Home | About Journal | Editorial Board | Instruction | Subscribe | Advertisement | Messages Board | Self-test of coincidence rate of papers | Contact Us | Download | 中文
        Office Online
        Journal
Just Accepted
Current Issue
Archive
Advanced Search
Most Read
Most Download
Email Alert
2016 Vol. 24, No. 3
Published: 2016-03-20
 
185 Synthesis and Anti-platelet Aggregation Activities of Novel Triazolo［4,5-d］pyrimidin Compounds
WANG Bing, YANG Jing, JIANG Xi-ming, LIU Ying, LIU Deng-ke, WANG Ping-bao
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15379
The aminopyrimidines(2) were obtained via the substitution reaction of 4,6-dichloro-2-(propylthio)pyrimidin-5-amine with primary amines. Diazotization and coupling reaction of 2 provided thiazoles(3). Twenty-six novel triazolo［4,5-d］pyrimidin compounds(6a~6z) were synthesized by the nucleophilic subsititution reaction of 3 with substituted amines and hydrolysis orderly. The structures were characterized by 1H NMR and ESI-MS. The anti-platelet aggregation activities were evaluated by platelet aggregation inhibition tests in rats. The results showed that 6a~6z exhibited certain anti-platelet aggregation activities. The inhibition rates of 6d, 6i and 6l were 61.9%, 69.3% and 71.2%,  respectively.
2016 Vol. 24 (3): 185-191 [Abstract] ( 428 ) HTML (1 KB)  PDF (832 KB)  ( 432 )
192 Synthesis of Novel Tetrandrine Derivatives and Their Biological Activities
WEI Xiao, YANG Yi-fang, ZHAO Zheng-bao
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15405
Six novel tetrandrine derivatives(4a~4f) were synthesized by Suzuki coupling reaction of boronic acid derivatives and 5-bromotetrandrine， which was obtained by bromination, using tetrandrine as the starting material. The structures were characterized by  1H NMR, 13C NMR and ESI-MS. The inhibition activities of 4a~4f against A549 and HL60 cancer cell lines were investigated by CCK-8 assay. The compounds which had better inhibition activities were secondary screened by MTT assay. The inhibitory activities of 4a~4f against PTKs were tested by ELISA. The results showed that 4b, 4c and 4e exhibited well inhibition activities against the two cancer cell lines. 4b and 4c showed better inhibition activities against FGFR1.
2016 Vol. 24 (3): 192-197 [Abstract] ( 419 ) HTML (1 KB)  PDF (557 KB)  ( 352 )
198 Synthesis and Application of A New Photolabile Protecting Group for Phosphate Derivatives
LIU Shan-shan, MA Chi, LI Jun-ru, HONG Li-hong, ZHANG You-lai
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15351
4-Oxo-3-phenyl-4H-thiochromene-2-carbaldehyde(4) was prepared by dehydration reaction, iodine substitution reaction, Suzuki-Miyaura coupling and oxidation， using thiophenol and ethyl acetoacetate as starting material. Furthermore oxidation of the sulfur atom of 4 with m-CPBA, and then reaction with TsNHNH2 to obtain tosylhydrazone(6). 2-Diazomethyl-3-phenyl-4H-thiochromen-4-one 1,1-dioxide(7) was synthesized by Bamford-Stevens reaction from 6. The structures were characterized by 1H NMR, 13C NMR and HR-MS. 7 was designed as a novel photolabile protecting group for the protection and photodeprotection of phosphate derivatives. Protection reaction proceeded smoothly under mild reaction. The photodeprotection yields were more than 95% in 15 min monitored by UV-Vis and fluorescence spectroscopies.
2016 Vol. 24 (3): 198-202 [Abstract] ( 324 ) HTML (1 KB)  PDF (826 KB)  ( 345 )
203 Synthesis of Benzene Propylene O-Glycosides and Their Anti-hypoxic Activities
MA Chen, ZHANG Wen-bin, LI Xia, LI Ling-zhi, WU Yu-qiang, ZHANG Yong-liang, GE Xiao-jian
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15374
Twenty four benzene propylene O-glycosides(5a~5x) were designed and synthesized by Koenigs-Knorr reaction of 3-phenyl-2-propen-1-ol derivatives (3a~3x) with bromo acetyl glucose and deacetylation. 3a~3x were prepared by two methods. 3a~3t were prepared by Knoevenagel condensation， esterification， and reduction from substituted benzaldehyde. And 3u~3x were prepared by reduction from cinnamic aldehyde derivatives. 5c， 5f ~ 5x were new compounds. The structures were characterized by 1H NMR and ESI-MS. The anti-hypoxic activities of 5 on hypoxia exposure endothelial cells(EA.hy926) were evaluated by MTT assays. The results indicated that 5b, 5e, 5g, 5p, 5q, 5s, 5t and 5y exhibited better anti-hypoxic activity than salidroside.
2016 Vol. 24 (3): 203-210 [Abstract] ( 343 ) HTML (1 KB)  PDF (645 KB)  ( 358 )
211 Synthesis of Phloretamide and Its Derivatives and Their Antioxidant Activities
WU Dong-dong, FAN Zhi-qiang, REN Jie, HU Kun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15068
A series of Phloretamide derivatives were designed and synthesized using 3-(4-hydroxyphenyl)propan-amide as the lead compound. They were synthesized by amidation reaction， using cinnamon acids as the raw materials. 3-(3,4,5-trihydroxyphenyl)acrylamide(2f), 3-(2,3,4-trihydroxyphenyl) propanamide(3e) and 3-(3,4,5-trihydroxyphenyl) propanamide(3f) are new compounds. The structures were characterized by 1H NMR, 13C NMR and ESI-MS. The antioxidant activities of these compounds were investigated. The results showed that 3-(3,4-dihydroxyphenyl)acrylamide(2b), 3-(3,4,5-trihydroxy-phenyl)acryl-amide(2f) and 3-(3,4,5-trihydroxyphenyl)propanamide(3f) had good antioxidant activities with radical scavenging ratio of 66.8%, 59.8% and 69.4% at 10 μmol·L-1, respectively， better than caffeic acid, caffeic acid phenethyl ester and Vc.
2016 Vol. 24 (3): 211-214 [Abstract] ( 418 ) HTML (1 KB)  PDF (459 KB)  ( 302 )
215
Synthesis of N-(2-chloroethyl)-N′-2-(O6-benzyl-9-guanineyl)ethyl-N-nitrosourea
Synthesis of N-(2-chloroethyl)-N′-2-(O6-benzyl-9-guanineyl)ethyl-N-nitrosourea[J]. journal1, 2016,24(3): 215-218')" href="#"> WANG Ya-meng, REN Ting, SONG Xiu-qing, ZHAO Li-jiao, ZHONG Ru-gang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15104
N-9-(2-amino)ethyl-O6-benzylguanine(4) was obtained through substitution and Gabriel reaction, using O6-benzylguanine as the starting material. N-(2chloroethyl)-N′-2-(O6-benzyl-9-guanine)ethyl-N-nitrosourea(6) was synthesized by isocyanate substitution of 4, followed by a nitrosation reaction. 4 and 6 were new compounds. And their structures were characterized by UV- Vis, 1H NMR, 13C NMR, IR and HR-ESI-MS.
2016 Vol. 24 (3): 215-218 [Abstract] ( 409 ) HTML (1 KB)  PDF (556 KB)  ( 341 )
219 Synthesis of Novel ［60］Fullerene Derivatives Containing Fluorene              
HAN Lu， LIU Feng-li， DING Min-yuan， XU Yu-jie， LI hui
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15103
Three novel ［60］fullerene derivatives containing fluorene were synthesized by Suzuki coupling reaction, hydrazone reaction and 1,3dipolar cycloaddition reaction, using 2,7-dibromofluoren-9-one as the starting material. The structures were characterized by UV-Vis， 1H NMR， 13C NMR， FT-IR and MALDI-TOF-MS．
2016 Vol. 24 (3): 219-222 [Abstract] ( 308 ) HTML (1 KB)  PDF (492 KB)  ( 365 )
223 Synthesis of Enantioenriched Analogues of Novel Rh2(esp)2 Ligand
HUANG Ze-ao, LU Chong-dao
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15115
A synthetic approach toward the enantioenriched Analogues of α,α,α′,α′-tetramethyl-1,3-benzene-dipropionic acid that was the ligand of Rh2(esp)2 catalyst was reported. In this process, the chiral (R)-tert-butanesulnyl diimine derived from 1,3-benzenedialdehyde was used in the nucleophilic additions of lithium ester enolates to give two novel chiral analogues of the “esp” esters that are (Rs,Rs′,R,R′)-β-amino esters and (Rs,Rs′,R,R′,R,R′)-α,β- aziridinyl esters in yields of 96% and 65% with excellent diastereoselectivity(dr>20 ：1). The structures were characterized by 1H NMR and 13C NMR.
2016 Vol. 24 (3): 223-226 [Abstract] ( 316 ) HTML (1 KB)  PDF (597 KB)  ( 288 )
227 Asymmetric Synthesis of (S)-(+)-4-phenyl-2-butanol by Carbonyl Reduction with Microbial Enzymes
YANG Min, LI Ke, ZHOU Xiao-jian, CUI Bao-dong, CHEN Yong-zheng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.16090
Pseudomonas monteilii TA-5 cultivated with LB medium was employed as the biocatalysts（Cat) for the synthesis of (S)-(+)-4-phenyl-2-butanol with high enantioselectivity by asymmetric reduction. In this paper, the optimal reaction conditions for bioreduction of 4-phenyl-2-butanone（1） were optimized. Under the optimized reaction conditions［1 10 mmol·L-1, c(Cat) 30 g·cdw·L-1, 10% glycerol as the cosolvent, pH 8.0, 300 r·min-1, at 30 ℃ for 4 h］, the conversion was 82% and the ee was 91%.
2016 Vol. 24 (3): 227-230 [Abstract] ( 382 ) HTML (1 KB)  PDF (604 KB)  ( 341 )
231 Synthesis and Fluorescence Property of the GFP Chromophores’ Derivatives
YE Jian-heng, WANG Chao, DI Xiao, SUN Jian, TANG Zhuo
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15135
Eight novel analogs(5a~5h) of fluorescent protein chromophore were designed and synthesized by condensation between aromatic aldehydes and imidazolinone, which were obtained by acetylation, substitution and Wittiong reaction, starting from N-methylacetamide or N-methylbenzamide. The structures were characterized by 1H NMR and 13C NMR. The optical study showed that the fluorescent emission wavelengths of most compounds were red-shifted compared with p-hydroxybenzylideneimidazolinone. The emission wavelength of (Z)-4-(2-hydroxy-5-nitrobenzylidene)-1-methyl-2-phenyl-1H-imidazol-5(4H)-one (5f) was 614 nm.
2016 Vol. 24 (3): 231-234 [Abstract] ( 503 ) HTML (1 KB)  PDF (424 KB)  ( 311 )
235 Preparation of Novel Benzimidazole Heteropolyanion-based Ionic Liquid and Their Application in the Catalytic Synthesizing Adipic Acid
HU Hai-yan, GUO Zong-yang, LIU Wen-bo,ZHANG Yong-hong, LIU Chen-jiang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15139

Five novel heteropolyacid-based ionic liquids ［BSbBim］4SiW12O40(4a), ［BSbBim］3PW12O40(4b), ［BSbBim］3PMo12O40(4c), ［CMbBim］4SiW12O40(5) and ［BbBim］4SiW12O40 (6) were synthesized by reaction of heteropolyacid and ［BSbBim］(1), ［CMbBim］Cl(2), ［BbBim］Br(3), which were prepared from 1-butyl-1H-benzo［d］imidazole. The structures were characterized by 1H NMR, 13C NMR and IR. Oxidation of cyclohexene to adipic acid with hydrogen peroxide catalyzed by 4~6 were investigated. And the results showed that 4b has the best catalytic activity. The yield of adipic acid was up to 71％ under the optimized conditions that cyclohexene was 20 mmol， 4b was 0.16 mmol, n(cyclohexene) : n(H2O2) : n(ILs)=1 :4.4 :0.008.
2016 Vol. 24 (3): 235-239 [Abstract] ( 347 ) HTML (1 KB)  PDF (469 KB)  ( 305 )
240 The Efficient Green Synthesis of N-ethylcarbazole
ABDUKADER Ablimit， ZHANG Yong-hong, LIU Chen-jiang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15368
Diethyl carbonate as the alkylating reagent, the efficient green Cs2CO3/TEBAC dual-catalyzed synthetic method of N-ethylcarbazole was developed. The structure was confirmed by 1H NMR and HR-ESI-MS． Under the optimized conditions［carbazole 200 mmol， diethyl carbonate 1.2eq， Cs2CO3 0.05 eq., TEBAC 0.05 eq.， at 180 ℃ for 3 h］, the yield was up to 99%.
2016 Vol. 24 (3): 240-242 [Abstract] ( 452 ) HTML (1 KB)  PDF (422 KB)  ( 482 )
243 Preparation and Characterization of Poly(lactide-co-glycolide-co-caprolactone)s Random Terpolymer
YANG Huan, HUANG Dong-ling, CHEN Dong-liang, XIONG Cheng-dong, ZHANG Qi， PANG Xiu-bing， XIONG Zuo-chun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15168
Random terpolymers(P) of L-lactide, glycolide and caprolactone had been prepared by bulk ring-opening copolymerization initiated by stannous octoate under high vacuum. The sttucture and properties had been investigated by  1H NMR, IR， DSC and viscosimetry. The results indicated that the glass transition temperature of P can be controlled by adjusting the monomer ration. The submicron fiber membrane of P can be obtained easily through electrospinning.
2016 Vol. 24 (3): 243-246 [Abstract] ( 319 ) HTML (1 KB)  PDF (930 KB)  ( 313 )
247 Synthesis of Hydrazone Compounds
GUO Ya-ning
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15388
Five hydrazones(3a~3e) were synthesized by nucleophilic addition-elimination reaction of aromatic aldehydes and substituted hydrazine. 3-(Iminomethyl)-2-methoxyphenol(3a) was a new compound and its structure was characterized by 1H NMR, 13C NMR, IR and elemental analysis.
2016 Vol. 24 (3): 247-249 [Abstract] ( 554 ) HTML (1 KB)  PDF (308 KB)  ( 458 )
250 Synthesis of C-aryl Glycosides Catalyzed by CuI/TMEDA
MAO Ze-wei, RAO Gao-xiong
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15088
C-aryl glycosides（2a~2c） were stereoselectively synthesized by substitution reaction of 2,3,4,6- tetra-O- acetyl-α-D-glucopyranosyl bromide and aryl Grignard reagents, using THF as the solvent and CuI/TMEDA as the catalyst. The structures were confirmed by 1H NMR and 13C NMR. Under the optimized reaction conditions(THF as the solvent, 10％CuI and 10%TMEDA as the catalyst, and the reaction temperature was 0 ℃), the yields of 2a~2c were 58%~71% and α/β were 1/6.5~1/7.1.
2016 Vol. 24 (3): 250-252 [Abstract] ( 420 ) HTML (1 KB)  PDF (275 KB)  ( 289 )
253 Process Improvement on the Synthesis of 1-(3,5-Dimethylphenyl)-1-［(1S,4S)-1,7,7-trimethyl-bicyclo［2.2.1］heptan-2-yl］hydrazine
WANG Kai, CHEN Qiang, ZHANG Xiu-qin, YUE Bang-yi
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15087
3,5-Dimethyl-N-［(1S,4S)-1,7,7-trimethylbicyclo［2.2.1］heptan-2-ylidene］aniline(1) was prepared by microwave-assisted condensation of 3,5-dimethylaniline with 2-camphonone. 1-(3,5-Dimethylphenyl)-1-［(1S,4S)-1,7,7-trimethylbicyclo［2.2.1］heptan-2-yl］hydrazine in total yield of 70.4% was synthesized by reduction of 1 by NaBH4 followed by amination with hydroxylamine O-sulfonic acid. The structures were confirmed by 1H NMR and ESI-MS.
2016 Vol. 24 (3): 253-255 [Abstract] ( 310 ) HTML (1 KB)  PDF (349 KB)  ( 322 )
256 Synthesis of Novel Cationic Surfactant of Triethyl Ammonium Chloride and the Interfacial Properties
MIAO Zong-cheng, ZHAI Peng-fei, SU Ting-ting, ZHAO Yang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15384
In order to realize the reasonable utilization and eliminate the harm of waste oil, waste oil was used to synthesize a novel cationic surfactant(4) through hydrolysis, open loop esterification of epichlorohydrin, and quaternization of triethylamin. The structure was characterized by 1H NMR and IR. The interfacial properties were investigated. The results showed that he critical micelle concentration of 4 was 4.16×10-3 mol·L-1, and the γcmc was 38.36 mN·m-1. The foaming ability and foam stability of 4 was similar to n-hexadecyltrimethylammonium chloride.
2016 Vol. 24 (3): 256-258 [Abstract] ( 368 ) HTML (1 KB)  PDF (648 KB)  ( 440 )
259 A New Method for Synthesis of Multiple Fluorine Substituted Biaryl Compounds
JI Yan-ping, YANG Yun, GAO Guang-chun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15359
A new one-pot synthetic method to prepare multiple fluorine substituted biaryl compounds(3a~3f) by diazotization/cross-coupling of aromatic anilines with poly-uoroarenes had been developed. The yields were 56%~82%. The structures were confirmed by 1H NMR, 19F NMR and EI-MS．Under the optimized conditions［1a 2 mmol, 20%CuI as the catalyst，150%Bu4NI as the iodide reagent， V(DMSO）: V （MeCN）=1 : 1 as the solvent， at 130 ℃ for 4 h］, the yield of 3a was 75%.
2016 Vol. 24 (3): 259-262 [Abstract] ( 420 ) HTML (1 KB)  PDF (358 KB)  ( 394 )
263 Synthesis of Deuterated AZD9291
KANG Fang-yuan, PANG Xue-hai, WANG Ying-wei, CHEN Yuan-wei
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15155
The synthesis of deuterated AZD9291 was reported. 3-(2-Chloropyrimidin-4-yl)-1H- indole(1) was prepared by coupling reaction of indole with 2,4-dichloropyrimidine. 3-(2-Chloropyrimidin-4-yl)-1-(methyl-d3)-lindole(2) was obtained by substitution reaction of 1 with iodomethane-d3. N′-(2-dimethylaminoethyl)-2-methoxy-N′-methyl-N-{［4-(1- methyl-d3)indol-3-yl］pyrimi- din-2-yl}benzene-1,2,4-triamine(4) was obtained by two substitution reactions from 2. Then deuterated AZD9291 in total yield of 8.5% was synthesized by condensation reaction following reduction of 〖STHZ〗4〖STBZ〗. The structures were confirmed by 1H NMR, 13C NMR and ESI-MS.
2016 Vol. 24 (3): 263-265 [Abstract] ( 580 ) HTML (1 KB)  PDF (478 KB)  ( 493 )
266 Research Progress of Synthesis and Applications of Tartaric Esters
LIU Bing, ZHAO Jian-qiang, ZHOU Ming-qiang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.03.15410
The synthetic methods of twelve kinds of tartaric esters and the applications of tartaric esters in chiral auxiliaries, chiral ligands, synthesis of ligands as chiral pools and chiralselector extraction were reviewed with 69 references. Future research orientation and application prospect are proposed.
2016 Vol. 24 (3): 266-276 [Abstract] ( 427 ) HTML (1 KB)  PDF (1330 KB)  ( 785 )
Copyright © Editorial Board of Chinese Journal of Synthetic Chemistry
Supported by:Beijing Magtech