基于咔唑-三嗪并吲哚的N-酰腙衍生物的NMR数据归属

doi:10.11938/cjmr20202803

波谱学杂志 ›› 2020, Vol. 37 ›› Issue (4): 496-504.doi: 10.11938/cjmr20202803

基于咔唑-三嗪并吲哚的N-酰腙衍生物的NMR数据归属

李英俊¹, 杨鸿境¹, 刘季红², 靳焜³, 林乐弟¹, 刘雪洁¹

1. 辽宁师范大学化学化工学院, 辽宁大连 116029;
2. 大连理工大学化学分析测试中心辽宁大连 116024;
3. 大连理工大学精细化工国家重点实验室, 辽宁大连 116023

收稿日期:2020-01-19 出版日期:2020-11-05 发布日期:2020-03-23
通讯作者: 李英俊,Tel:0411-82158329,E-mail:chemlab.lnnu@163.com. E-mail:chemlab.lnnu@163.com
基金资助:
辽宁省自然科学基金资助项目（20102126）.

Assignments of NMR Spectral Data of a Novel Carbazole-Triazinoindole Based N-Acylhydrazone Derivative

LI Ying-jun¹, YANG Hong-jing¹, LIU Ji-hong², JIN Kun³, LIN Le-di¹, LIU Xue-jie¹

1. College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China;
2. Chemistry Analysis and Inspection Center, Dalian University of Technology, Dalian 116024, China;
3. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, China

Received:2020-01-19 Online:2020-11-05 Published:2020-03-23

摘要/Abstract

摘要： N-酰腙类化合物在极性溶剂中存在着E/cis和E/trans两种异构体，本文利用元素分析、红外光谱、1D和2D核磁共振（NMR）波谱（包括¹H NMR、¹³C NMR、¹H-¹H COSY、¹H-¹³C HSQC、¹H-¹³C HMBC和NOESY）等技术，对基于咔唑-三嗪并吲哚的新型N-酰腙衍生物3，即2-（5H-[1，2，4]三嗪[5，6-b]吲哚-3-硫基）-N'-（9-乙基咔唑-3-亚甲基）乙酰肼的两种异构体（E/cis和E/trans）的¹H和¹³C NMR信号进行了全归属，测量了其偶合常数（J值）及两种异构体的含量，确定了其空间结构.

关键词: 核磁共振（NMR）, 归属, 2D NMR, 咔唑-三嗪并吲哚, N-酰腙衍生物

Abstract: N-acylhydrazone compounds have two isomers, E/cis and E/trans, in polar solvents. In this work, ¹H and ¹³C nuclear magnetic resonance (NMR) signals, coupling constants (J), and the spatial structures of the two isomers (E/cis and E/trans) of a novel carbazole-triazinoindole based N-acylhydrazone derivative 3, 2-(5H-[1,2,4] triazine[5,6-b]indol-3-ylthio)-N'-(9-ethylcarbazol-3-ylmethylene)acetylhydrazine, were obtained by one-dimensional and two-dimensional NMR techniques, infrared spectroscopy (IR) and elemental analysis. The ratios of the two isomers were determined.

Key words: nuclear magnetic resonance (NMR), assignment, 2D NMR, carbazole-triazinoindole, N-acylhydrazone derivative

中图分类号:

O482.53

李英俊, 杨鸿境, 刘季红, 靳焜, 林乐弟, 刘雪洁. 基于咔唑-三嗪并吲哚的N-酰腙衍生物的NMR数据归属[J]. 波谱学杂志, 2020, 37(4): 496-504.

LI Ying-jun, YANG Hong-jing, LIU Ji-hong, JIN Kun, LIN Le-di, LIU Xue-jie. Assignments of NMR Spectral Data of a Novel Carbazole-Triazinoindole Based N-Acylhydrazone Derivative[J]. Chinese Journal of Magnetic Resonance, 2020, 37(4): 496-504.

参考文献

[1] KUMAR V. Hydrazone:A promising pharmacophore in medicinal chemistry[J]. J Pharmacogn Phytochem, 2018, 7(2):40-43.
[2] JADNA SILVA FREDERICO M, JHONATAN GOMES CASTRO A, MASCARELLO A, et al. Acylhydrazones contribute to serum glucose homeostasis through dual physiological targets[J]. Curr Top Med Chem, 2012, 12(19):2049-2058.
[3] CERQUEIRA J V, MEIRA C S, DE SOUZA SANTOS E, et al. Anti-inflammatory activity of SintMed65, an N-acylhydrazone derivative, in a mouse model of allergic airway inflammation[J]. Int Immunopharmacol, 2019, 75:105735.
[4] ISSA S, PRANDINA A, BEDEL N, et al. Carbazole scaffolds in cancer therapy:a review from 2012 to 2018[J]. J Enzyme Inhib Med Chem, 2019, 34(1):1321-1346.
[5] LI Y J, WANG S Y, JIN K, et al. Synthesis and Cdc25B/PTP1B inhibitory activity evaluation of novel acylhydrazone derivatives containing carbazole moity[J]. Chin J Org Chem, 2019, 39(2):491-499. 李英俊, 王思远, 靳焜, 等. 新型含咔唑环酰腙衍生物的合成及Cdc25B/PTP1B抑制活性评价[J]. 有机化学, 2019, 39(2):491-499.
[6] LI Y J, ZHAO Y, JIN K, et al. Synthesis and PTP1B/TCPTP Inhibitory Activity Evaluation of Novel 2,5-Disubstituted-1,3,4-thiadiazolamide Derivatives Containing Carbazole/Benzimidazole Moity[J]. Chin J Org Chem, 2019, 39(9):2599-2608. 李英俊, 赵月, 靳焜, 等. 含咔唑/苯并咪唑环的2,5-二取代-1,3,4-噻二唑酰胺衍生物的合成及对PTP1B/TCPTP抑制活性的评价[J]. 有机化学, 2019, 39(9):2599-2608.
[7] TANG Y B, LIU J Z, ZHANG S E, et al. 3-Phenylpropanoic acid-based phosphotyrosine (pTyr) mimetics:Hit evolution to a novel orally active protein tyrosine phosphatase 1B (PTP1B) inhibitor[J]. Chem Med Chem, 2014, 9(5):918-921.
[8] CARUSO A, CERAMELLA J, IACOPETTA D, et al. Carbazole derivatives as antiviral agents:An overview[J]. Molecules, 2019, 24(10):1912.
[9] SHAIKH M S, KANHED A M, CHANDRASEKARAN B, et al. Discovery of novel N-methyl carbazole tethered rhodanine derivatives as direct inhibitors of Mycobacterium tuberculosis InhA[J]. Bioorg Med Chem Lett, 2019, 29(16):2338-2344.
[10] TAMENE D, ENDALE M. Antibacterial activity of coumarins and carbazole alkaloid from roots of clausena anisata[J]. Adv Pharmacol Sci, 2019:5419854.
[11] MAHAPATRA D K, DADURE K M, SHIVHARE R S. Edema reducing potentials of some emerging Schiff's bases of murrayanine[J]. MOJ Bioorg Org Chem, 2018, 2(4):171-174.
[12] ZHANG Q, DING D, ZENG S X, et al. Structure and activity analysis of Inauhzin analogs as novel antitumor compounds that induce p53 and inhibit cell growth[J]. PLoS one, 2012, 7(10):e46294.
[13] ALI R, SAAD H. Synthesis of some novel fused pyrimido[4'',5'':5',6']-[1,2,4] triazino[3',4':3,4] [1,2,4] triazino[5,6-b]indoles with expected anticancer activity[J]. Molecules, 2018, 23(3):693.
[14] ZHAN J Y, MA K, ZHENG Q C, et al. Exploring the interactional details between aldose reductase (AKR1B1) and 3-mercapto-5H-1,2, 4-triazino[5,6-b]indole-5-acetic acid through molecular dynamics simulations[J]. J Biomol Struct Dyn, 2019, 37(7):1724-1735.
[15] RAHIM F, TARIQ S, TAHA M, et al. New triazinoindole bearing thiazole/oxazole analogues:Synthesis, α-amylase inhibitory potential and molecular docking study[J]. Bioorg Chem, 2019, 92:103284.
[16] SHRUTHI N, POOJARY B, KUMAR V, et al. Synthesis and biological evaluation of N-(substituted phenyl)-2-(5H-[1,2,4] triazino[5,6-b] indol-3-ylsulfanyl)acetamides as antimicrobial, antidepressant, and anticonvulsant agents[J]. Russ J Bioorg Chem, 2015, 41(2):223-230.
[17] SHELKE S M, BHOSALE S H, MAHADIK K R. 3-(5H-[1,2,4] Triazino[5,6-b]indol-3-ylthio)-N-(substituted phenyl)propionamides:Synthesis and antidepressant activity evaluation[J]. Der Pharma Chemica, 2010, 2(4):169-177.
[18] ASWAR U M, KALSHETTI P P, SHELKE S M, et al. Effect of newly synthesized 1,2,4-triazino[5,6-b]indole-3-thione derivatives on olfactory bulbectomy induced depression in rats[J]. Asian Pac J Trop Biomed, 2012, 2(12):992-998.
[19] KGOKONG J L, SMITH P P, MATSABISA G M. 1,2,4-Triazino[5,6-b]indole derivatives:effects of the trifluoromethyl group on in vitro antimalarial activity[J]. Bioorg Med Chem, 2005, 13(8):2935-2942.
[20] SIVENDRAN S, JONES V, SUN D, et al. Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-D-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC)[J]. Bioorg Med Chem, 2010, 18(2):896-908.
[21] LI Y J, LIU X J, LIU J H, et al. Synthesis and PTP1B inhibitory activity evaluation of novel carbazole-based carbohydrazone derivatives[J]. Chin J Org Chem, 2020, 40(2):478-488. 李英俊, 刘雪洁, 刘季红, 等. 基于咔唑的新型碳酰腙衍生物的合成及PTP1B抑制活性评价[J]. 有机化学, 2020, 40(2):478-488.
[22] HAMID H M A. Functionalised 1,2,4-triazino[5,6-b]indoles[J]. J Chem Res, 2004, 2004(3):183-185.
[23] ZHOU M, EUN Y J, GUZEI I A, et al. Structure-activity studies of divin:an inhibitor of bacterial cell division[J]. ACS Med Chem Lett, 2013, 4(9):880-885.
[24] HIZLIATEŞ C G. Arylidene carbazole carbohydrazides:Synthesis and characterization[J]. Hacettepe J Biol Chem, 2018, 46(2):169-175.
[25] LI Y J, YANG K D, JIN K, et al. NMR study of a novel carbazole-isatin based bis-thiocarbohydrozone derivative[J]. Chinese J Magn Reson, 2019, 36(1):83-92.李英俊, 杨凯栋, 靳焜, 等. 基于咔唑-靛红双-硫代碳酰腙衍生物的NMR研究[J]. 波谱学杂志, 2019, 36(1):83-92.
[26] YIN T P, WANG Z, CHEN Y, et al. An NMR analysis of 10-indol cytochalasin chaetoglobosin F[J]. Chinese J Magn Reson, 2019, 36(1):74-82. 尹田鹏, 汪泽, 陈阳, 等. 10-吲哚细胞松弛素chaetoglobosin F的NMR解析[J]. 波谱学杂志, 2019, 36(1):74-82.
[27] LI Y J, LI J Y, JIN K, et al. An NMR study of a novel N-acylhydrazone derivative containing benzimidazole moiety[J]. Chinese J Magn Reson, 2017, 34(1):25-34.李英俊, 李继阳, 靳焜, 等. 含苯并咪唑环N-酰腙衍生物的NMR研究[J]. 波谱学杂志, 2017, 34(1):25-34.

基于咔唑-三嗪并吲哚的N-酰腙衍生物的NMR数据归属

Assignments of NMR Spectral Data of a Novel Carbazole-Triazinoindole Based N-Acylhydrazone Derivative

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	柯汉平, 蔡宏浩. 基于哈德曼编码的新型高分辨定域谱[J]. 波谱学杂志, 2020, 37(4): 524-532.
[2]	刘思, 安艳捧, 唐惠儒. 冷冻干燥对人类体液代谢组影响的NMR研究[J]. 波谱学杂志, 2020, 37(4): 484-489.
[3]	刘欢, 徐锦绣, 郑炀, 熊镭. 渤海J油田储层核磁共振测井孔隙度影响因素分析及校正[J]. 波谱学杂志, 2020, 37(3): 370-380.
[4]	王思宏, 张敬东, 尹秀梅, 李东浩, 阚玉和, 胡伟. 6-(4-氯苯氧基)四唑并[5,1-a]酞嗪的核磁共振谱峰归属[J]. 波谱学杂志, 2020, 37(3): 390-398.
[5]	尹田鹏, 李幸, 汪泽, 王雅溶, 王敏. 石斛属植物中石斛碱类成分的波谱学特征[J]. 波谱学杂志, 2020, 37(3): 381-389.
[6]	张宫, 何宗斌, 曹文倩, 陈瑶. 回波间隔对核磁共振表观孔隙度的影响及矫正方法[J]. 波谱学杂志, 2020, 37(2): 172-181.
[7]	张一鸣, 陈志雪, 杨晓云. 丁氟螨酯的波谱学数据解析与结构确证[J]. 波谱学杂志, 2020, 37(2): 224-231.
[8]	刘慧霞, 辛家祥, 魏达秀, 姚叶锋. 核自旋单重态的制备及其转化效率和寿命的影响因素分析[J]. 波谱学杂志, 2020, 37(2): 182-192.
[9]	闫松, 屠小青, 彭梅. 光泵抽运³He极化程度监控系统的设计与实现[J]. 波谱学杂志, 2020, 37(1): 114-122.
[10]	李震, 蔡宏浩, 雷国伟, 赖宗英, 吴孟键, 闫瑾, 潘邵斌. 不均匀场下基于分子间双量子相干核磁共振技术的果肉检测[J]. 波谱学杂志, 2019, 36(4): 563-570.
[11]	赵智慧, 刘表兰, 闫小双, 武帅帅, 茹阁英, 毛诗珍, 冯继文. PSSS₅₀-b-PNIPAM₃₀₀嵌段共聚物在二元溶剂中自组装的NMR研究[J]. 波谱学杂志, 2019, 36(4): 502-509.
[12]	方仲佩, 孙鹏, 王倩文, 张亮, 刘买利, 张许. 天然同位素丰度野生型酵母细胞色素c构象变化的核磁共振检测[J]. 波谱学杂志, 2019, 36(4): 481-489.
[13]	杨盈, 黄少华, 冯继文. 核磁共振氢谱中二苯基乙二胺衍生物手性识别其结构类似物[J]. 波谱学杂志, 2019, 36(4): 525-533.
[14]	王亚兰, 王晓静, 王志伟. 阿齐沙坦的波谱学数据及结构确证[J]. 波谱学杂志, 2019, 36(3): 350-358.
[15]	刘季红, 靳焜, 王平, 罗根. 七叶亭及其衍生物的NMR研究[J]. 波谱学杂志, 2019, 36(3): 341-349.