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Synthesis, Crystal, Calculated Structure and Biological Activity of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-N-(1-adamantyl)-3-(dimethylamino) Propanamide
Alternative TitleSynthesis, Crystal, Calculated Structure and Biological Activity of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl) methyl)-N-(1-adamantyl)-3-(dimethylamino) Propanamide
Bai YueFei1; Yuan Lei1; Wang LiJuan2; Gao Jian1; Wang ZhiQiang1; Wang XiaoFei1; Sun TieMin1
2012
Source PublicationCHINESE JOURNAL OF STRUCTURAL CHEMISTRY
ISSN0254-5861
Volume31Issue:2Pages:205-210
AbstractThe 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-3-4-yl)(phenyl)methyl)-N-(1-adamantyl)-3-(dimethylamino) propanamide-(C32H38BrN3O2, M-r = 576.56), and its structure was confirmed by elemental analysis, IR,H-1 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) angstrom, beta = 113.969(16)degrees, V = 2851.0(18) angstrom(3), Z = 4, D-c = 1.343 g/cm(3), F(000) = 1208, mu(MoK alpha) = 1.475 mm(-1), the final R = 0.0645 and wR = 0.2039. In total, 4681 independent reflections including 3164 observed ones with I > 2 sigma(I) were collected. The dihedral angle between substituted quinolyl and phenyl is 64.0 degrees. Through C-H center dot center dot center dot O, C-H center dot center dot center dot N and C-H center dot center dot center dot 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.
Other AbstractThe 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.
KeywordMYCOBACTERIUM-TUBERCULOSIS ATP SYNTHASE CYTOTOXICITY DERIVATIVES synthesis X-ray diffraction DFT biological activity
Indexed ByCSCD
Language英语
CSCD IDCSCD:4448706
Citation statistics
Cited Times:2[CSCD]   [CSCD Record]
Document Type期刊论文
Identifierhttp://ir.imr.ac.cn/handle/321006/142257
Collection中国科学院金属研究所
Affiliation1.中国科学院金属研究所
2.中山大学
Recommended Citation
GB/T 7714
Bai YueFei,Yuan Lei,Wang LiJuan,et al. Synthesis, Crystal, Calculated Structure and Biological Activity of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-N-(1-adamantyl)-3-(dimethylamino) Propanamide[J]. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY,2012,31(2):205-210.
APA Bai YueFei.,Yuan Lei.,Wang LiJuan.,Gao Jian.,Wang ZhiQiang.,...&Sun TieMin.(2012).Synthesis, Crystal, Calculated Structure and Biological Activity of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-N-(1-adamantyl)-3-(dimethylamino) Propanamide.CHINESE JOURNAL OF STRUCTURAL CHEMISTRY,31(2),205-210.
MLA Bai YueFei,et al."Synthesis, Crystal, Calculated Structure and Biological Activity of N-((6-bromo-2-methoxyquinolin-3-yl)(phenyl)methyl)-N-(1-adamantyl)-3-(dimethylamino) Propanamide".CHINESE JOURNAL OF STRUCTURAL CHEMISTRY 31.2(2012):205-210.
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