有机锡2-[(1,2,4-三唑-1-基)甲基硫代]苯甲酸酯的合成与生物活性

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (6): 1162.

有机锡2-[(1,2,4-三唑-1-基)甲基硫代]苯甲酸酯的合成与生物活性

张晓燕, 杨光, 张俊, 曾广同, 唐良富

南开大学化学系, 元素有机化学国家重点实验室, 天津 300071

收稿日期:2009-08-04 出版日期:2010-06-10 发布日期:2010-06-10
通讯作者: 唐良富, 男, 博士, 教授, 主要从事金属有机化学研究. E-mail: lftang@nankai.edu.cn
基金资助:
国家自然科学基金(批准号: 20721062)资助.

Synthesis and Biological Activities of Organotin 2-[(1,2,4-Triazol-1-yl)methylthio]benzoates

ZHANG Xiao-Yan, YANG Guang, ZHANG Jun, ZENG Guang-Tong, TANG Liang-Fu*

Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Received:2009-08-04 Online:2010-06-10 Published:2010-06-10
Contact: TANG Liang-Fu. E-mail: lftang@nankai.edu.cn
Supported by:
国家自然科学基金(批准号: 20721062)资助.

摘要/Abstract

摘要：

通过硫代水杨酸与(1-氯甲基)-1,2,4-三唑盐酸盐在碱性条件下的反应, 合成了2-[(1,2,4-三唑-1-基)甲基硫代]苯甲酸. 利用该酸与(R₃Sn)₂O(R=Et, n-Bu, Ph), Cy₃SnOH(Cy为环己基)或Et₂SnO反应, 得到了5个有机锡羧酸酯. 用X射线单晶衍射测定了三正丁基锡2-[(1,2,4-三唑-1-基)甲基硫代]苯甲酸酯的晶体结构. 在该化合物中, 锡为五配位的三角双锥结构. 该化合物通过三唑四位氮原子与锡配位, 形成一维链状配位高分子. 初步的生物活性测试结果表明, 所有的有机锡化合物都表现出了明显的抗真菌活性.

关键词: 有机锡羧酸酯; 1,2,4-三唑; 晶体结构; 抗真菌活性

Abstract:

Triazole and its derivatives have attracted broad attention owing to their good coordination ability as well as extensive biological activities. In this paper, a new carboxylic acid with triazole moiety, namely 2-[(1,2,4-triazol-1-yl)methylthio]benzoic acid, was synthesized by the reaction of thiosalicylic acid with 1-chloromethyl-1,2,4-triazole-HCl. Five organotin 2-[(1,2,4-triazol-1-yl)methylthio]benzoates were obtained upon treatment this acid with (R₃Sn)₂O(R=Et, n-Bu, Ph), Cy₃SnOH(Cy=cyclohexyl) and Et₂SnO. The molecular structure of tri(n-butyl)tin 2-[(1,2,4-triazol-1-yl)methylthio]benzoate determined by X-ray crystallography showed that the tin atom was a five-coordinate distorted trigonal bipyramidal geometry with the exodentate nitrogen atom on 4-position of triazole ring and carboxyl oxygen atom occupying the apical position. Moreover, this complex formed a linkage coordination polymer through the intermolecular Sn…N interactions. All these complexes displayed good antifungal activities in vitro against Alternaria solani, Cercospora arachidicola, Gibberella zeae, Physalospora piricola and Botrytis cinerea.

Key words: Organotin carboxylate; 1,2,4-Triazole; Crystal structure; Fungicidal activity

TrendMD:

张晓燕, 杨光, 张俊, 曾广同, 唐良富. 有机锡2-[(1,2,4-三唑-1-基)甲基硫代]苯甲酸酯的合成与生物活性. 高等学校化学学报, 2010, 31(6): 1162.

ZHANG Xiao-Yan, YANG Guang, ZHANG Jun, ZENG Guang-Tong, TANG Liang-Fu* . Synthesis and Biological Activities of Organotin 2-[(1,2,4-Triazol-1-yl)methylthio]benzoates. Chem. J. Chinese Universities, 2010, 31(6): 1162.

参考文献

[1]Hadjikakou S. K., Hadjiliadis N.. Coord. Chem. Rev.[J], 2009, 253: 235—249
[2]Baul T. S. B.. Appl. Organometal. Chem.[J], 2008, 22: 195—204
[3]Chandrasekhar V., Gopal K., Thilagar P.. Acc. Chem. Res.[J], 2007, 40: 420—434
[4]Chandrasekhar V., Nagendran S., Baskar V.. Coord. Chem. Rev.[J], 2002, 235: 1—52
[5]Gielen M.. Appl. Organometal. Chem.[J], 2002, 16: 481—494
[6]Tiekink E. R. T.. Appl. Organometal. Chem.[J], 1991, 5: 1—23
[7]Ma C., Wang Q., Zhang R.. Inorg. Chem.[J], 2008, 47: 7060—7061
[8]Chandrasekhar V., Thirumoorthi R.. Organometallics[J], 2009, 28: 2096—2106
[9]WANG Yan-Hua(王艳华), DU Xi-Guang(杜锡光), WU Xiao-Yan(吴晓燕), ZHU Chao-Guang(朱超光), DU Da-Feng(杜大峰), ZHU Dong-Sheng(朱东升). Chem. J. Chinese Universities(高等学校化学学报)[J], 2008, 29(9): 1781—1785
[10]Yin H. D., Wang C. H., Xing Q. J.. Polyhedron[J], 2004, 23: 1805—1810
[11]Rauf M. K., Saeed M. A., Imtiaz-ud-Din, Bolte M., Badshah A., Mirza B.. J. Organomet. Chem.[J], 2008, 693: 3043—3048
[12]Amini M. M., Azadmehr A., Alijani V., Khavasi H. R., Hajiashraf T.. Inorg. Chim. Acta[J], 2009, 362: 355—360
[13]Lu J. T., Chen S. S., Du M., Tang L. F.. Appl. Organometal. Chem.[J], 2006, 20: 448—453
[14]Zhang X. Y., Song H. B., Li Q. S., Liu X. F., Tang L. F.. Polyhedron[J], 2007, 26: 3743—3749
[15]GAN Xian-Xue(甘贤雪), WANG Xi(王希), ZHANG Hai-Ke(张海科), TANG Liang-Fu(唐良富). Chinese J. Inorg. Chem.(无机化学学报)[J], 2008, 24: 1504—1509
[16]Duong Q., Song X., Mitrojorgji E., Gordon S., Eng G.. J. Organomet. Chem.[J], 2006, 691: 1775—1779
[17]Holeek J., Lyka A.. Inorg. Chim. Acta[J], 1986, 118: L15—L16
[18]Willem R., Bouhdid A., Biesemans M., Martins J. C., Vos D., Tiekink E. R. T., Gielen M.. J. Organomet. Chem.[J], 1996, 514: 203—212
[19]Szorcsik A., Nagy L., Deák A., Scopelliti M., Fekete Z. A., Császár A., Pellerito C., Pellerito L.. J. Organomet. Chem.[J], 2004, 689: 2762— 2769