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2016 Vol. 24, No. 1
Published: 2016-01-20
 
1 Synthesis and Biological Activities of Novel GPR40 Agonists
HUANG Jing， GUO Bin， ZHOU Xian-li
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15057
Methyl 2-｛6-［4-(tert-butyldimethylsilyloxy)but-2-ynyloxy］-2,3-dihydrobenzofuran-3-yl｝acetate（3） was prepared by protection of 2-butyne-1,4-diol with tertbutyldimethylsilyl chloride, then Mitsunobu reaction with methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate. Six novel benzo-dihydrofuran derivatives(7a~7f) were synthesized by deprotection, Mitsunobu reaction with phenol derivatives and hydrolysis from 3. The structures were characterized by 1H NMR， 13C NMR and HR-EI-MS. The activities of 7a~7f were tested in GPR40- transfected HEK293 cells. The results showed that 7a~7f all exhibited agonistic activities on GPR40, 7e and 7f were the most potent componds, with the EC50 of 0.593 μmol·L-1 and 0.596 μmol·L-1, respectively.
2016 Vol. 24 (1): 1-5 [Abstract] ( 608 ) HTML (1 KB)  PDF (3728 KB)  ( 376 )
6 Synthesis and Antifungal Activities of Novel Acrylpimaric Acid-based Dithiadiazole Compounds
CEN Bo, WEI You-jie, DUAN Wen-gui, LIN Gui-shan, LIU Lu-zhi, YANG Zhang-qi
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15046
Acrylpimaric acid(1) was synthesized by Diels-Alder cycloaddition reaction of rosin with acrylic acid, then converted to its dichloride(2). Eight novel acrylpimaric acid-based dithiadiazole compounds(4a~4h) were synthesized by N-acylation reaction of 2 with 2-amino-5-substituted phenyl-1,3,4-thiadiazoles. The structures were characterized by 1H NMR, 13C NMR, IR and elemental analysis. Antifungal activities tests showed that inhibition rates of  4d(R=m-Cl) against  Physalospora piricola, Cercospora arachidicola and Fusarium graminearum were 66.9%, 57.8% and 52.9%, respectively, at 50 μg·mL-1.
2016 Vol. 24 (1): 6-11 [Abstract] ( 412 ) HTML (1 KB)  PDF (4113 KB)  ( 366 )
12 Synthesis of Novel Benzoxazole Heteroaryl Thioether Compounds and Their Effects on Wheat Seed Germination Rate
LIU Xia, MA Cai-lian, YI Ze
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.14406
Nine benzoxazole heteroaryl thioether compounds(6, 10a and 10d were novel compounds) were designed and syntheiszed by active group combination principle with SCH2 as “bridge group”, using 2-amino-4-methylphenol and 2-amino-phenol as materials. The structures were characterized by 1H NMR, 13C NMR, IR and elemental analysis. Effects of 6 and 10 on wheat seed germination rate were investigated by petri dish-filter paper germination method. The results indicated that 6 and 10 could promote wheat seed germination rate at proper concentration.
2016 Vol. 24 (1): 12-15 [Abstract] ( 392 ) HTML (1 KB)  PDF (3030 KB)  ( 352 )
16 Synthesis of Pyridinyl-triazole Metal Complexes and Their Catalytic Activity for Ethylene Polymerization
XU Ma-li, QIN Lu, YAN Tao, CHEN Xia
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15307
The novel ligand, 1-benzyl-4-［o-pyridyl］-［1,2,3］-triazole(1), was synthesized via click reaction of benzyl chloride, 2-ethynylpyridine and sodium azide， using Cu(I) as the catalyst. Treatment of 1 with anhydrous FeCl2, CoCl2 or NiBr2·DME afforded the corresponding novel pyridyl-triazole metal complexes(2~4), respectively. The structures were characterized by 1H NMR, 13C NMR, IR and elemental analysis. The catalytic performance of 2~4 on ethylene polymerization indicated that 4 exhibited the highest activity with catalytic activity of 8.8 × 105 g·mol-1·h-1 under the condition of methylaluminoxane as cocatalyst, at 20 ℃ and Al/Ni ratio was 2 500/1.
2016 Vol. 24 (1): 16-20 [Abstract] ( 423 ) HTML (1 KB)  PDF (3681 KB)  ( 329 )
21 Synthesis of CdTe Quantum Dots and Their Interaction with Pb2+
YI Kui-yu, WEI Chun-sheng, SONG Zi-jia, WANG Meng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15050
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Thioglycolic acid and mercaptopropionic acid capped water-soluble CdTe quantum dots(QDs) were synthesized via hydrothermal process. The interaction between CdTe QDs and Pb2+ were investigated by fluorescence spectroscopic approaches. The results showed that the fluorescence of CdTe QDs could be irreversibly quenched by Pb2+. According to Stern-Volmer and double logarithm regression curve, the mechanism was discussed. The results showed that the intensity of CdTe QDs could be quenched by Pb2+ significantly, the quenching mechanism was intrinsic fluorescence of static quenching.
2016 Vol. 24 (1): 21-25 [Abstract] ( 324 ) HTML (1 KB)  PDF (6508 KB)  ( 358 )
26 Synthesis and Thermal Stability of A Novel Halogen-free Si-N Charring Agent
WANG Wen-tao, XIONG Kuan-kuan, ZHAO Bin, ZHAO Pei-hua, LIU Ya-qing
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15320
2-Chloro-4,6-di(3-triethoxysiloxy-1-aminoproply)-1,3,5-triazine(3) was prepared by substitution reaction of cyanuric chloride with γ-aminopropyl triethoxysilane. A novel halogen-free and high silicon content of charring agent(5) was synthesized by reaction of 3 with diethylenetriamine(4). The structure and thermal properties were characterized by 1H NMR, FT-IR and TGA. Effects of molar ratio of raw materials, acid-blinding agent, reaction time, reaction solvent and reaction temperature on the yield of 5 were investigated. The optimum reaction conditions were as followed: toluene was solvent, triethylamine was acid-binding agent, and n(3) : n(4) was 3.3:1, at 100 ℃ for 11 h, the yield was 62.7%. The initial decomposition temperature of 5 was 197 ℃, and the char yield was about 36.7% at 700 ℃.
2016 Vol. 24 (1): 26-29 [Abstract] ( 446 ) HTML (1 KB)  PDF (4008 KB)  ( 1090 )
30 Total Synthesis and Cytotoxicity of Tylophorine Analogue DCB-3501
LI Song-tao, LIU Jiang, HUANG Xue-shi
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15279
The tylophorine analogue DCB-3501 was totally synthesized by a seven-step reaction including Perkin condensation, free radical oxidative coupling, Swern oxidation, reductive amination and Fridel-Crafts acylation, using 3,4-dimethoxy-benzaldehyde and 3,4-dimethoxy-phenylacetic acid as the raw materials. The structure was confirmed by 1H NMR and ESI-MS. The in vitro cytotoxicity results showed that the IC50 of DCB-3501 against human colon cancer cell HCT116, human gastric cancer cell BGC-823, human hepatic cancer cell HepG-2, human cervical cancer cell HeLa and human large-cell lung cancer cell H460 were 20.0 μmol·L-1, 50.9 μmol·L-1, 2.1 μmol·L-1, 65.8 μmol·L-1 and 30.8 μmol·L-1, respectively.
2016 Vol. 24 (1): 30-34 [Abstract] ( 432 ) HTML (1 KB)  PDF (3812 KB)  ( 332 )
35 Synthesis and Crystal Structures of Novel Asymmetric Bis-Schiff Bases
YU Rong-hua, LIN Jia-huang, NI Qing-ling,XIE Yao, WANG Ya-na, LIANG Guang-ming
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15325
Two novel asymmetric bis-schiff bases, 2-【1,2-bis{［(E)-(2-hydroxyphenyl)ymethylidene］amino}-2-(2-pyridinyl)ethyl】phenol(2a) and 2-【1,2-bis{［(E)-(2-hydroxyphenyl)methylidene］amino}-2-(4-pyridinyl)ethyl】phenol(2b), were synthesized via one-pot method by condensation of sailcylaldehyde and NH3 with 2-aminomethylpyridine or 4-aminomethylpyridine, respectively. The structures were characterized by 1H NMR, 13C NMR, IR and X-ray single crystal diffraction(2b). 2b(CCDC： 1 423 247) belongs to monoclinic system, space group P2(1)/n with a=10.764(3) ， b=9.725(2) ， c=21.934(5) ， β=93.291(9) °， V=2 292.2(9) 3， Dc=1.268 mg·cm-3， Z=4， F(000)=920， μ=0.084 mm-1.
2016 Vol. 24 (1): 35-38 [Abstract] ( 481 ) HTML (1 KB)  PDF (2818 KB)  ( 586 )
39 Synthesis of Photo-sensitive Supported-Proline and Their Application in Asymmetric Aldol Reaction in Water
LI Guang-feng， HUANG Yan-gen
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15039
RAFT polymerization was successfully applied to the synthesis of the photo-sensitive supported catalysts(P) containing L-proline, coumarin and polyethylene glycol. The structures were characterized by 1H NMR and elemental analysis. UV spectra showed that the structures of P changed before and after UV irradiation. The catalytic performance indicated that Aldol reaction between cyclohexanone and 4-nitrobenzaldehyde in water can be achieved under the catalysis of P both before and after UV irradiation. The yields were 65%~76%, dr>93/7, and ee>95%.
2016 Vol. 24 (1): 39-42 [Abstract] ( 459 ) HTML (1 KB)  PDF (3344 KB)  ( 664 )
43 Synthesis of Novel 3,4-Disubstituted Pyrrolidine-3-carboxylic Acid Derivatives
ZHANG Wei， XU Liang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15099
Ten novel cis-trans-2,4-disubstituted pyrrolidine-3-carboxylic acid derivatives（3a~3j） in yield of 65%~75% were synthesized by 1,3-dipolar cycloaddition reaction of N-(trimethylsilylmethyl)benzaldehyde imine with α,β-unsaturated oxazolidinone amides, using phosphoric acid as catalyst. The structures were characterized by 1H NMR， 13C NMR and HR-MS. The stereochemical structure of 3b was confirmed by Xray  single crystal diffraction.
2016 Vol. 24 (1): 43-46 [Abstract] ( 560 ) HTML (1 KB)  PDF (3074 KB)  ( 364 )
47 Synthesis of Novel 2′-Bromo-biphenyl-2-ol Compounds
WU Hai-jian, SUN Xiao-qiang, WANG Zhi-ming
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15045
A series of 2′-bromo-biphenyl-2-ol compounds (3a~3i) were synthesized by Suzuki coupling reaction of 2-hydroxyphenylboronic acid compounds with dibromobenzen compounds at 90 ℃ in the mixtures of toluene/ethanol/water, using Pd(PPh3)4 as the catalyst and Na2CO3  as the base. 3b~3i were new compounds. The structures were characterized by 1H NMR, 13C NMR and ESI-MS.
2016 Vol. 24 (1): 47-50 [Abstract] ( 479 ) HTML (1 KB)  PDF (3769 KB)  ( 339 )
51 Synthesis and Properties of A Mo-V Dipolymer Polyoxometalate  
SHI Shu-yun, YANG Dong-lin
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15221
The novel polyoxometalate,(H2NC4H8NH2)6［MoVI16VV12P2O84］·5H2O(1), was hydrothermally synthesized using NH4VO3, H3PMo12O40·xH2O, Cu(NO3)2 and piperazine as the starting materials. The structure and properties were characterized by UV-Vis， IR, XRD, XPS spectra and TG analysis. 1 belongs to monoclinic system, space group a=20.450(4) , b=24.989(5) , c=20.450(4) , β=93.89 °, V=10 427(4) 3, Fw=4 159.18, Dc=2.650 g·cm-3, μ=3.018 mm-1, F(000)=7 952, Gof=1.029.〖JP〗 The results showed that the polyanion ［P2Mol6V12O84］14- was a dipolymer formed by two ［PMo8V6O42］7- units. 1 exhibited a novel 3-D supramolecular arrays constructed from dipolymer anions and organic ligands via hydrogen bonds.
2016 Vol. 24 (1): 51-54 [Abstract] ( 409 ) HTML (1 KB)  PDF (4002 KB)  ( 343 )
55 Synthesis and Photoelectric Properties of  A Novel Nickel(Ⅱ) Complex Containing Crown Ether Annelated Dithiolate Ligand
ZHANG Rui, GU Xiao-long， XU Zhong-juan, JI Yong, XU Ming
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15040

A novel nickel(Ⅱ) complex(1) containing dithiolate ligand was synthesized by reaction of 5,8,11,14-tetraoxa-2,17,19,21-tetrathiabicy-clo［16.3.0］heneicosa-1(18)-en-20-one with Ni(dbbpy)Cl2(dbbpy=4,4′-di-tert-butyl-2,2′-bipyridine) in solution of CsOH and MeOH/THF. The structure was characterized by 1H NMR, IR, MS and elemental analysis. 1 exhibited a significant response for Na+ with △E11/2 of 100 mV(20 times of Na+) and 125 mV(30 times of Na+), and displayed solvatochromic behavior at room temperature. 1 was very sensitive in detecting Na+ with an obvious change in color.
2016 Vol. 24 (1): 55-58 [Abstract] ( 463 ) HTML (1 KB)  PDF (3149 KB)  ( 415 )
59 Synthesis and Properties of A Novel Amphoteric Betaine Surfactant
ZHOU Yang, PAN Zhong-wen, CHEN Geng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15310
N,N-dimethyl-N′-(acyl-methoxy-propyl)-1,3-propanediamine(2) was prepared by reaction of N,N-dimethyl-1,3-propanediamine with methyl acrylate. A novel amphoteric betaine surfactant(6) was obtained by amino protection， quaterisation and hydrolysis from 2. The structure was characterized by 1H NMR, IR and ESI-MS. The surface properties of 6 were investigated. The results showed that the critical micelle concentration(CMC) was 1.48×10-4 mol·L-1, the surface tension(γCMC) was 39.99 mN·m-1, and the Krafft point was below 0 ℃. Moreover, 6 exhibited good surface activities, excellent emulsifying capacity and forming capacity.
2016 Vol. 24 (1): 59-62 [Abstract] ( 373 ) HTML (1 KB)  PDF (3094 KB)  ( 471 )
63 Synthesis of A Novel Thermosensitivity Ionic Liquid and Its Catalytic Activity in Esterification Reaction of Long-chain Fatty Acids
PENG Lin-cai, PU Ling-xiang, HOU Zheng-bo, SONG Hang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15077
A novel ionic liquid(1) based on 8-hydroxyquinoline cation and HSO4- anion was firstly synthesized. The structure was characterized by 1H NMR, FT-IR, ESI-MS and elemental analysis. The physical properties and catalytic activity in esterification reaction of long-chain fatty acids were studied. The results showed that 1 exhibited low moisture absorption, obvious thermosensitivity in ethanol, and good catalytic activity for esterification reaction of long-chain fatty acids and ethanol. The yield of cetylic acid was up to 95.5%.
2016 Vol. 24 (1): 63-66 [Abstract] ( 371 ) HTML (1 KB)  PDF (3111 KB)  ( 355 )
67 Preparation of H2SO4/MCM-41 Catalysts and Their Application in Dehydration of Glycerol into Acrolein
ZHU Ye-nan, MA Tian-lin, DING Jian-fei
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15313
The mesoporous MCM-41 catalyst was grafted by sulphuric acid via equal volume impregnation method to prepare the H2SO4/MCM-41 catalysts. The structures and properties were characterized by pyridineIR, XRD, N2 adsorption-desorption and NH3-TPD. The results indicated that the best yield of acrolein was 85.5% over H2SO4/MCM-41 catalyst with 10%H2SO4. The mesoporous structures of the catalysts were maintained after modifying, and the acidity and the ratio of Brnsted acid were improved.
2016 Vol. 24 (1): 67-70 [Abstract] ( 388 ) HTML (1 KB)  PDF (4049 KB)  ( 367 )
71 Synthesis of Androstane-2-eno［3,2-b］-indol-17-ol
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15026
Androstane-2-eno［3,2-b］-indol-17-ol(5) with the total yield of 43.2% was synthesized by hydroxyl oxidation, carbonyl protection, carbonyl reduction and Fischer indole synthesis using dehydroepiandrosterone as the starting material. The structure was confirmed by 1H NMR, IR and MS. The results of the biological activity tests on culex pippens showed that comparing with dihydrotestosterone, the insecticidal activity of 5 increased significantly, and the insecticidal rate was 41.5％ at 400 mg·L-1.
2016 Vol. 24 (1): 71-74 [Abstract] ( 539 ) HTML (1 KB)  PDF (3098 KB)  ( 2018 )
75 Process Improvement on the Synthesis of (Z)-2-(2-tritylaminothiazol-4-yl)-2-(1,5-dibenzhydryloxy-4-pyridon-2-ylmethoxyimino)acetic Acid
TAO Yun-liang, YANG Yu-she, WANG Hai-dong
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15044
The key intermediate of BAL30072, (Z)-2-(2-tritylaminothiazol-4-yl)-2-［(1,5-dibenz-hydryloxy）-4-pyridon-2-ylmethoxyimino］acetic acid with overall yield of 23%, was synthesized by protection of phenolic hydroxyl group, Michael addition, nucleophilic substitution, Mitsunobu reaction, hydrazinolysis, condensation reaction and so on, using kojic acid as the starting material. The structure was confirmed by 1H NMR and MS.
2016 Vol. 24 (1): 75-78 [Abstract] ( 555 ) HTML (1 KB)  PDF (3229 KB)  ( 380 )
79 Process Improvement on the Synthesis of Halofuginone Intermediate
WANG Chao-jie, WAN Yang, SONG Wei-qiang, LU Qun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15016
Halofuginone intermediate, 1-(3-methoxypiperidin-2-yl)propan-2-one, was synthesized by ring-expansion, methylation, deprotonation, nucleophilic addition, ketalation, hydrogenation and hydrolysis, using 2-acetylfuran as the starting material. The overall yield was 40.2%. The structure was confirmed by 1H NMR and ESI-MS.
2016 Vol. 24 (1): 79-83 [Abstract] ( 573 ) HTML (1 KB)  PDF (3633 KB)  ( 401 )
84 Synthesis of 17α,21-Dihydroxypregn-4-ene-3,20-dione-17-valerate
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15009
The intermediate of hydrocortisone, 17α,21-dihydroxypregn-4-ene-3,20-dione-17-valerate, was synthesized by a seven-step reaction of addition, silicon etherification, cycloaddition-protiodesilylation and so on, using androstendione as the starting material. The total yield was about 75% and purity was more than 96%. The structure was confirmed by 1H NMR and ESI-MS.
2016 Vol. 24 (1): 84-87 [Abstract] ( 388 ) HTML (1 KB)  PDF (3130 KB)  ( 344 )
87 Research Progress on Application of Microwave Irradiation in Non-aqueous Enzymatic Catalysis
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.01.15341
Research progress on application of microwave irradiation in non-aqueous enzymatic catalysis were reviewed with 43 references. The influence of microwave irradiation on enzyme catalytic reaction kinetics, reaction yields, selectivity and enzymology properties in organic solvent were discussed in detail.
2016 Vol. 24 (1): 87-92 [Abstract] ( 419 ) HTML (1 KB)  PDF (4999 KB)  ( 358 )
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