Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases

Yusof, Enis Nadia Md; Ishak, Nurul N. M.; Latif, Muhammad; Tahir, Mohamed Ibrahim Mohamed; Sakoff, Jennette A.; Page, Alister J.; Tiekink, Edward R. T.; Ravoof, Thahira Begum S. A.

doi:10.1007/s11164-020-04095-x

Cited by 4 publications

(2 citation statements)

References 62 publications

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“…Schiff base molecules can be derived from the condensation of S-alkyl-dithiocarbazate derivatives with heterocyclic aldehydes and ketones to form molecules of the general formula RSC( S)N(H)N C(R 0 )R 00 , where R 0 , R 00 = alkyl and aryl. These molecules are effective ligands for a variety of metals and the motivation for complexation largely stems from the promising biological activity exhibited by the derived metal complexes (Low et al, 2016;Ravoof et al, 2017;Yusof et al, 2020). However, these Schiff bases are susceptible to oxidation resulting in the formation of a disulfide bond, as has been observed previously (Amirnasr et al, 2014;Sohtun et al, 2018).…”

Section: Chemical Contextmentioning

confidence: 98%

2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

Paulus¹,

Kwong²,

Crouse³

et al. 2020

Acta Cryst E

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The complete molecule of the title hydrazine carbodithioate derivative, C32H30N4O2S4, is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)° indicating an orthogonal relationship between the symmetry-related halves of the molecule. The conformation about the imine bond [1.282 (2) Å] is E and there is limited delocalization of π-electron density over the CN2C residue as there is a twist about the N—N bond [C—N—N—C torsion angle = −166.57 (15)°]. An intramolecular hydroxyl-O—H...N(imine) hydrogen bond closes an S(6) loop. In the crystal, methylene-C—H...π(tolyl) contacts assemble molecules into a supramolecular layer propagating in the ab plane: the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H...H contacts, which contribute 46.7% of all contacts followed by H...C/C...H contacts [25.5%] reflecting, in part, the C—H...π(tolyl) contacts. The calculation of the interaction energies confirm the importance of the dispersion term and the influence of the stabilizing H...H contacts in the inter-layer region.

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Section: Chemical Contextmentioning

confidence: 98%

2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

Paulus¹,

Kwong²,

Crouse³

et al. 2020

Acta Cryst E

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“…Dithiocarbazato Schiff bases and their metal complexes show a wide range of anti-bacterial (da Silva et al, 2011), anti-fungal (Nazimuddin et al, 1992), anti-viral (Pandeya et al, 1999) and anti-malarial (Dutta et al, 2006) activities. In addition, some dithiocarbazate derivatives display cytotoxicity towards a variety of cancer cell lines (Yusof et al, 2020) and some exhibit varying degrees of analgesic and anti-inflammatory activities (Zangrando et al, 2015).…”

Section: Chemical Contextmentioning

confidence: 99%

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

et al. 2020

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The title hydrazine carbodithioate chloroform hemisolvate, 2C15H14N2O2S2·CHCl3, comprises two independent hydrazine carbodithioate molecules, A and B, and a chloroform molecule; the latter is statistically disordered about its molecular threefold axis. The common features of the organic molecules include an almost planar, central CN2S2 chromophore [r.m.s. deviation = 0.0203 Å (A) and 0.0080 Å (B)], an E configuration about the imine bond and an intramolecular hydroxyl-O—H...N(imine) hydrogen bond. The major conformational difference between the molecules is seen in the relative dispositions of the phenyl rings as indicated by the values of the dihedral angles between the central plane and phenyl ring of 71.21 (6)° (A) and 54.73 (7)° (B). Finally, a difference is seen in the disposition of the outer hydroxyl-H atoms, having opposite relative orientations. In the calculated gas-phase structure, the entire molecule is planar with the exception of the perpendicular phenyl ring. In the molecular packing, the A and B molecules assemble into a two-molecule aggregate via N—H...S hydrogen bonds and eight-membered {...HNCS}2 synthons. The dimeric assemblies are connected into supramolecular chains via hydroxyl-O—H...O(hydroxyl) hydrogen bonds and these are linked into a double-chain through hydroxy-O—H...π(phenyl) interactions. The double-chains are connected into a three-dimensional architecture through phenyl-C—H...O(hydroxyl) and phenyl-C—H...π(phenyl) interactions. The overall assembly defines columns along the a-axis direction in which reside the chloroform molecules, which are stabilized by chloroform–methine-C—H...S(thione) and phenyl-C—H...Cl contacts. The analysis of the calculated Hirshfeld surfaces, non-covalent interaction plots and interaction energies confirm the importance of the above-mentioned interactions, but also of cooperative, non-standard interactions such as π(benzene)...π(hydrogen-bond-mediated-ring) contacts.

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Comparative investigation of Cu(II) complexes with dithiocarbazate: Structural design, theoretical calculation, and in vitro antitumor activity

Cavalcante

García

Mota

et al. 2022

Journal of Inorganic Biochemistry

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Selective cytotoxicity of organotin(IV) compounds with 2,3-dihydroxybenzyldithiocarbazate Schiff bases

Cited by 4 publications

References 62 publications

2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

4-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]benzene-1,3-diol chloroform hemisolvate: crystal structure, Hirshfeld surface analysis and computational study

Comparative investigation of Cu(II) complexes with dithiocarbazate: Structural design, theoretical calculation, and in vitro antitumor activity

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