2-(2-苯并噁唑啉酮-3-甲基)-6-芳基-咪唑[2,1-b][1,3,4]噻二唑的NMR谱研究

波谱学杂志 ›› 2010, Vol. 27 ›› Issue (4): 617-622.

2-(2-苯并噁唑啉酮-3-甲基)-6-芳基-咪唑[2,1-b][1,3,4]噻二唑的NMR谱研究

李英俊^*，李春燕，靳焜，安静，王雷雷，赵星

辽宁师范大学化学化工学院，辽宁大连 116029

收稿日期:2010-01-18 修回日期:2010-02-23 出版日期:2010-12-05 发布日期:2010-12-05
基金资助:
Natural Science Foundation of Liaoning Province (20102126) and Education office Foundation of Liaoning Province (2008345)

An NMR Study on 2-[(2-Benzoxazolinone-3-yl)methyl]-6-phenyl-imidazo[2,1-b][1,3,4]thiadiazole

LI Ying-Jun^*, LI Chun-Yan, JIN Kun, AN Jing, WANG Lei-Lei, ZHAO Xing

College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China

Received:2010-01-18 Revised:2010-02-23 Online:2010-12-05 Published:2010-12-05
Supported by:
Natural Science Foundation of Liaoning Province (20102126) and Education office Foundation of Liaoning Province (2008345)

摘要/Abstract

摘要：

许多文献已报道，含有咪唑[2,1-b][1,3,4]噻唑环的衍生物具有抗癌、抗结核、抗菌、抗真菌、抗惊厥、止痛等活性. 该文合成了一个新的在医药方面具有潜在应用价值的咪唑[2,1-b][1,3,4]噻二唑衍生物，即2-(2-苯噁唑啉酮-3-甲基)-6-苯基-咪唑[2,1-b][1,3,4]噻二唑，并利用2D NMR技术对其¹H NMR 和¹³C NMR谱进行了全归属. 

关键词: 核磁共振（NMR), 归属, 2D NMR, 2-苯并噁唑啉酮, 咪唑[2,1-b][1,3,4]噻二唑

Abstract:

Many compounds containing imidazo[2,1-b][1,3,4]thiadiazole ring showed pharmacological properties such as anticancer, antitubercular, antibacterial, antifungal, anticonvulsant, analgesic activities. In this paper, a novel compound which may have potential pharmaceutical applications, 2-[(2-benzoxazolinone-3-yl)methyl]-6-phenyl-imidazo[2,1-b][1,3,4] thiadiazole, was synthesized. Its ¹H and ¹³C NMR chemical shifts were assigned using 2D NMR techniques, including gHMQC, gHMBC and ¹H-¹H COSY.

Key words: NMR, assignment, 2D NMR, 2-benzoxazolinone, imidazo[2,1-b][1,3,4]thiadiazole

中图分类号:

O641

李英俊, 李春燕, 靳焜, 安静, 王雷雷, 赵星. 2-(2-苯并噁唑啉酮-3-甲基)-6-芳基-咪唑[2,1-b][1,3,4]噻二唑的NMR谱研究[J]. 波谱学杂志, 2010, 27(4): 617-622.

LI Ying-Jun, LI Chun-Yan, JIN Kun, AN Jing, WANG Lei-Lei, ZHAO Xing. An NMR Study on 2-[(2-Benzoxazolinone-3-yl)methyl]-6-phenyl-imidazo[2,1-b][1,3,4]thiadiazole[J]. Chinese Journal of Magnetic Resonance, 2010, 27(4): 617-622.

参考文献

[1] Jadhav V B, Kulkarni M V, Rasal V P, et al. Synthesis and anti-inflammatory evaluation of methylene bridged benzofuranyl imidazo[2,1-b][1,3,4]thiadiazoles[J]. Eur J Med Chem, 2008, 43: 1 721-1 729.

[2] Ravi S L, Nitinkumar S S, Ravindra R K, et al. Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives[J]. Eur J Med Chem, 2009, 44: 2 828-2 833.

[3] Wang X C, Wang M G, Quan Z J, et al. A neat and rapid synthesis of 2-aryloxymethylene-6-arylimidazo[2,1-b]-1,3,4-thiadiazole under microwave irradiation[J]. Synth Commun, 2005, 35: 2 881-2 888.

[4] Gundurao K, Vinayak H, Imtiyaz ahmed K, et al. Synthesis and evaluation of antitubercular activity of imidazo[2,1-b][1,3,4]thiadiazole derivatives[J]. Bioorg Med Chem, 2006, 14: 3 069-3 080.

[5] Gokhan N, Erdogan H, Tugba Durlu N, et al. Analgesic activity of acylated 2-benzoxazolinone derivatives[J]. Il Farmaco, 1999, 54: 112-115. \

[6] Said Y, Jacques H P, Isabelle L, et al. AlCl₃-DMF reagent in the Friedel-Crafts reaction. Application to the acylation reaction of 2(3H)benzothiazolones[J]. J Org Chem, 1994, 59: 1 574-1 576.

[7] Cals Ü, Gokhan N, Erdogan H. Synthesis of some novel 3-methyl-6-(2-substituted propanoyl/propyl)-2-benzoxazolinone derivatives and anti-nociceptive activity[J]. Il Farmaco, 2001, 56: 719-724.

[8] Ünlü S, nkol T, Dündar Y, et al. Synthesis and analgesic and anti-inflammatory activity of some new (6-acyl-2-benzoxazolinone and 6-acyl-2-benzothiazolinone derivatives with acetic acid and propanoic acid residues[J]. Arch Pharm Pharm Med Chem, 2003, 336: 353-361.

[9] Salgn-Goksen U, Gokhan-Kelekci N, Goktas, et al. 1-Acylthiosemicarbazides,1,2,4-triazole-5(4H)-thiones, 1,3,4-hiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic-anti-inflammatory and antimicrobial activities[J]. Bioorg Med Chem, 2007, 15: 5 738-5 751.

[10] Chiarotto I, Feroci M, Orsini M, et al. Electrogenerated N-heterocyclic carbenes: N-functionalization of benzoxazolones[J]. Tetrahedron, 2009, 65: 3 704-3 710.

[11] Mésangeau C, Narayanan S, Green A M, et al. Conversion of a highly selective sigma-1 receptor-ligand to sigma-2 receptor preferring ligands with anticocaine activity[J]. J Med Chem, 2008, 51: 1 482-1 486.

[12] Li Ying-jun(李英俊), Sun Ya zhen(孙亚珍), Xu Yong-ting(许永廷), et al. An NMR study on 1-(4-nitro-phenylaminoacetyl)-4-phenylacetyl thiosemicarbazide(1-(4-硝基苯氨基乙酰基)-4-苯乙酰基氨基硫脲的NMR谱研究)[J]. Chinese J Magn Reson(波谱学杂志), 2006, 23(4): 517-522.

[13] Jin Kun(靳焜), Wang Pei(王沛), Peng Qin-ji(彭勤纪), et al. Characterization of phthalazinone moiety containing methoxyl side group by NMR spectroscopy(含甲氧基二氮杂萘酮结构类双酚单体的波谱表征) [J]. Chinese J Magn Reson(波谱学杂志), 2006, 23(2): 193-198.

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