基于咔唑-靛红双-硫代碳酰腙衍生物的NMR研究

doi:10.11938/cjmr20182665

波谱学杂志 ›› 2019, Vol. 36 ›› Issue (1): 83-92.doi: 10.11938/cjmr20182665

基于咔唑-靛红双-硫代碳酰腙衍生物的NMR研究

李英俊¹, 杨凯栋¹, 靳焜², 刘季红³, 王思远¹, 张楠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, 精细化工国家重点实验室, 辽宁大连 116012;
3. 大连理工大学化学分析测试中心, 辽宁大连 116023

收稿日期:2018-06-18 出版日期:2019-03-05 发布日期:2018-08-21
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）.

NMR Study of A Novel Carbazole-Isatin Based Bis-Thiocarbohydrozone Derivative

LI Ying-jun¹, YANG Kai-dong¹, JIN Kun², LIU Ji-hong³, WANG Si-yuan¹, ZHANG Nan¹

1. College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China;
2. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, China;
3. Chemistry Analysis and Inspection Center, Dalian University of Technology, Dalian 116023, China

Received:2018-06-18 Online:2019-03-05 Published:2018-08-21

摘要/Abstract

摘要： 采用多种核磁共振（NMR）技术（包括¹H NMR、¹³C NMR、¹H-¹H COSY、¹H-¹³C HSQC、¹H-¹³C HMBC），对基于咔唑-靛红双-硫代碳酰腙新型衍生物2，即1-[（3Z）-2-氧代吲哚-3-亚基]-5-[（9-己基-3-咔唑基）亚基]硫代碳酰腙的¹H和¹³C NMR信号进行了全归属，确定了其结构．

关键词: 核磁共振(NMR), 归属, 咔唑, 靛红, 硫代碳酰腙衍生物

Abstract: The ¹H and ¹³C NMR signals of a novel carbazole-isatin based bis-thiocarbohydrozone derivative 2, 1-[(3Z)-2-oxoindoline-3-ylidene]-5-[(9-hexyl-3-carbazolyl)ylidene]thiocarbohydrazone, were assigned, and the structure of the compound was confirmed.

Key words: nuclear magnetic resonance (NMR), chemical shift assignment, carbazole, isatin, thiocarbohydrozone derivative

中图分类号:

O482.53

李英俊, 杨凯栋, 靳焜, 刘季红, 王思远, 张楠. 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.

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.

参考文献

[1] BROCKMAN R W, THOMSON J R, BELL M J, et al. Observations on the antileukemic activity of pyridine-2-carboxaldehyde thiosemicarbazone and thiocarbohydrazone[J]. Cancer Res, 1956, 16(2):167-170.
[2] BOŽIĆ A, MARINKOVIĆ A, BJELOGRLIĆ S, et al. Quinoline based mono-and bis-(thio)carbohydrazones:synthesis, anticancer activity in 2D and 3D cancer and cancer stem cell models[J]. RSC Adv, 2016, 6(106):104763-104781.
[3] GABR M T, EL-GOHARY N S, EL-BENDARY E R, et al. Isatin-β-thiocarbohydrazones:Microwave-assisted synthesis, antitumor activity and structure-activity relationship[J]. Eur J Med Chem, 2017, 128, 36-44.
[4] TEJASREE C, KIRAN G, RAJYALAKSHMI G, et al. Antidiabetic activity of 1-(4-(dimethylamino)benzylidene)-5-(2-oxo indolin-3-ylidene) thiocarbohydrazone in rats[J]. Int J Pharm Sci Res, 2014, 5(7):2738-2743.
[5] GANGARAPU K, MANDA S, JALLAPALLY A. Synthesis of thiocarbohydrazide and carbohydrazide derivatives as possible biologically active agents[J]. Med Chem Res, 2014, 23(2):1046-1056.
[6] ESSA H H, KANDIL F, FALAH A. Synyhesis and identification of schiff bases and bilogical activity new study[J]. Iraqi J Sci, 2012, 53(2):230-240.
[7] SHI Z C, ZHAO Z G, LIU M, et al. Solvent-free synthesis of novel unsymmetric chenodeoxycholic acid bis thiocarbazone derivatives promoted by microwave irradiation and evaluation of their antibacterial activity[J]. CR Chimie, 2013, 16(11):977-984.
[8] LI L, JIANG Y J, Liu X L, et al. Microwave-assisted synthesis and antibacterial activity of unsymmetrical indolyl/aryl bis-thiosemicarbazones[J]. J Chem Res, 2013, 37(6):372-374.
[9] KIRAN G, MANESHWAR T, RAJESHWAR Y, et al. Microwave-assisted synthesis, characterization, antimicrobial and antioxidant activity of some new isatin derivatives[J]. J Chem, 2013, doi:10.1155/2013/192039.
[10] RIYADH S M, GOMHA S M, MAHMMOUD E A. Recent trends in chemistry of ethylidene thiocarbonohydrazides[J]. World J Pharm Pharm Sci, 2015, 4(6):192-201.
[11] WANG J B, YUN D, YAO J L, et al. Design, synthesis and QSAR study of novel isatin analogues inspired Michael acceptor as potential anticancer compounds[J]. Eur J Med Chem, 2018, 144:493-503.
[12] SOLOMON V R, HU C, LEE H. Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity[J]. Bioorg Med Chem, 2009, 17(21):7585-7592.
[13] WANG G C, CHEN M, QIU J, et al. Synthesis, in vitro α-glucosidase inhibitory activity and docking studies of novel chromone-isatin derivatives[J]. Bioorg Med Chem Lett, 2018, 28(2):113-116.
[14] TEHRANI K H M E, HASHEMI M, Hassan M, et al. Synthesis and antibacterial activity of schiff bases of 5-substituted isatins[J]. Chin Chem Lett, 2016, 27(2):221-225.
[15] ANDREANI A, BURNELLI S, GRANAIOLA M, et al. New isatin derivatives with antioxidant activity[J]. Eur J Med Chem, 2010, 45, 1374-1378.
[16] MURALI K, SPARKES, H A, PRASAD K J R. Synthesis of hetero annulated isoxazolo-, pyrido-and pyrimido carbazoles:Screened for in vitro antitumor activity and structure activity relationships, a novel 2-amino-4-(3'-bromo-4'-methoxyphenyl-8-chloro-11H-pyrimido[4,5-a] carbazole as an antitumor agent[J]. Eur J Med Chem, 2017, 128, 319-331.
[17] SUN L Q, WU Y B, LIU Y H, et al. Novel carbazole sulfonamide derivatives of antitumor agent:Synthesis, antiproliferative activity and aqueous solubility[J]. Bioorg Med Chem Lett, 2017, 27(2):261-265.
[18] DINESHKUMAR B, MITRA A, MAHADEVAPPA M. Antidiabetic and hypolipidemic effects of mahanimbine (carbazole alkaloid) from murraya koenigii (rutaceae) leaves[J]. Int J Phytomed, 2010, 2(1):22-30.
[19] WANG G C, WANG J, HE D X, et al. Synthesis and biological evaluation of novel 1,2,4-triazine derivatives bearing carbazole moiety as potent a-glucosidase inhibitors[J]. Bioorg Med Chem Lett, 2016, 26(12):2806-2809.
[20] KONG X Q, ZHANG H Z, CAO C S, et al. Synthesis of fluorinated carbazoles via C-H arylation catalyzed by Pd/Cu bimetal system and their antibacterial activities[J]. Bioorg Med Chem, 2016, 24(6):1376-1383.
[21] BANDGAR B P, ADSUL L K, CHAVAN H V, et al. Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents[J]. Bioorg Med Chem Lett, 2012, 22(18):5839-5844.
[22] ZHU D Q, CHEN M H, LI M, et al. Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity[J]. Eur J Med Chem, 2013, 68:81-88.
[23] HIEDA Y, ANRAKU M, CHOSHI T, et al. Antioxidant effects of the highly-substituted carbazole alkaloids and their related carbazoles[J]. Bioorg Med Chem Lett, 2014, 24(15):3530-3533.
[24] BÖRGER C, BRÜTTING C, JULICH-GRUNER K K, et al. Anti-tuberculosis activity and structure-activity relationships of oxygenated tricyclic carbazole alkaloids and synthetic derivatives[J]. Bioorg Med Chem, 2017, 25(22):6167-6174.
[25] LI Y J, WANG S Y, JIN K, et al. Synthesis and cell division cycle 25B phosphatase/protein tyrosine phosphatase 1B inhibitory activity evaluation of novel acylthiourea derivatives[J]. Chin J Org Chem, 2018, 38(5):1242-1250. 李英俊, 王思远, 靳焜, 等. 新型酰基硫脲衍生物的合成及细胞分裂周期25B磷酸酶和蛋白酪氨酸磷酸酶1B抑制活性研究[J]. 有机化学, 2018, 38(5):1242-1250.
[26] 李继阳. 新型基于咔唑-希夫碱/酰腙衍生物的合成、表征及性能[D]. 大连:辽宁师范大学, 2017.
[27] LI Y Q, SHI W, MA J C, et al. A novel optical probe for Hg²⁺ in aqueous media based on mono-thiosemicarbazone Schiff base[J]. J Photochem Photobioi A, 2017, 338:1-7.
[28] LI Y J, LUO T C, XU Y T, et al. NMR spectroscopic characterization of 2-aryloxymethyl-1H-benzimidazole acetic acid hydrazides[J]. Chinese J Magn Reson, 2013, 30(2):233-246. 李英俊, 罗潼川, 许永廷, 等. 2-芳氧甲基苯并咪唑-1-乙酰肼的NMR谱的表征[J]. 波谱学杂志, 2013, 30(2):233-246.
[29] 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.
[30] ZHOU Z G, YUAN Y Y, LIU H B, et al. An NMR study on prucalopride[J]. Chinese J Magn Reson, 2018, 35(1):119-127. 周中高,元洋洋,刘红波, 等. 普卡必利的NMR研究[J]. 波谱学杂志, 2018, 35(1):119-127.
[31] FAN H Y. Spectral analyses of a novel Ibuprofen-phillygenin ester[J]. Chinese J Magn Reson.. 2018, 35(1):98-108. 樊宏宇. 新型连翘脂素-布洛芬酯合物的波谱学数据解析[J]. 波谱学杂志, 2018, 35(1):98-108.

基于咔唑-靛红双-硫代碳酰腙衍生物的NMR研究

NMR Study of A Novel Carbazole-Isatin Based Bis-Thiocarbohydrozone 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]	胡坤, 孙汉董, 普诺·白玛丹增. 量子化学计算核磁共振参数在天然产物结构鉴定中的应用[J]. 波谱学杂志, 2019, 36(3): 359-376.
[2]	尹田鹏, 王雅溶, 王敏, 石文智, 张正茜, 何莎莎. 三个C₁₉-二萜生物碱的NMR数据全归属[J]. 波谱学杂志, 2019, 36(3): 331-340.
[3]	杨云汉, 杜瑶, 应飞祥, 杨俊丽, 夏大真, 夏福婷, 杨丽娟. 柚皮素/β-环糊精超分子体系的包合行为[J]. 波谱学杂志, 2019, 36(3): 319-330.
[4]	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.
[5]	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.
[6]	曹园, 吴永平, 陈东军. 卷柏属Selaginellin类化合物互变异构的波谱学研究[J]. 波谱学杂志, 2019, 36(2): 155-163.
[7]	寇新慧, 刘乙祥, 刘兴弘, 李从刚, 刘买利, 姜凌. 探测应答调控蛋白PhoB_N^F20D自由态中存在的Pre-Active构象[J]. 波谱学杂志, 2019, 36(2): 164-171.
[8]	陈晓瑛, 俞刚金, 毛诗珍, 刘买利, 杜有如. 利用¹H NMR探究混合离子型/非离子型表面活性剂临界胶束浓度降低的实质[J]. 波谱学杂志, 2019, 36(2): 219-224.
[9]	迟秀娟, 乔晓亚, 刘颖, 刘惠丽, 陈雷, 王际辉, 艾选军. 拟南芥AtGrp7 RRM结构域的纯化及其结构与结合的初步分析(英文)[J]. 波谱学杂志, 2019, 36(1): 1-14.
[10]	尹田鹏, 汪泽, 陈阳, 邵娅婷, 邓亮, 黎唯. 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.
[11]	尹田鹏, 罗智慧, 蔡乐, 丁中涛. 天然C₁₉-二萜生物碱的研究进展及其核磁共振波谱特征[J]. 波谱学杂志, 2019, 36(1): 113-126.
[12]	冉梦琳, 覃凌云, 唐淳, 董旭. 磷酸化调控泛素单体与Rad23A/Ubiquilin-1中泛素结合域互作的检测[J]. 波谱学杂志, 2019, 36(1): 15-22.
[13]	魏会强, 于江, 毕常芬, 宁洪鑫, 李祎亮, 刘强. N-异丁酰基-3'-O-(1-氟-1,1,3,3-四异丙基-1,3-二硅氧烷-3-基)-2'-苄氧羰基鸟苷的NMR研究[J]. 波谱学杂志, 2019, 36(1): 93-102.
[14]	王伟宇, 胡涵, 徐君, 邓风. Pd-Cu双金属催化剂上加氢反应的仲氢诱导超极化研究[J]. 波谱学杂志, 2018, 35(3): 269-279.
[15]	朱云峰, 何为, 何传红, 王怡, 齐天昊, 陈柏冰, 徐征. 基于数字调制技术的核磁共振射频脉冲发生器[J]. 波谱学杂志, 2018, 35(3): 318-327.