关闭×
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. 4
Published: 2016-04-20
277
Synthesis and Biological Evaluation of Novel PARP-1 Inhibitors with Indazole Skeleton
LONG Wei, QIU Wen-ge, HU Yun-yan, SONG Li-yun, LI Hai-jun, HE Hong
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.16016
Methyl 1
H
-indazole-7-carboxylate(
3
) was obtained by two-step reaction from methyl 2-nitro-3-methylbenzoate. 3-Halogenated-
3
(
4b~4d
) were prepared by halogenation of
3
with POCl
3
, Br
2
or I
2
, respectively. 3-Fluoro（cyano)-
3
(
4a, 4e
) were prepared by fluorination or cyanation of
4d
with selectflor or Zn(CN)
2
. 3-Methyl（phenyl）-
3
(
5a, 5b
) were obtained by Suzuki coupling of
4d
with methylboronic acid or phenylboronic acid catalyzed by Pd(PPh
3
)
4
. Indazole derivatives(
6a~6n
) were synthesized by
N
-alkylation of
3
,
4a~4c, 4e
and
5
. Fourteen novel indazole derivatives(
7a~7n
) were synthesized by aminolysis and deprotection from
6a~6n
. The structures were characterized by
1
H NMR and ESI-MS. The results of biological evaluation indicated that seven target molecules displayed inhibitory activities against PARP-1 with IC
50
less than 30 nmol·L
-1
. Moreover, the indazoles bearing pyrrolidinyl at 2-position and hydrogen(
7e
) or fluorin(
7f
) at 3-position displayed inhibitory activities against PARP-1 with IC
50
of 4.2 nmol·L
-1
and 4.6 nmol·L
-1
, respectively.
2016 Vol. 24 (4): 277-282 [
Abstract
] (
403
)
HTML
(1 KB)
PDF
(1097 KB) (
344
)
283
Synthesis and Antitumor Activities of Novel
N
6
-Piperazine Substituted Adenosine Analogues
ZHOU Gao-hui, LUO Ming-ming, ZHANG Yang,YU Xiao-qin, TAO Li-ming, XU Wen-ping
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15151
The intermediate, {(3
R
,4
R
,6
R
,6
R
)-2,2-dimethyl-6-［6-(piperazin-1-yl)-9
H
-purin-9-yl］ tetrahydrofuro［3,4-
d
］［1,3］dioxol-4-yl}methanol(
4
), was synthesized by three steps including adjacent hydroxyl protection, chlorination and introduction of piperazine at
N
6
- position, using adenosine as starting material. Eight novel
N
6
-piperazine substituted adenosine analogues(
8a~8h
) were synthesized by coupling reaction of
4
with
6a~6h
, then deprotection of hydroxyl. The structures were characterized by
1
H NMR，
13
C NMR and HR-ESI-MS. Biological evaluation showed that 8a~8h exhibited antitumor activities on Hela cells, especially, 2-｛4-［9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9
H
-purin-6-yl］-piperazin-1-yl｝-
N
-(3-fluoro-phenyl)-acetamide(
8e
) exhibited the strongest inhibitory activity with IC
50
of 21.74 μmol·L
-1
.
2016 Vol. 24 (4): 283-287 [
Abstract
] (
321
)
HTML
(1 KB)
PDF
(797 KB) (
283
)
288
Synthesis and Biologial Activities of Novel Magnolol -2-Azomethine Derivatives
MEI Fan, ZHAI Ting, ZHENG Nian, LI Yan, CHEN Yong, LOU Zhao-wen
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15145
The formoxyl was introduced into the ortho-position of magnolol hydroxy by the Reimer-Tiemann method using magnolol as the raw material. Four novel mono-substituted and one bis substituted magnolol 2-azomethine derivatives were synthesized by reaction of the formylated magnolol with glycine, glutamic acid, arginine and sulfanilamide, respectively. The structures were characterized by UV-Vis,
1
H NMR, IR, MS and elemental analysis. The myoblast cell toxicity and the effects on CYPs in liver microsomes
in vitro
human were investigated. The results showed that 2-(
N
-glycine)magnolol azomethine(
3a
) exhibited certain tomyoblasts toxicity. At 64 μmol·L
-1
, the inhibition rate of 2-［
N
-(4-sulfamoyl-phenyl)］-magnolol azomethine(
3d
) on CYP2D6 and CYP1A2 was 42.9% and 36.8%, respectively.
2016 Vol. 24 (4): 288-292 [
Abstract
] (
381
)
HTML
(1 KB)
PDF
(653 KB) (
322
)
293
Synthesis and Antitumor Activities of Novel Indazole Derivatives
ZHOU Yun-peng, HE Chang, SONG Duan-zheng, CHEN Ye, LIU Ju, ZHANG Qiu-shi, WANG Yang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.16019
2-Fluoro-6-morpholinobenzonitrile(
1
) was prepared by reaction of 2,6-difluorobenzonitrile with morpholine. 4-Morpholino-1
H
-indazol-3-amine(
2
) was synthesized by cyclization of
1
with hydrazine.
2
was coupled with various carboxylic acids to afford eight novel indazole derivatives(
4a~4h
). The structures were characterized by
1
H NMR， IR and HR-ESI-MS. The antitumor activities were investigated. The results showed that 4-(4-methylpiperazin-1-yl)-
N
-(4-morpholino-1
H
-indazol-3-yl)-4-oxobutanamide(〖WTHZ〗〖STHZ〗4a〖STBZ〗〖WTBZ〗) exhibited potent antitumor activities against K-562, SMMC7721 and T-47D tumor cell lines with IC
50
of 0.056 μmol·L
-1
, 0.062 μmol·L
-1
and 0.086 μmol·L
-1
, respectively.
2016 Vol. 24 (4): 293-296 [
Abstract
] (
428
)
HTML
(1 KB)
PDF
(588 KB) (
295
)
297
Synthesis and Anti-platelet Aggregation Activities of Novel Thienopyridine Derivatives
FAN Meng-lin, JIANG Xi-ming, LIU Ying, LIU Deng-ke, WANG Ping-bao
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15393
Novel thienopyridine derivatives(
3b~3e, 3g
and
5a~5g
) were synthesized by substitution reaction of tetrahydrothieno［3,2-
c
］pyridine or tetrahydrothieno［2,3-
c
］pyridine with substituted benzyl bromides, and salt forming reaction with ethereal hydrochloric acid. Novel thienopyridine derivatives(
7d, 7e, 7g~7i
) were synthesized by substitution reaction of tetrahydrothieno［3,2-
c
］pyridone with substituted benzyl bromides, and condensation with acetic anhydride, then salt forming with 2 mol·L
-1
ethereal hydrochloric acid. The structures were characterized by
1
H NMR and ESI-MS. The results in platelet aggregation inhibition tests
in vivo
showed that the compounds exhibited certain activities,
7d, 7h
and
7i
showed better activities than the positive control drug ticlopidine, and the inhibitory rate were 66.2%, 86.8% and 88.3%, respectively.
2016 Vol. 24 (4): 297-301 [
Abstract
] (
371
)
HTML
(1 KB)
PDF
(643 KB) (
328
)
302
Preparation of Three-dimensional Porous Reduced Graphene Oxide Aerogel and Its Application in Lithium-ion Batteries
DENG Xiao-mei, WEN Hao, ZHANG Chu-hong, DENG Jian-guo, GAO Li-zhen
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15073
Reduced graphene oxide(rGO) aerogel with a three-dimensional porous monolithic structure was synthesized via self-assembly using L-ascorbic acid as reductant from graphene oxide, which was prepared by a modified Hummers method using natural graphite as starting material. The morphological and structure were characterized by FT-IR, SEM, TEM, XRD and XPS. The electrochemical performances as lithium ion battery anode were tested. The results showed that the rGO aerogel exhibited high specific capacities and a good cyclability, the initial discharge and charge specific capacities reached 1 700 mAh·g
-1
and 710 mAh·g
-1
, respectively, at a current density of 100 mA·g
-1
. After 100 cycles the reversible discharge specific capacity could still retain at 450 mAh·g
-1
along with the coulombic efficiency at 98%.
2016 Vol. 24 (4): 302-307 [
Abstract
] (
534
)
HTML
(1 KB)
PDF
(1673 KB) (
917
)
308
Synthesis of Novel Choline Derivatives and Their
in vitro
Antimalarial Activities
WANG Fang, ZHAO Qing, CHEN Hui-fang, ZHANG Shu-qiu
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15415
Six novel choline derivatives of quaternary ammonium salts(
3a~3f
) were synthesized by reaction of
N,N
-dimethyl ethanolamine or
N,N
-diethyl ethanolamine with brominated alkanes of different carbon chain length under reflux condition. The structures were characterized by UV-Vis，
1
H NMR and HR-MS. The antimalarial activities test showed that
3a~3f
demonstrated different degrees of inhibiting effect on the growth of plasmodium falciparum 3D7
in vitro
, and (1-hydroxy) diethyl -
n
-butyl ammonium bromide(
3f
) exhibited the strongest antimalarial activity with IC
50
of (68.1±6.5) nmol·L
-1
, but lower than Artemisinin［IC
50
(5.7±1.54）nmol·L
-1
］.
2016 Vol. 24 (4): 308-311 [
Abstract
] (
263
)
HTML
(1 KB)
PDF
(582 KB) (
286
)
312
Synthesis of A Novel Mono-hydroxyl Chloro-corrole and Its Photocleavage of DNA
SHI Lei, YANG Wen-cong, ZENG Shu-ying,MO Ting-ting, WANG Hua-hua, LIU Hai-yang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15408
5-(Pentafluoro-phenyl)-dipyrromethane(
1
) was prepared by condensation reaction of pentafluorobenzaldehyde with pyrrole. A novel mono-hydroxyl corrole, 10-(3-chloro-4-hydroxylphenyl)-5,15-bis(pentafluorophenyl) corrole(
2
) with yield of 12.0%, was synthesized by condensation reaction of
1
with 3-chloro-4-hydroxylbenzaldehyde. The structure was characterized by UV-Vis，
1
H NMR，
19
F NMR, HR-ESI-MS and X-ray single crystal diffraction. Agarose gel electrophoresis showed that
2
could cleave 68% supercoiled DNA(form I) to give nicked-circular DNA(form II) under irradiation at 100 μmol·L
-1
.
2016 Vol. 24 (4): 312-315 [
Abstract
] (
340
)
HTML
(1 KB)
PDF
(695 KB) (
265
)
316
Synthesis of Novel Potassium(3-fluoro-2-amino-substituted pyridin-4-yltrifluoroborates)
TENG Ming-gang, ZHAO Chun-shen, DUAN Lian, CHAI Hui-fang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15146
2-Substituted-amino-3-fluoropyridine compounds(
2a~2g
) were synthesized by substitution and reduction from 2,3-difluoro-5-chloropyridine. A series of pyridine boric acid compounds(
3a~3g
)were obtained by reaction of
2
with
n
-butyllithium and triisopropyl borate. Finally， seven novel potassium(3-fluoro-2-amino substituted pyridin-4-yltrifluoroborates) were synthesized by substitution of
3a~3g
with potassium hydrogen fluoride， respectively． The structures were characterized by
1
H NMR,
13
C NMR, IR, ESI-MS and elemental analysis.
2016 Vol. 24 (4): 316-320 [
Abstract
] (
358
)
HTML
(1 KB)
PDF
(583 KB) (
330
)
321
Synthesis of Xanthenes Catalyzed by Ionic Liquid 1-Ethyl-3-(4-sulfobutyl)-1
H
-imidazol-3-ium -p-Toluenesulfonate
TIAN Xiao-yue, ZHANG Yong-hong, SUN Ya-dong, WANG Duo-zhi, LIU Chen-jiang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15153
Brnsted acidic ionic liquid, 1-ethyl-3-(4-sulfobutyl)-1
H
-imidazol-3-ium -p-toluenesulfonate(
IL1
), was prepared using 1-ethylimidazole as raw material. A series of xanthenes were synthesized by condensation reaction of aromatic aldehydes with 5,5-dimethyl-1,3-cyclohexanedione or 1,3-cyclohexanedione catalyzed by
IL1
under solvent-free conditions. The structures were characterized by
1
H NMR,
13
C NMR and ESI-MS. The results indicated that 5 mol%
IL1
as catalyst, reaction at 80 ℃ for 40 min, the yields were 78%~95%. The catalytic activity of
IL1
keep stable with the yields of 86%~89% after recycling of three times.
2016 Vol. 24 (4): 321-325 [
Abstract
] (
326
)
HTML
(1 KB)
PDF
(654 KB) (
474
)
326
A New Synthetic Method of
α-
Sulfo-
β
-amino Acid Esters
HU Xiao-yan, HU Fang-zhi, YUAN Wei-cheng, ZHANG Xiao-mei
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15164
Five novel
α
-sulfo-
β
-enamioesters(
3a~3e
) were synthesized by oxidative coupling reaction of
β
-enamioesters and
N
-(thio)succinimide, using CuBr
2
as the catalyst. Then they were hydrosilylated to afford five α-sulfo
-β
-amino acid moieties(
4a~4e
). The structures were characterized by
1
H NMR. Under the optimized reaction conditions(
3
0.1 mmol， HSiCl
3
2.0 eq., DCE 1 mL， at room temperature for 12 h), the yield of
4a
was 97%.
2016 Vol. 24 (4): 326-329 [
Abstract
] (
339
)
HTML
(1 KB)
PDF
(332 KB) (
286
)
330
Organocatalytic Asymmetric Michael Addition of Barbituric Acid to
β
-Nitroalkenes
GUI Yong-yuan, LIU Kang-qiong, WANG Xiao, TIAN Fang, PENG Lin, WANG Li-xin
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15183
Organocatalytic asymmetric Michael addition of 1,3-dimethylbarbituric acid to
β-
nitroalkenes was studied using chiral squaric amide as the catalyst. The influence of substrate structure on the enantioselectivity of the reaction was investigated. The addition products were obtained in high yields (80%~100%) and moderate to good enantioselectivity (
ee
43%~90%). The structures were characterized by
1
H NMR and
13
C NMR.
2016 Vol. 24 (4): 330-332 [
Abstract
] (
368
)
HTML
(1 KB)
PDF
(535 KB) (
313
)
333
Poly(
p
-dioxanone-
co
-
N
ε
-carbobenzoxy-L-lysine):Synthesis and Mechanism of Copolymerization
WANG Bing, DONG Jun, CHEN Dong-liang, XIONG Cheng-dong
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15149
The copolymers(PPCLAs), poly(
p
-dioxanone-
co
-
N
ε
-
carbobenzoxy-L-lysine), were synthesized by bulk copolymerization of
p
-dioxanone with
N
ε-
carbobenzoxy-L-lysine
-N
-carboxyanhydride. The structures were characterized by
1
H NMR and GPC. The effects of catalyst quantities and reaction time on the average molecular weights of PPCLAs were investigated. The copolymerization mechanism was deduced as “competitive initiate-condensation polymerization between macromolecules”.
2016 Vol. 24 (4): 333-337 [
Abstract
] (
293
)
HTML
(1 KB)
PDF
(1629 KB) (
311
)
338
Synthesis and Photoisomerization Behavior of Azobenzene Compounds Containing Various Groups
LIU Jia, TIAN Jin-tao
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15094
Four kinds of azobenzene compounds(
1~4
) containing nitro, amino, and different number of azo groups were synthesized by diazo coupling reaction from aniline or 4-nitroaniline. The structures were confirmed by
1
H NMR and FT-IR. The UV-Vis spectra of
1~4
under UV irradiation were investigated. The results showed that the photoisomerization rate of the compounds linked with electron-donating group(NH
2
) was faster than those linked with electron withdrawing group(NO
2
). The photoisomerization was therefore restrained by NO
2
. The
cis/trans
isomerization process was also affected by the number of azo couples.
2016 Vol. 24 (4): 338-341 [
Abstract
] (
571
)
HTML
(1 KB)
PDF
(1119 KB) (
646
)
342
Synthesis of Novel Sulfinyl-NH-olefine Ligands and Their Application in Transfer Hydrogenation Reaction
LIN Zhe-chao, TANG Lei, HUANG Qing-fei, WANG Qi-wei, DENG Jin-gen
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15128
Two novel flexible tert-butylsulfinyl-NH-olefine tridentate ligands(
4a, 4b
) were synthesized by condensation and reduction starting with 2-tert-butylsulfinylbenzylamine and 2-vinyl-benzaldehyde or 2-styrylphenyl-benzaldehyde. The structures were characterized by
1
H NMR，
13
C NMR and HR-MS. The catalytic activities of
4a
and
4b
with iridium in transfer hydrogenation reaction of acetophenone were investigated. The conversion were 94% and 51%, respectively.
2016 Vol. 24 (4): 342-346 [
Abstract
] (
310
)
HTML
(1 KB)
PDF
(487 KB) (
347
)
346
Synthesis and Crystal Structure of 2-(
N
-cyclohexylamine)-6-trifluoromethoxy-benzothiazole
WU Xiang-long, LIU Liu, LI You-jia, LUO Jie,GAI Dong-wei, MA Jing-chuan, MEI Qi-bing
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15404
Riluzole was firstly transformed into (6-trifluoromethoxy-benzothiazol-2-yl)-hydrazine, then was chloridized by SOCl
2
to obtain 2-chloro-6-trifluoromethoxybenzothiazole(
3
). The novel compound, 2-(
N
-cyclohexylamine)-6-trifluoromethoxybenzothiazole(
4
), was synthesized by substitution reaction of
3
with cyclohexylamine. The structure was characterized by
1
H NMR, IR, elemental analysis and X-ray single crystal diffraction.
4
(CCDC： 1 440 686) belongs to triclinic system, space group
P
-1 with
a
=10.617(3) ，
b
=13.607(4) ，
c
=16.619(5) ，
V
=2 201.8
3
，
Dc
=1.422 g·cm
-3
，
Z
=6，
R
1
=0.082 0，
wR
2
=0.235 1.
2016 Vol. 24 (4): 346-349 [
Abstract
] (
405
)
HTML
(1 KB)
PDF
(890 KB) (
384
)
350
Asymmetric Hydroxylation of 1,2,3,4- Tetrahydroquinoline by Hydroxylase-catalyzed Hydroxylation in Two-phase Reaction System
LI Ke， YANG Min， CUI Bao-dong, CHEN Yong-zheng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.16010
(
R
)-4-hydroxy-1,2,3,4-tetrahydroquinoline was synthesized by hydroxylation of 1,2,3,4-tetrahydroquinoline using the whole-cell of
Pseudomonas plecoglossicidas
ZMU-T02 as biocatalyst. The structure was confirmed by
1
H NMR,
13
C NMR, HR-MS and HPLC. Under the optimized reaction conditions［cell density 30 g cdw·L
-1
, pH 9.0, 50%(
V
/
V
) hexadecane as co-solvent］, when substrate concentration was 10 mmol·L
-1
, the yield and
ee
were 37% and 98%, respectively.
2016 Vol. 24 (4): 350-354 [
Abstract
] (
355
)
HTML
(1 KB)
PDF
(628 KB) (
336
)
355
Synthesis of (3
S
,4
S
)-4-amino-3-hydroxy-5-phenylpentanoic Acid Derivatives Catalyzed by D-proline
BAO Ke-ting, ZHANG Wei, LI Ying-xia, HU Chun
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.16006
A new route for the synthesis of (3
S
,4
S
)-4-amino-3-hydroxy-5-phenylpentanoic acid derivatives was reported. The target compounds with overall yields of 5.8%~6.7% were synthesized by condensation with Weinreb amide, reduction, aldol condensation reaction and bromine imitation reaction, using amino-protected L-phenylalanine as starting material. The structures were confirmed by
1
H NMR，
13
C NMR and ESI-MS. The exploration of reaction conditions showed that the loading amount of D-proline had no evident effect on the yield, but on stereoselectivity. Larger size protecting groups in substrate can enhanced the stereoselectivity.
2016 Vol. 24 (4): 355-358 [
Abstract
] (
364
)
HTML
(1 KB)
PDF
(523 KB) (
404
)
359
A Novel Synthetic Method for Ginkgolic Acid
ZHAO Jian-yang, WANG Ting, LIU Qing-qing,ZHU Jin, HUANG Qing-fei, WANG Qi-wei
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.15395
A novel method for the synthesis of the ginkgolic acid was reported. 2-Methoxy-6-tridec-1-enylbenzoic acid methyl este(
6a
) and 2-methoxy-6-pentadec-1-enylbenzoic acid methyl ester(
6b
) were synthesized by methlation,
N
-bromosuccinimide substitution and constructing different long chain olefins via Wittig reaction from 2-methy-5-hydroxy benzoic acid. Two ginkgolic acids with different long chains were synthesized by reduction of carbon carbon double bond of
6
with palladium carbon then demethylating, the total yield were 46% and 40%, respectively. The structures were confirmed by
1
H NMR and ESI-MS.
2016 Vol. 24 (4): 359-361 [
Abstract
] (
357
)
HTML
(1 KB)
PDF
(496 KB) (
333
)
362
Research Process on Preparation ofNovel Macromolecular by ATRP/CuAAC Technique
WEI Ke-yao, JI Hu, WU Qi, ZHAO Xin,DUAN Ran, LEI Liang-cai, LI Hai-ying
DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.04.16003
The application of CuAAC and ATRP in polymer synthesis in recent years were reviewed with 31 references. Preparation of cyclic, block and graft polymers, one-pot ATRP-CuAAC and the application of CuAAC and ATRP hyphenated techniques in biological chemistry were discussed in detail.
2016 Vol. 24 (4): 362-368 [
Abstract
] (
395
)
HTML
(1 KB)
PDF
(1735 KB) (
404
)
Copyright © Editorial Board of Chinese Journal of Synthetic Chemistry
Supported by:
Beijing Magtech
