Synthesis, characterization and antifertility activity of new unsymmetrical macrocyclic complexes of tin(II)

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Abstract

A new series of unsymmetrical macrocyclic complexes of tin(II) has been prepared by the template process using bis(3-oxo-2-butylidene)propane-1,3-diamine as precursor. This affords as method to synthesize these complexes with various ring sizes. The tetradentate macrocyclic precursor [N4mL] reacts with SnCl2 and different diamines in a 1:1:1 molar ratio in refluxing methanol to give complexes of the type [Sn(N4mL)Cl22]. The ring expansion has been achieved by varying the diamine between the two diacetyl amino nitrogen atoms. The macrocyclic precursor and its metal complexes have been characterized on the basis of elemental analysis, molar conductance, molecular weight determinations, IR, 1H NMR, 13C NMR, 119Sn NMR and electronic spectral studies. An octahedral geometry around the meral ion is suggested for these complexes. On the basis of molecular weights and conductivity measurements, their monomeric and non-electrolytic nature has been confirmed. The precursor and complexes have been screened in vitro against a number of pathogenic fungi and bacteria to assess their growth inhibiting potential. The testicular sperm density and testicular sperm morphology, sperm motility, density of cauda epididymal spermatozoa and fertility in mating trails and biochemicals parameters of reproductive organs have been examined and discussed.

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  • Table I: Physical Properties and Analytical Data of Precursor and its Compounds Analysis(%) Found.(Cacd.). Compound Colour M.P. (*C) M N Ci C H Mol.Wt. Found (Caicd) CH18N202 Reddish 167-169
  • Table II" Fungicidal Screening Data of Precursor and its Compounds (percentage inhibition after 96 h) Compound Fusarium oxysporum Macrophominaphaseolina
  • Table 111: Antibacterial Activity of Precursor and its Compounds [percentage inhibition (mm) after 24 hi (Conc. in ppm)
  • Table IV: H NMR Data (b, ppm) of Precursor and its Compounds (in DMSO-d6) Compound >N-CH2(bs) R -CH3(s) >NH -CH2CHsN202 3.14 (4H) 1.23 (12H) 2.13 (2H) [Sn(CTH22N4)CI2] 3.45 (4H) 8.15(H2,5 d) 7.30(H3,4 d) 1.57 (12H) 2.19 (2H) [Sn(C6H23Ns)Ci2] 3.36 (4H) 8.00(H2,4 s) 7.38 (H3 d) 1.68 (12H) 2.05 (2H) [Sn(CsH27Ns)CI2] 3.40 (12H) 1.28 (12H) 4.33 2.16 (2H) [Sn(C2tH24N4)CI2] 3.56 (4H) 8.3(H2,7 b) 7.30 (H3,6 d) 1.46 (12H) 2.10 (2H) 7.28 (H4,5 d)
  • Table V: 13C NMR Spectral Data (, ppm) of Precursor and its Compounds Compound >C=O >N-CH2 >C=N -CH3 R
  • Table VI Changes in the Body Weight of Reproductive Organs after Treatment with Various Compounds
  • Table VII: Sperm Motility, Concentration and Fertility after Treatment with Precursor and Compounds
  • Table VIII: Effects of Various Compounds on Total Protein and Sialic acid Contents of Various Reproductive Organs of Male Rats

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Sharma, K., Joshi, S. C., & Singh, R. V. (2000). Synthesis, characterization and antifertility activity of new unsymmetrical macrocyclic complexes of tin(II). Metal-Based Drugs, 7(5), 237–243. https://doi.org/10.1155/MBD.2000.237

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