Synthesis and Absolute Configuration of(2R,3S,4Z,6Z)-1,3-bis(benzyloxy)-8-chloro-7-((E)-(2-(2, 4-dinitro-phenyl)hydrazono)methyl)octa-4,6-dien-2-ol

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摘要 Lewis acid-catalyzed [1,3]-sigmatropic O→C rearrangement was used to synthesize C-glycosides derivatives. The structure of the target compound was characterized by NMR and HR-ESI-MS, and its absolute configuration was confirmed. Compound 8 (C29H29ClN4O7): monoclinic system, space group P212121, a = 6.1484(2), b = 12.3625(3), c = 37.0127(8) Å, V = 2813.32(13) Å3, Z = 4, F(000) = 1216.0, Dc = 1.372 g/cm3, μ = 1.662 mm−1, R = 0.0522 and wR = 0.1358 for 5611 independent reflections (Rint = 0.0778) and 5169 observed ones (I > 2σ(I)).

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	ABDULMAJED OTHMAN Karwan
	蔡津津
	解瑞
	周新燃
	姚辉
	黄年玉

关键词 ： X-ray diffraction, crystal structure, absolute configuration, conjugated aliphatic imine, cytotoxity

Abstract：

Lewis acid-catalyzed [1,3]-sigmatropic O→C rearrangement was used to synthesize C-glycosides derivatives. The structure of the target compound was characterized by NMR and HR-ESI-MS, and its absolute configuration was confirmed. Compound 8 (C29H29ClN4O7): monoclinic system, space group P212121, a = 6.1484(2), b = 12.3625(3), c = 37.0127(8) Å, V = 2813.32(13) Å3, Z = 4, F(000) = 1216.0, Dc = 1.372 g/cm3, μ = 1.662 mm−1, R = 0.0522 and wR = 0.1358 for 5611 independent reflections (Rint = 0.0778) and 5169 observed ones (I > 2σ(I)).

Key words： X-ray diffraction crystal structure absolute configuration conjugated aliphatic imine cytotoxity

收稿日期: 2020-02-19 出版日期: 2020-10-10

基金资助:This project was supported by the National Natural Science Foundation of China (No. 21602123) and Youth Talent Development Foundation of China Three Gorges University

通讯作者: yaohui@ctgu.edu.cn E-mail: yaohui@ctgu.edu.cn

引用本文:

ABDULMAJED OTHMAN Karwan;蔡津津;解瑞;周新燃;姚辉;黄年玉. Synthesis and Absolute Configuration of(2R,3S,4Z,6Z)-1,3-bis(benzyloxy)-8-chloro-7-((E)-(2-(2, 4-dinitro-phenyl)hydrazono)methyl)octa-4,6-dien-2-ol[J]. 结构化学, 2020, 39(10): 1781-1787.
ABDULMAJED OTHMAN Karwan;CAI Jin-Jin;XIE Rui;ZHOU Xin-Ran;YAO Hui;HUANG Nian-Yu. Synthesis and Absolute Configuration of(2R,3S,4Z,6Z)-1,3-bis(benzyloxy)-8-chloro-7-((E)-(2-(2, 4-dinitro-phenyl)hydrazono)methyl)octa-4,6-dien-2-ol. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39(10): 1781-1787.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2020/V39/I10/1781

REFERENCES
(1) Olgen, S. Overview on anticancer drug design and development. Curr. Med. Chem. 2018, 25, 17041719.
(2) Diethelm-Varela, B.; Ai, Y.; Liang, D.; Xue, F. Nitrogen mustards as anticancer chemotherapies: historic perspective, current developments and future trends. Curr. Top Med. Chem. 2019, 19, 691712.
(3) Singh, R. K.; Kumar, S.; Prasad, D. N.; Bhardwaj, T. R. Therapeutic journery of nitrogen mustard as alkylating anticancer agents: historic to future perspectives. Eur. J. Med. Chem. 2018, 151, 401433.
(4) Hou, X. M.; Wang, C. Y.; Gerwick, W. H.; Shao, C. L. Marine natural products as potential anti-tubercular agents. Eur. J. Med. Chem. 2019, 165, 273292.
(5) Davison, E. K.; Brimble, M. A. Natural product derived privileged scaffolds in drug discovery. Curr. Opin. Chem. Biol. 2019, 52, 18.
(6) Le Goff, G.; Ouazzani, J. Natural hydrazine-containing compounds: biosynthesis, isolation, biological activities and synthesis. Bioorg. Med. Chem. 2014, 22, 65296544.
(7) Akhtar, M. J.; Yar, M. S.; Khan, A. A.; Ali, Z.; Haider, M. R. Recent advances in the synthesis and anticancer activity of some molecules other than nitrogen containing heterocyclic moeities. Mini. Rev. Med. Chem. 2017, 17, 16021632.
(8) Parshikov, I. A.; Silva, E. O.; Furtado, N. A. Transformation of saturated nitrogen-containing heterocyclic compounds by microorganisms. Appl. Microbiol. Biotechnol. 2014, 98, 14971506.
(9) Yu, J.; Maliutina, K.; Tahmasebi, A. A review on the production of nitrogen-containing compounds from microalgal biomass via pyrolysis. Bioresour Technol. 2018, 270, 689701.
(10) Paik, J.; Blair, H. A. Dapagliflozin: a review in type 1 diabetes. Drugs 2019, 79, 18771884.
(11) Bouloc, A.; Roo, E.; Moga, A.; Chadoutaud, B.; Zouboulis, C. C. A compensating skin care complex containing pro-xylane in menopausal women: results from a multicentre, evaluator-blinded, randomized study. Acta Derm. Venereol. 2017, 97, 541542.
(12) Janssens, J.; Decruy, T.; Venken, K.; Seki, T.; Krols, S.; Van der Eycken, J.; Tsuji, M.; Elewaut, D.; Van Calenbergh, S. Efficient divergent synthesis of new immunostimulant 4΄΄-modified α-galactosylceramide analogues. ACS Med. Chem. Lett. 2017, 8, 642647.
(13) Liao, H. Z.; Ma, J. M.; Yao, H.; Liu, X. W. Recent progress of C-glycosylation methods in the total synthesis of natural products and pharmaceuticals. Org. Biomol. Chem. 2018, 16, 17911806.
(14) Yang, Y.; Yu, B. Recent advances in the chemical synthesis of C-glycosides. Chem. Rev. 2017, 117, 1228112356.
(15) Lai, M. N.; Othman, K. A.; Yao, H.; Wang, Q. Y.; Feng, Y. K.; Huang, N. Y.; Liu, M. G.; Zou, K. Open-air stereoselective construction of C-aryl glycosides. Org. Lett. 2020, 22, 11441148.
(16) Kona, C. N.; Ramana, C. V. Gold(I)-catalysed [1,3] O→C rearrangement of allenyl ethers. Chem. Commun. 2014, 50, 21522154.
(17) Freitas, J. C.; Couto, T. R.; Paulino, A. A.; Freitas Filho, J. R.; Malvestiti, I.; Oliveira, R. A.; Menezes, P. H. Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions. Tetrahedron 2012, 68, 1061110620.
(18) Moons, S. J.; Mensink, R. A.; Bruekers, J. P. J.; Vercammen, M. L. A.; Jansen, L. M.; Boltje, T. J. α-Selective glycosylation with β-glycosyl sulfonium ions prepared via intramolecular alkylation. J. Org. Chem. 2019, 84, 44864500.
(19) Sheldrick, G. M. SHELXS 97, Program for Crystal Structure Determinations. University of Göttingen, Germany 1997.
(20) Sheldrick, G. M. SHELXL 97, Program for the Refinement of Crystal Structure. University of Göttingen, Germany 1997.
(21) Stockert, J. C.; Blázquez-Castro, A.; Cañete, M.; Horobin, R. W.; Villanueva, Á. MTT assay for cell viability: intracellular localization of the formazan product is in lipid droplets. Acta Histochem. 2012, 114, 785–796.
(22) Paolini, J. P. The bond order-bond length relationship. J. Comput. Chem. 1990, 11, 1160–1163.
(23) Yao, Y.; Xiong, C. P.; Zhong, Y. L.; Bian, G. W.; Huang, N. Y.; Wang, L.; Zou, K. Intramolecular and Ferrier rearrangement strategy for the construction of C1-β-D-xylopyranosides: synthesis, mechanism and biological activity study. Adv. Syn. Cat. 2019, 361, 1012–1017.
(24) Jian, S. X.; Tian, Y. Y.; Wang, J. Z.; Hu, W. M.; Huang, N. Y. Research progress on the natural anti-peptic ulcer chemical structures. Chin. J. Struct. Chem. 2018, 37, 1703–1710.
(25) Huang, N. Y.; Wang, W. B.; Chen, L.; Luo, H. J.; Wang, J. Z.; Deng, W. Q.; Zou, K. Design, synthesis and biological evaluation of bisabolonalone oxime derivatives as potassium-competitive acid blockers (P-CABs). Bioorg. Med. Chem. Lett. 2016, 26, 2268–2272.
(26) Cumming, G.; Fidler, F.; Vaux, D. L. Error bars in experimental biology. J. Cell Biol. 2007, 177, 7–11.
(27) West, B. T. Analyzing longitudinal data with the linear mixed models procedure in SPSS. Eval. Health Prof. 2009, 32, 207–228.