectra. This new compound showed cytotoxicity against human tumor cell lines 95-D and HeLa with IC50 values of 27.08 μmol/L and 20.12 μmol/L, respectively.

2010 Vol. 21 (05): 590-592 [Abstract] ( 1297 ) HTML (1 KB)  PDF  (0 KB)  ( 562 )
593 A novel antimicrobial flavonoidic glycoside from the leaves of Alstonia macrophylla Wall ex A. DC (Apocynaceae)
Mehtab Parveen, Zakia Khanam, Akhtar Ali, Syed Mohmud Ahmad

A new flavonoidic glycoside, tricin-4′-O-β-L-arabinoside (1) was isolated from the leaves of Alstonia macrophylla along with two known flavonoids, vitexin and myricetin-3′-rhamnoside-3-O-galactoside. Their structures were established by chemical and spectral evidences. The known compounds were reported for the first time from this plant. Moreover compound 1 was tested for antifungal and antibacterial avtivities.

2010 Vol. 21 (05): 593-595 [Abstract] ( 1290 ) HTML (1 KB)  PDF  (0 KB)  ( 581 )
596 Evodiagenine and dievodiamine, two new indole alkaloids from Evodia rutaecarpa
Qi Zhi Wang, Jing Yu Liang, Xu Feng

Two new indole alkaloids, evodiagenine 1 and dievodiamine 2 were isolated from the fruits of Evodia rutaecarpa (Juss.) Benth. The structure of compounds 1 and 2 were elucidated by comprehensive spectroscopic analysis and compound 1 was confirmed by X-ray crystallographic analysis.

2010 Vol. 21 (05): 596-599 [Abstract] ( 911 ) HTML (1 KB)  PDF  (0 KB)  ( 556 )
600 A new triterpenoid from the roots of Tripterygium Wilfordii
Lin Mei Zhou, Jiang Du, Chun Min Wu

A new triterpenoid 3, 4, 6-trihydroxy-2-oxo-1(10), 3, 5, 7-tetraen-23, 24-nor-D: A-friedooleana-29-oic acid, as well as twelve known terpenes were isolated from the roots of Tripterygium wilfordii. Its structure was established on the basis of spectroscopic methods.

2010 Vol. 21 (05): 600-602 [Abstract] ( 1183 ) HTML (1 KB)  PDF  (0 KB)  ( 509 )
603 A new pteridinedione from Whitmania pigra
Yun Feng Zheng, Cun Yu Li, Guo Ping Peng, Hong Yang Li
2010 Vol. 21 (05): 603-605 [Abstract] ( 919 ) HTML (1 KB)  PDF  (0 KB)  ( 533 )
606 A new cerebroside and its anti-proliferation effect on VSMCs from the radix of Cyperus rotundus L.
Pei Liu, Li Liu, Yu Ping Tang, Jin Ao Duan, Nian Yun Yang

A new cerebroside, 1-O-(β-D-glucopyranosyloxy)-(2S,3R,4E,8Z)-2-[(2´R)-2´-hydroxylignoceranoylamino]-4,8- tetradecene-3-diol was isolated from the 60% EtOH extract of traditional Chinese medical plant Cyperus rotundus L.. Its structure was determined on basis of spectroscopic data. This new compound showed anti-proliferation effect on vascular smooth muscle cells (VSMCs).

2010 Vol. 21 (05): 606-609 [Abstract] ( 976 ) HTML (1 KB)  PDF  (0 KB)  ( 605 )
610 New diterpenoids from Isodon excisoides
Yong Xue Wang, Lin Lin Zhu, Zhi An He, Ji Xia Zhang

Two new ent-kaurane diterpenoids, taihangexcisoidesin C (1) and it’s acetonide, taihangexcisoidesin D (2) were isolated from the leaves of Isodon excisoides. Their structures were determined by 1D and 2D spectroscopic analysis.

2010 Vol. 21 (05): 610-612 [Abstract] ( 1152 ) HTML (1 KB)  PDF  (0 KB)  ( 548 )
613 Fischelactone: a novel eremophilane dimer from Ligularia fischeri
Hong Zhao, Cheng Wu Weng, Xin Tian, Peng Xiang Lai, Jian Jun Huang, Wei Dong Xie

A novel eremophilane dimer, named fischelactone (1), was isolated from the roots of Ligularia fischeri. Complete structural elucidation of this compound was performed by HRESIMS, IR, 1D NMR and 2D NMR (1H-1H COSY, HMBC, HMQC and NOESY) data.

2010 Vol. 21 (05): 613-615 [Abstract] ( 990 ) HTML (1 KB)  PDF  (0 KB)  ( 599 )
616 A novel associative latex thickener using ethoxylated behenyl methacrylate as functional monomer
Xiang Zheng Kong, Chen Wang, Xu Bao Jiang, Xiao Li Zhu

Alkali soluble associative latex thickeners modified with hydrophobic long chain alkyl groups were prepared using common acrylics and varying amount of a functional monomer, ethoxylated behenyl methacrylate (BEM), through emulsion polymerization. It was found that the size of the emulsion particle became larger with addition of BEM. The light transmittance of the thickener latex sharply increased with pH varied from 6 to 7. The associative latex thickener manifested a higher viscosity when solids in the latex thickeners were kept at 0.5 wt% or higher, and the optimal amount of BEM was found to be around 2.5 wt%, or 0.16 mol%. Effective thickening was achieved in a styrene-acrylic copolymer latex.

2010 Vol. 21 (05): 616-619 [Abstract] ( 1288 ) HTML (1 KB)  PDF  (0 KB)  ( 550 )
620 One pot synthesis of a soluble polymer for zirconium carbide
Xue Yu Tao, Wen Feng Qiu, Hao Li, Tong Zhao

A new polymer, polyzirconoxanesal (PZS), is synthesized from the reaction of zirconium oxychloride octahydrate (ZrOCl2•8H2O) with acetylacetone (Hacac) and salicyl alcohol (SA) by one-pot protocol. The polymer is soluble in common organic solvents, such as ethanol, methanol, acetone, tetrahydrofuran and chloroform, and exhibits rheology with viscosity of 100~300mpa•s at 25°C. These properties are suitable for uses in fabrication of ceramic matrix fiber composites. Pyrolysis of this polymer at 1300°C in argon provides nanosized ZrC with spherical morphology and size of 20~100nm.

2010 Vol. 21 (05): 620-623 [Abstract] ( 1054 ) HTML (1 KB)  PDF  (0 KB)  ( 555 )
624 Hydrothermal synthesis and fluorescence of YF3: Eu3+
Guo Xian Zhua, Yong Da Li, Hong Zhou Lian, Yi Zhao Chen, Sheng Gui Liu

Europium (Ⅲ) -doped YF3 is prepared by a hydrothermal process at 200 °C. X-ray diffraction (XRD) pattern identifies the formation of YF3 phase without detectable impurity. Environment scanning electron microscopy (ESEM) image shows the even size distribution of the samples with cubic morphology. The excitation and emission spectra of the rare earth ions doped YF3 is investigated by fluorescence spectrophotometer. The excitation spectrum for 591 nm emission has several excitation bands at 320,365,386, 397 and 467,and the main peak value was 397 nm. Typical Eu3+ emission peaks at 591 nm(5D07F1) and 612 nm(5D07F2) are observed when excited by 397 nm, and the strongest emission is 591 nm, demonstrating that the rare earth ions occupy the centrosymmetrical sites in YF3.

2010 Vol. 21 (05): 624-627 [Abstract] ( 1437 ) HTML (1 KB)  PDF  (0 KB)  ( 558 )
628 Microwave-assisted synthesis of high aspect ratio ruthenium nanorods
Shu Ge Peng, Xi Ping Gao, Yong Ke Guo, Yu Qing Zhang, Han Fan Liu

Poly (N-vinyl-2-pyrrolidone) (PVP) –stabilized ruthenium nanorods with high aspect ratio by refluxing ruhenium(Ⅲ) chloride in n-propanol have been successfully prepared by means of a facile and rapid microwave heating for the first time. The structure and morphology of the obtained products were characterized by transmission electron microscopy (TEM), select area electron diffraction (SAED), ultraviolet-visible spectrophotometry (UV-vis), X-ray photoelectron spectroscopy (XPS) and Fourier transform spectroscopy (FT-IR). XPS analysis reveals that the nanorods were in the metallic state. TEM images showed that ruthenium nanorods had an obvious one-dimensional structure with the aspect ratio ranged from 5-40 nm and length up to 600 nm. SAED patterns indicated that the nanorods were single-crystalline with a hexagonal structure.

2010 Vol. 21 (05): 628-631 [Abstract] ( 1300 ) HTML (1 KB)  PDF  (0 KB)  ( 554 )
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