Synthesis, characterization, X-ray structure and in vitro antifungal activity of triphenyltin complexes based on pyrazole dicarboxylic acid derivatives

Abstract

A series of new ditriphenyltin(IV) dicarboxylate complexes of general formula (Ph3SnOOC-Pz)2R with Pz: pyrazole and R: alkyl or ether, have been synthesized from bipyrazoledicarboxylic acid and hydroxytripheyltin. These complexes, noted C1-C7, have been characterized by IR, 1 H and 13 C NMR spectroscopies. The molecular structures of C3: 1,3-Bis[(5-methyl-2-H-3-triphenyltincarboxylate pyrazol)]propane and C7: Bis[(2-methyl-2H-3triphenyltincarboxylate pyrazol)ethyl]oxide have been confirmed by single crystal X-ray diffraction. Both compounds crystallize in the monoclinic symmetry: C3 in P21 space group with a = 15.915(1) Å, b = 10.0791(8) Å, c = 13.823(1) Å, α = 90°, β = 100.459(3)°, γ = 90° and C7 in P21/n space group, with a = 15.0951(7) Å, b = 8.9847(3) Å, c = 34.244(1) Å, α = 90°, β = 101.421(2)°, γ = 90°.. The two cristallographically independent Sn1 and Sn2 atoms are tetra coordinated within distorted tetrahedral environments, very similar in the two compounds. The antifungal activity of these organotin complexes and their corresponding bipyrazoledicarboxylic acid (ligands) has been evaluated against the pathogenic Fusarium oxysporum f. sp. albedinis. This activity greatly depends on the nature of ligands and on the dose used. The presence of triphenyltin moiety improves considerably the antifungal activity becoming close to that of the benomyl (fungicide).

Two novel macrocyclic organotin (IV) carboxylates based on bipyrazoledicarboxylic acid derivatives: Syntheses, crystal structures and antifungal activities

“…This proves the presence of two butyl categories and the result agrees with the crystal structures determined for the complexes C1 and C2. As well, the above remark is also confirmed by the 13 C NMR spectra (Fig. 3.)…”

“…A spectrometer BRÜKER AC 300 was used to record the NMR spectra. Spin resonances are given in the form of chemical shifts () in parts per million (ppm) with reference to the residual peak of the solvent used as an internal standard, namely CDCl 3 7.27 ppm and DMSO-d 6 2.50 ppm for 1 H NMR, and 77 ppm 39.5 ppm for 13 C NMR. Spin multiplicity is presented by s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet.…”

“…albedinis (FAO) using the agar diffusion technique, as reported in our recent work. 13 Potato dextrose agar (PDA) medium was mixed with different volumes (40, 160, and 500 μ ) of DMSO solutions of the complexes and the corresponding ligands. Then, discs (6 mm in diameter) of the microorganism (FAO) were put in the middle of these Petri plates.…”

“…[1][2][3][4][5][6] This is due to their structural diversity and their potential application in several fields, [7][8][9] especially in medicinal chemistry. 8,9 In fact, the literature reports that organotin carboxylates can act as antitumor, 8,9 antiviral, 10,11 antifungal, 12,13 antibacterial, 14,15 anti-proliferative, 16,17 anti-inflammatory, 18 and antioxidant potent agents. 19,20 Among the studies reporting on the various types of organotin complexes, only a few describe the synthesis and characterization of macrocyclic organotin compounds.…”

Synthesis and characterization of new pyrazole–tetrazole derivatives as new vasorelaxant agents

“…N ‐heterocyclic compounds have attracted much interest in several fields and more especially in medicinal chemistry (Brown, 1998). In fact, they have been found to act as potent antimicrobial (Ardeleanu et al, 2018; Dahmani et al, 2021; Harit, Bellaouchi, Mokhtari, et al, 2017), antiviral (Carta et al, 2019), anti‐inflammatory (Kumbar et al, 2018), antitumor (Zhang et al, 2019), and enzyme agents (Kattimani et al, 2020). In this context, several N ‐heterocyclic molecules with well‐defined architectures possessing good biological activities have been investigated in our laboratory, including macrocycles (Harit et al, 2018; Harit, Bellaouchi, Rokni, et al, 2017) and tripods (Harit et al, 2012; Malek et al, 2014).…”