Synthesis, Crystal, Calculated Structure and Biological Activity of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl) methyl)-N-(1-adamantyl)-3-(dimethylamino) Propanamide
查看参考文献13篇
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文摘
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The halogenated hydrocarbon amination reaction between the original raw material N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-3-chloro-N-(1-adamantyl) propanamide and dimethylamine hydrochloride produces the target molecule N-((6-bromo-2-methoxyquinolin-3- yl)(phenyl)methyl)-N-(1-adamantyl)-3-(dimethylamino) propanamide (C_(32)H_(38)BrN_3O_2, M_r = 576.56), and its structure was confirmed by elemental analysis, IR, ~1H NMR, MS, and X-ray diffraction. This crystal is of monoclinic system, space group P2_1/c with a = 10.760(5), b = 14.768(5), c = 19.635(5)A, β = 113.969(16)°, V = 2851.0(18)A~3, Z = 4, D_c = 1.343 g/cm~3, F(000) = 1208, μ(MoKα) = 1.475 mm~(-1), the final R = 0.0645 and wR = 0.2039. In total, 4681 independent reflections including 3164 observed ones with I > 2σ(I) were collected. The dihedral angle between substituted quinolyl and phenyl is 64.0°. Through C-H···O, C-H···N and C-H···Br weak hydrogen bonds among molecules, the whole molecule is stacked into a three-dimensional structure. The optimized geometric bond lengths and bond angles obtained by using density functional theory (DFT) have been compared with X-ray diffraction values. In addition, the preliminary biological test showed that the title compound has anti-Mycobacterium phlei 1180 activity. |
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来源
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Chinese Journal of Structural Chemistry
,2012,31(2):205-210 【核心库】
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关键词
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synthesis
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X-ray diffraction
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DFT
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biological activity
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地址
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1.
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Key Laboratory of Original New Drug Design & Discovery Ministry of Education, Shenyang, 110016
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Jilin University, State Key Laboratory of Supramolecular Structure and Materials, Changchun, 130012
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语种
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英文 |
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文献类型
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研究性论文 |
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ISSN
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0254-5861 |
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学科
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化学 |
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文献收藏号
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CSCD:4448706
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参考文献 共
13
共1页
|
|
1.
Biava M. Antimycobacterial agents. Novel diarylpyrrole derivatives of BM212 endowed with high activity toward mycobacterium tuberculosis and low cytotoxicity.
J. Med. Chem,2006,49:4946-4952
|
被引
5
次
|
|
|
|
|
2.
Rivers E C. New anti-tuberculosis drugs in clinical trials with novel mechanisms of action.
Drug Discovery Today,2008,13:1090-1098
|
被引
14
次
|
|
|
|
|
3.
Koul A. Diarylquinolines target subunit c of mycobacterial ATP synthase.
Nature Chemical Biology,2007,3:323-324
|
被引
13
次
|
|
|
|
|
4.
Upadhayaya R S. Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against mycobacterium tuberculosis. Bioorg. Med.
Chem,2009,17:2830-2841
|
被引
1
次
|
|
|
|
|
5.
Andries K. A diarylquinoline drug active on the ATP synthase of mycobacterium tuberculosis.
Science,2005,307:223-227
|
被引
65
次
|
|
|
|
|
6.
Lilienkampf A. Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating mycobacterium tuberculosis.
J. Med. Chem,2009,52:2109-2118
|
被引
5
次
|
|
|
|
|
7.
Wang T. A combined experimental and theoretical study on weisiensin B with cytotoxicity.
J. Mol. Struct,2011,994:137-143
|
被引
2
次
|
|
|
|
|
8.
Foresman J B.
Exploring Chemistry with Electronic Structure Methods (Second Ed.),1996
|
被引
1
次
|
|
|
|
|
9.
Frisch M J.
Gaussian 09, Revision A. 1,2009
|
被引
17
次
|
|
|
|
|
10.
Frish A.
Gauss View User Manual,2011
|
被引
2
次
|
|
|
|
|
11.
Sheldrick G M.
SHELXS 97, Program for the Solution of Crystal Structure,1997
|
被引
160
次
|
|
|
|
|
12.
Sheldrick G M.
SHELXL 97, Program for the Refinement of Crystal Structure,1997
|
被引
135
次
|
|
|
|
|
13.
Bai Y F. Synthesis, crystal, computational study and in vitro anti-tuberculosis activity of N-(furan-2-yl-methyl)-N-(phenyl(quinolin-3-yl)methyl) acetamide derivatives.
J. Mol. Struct,2011
|
被引
1
次
|
|
|
|
|
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