A Spectroscopy Study on Novel Daidzein [1,3] Oxazin Derivatives

doi:10.11938/cjmr20160214

Abstract

Abstract:

Two novel daidzein[1,3] oxazine derivatives were synthesized by a one-pot approach using daidzein, n-butyl amine and 37% aqueous solution of formaldehyde as the raw materials under ultrasonic radiation. The ¹H and ¹³C NMR chemical shifts of the title compounds were assigned by two-dimensional NMR techniques, including DEPT, ¹H-¹H COSY, ¹H-¹³C HSQC and ¹H-¹³C HMBC. The reactive sites in daidzein were determined.

Key words: nuclear magnetic resonance (NMR), assignment, daidzein oxazin derivative

CLC Number:

O482.53

YUAN Jin-wei, YIN Qiu-yue, LI Yuan-zhe, MAO Pu, YANG Liang-ru, XIAO Yong-mei, QU Ling-bo. A Spectroscopy Study on Novel Daidzein [1,3] Oxazin Derivatives[J]. Chinese Journal of Magnetic Resonance, 2016, 33(2): 327-336.

References

[1] Wu S Y, Brewer M S. Soy protein isolate antioxidant effect on lipid peroxidation of grouond beef and microsomal lipids[J]. J Food Sci, 1994, 59(4):702-706.

[2] Colditz G A, Stampfer M J, Willett W C, et al. Type of postmenopausal hormone use and risk of breast cancer:12-year follow-up from the nurses' health study[J]. Cancer Causes Control, 1992, 3(5):433-439.

[3] Yadav D K, Gautam A K, Kureel J, et al. Synthetic analogs of daidzein, having more potent osteoblast stimulating effect[J]. Bioorg Med Chem Lett, 2011, 21(2):677-681.

[4] Peng You(彭游), Deng Ze-yuan(邓泽元), Ye Zhi-gang(叶志刚). Progress in prodrug modification of daidzein(大豆苷元的前药修饰研究进展)[J]. Chemistry(化学通报), 2011, 74(6):508-512.

[5] Chen Xiao-lan(陈晓岚), Shi Xiao-na(石晓娜), Qu Ling-bo(屈凌波), et al. The phosphorylation reaction between daidzein and diisopropyl phosphite studied by NMR and ESI MS/MS(大豆苷元磷酰化产物的结构确定)[J]. Chinese J Magn Reson(波谱学杂志), 2007, 24(1):85-90.

[6] Liu Qian-guang(刘谦光), Zhang Zun-ting(张尊听), Xue Dong(薛东). Synthesis, crystal structure and activity of sulfated daidzein(大豆苷元磺化物的合成、晶体结构及活性研究)[J]. Chem J Chinese U(高等学校化学学报), 2003, 24(5):820-825.

[7] Wang S, Li Y, You Q, et al. Novel hexacyclic camptothec in derivatives. Part 1:Synthesis and cytotoxicity of camptothecins with an a-ring fused 1,3-oxazine ring[J]. Bioorg Med Chem, 2008, 18(14):4095-4097.

[8] Tang Zi-long(唐子龙), Xia Zan-wen(夏赞稳), Wang Hong-qing(王宏清), et al. Synthesis and fungicidal activities of 2,3-diaryl-1,3-benzoxazines(2,3-二芳基-1,3-苯并噁嗪的合成及杀菌活性)[J]. Chin J Appl Chem(应用化学), 2015, 32(2):143-150.

[9] Chen S, Li X, Wan S, et al. Synthesis of novel benzoxazinone compounds as epidermal growth factor receptor (EGRF) tyrosine kinase inhibitors[J]. Synthetic Commun, 2012, 42(19):2937-2946.

[10] Zhao Tian-zeng(赵天增). Proton NMR Spectroscopy(核磁共振氢谱)[M]. Beijing(北京):Peking University Press(北京大学出版社), 1983:107-173.

[11] Ning Yong-cheng(宁永成). Structural Identification of Organic Compounds and Organic Spectroscopy(有机化合物结构鉴定与有机波谱学)[M]. Beijing(北京):Science Press(科学出版社), 2000.

[12] Yuan Jin-wei(袁金伟), Chen Xiao-lan(陈晓岚), Qu Ling-bo(屈凌波), et al. Spectroscopic characterization of a novel quinoline-4-phosphoramidate derivative(一种新型的喹啉-4-氨基磷酸酯衍生物的波谱学研究)[J]. Chinese J Magn Reson(波谱学杂志), 2009, 26(1):95-102.

[1]	HU Kun, SUN Han-dong, PUNO Pema-tenzin. Application of Quantum Chemical Calculation of Nuclear Magnetic Resonance Parameters in the Structure Elucidation of Natural Products [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 359-376.
[2]	YIN Tian-peng, WANG Ya-rong, WANG Min, SHI Wen-zhi, ZHANG Zheng-qian, HE Sha-sha. Complete Assignments of NMR Spectral Data of Three C₁₉-Diterpenoid Alkaloids [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 331-340.
[3]	YANG Yun-han, DU Yao, YING Fei-xiang, YANG Jun-li, XIA Da-zhen, XIA Fu-ting, YANG Li-juan. Inclusion Behavior of Naringenin/β-Cyclodextrin Supramolecular Complex [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 319-330.
[4]	WANG Ya-lan, WANG Xiao-jing, WANG Zhi-wei. Spectral Analyses and Structural Elucidation of Azilsartan [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 350-358.
[5]	LIU Ji-hong, JIN Kun, WANG Ping, LUO Gen. An NMR Study on Esculetin and It's Derivatives [J]. Chinese Journal of Magnetic Resonance, 2019, 36(3): 341-349.
[6]	CAO Yuan, WU Yong-ping, CHEN Dong-jun. A Spectroscopic Study on Tautomerism of Selaginellins from Selaginella [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 155-163.
[7]	KOU Xin-hui, LIU Yi-xiang, LIU Xing-hong, LI Cong-gang, LIU Mai-li, JIANG Ling. Visualizing the Pre-Active Conformation of Response Regulator PhoB_N^F20D in Its apo State [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 164-171.
[8]	CHEN Xiao-ying, YU Gang-jin, MAO Shi-zhen, LIU Mai-li, DU You-ru. Mixing-Induced Decreases in Critical Micelle Concentration in Aqueous Solution of Surfactants:Probing into the Mechanisms with ¹H NMR Spectroscopy [J]. Chinese Journal of Magnetic Resonance, 2019, 36(2): 219-224.
[9]	CHI Xiu-juan, QIAO Xiao-ya, LIU Ying, LIU Hui-li, CHEN Lei, WANG Ji-hui, AI Xuan-jun. Purification of the AtGrp7 RRM Domain from Arabidopsis thaliana and Its Preliminary Structure and Binding Analysis [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 1-14.
[10]	YIN Tian-peng, WANG Ze, CHEN Yang, SHAO Ya-ting, DENG Liang, LI Wei. An NMR Analysis of 10-Indol Cytochalasin Chaetoglobosin F [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 74-82.
[11]	YIN Tian-peng, LUO Zhi-hui, CAI Le, DING Zhong-tao. Research Progress and NMR Spectral Features of Natural C₁₉-Diterpenoid Alkaloids [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 113-126.
[12]	RAN Meng-lin, QIN Ling-yun, TANG Chun, DONG Xu. Regulation of Inter-Protein Interactions Between Ubiquitin and Ubiquitin-Associated Domains in Rad23A/Ubiquilin-1 by Phosphorylation [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 15-22.
[13]	WEI Hui-qiang, YU Jiang, BI Chang-fen, NING Hong-xin, LI Yi-liang, LIU Qiang. An NMR Study of N-isobutyryl-3'-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-2'-benzyloxycarbonyl-guanosine [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 93-102.
[14]	LI Ying-jun, YANG Kai-dong, JIN Kun, LIU Ji-hong, WANG Si-yuan, ZHANG Nan. NMR Study of A Novel Carbazole-Isatin Based Bis-Thiocarbohydrozone Derivative [J]. Chinese Journal of Magnetic Resonance, 2019, 36(1): 83-92.
[15]	WANG Wei-yu, HU Han, XU Jun, DENG Feng. Hydrogenation Reaction on Pd-Cu Bimetallic Catalysts: A Parahydrogen-Induced Polarization Study [J]. Chinese Journal of Magnetic Resonance, 2018, 35(3): 269-279.