基于咔唑-靛红双-硫代碳酰腙衍生物的NMR研究
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摘要
采用多种核磁共振(NMR)技术(包括~1H NMR、~(13)C NMR、~1H-~1H COSY、~1H-~(13)C HSQC、~1H-~(13)C 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~(13)C NMR信号进行了全归属,确定了其结构.
The ~1H and ~(13)C NMR signals of a novel carbazole-isatin based bis-thiocarbohydrozone derivative 2, 1-[(3 Z)-2-oxoindoline-3-ylidene]-5-[(9-hexyl-3-carbazolyl)ylidene]thiocarbohydrazone, were assigned, and the structure of the compound was confirmed.
The ~1H and ~(13)C NMR signals of a novel carbazole-isatin based bis-thiocarbohydrozone derivative 2, 1-[(3 Z)-2-oxoindoline-3-ylidene]-5-[(9-hexyl-3-carbazolyl)ylidene]thiocarbohydrazone, were assigned, and the structure of the compound was confirmed.
引文
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[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.
[2]BO?I?A,MARINKOVI?A,BJELOGRLI?S,et al.Quinoline based mono-and bis-(thio)carbohydrazones:synthesis,anticancer activity in 2Dand 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 vitroα-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]B?RGER 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 JMagn 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.
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