Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of <i>N-</i>(3,5-Dibromosalicylidene)valine

Citation: TIAN Lai-Jin, YAO Yan-Ze, LIU Qing-Tao, ZHENG Xiao-Feng. Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3,5-Dibromosalicylidene)valine[J]. Chinese Journal of Structural Chemistry, 2016, 35(6): 849-856. doi: 10.14102/j.cnki.0254-5861.2011-1058 shu

Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3,5-Dibromosalicylidene)valine

1.
Department of Chemistry, Qufu Normal University, Qufu 273165, China

通讯作者: TIAN Lai-Jin,

基金项目:

ong Provincial Natural Science Foundation (ZR2013BM007) (ZR2013BM007)

ong Province (BS2014CL015) (BS2014CL015)

the National Natural Science Foundation of China (21302110) (21302110)

摘要: Three cyclohexyltin complexes of N-(3,5-dibromosalicylidene)valine (H₂L), Cy₃Sn(HL) (1), Cy₂SnL (2), and Cy₂SnL·Cy₃SnCl (3) (Cy = cyclohexyl), have been synthesized and characterized by elemental analysis, IR, and ¹H and^{13C NMR spectra.}The crystal structures of 2 and 3 have been determined. Complex 2 belongs to the monoclinic system, space group P2₁/n with a = 21.250(8), b = 10.837(4), c = 23.050(8) Å, b = 93.193(9)°, V = 5300(3) Å³, Z = 8, D_c= 1.659 g/cm³, m ＝ 4.004 mm^-1, F(000) = 2624, R = 0.0471 and wR = 0.1015. Complex 3 belongs to the monoclinic system, space group P2₁ with a = 10.3452(10), b = 18.7665(18), c = 12.1483(12) Å, b = 103.374(2)°, V = 2294.5(4) Å³, Z = 2, D_c= 1.542 g/cm³, m = 2.923 mm^-1, F(000) = 1072, R = 0.0428 and wR = 0.0936. Complex 2 has a distorted trigonal bipyramidal geometry with the axial locations occupied by one carboxylate oxygen and a phenolic oxygen of the ligand, and 3 reveals that the two tin atoms are joined via the carbonyl atom of the ligand to form a mixed organotin binuclear complex. Bioassay results show that 1 and 2 have good in vitro antibacterial activity against Escherichia coli.

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English

Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3,5-Dibromosalicylidene)valine

1.
Department of Chemistry, Qufu Normal University, Qufu 273165, China

Corresponding author: TIAN Lai-Jin,

Received Date: 20 November 2015
Fund Project:

Abstract: Three cyclohexyltin complexes of N-(3,5-dibromosalicylidene)valine (H₂L), Cy₃Sn(HL) (1), Cy₂SnL (2), and Cy₂SnL·Cy₃SnCl (3) (Cy = cyclohexyl), have been synthesized and characterized by elemental analysis, IR, and ¹H and^{13C NMR spectra.}The crystal structures of 2 and 3 have been determined. Complex 2 belongs to the monoclinic system, space group P2₁/n with a = 21.250(8), b = 10.837(4), c = 23.050(8) Å, b = 93.193(9)°, V = 5300(3) Å³, Z = 8, D_c= 1.659 g/cm³, m ＝ 4.004 mm^-1, F(000) = 2624, R = 0.0471 and wR = 0.1015. Complex 3 belongs to the monoclinic system, space group P2₁ with a = 10.3452(10), b = 18.7665(18), c = 12.1483(12) Å, b = 103.374(2)°, V = 2294.5(4) Å³, Z = 2, D_c= 1.542 g/cm³, m = 2.923 mm^-1, F(000) = 1072, R = 0.0428 and wR = 0.0936. Complex 2 has a distorted trigonal bipyramidal geometry with the axial locations occupied by one carboxylate oxygen and a phenolic oxygen of the ligand, and 3 reveals that the two tin atoms are joined via the carbonyl atom of the ligand to form a mixed organotin binuclear complex. Bioassay results show that 1 and 2 have good in vitro antibacterial activity against Escherichia coli.

Key words:

1. [1]
  (1) Davis, A. G. Organotin Chemistry. 2nd ed., Wiley-VCH, Weinheim 2004, pp 8–23.(1) Davis, A. G. Organotin Chemistry. 2nd ed., Wiley-VCH, Weinheim 2004, pp 8–23.
2. [2]
  (2) Davies, A. G.; Gielen, M.; Pannell, K. H.; Tiekink, E. R. T. Tin chemistry: fundamentals, frontiers, and applications. John Wiley& Sons, Chichester, U.K. 2008.(2) Davies, A. G.; Gielen, M.; Pannell, K. H.; Tiekink, E. R. T. Tin chemistry: fundamentals, frontiers, and applications. John Wiley& Sons, Chichester, U.K. 2008.
3. [3]
  (3) Arjmand, F.; Parveen, S.; Tabassum, S.; Pettinari, C. Organotin antitumor compounds: their present status in drug development and future perspectives. Inorg. Chim. Acta 2014, 423, 26–37.(3) Arjmand, F.; Parveen, S.; Tabassum, S.; Pettinari, C. Organotin antitumor compounds: their present status in drug development and future perspectives. Inorg. Chim. Acta 2014, 423, 26–37.
4. [4]
  (4) Hadjikakou, S. K.; Hadjiliadis, N. Antiproliferative and anti-tumor activity of organotin compounds. Coord. Chem. Rev. 2009, 253, 235–249.(4) Hadjikakou, S. K.; Hadjiliadis, N. Antiproliferative and anti-tumor activity of organotin compounds. Coord. Chem. Rev. 2009, 253, 235–249.
5. [5]
  (5) Nath, M.; Saini, P. K. Chemistry and applications of organotin(IV) complexes of Schiff bases. Dalton Trans. 2011, 40, 7077–7121.(5) Nath, M.; Saini, P. K. Chemistry and applications of organotin(IV) complexes of Schiff bases. Dalton Trans. 2011, 40, 7077–7121.
6. [6]
  (6) Zamudio-Rivera, L. S.; George-Tellez, R.; Lopez-Mendoza, G.; Morales-Pacheco, A.; Flores, E.; Hopfl, H.; Barba, V.; Fernandez, F. J.; Cabirol, N.; Beltran, H. I. Synthesis, characterization, biocide and toxicological activities of dibutyl- and diphenyl-tin-salicyliden-a-amino alcohol derivatives. Inorg. Chem. 2005, 44, 5370–5378.(6) Zamudio-Rivera, L. S.; George-Tellez, R.; Lopez-Mendoza, G.; Morales-Pacheco, A.; Flores, E.; Hopfl, H.; Barba, V.; Fernandez, F. J.; Cabirol, N.; Beltran, H. I. Synthesis, characterization, biocide and toxicological activities of dibutyl- and diphenyl-tin-salicyliden-a-amino alcohol derivatives. Inorg. Chem. 2005, 44, 5370–5378.
7. [7]
  (7) Mondal, S.; Ghosh, P.; Chakravorty, A. A family of α-amino acid salicylaldiminates incorporating the binuclear V₂O₃³⁺ core: electrosynthesis, structure and metal valence. Inorg. Chem. 1997, 36, 59–63.(7) Mondal, S.; Ghosh, P.; Chakravorty, A. A family of α-amino acid salicylaldiminates incorporating the binuclear V₂O₃³⁺ core: electrosynthesis, structure and metal valence. Inorg. Chem. 1997, 36, 59–63.
8. [8]
  (8) Muche, S.; Levacheva, I.; Samsonova, O.; Pham, L.; Christou, G.; Bakowsky, U.; Holynska, M. A chiral, low cytotoxic [Ni₁₅]-wheel complex. Inorg. Chem. 2014, 53, 7642–7649.(8) Muche, S.; Levacheva, I.; Samsonova, O.; Pham, L.; Christou, G.; Bakowsky, U.; Holynska, M. A chiral, low cytotoxic [Ni₁₅]-wheel complex. Inorg. Chem. 2014, 53, 7642–7649.
9. [9]
  (9) Dakternieks, D.; Basu Baul, T. S.; Dutta, S.; Tiekink, E. R. T. Synthesis, characterization, and X-ray structures of diphenyltin(IV) N-(2-hydroxyacetophenone)glycinate, its 1:1 adduct with triphenyltin chloride, and related systems. Organometallics 1998, 17, 3058–3062.(9) Dakternieks, D.; Basu Baul, T. S.; Dutta, S.; Tiekink, E. R. T. Synthesis, characterization, and X-ray structures of diphenyltin(IV) N-(2-hydroxyacetophenone)glycinate, its 1:1 adduct with triphenyltin chloride, and related systems. Organometallics 1998, 17, 3058–3062.
10. [10]
  (10) Beltran, H. I.; Zamudio-Rivera, L. S.; Mancilla, T.; Santillan, R.; Farfan, N. One-step preparation, structural assignment, and X-ray study of 2,2-di-nbutyl-and 2,2-diphenyl-6-aza-1,3-dioxa-2-stannabenzocyclononen-4-ones derived from amino acids. Chem. Eur. J. 2003, 9, 2291–2306.(10) Beltran, H. I.; Zamudio-Rivera, L. S.; Mancilla, T.; Santillan, R.; Farfan, N. One-step preparation, structural assignment, and X-ray study of 2,2-di-nbutyl-and 2,2-diphenyl-6-aza-1,3-dioxa-2-stannabenzocyclononen-4-ones derived from amino acids. Chem. Eur. J. 2003, 9, 2291–2306.
11. [11]
  (11) Rivera, J. M.; Reyes, H.; Cortes, A.; Santillan, R. Second-harmonic generation within the P2₁2₁2₁ space group, in a series of chiral (salicylaldiminato)tin Schiff base complexes. Chem. Mater. 2006, 18, 1174–1183.(11) Rivera, J. M.; Reyes, H.; Cortes, A.; Santillan, R. Second-harmonic generation within the P2₁2₁2₁ space group, in a series of chiral (salicylaldiminato)tin Schiff base complexes. Chem. Mater. 2006, 18, 1174–1183.
12. [12]
  (12) Basu Baul, T. S.; Masharing, C.; Ruisi, G.; Jirasko, R.; Holcapek, M.; Vos, D.; Wolstenholme, D.; Linden, A. Self-assembly of extended Schiff base amino acetate skeletons, 2-[[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino]phenylpropionate and 2-[[(E)-1-(2-hydroxyaryl)alkylidene]aminophenyl-propionate skeletons incorporating organotin(IV) moieties: synthesis, spectroscopic characterization, crystal structures, and in vitro cytotoxic activity. J. Organomet. Chem. 2007, 692, 4849–4862.(12) Basu Baul, T. S.; Masharing, C.; Ruisi, G.; Jirasko, R.; Holcapek, M.; Vos, D.; Wolstenholme, D.; Linden, A. Self-assembly of extended Schiff base amino acetate skeletons, 2-[[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino]phenylpropionate and 2-[[(E)-1-(2-hydroxyaryl)alkylidene]aminophenyl-propionate skeletons incorporating organotin(IV) moieties: synthesis, spectroscopic characterization, crystal structures, and in vitro cytotoxic activity. J. Organomet. Chem. 2007, 692, 4849–4862.
13. [13]
  (13) Kehie, P.; Chanu, O. B.; Duthie, A.; Hopfl, H. Synthesis and structural studies of diorganotin(IV) compounds derived from (E)-3-hydroxy-2-((2-hydroxybenzylidene)amino) propanoate and (E)-3-hydroxy-2-((1-(2-hydroxyphenyl)ethylidene)amino)propanoate. J. Organomet. Chem. 2013, 733, 36–43.(13) Kehie, P.; Chanu, O. B.; Duthie, A.; Hopfl, H. Synthesis and structural studies of diorganotin(IV) compounds derived from (E)-3-hydroxy-2-((2-hydroxybenzylidene)amino) propanoate and (E)-3-hydroxy-2-((1-(2-hydroxyphenyl)ethylidene)amino)propanoate. J. Organomet. Chem. 2013, 733, 36–43.
14. [14]
  (14) Tian, L.; Qian, B.; Sun, Y.; Zheng, X.; Yang, M.; Li, H.; Liu, X. Synthesis, structural characterization and cytotoxic activity of diorganotin (IV) complexes of N-(5-halosalicylidene)-α-amino acid. Appl. Organometal. Chem. 2005, 19, 980–987.(14) Tian, L.; Qian, B.; Sun, Y.; Zheng, X.; Yang, M.; Li, H.; Liu, X. Synthesis, structural characterization and cytotoxic activity of diorganotin (IV) complexes of N-(5-halosalicylidene)-α-amino acid. Appl. Organometal. Chem. 2005, 19, 980–987.
15. [15]
  (15) Tian, L.; Shang, Z.; Zheng, X.; Sun, Y.; Yu, Y.; Qian, B.; Liu, X. Synthesis, characterization and biological activity of diphenyltin(IV) complexes of N-(3,5-dibromosalicylidene)-α-amino acid and their diphenyltin dichloride adducts. Appl. Organometal. Chem. 2006, 20, 74–80.(15) Tian, L.; Shang, Z.; Zheng, X.; Sun, Y.; Yu, Y.; Qian, B.; Liu, X. Synthesis, characterization and biological activity of diphenyltin(IV) complexes of N-(3,5-dibromosalicylidene)-α-amino acid and their diphenyltin dichloride adducts. Appl. Organometal. Chem. 2006, 20, 74–80.
16. [16]
  (16) Tian, L.; Sun, Y.; Zheng, X.; Liu, X.; Yu, Y.; Liu, X; Qian, B. Synthesis, characterization and biological activity of diorganotin(IV) complexes of N-(3,5-dibromosalicylidene)-α-amino acid. Chin. J. Chem. 2007, 25, 312–318.(16) Tian, L.; Sun, Y.; Zheng, X.; Liu, X.; Yu, Y.; Liu, X; Qian, B. Synthesis, characterization and biological activity of diorganotin(IV) complexes of N-(3,5-dibromosalicylidene)-α-amino acid. Chin. J. Chem. 2007, 25, 312–318.
17. [17]
  (17) Tian, L. J.; Yang, H. J.; Wang, W.; Ni, Z. H. Syntheses and crystal structures of two diethyltin complexs of N-salicylidene-a-amino acid. Chin. J. Struct. Chem. 2009, 28, 663–668.(17) Tian, L. J.; Yang, H. J.; Wang, W.; Ni, Z. H. Syntheses and crystal structures of two diethyltin complexs of N-salicylidene-a-amino acid. Chin. J. Struct. Chem. 2009, 28, 663–668.
18. [18]
  (18) Tian, L.; Liu, X.; Zheng, X.; Sun, Y.; Yan, D.; Tu, L. Synthesis, characterization and cytotoxic activity of new diorganotin(IV) complexes of N-(3,5-dibromosalicylidene)tryptophane. Appl. Organometal. Chem. 2011, 25, 298–304.(18) Tian, L.; Liu, X.; Zheng, X.; Sun, Y.; Yan, D.; Tu, L. Synthesis, characterization and cytotoxic activity of new diorganotin(IV) complexes of N-(3,5-dibromosalicylidene)tryptophane. Appl. Organometal. Chem. 2011, 25, 298–304.
19. [19]
  (19) Dang, Y. Q.; Yang, H. J.; Tian, L. J. Syntheses and structural characterization of dimethyltin complexes of N-(3-methoxysalicylidene)-α-amino acid. Chin. J. Struct. Chem. 2012, 31, 479–484.(19) Dang, Y. Q.; Yang, H. J.; Tian, L. J. Syntheses and structural characterization of dimethyltin complexes of N-(3-methoxysalicylidene)-α-amino acid. Chin. J. Struct. Chem. 2012, 31, 479–484.
20. [20]
  (20) Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122.(20) Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122.
21. [21]
  (21) Zhang, H.; Yu, X.; Li, X.; Pan, X. A study of promotive and fungistatic actions of steroidal saponin by microcalorimetric method. Thermochim. Acta 2004, 416, 71–74.(21) Zhang, H.; Yu, X.; Li, X.; Pan, X. A study of promotive and fungistatic actions of steroidal saponin by microcalorimetric method. Thermochim. Acta 2004, 416, 71–74.
22. [22]
  (22) Deacon, G. B.; Phillips, R. J. Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord. Chem. Rev. 1980, 33, 227–250.(22) Deacon, G. B.; Phillips, R. J. Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord. Chem. Rev. 1980, 33, 227–250.
23. [23]
  (23) Tian, L.; Sun, Y.; Li, H.; Zheng, X.; Cheng, Y.; Liu, X.; Qian, B. Synthesis, characterization and biological activity of triorganotin 2-phenyl-1,2,3-triazole-4-carboxylates. J. Inorg. Biochem. 2005, 99, 1646–1652.(23) Tian, L.; Sun, Y.; Li, H.; Zheng, X.; Cheng, Y.; Liu, X.; Qian, B. Synthesis, characterization and biological activity of triorganotin 2-phenyl-1,2,3-triazole-4-carboxylates. J. Inorg. Biochem. 2005, 99, 1646–1652.
24. [24]
  (24) Nath, M.; Yadav, R.; Gielen, M.; Dalil, H.; Vos, D. D.; Eng, G. Synthesis, characteristic spectral studies and in vitro antimicrobial and antitumour activities of organotin complexes of Schiff bases derived from amino-acids. Appl. Organometal. Chem. 1997, 11, 727–736.(24) Nath, M.; Yadav, R.; Gielen, M.; Dalil, H.; Vos, D. D.; Eng, G. Synthesis, characteristic spectral studies and in vitro antimicrobial and antitumour activities of organotin complexes of Schiff bases derived from amino-acids. Appl. Organometal. Chem. 1997, 11, 727–736.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3,5-Dibromosalicylidene)valine

通讯作者: TIAN Lai-Jin,

English

Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3,5-Dibromosalicylidene)valine

Corresponding author: TIAN Lai-Jin,

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3,5-Dibromosalicylidene)valine

通讯作者: TIAN Lai-Jin,

English

Synthesis, Characterization and Antibacterial Activity of Cyclohexyltin Complexes of N-(3,5-Dibromosalicylidene)valine

Corresponding author: TIAN Lai-Jin,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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