(Z)-N,N-Dimethyl-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide

Jayakumar, K.; Sithambaresan, M.; Kurup, M.R. Prathapachandra

doi:10.1107/s1600536811045739

Cited by 4 publications

(3 citation statements)

References 10 publications

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“…This prevents the ligand from isomerizing to the E -form, where the three donor atoms are on the same side of the ligand. The intramolecular hydrogen bonding between the NH and the N of the pyridine ring in the neutral Z -isomeric Bp44mT ligand was preserved (Figure A) In fact, the conformation of the neutral ligand in [Cu(Bp44mT)(Bp44mT-H)]ClO 4 is almost the same as found in the free ligand, except the phenyl ring is rotated out of the plane of the ligand by the presence of the Cu atom. Two of the four independent perchlorate anions were well-defined, but the other two were disordered over several sites and refined with partial occupancies.…”

Section: Resultsmentioning

confidence: 94%

Structure–Activity Relationships of Di-2-pyridylketone, 2-Benzoylpyridine, and 2-Acetylpyridine Thiosemicarbazones for Overcoming Pgp-Mediated Drug Resistance

et al. 2016

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Multidrug resistance (MDR) mediated by P-glycoprotein (Pgp) represents a significant impediment to successful cancer treatment. The compound, di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT), has been shown to induce greater cytotoxicity against resistant cells than their nonresistant counterparts. Herein, the structure− activity relationships of selected thiosemicarbazones are explored and the novel mechanism underlying their ability to overcome resistance is further elucidated. Only thiosemicarbazones with electron-withdrawing substituents at the imine carbon mediated Pgp-dependent potentiated cytotoxicity, which was reversed by Pgp inhibition. Treatment of resistant cells with these thiosemicarbazones resulted in Pgp-dependent lysosomal membrane permeabilization (LMP) that relied on copper (Cu) chelation, reactive oxygen species generation, and increased relative lipophilicity. Hence, this study is the first to demonstrate the structural requirements of these thiosemicarbazones necessary to overcome MDR. We also demonstrate the mechanism that enables the targeting of resistant tumors, whereby thiosemicarbazones "hijack" lysosomal Pgp and form redox-active Cu complexes that mediate LMP and potentiate cytotoxicity.

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Section: Resultsmentioning

confidence: 94%

Structure–Activity Relationships of Di-2-pyridylketone, 2-Benzoylpyridine, and 2-Acetylpyridine Thiosemicarbazones for Overcoming Pgp-Mediated Drug Resistance

et al. 2016

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“…For their optical properties and applications, see: Tian et al (1997); Uesugi et al (1994). For a related structure, see: Jayakumar et al (2011…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methylidene]-N-cyclohexylhydrazinecarbothioamide

et al. 2014

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In the title compound, C17H20ClN3OS, the mean plane of the central thiourea core makes dihedral angles of 26.56 (9) and 47.62 (12)° with the mean planes of the chromene moiety and the cyclohexyl ring, respectively. The cyclohexyl ring adopts a chair conformation. The N–H atoms of the thiourea unit adopt an anti conformation. The chromene group is positioned trans, whereas the cyclohexyl ring lies in the cis position to the thione S atom, with respect to the thiourea C—N bond. In the crystal, molecules are linked by N—H⋯S hydrogen bonds, forming inversion dimers enclosing R 2 2(8) ring motifs. The dimers are linked by C—H⋯Cl hydrogen bonds, enclosing R 6 6(44) ring motifs, forming sheets lying parallel to (010).

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“…A variety of factors can be cited to be accountable for their flexibility in coordination, such as intramolecular hydrogen bonding, bulkier coligand, steric crowding on the azomethine carbon atom and π-π stacking interactions [44][45][46][47][48][49]. A potential donor atom or a functional group which is capable of furnishing a variety of coordination modes, present in the primary ligand systems, plays crucial role in providing flexibility to the ligands which can coordinate to the transition metal ion in a neutral or deprotonated form, producing mono or poly nuclear complexes with novel topologies and particular properties [50][51][52][53][54][55][56][57][58]. As a part of syntheses and characterizations of new thiosemicarbazones and their complexes and in continuation of our earlier publications [55,56], this communication is intended to report the synthesis, physico-chemical & spectroscopic characterization and antimicrobial studies of a series of Co(III) and Ni(II) complexes having different counter ions with the title ligand, HMPzNHex2, along with the X-ray crystallography and DFT study of [Co(MPzNHex2)2]ClO4·1.5H2O (I) and…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antimicrobial activities of Co(III) and Ni(II) complexes with 5-methyl-3-formylpyrazole-N(4)-dihexylthiosemicarbazone (HMPzNHex2): X-ray crystallography and DFT calculations of [Co(MPzNHex2)2]ClO4·1.5H2O (I) and [Ni(HMPzNHex2)2]Cl2·2H2O (II)

Saha

Mondal

Ghosh

et al. 2018

Inorganica Chimica Acta

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A new pyrazole containing ligand, 5-methyl-3-formylpyrazole-N(4)-dihexylthiosemicarbazone (HMPzNHex2), and a host of its cobalt(III) and nickel(II) complexes, [Co(MPzNHex2)2]X·mH2O and [Ni(HMPzNHex2)2]X2·nH2O (X= Cl, Br, ClO4, BF4 and NO3; m = 0 for Cl, Br, BF4 & NO3 and 1.5 for ClO4; n = 0 for Br, ClO4, BF4 & NO3 and 2 for Cl), respectively, have been synthesized and characterized by elemental analyses, magnetic measurements (polycrystalline state), 1 H NMR (for the ligand and its Co(III) complexes), electronic and IR spectral parameters. All the reported Co (III) and Ni(II) complexes are cationic in nature and behaving as 1:1 and 1:2 electrolytes, respectively, in MeOH. Electronic spectral data of the complexes categorize them as having distorted octahedral coordination geometry. IR spectral features (4000-/450 cm -1 ) specify a monodeprotonated / neutral tridentate (NNS) function of the ligand, HMPzNHex2 coordinating to the Co(III) / Ni(II) via the pyrazolyl (tertiary) ring nitrogen, azomethine nitrogen and thiolato / thioketo sulfur atom. 1 H NMR spectral data (in CDCl3 at 400 MHz) for the primary ligand and those of its Co(III) complexes are in agreement with the proposition of bonding sites evidenced from IR data. The single crystal x-ray data of I (C2/c (#15); monoclinic) and II (P-1 (#2); triclinic) have confirmed a CoN4S2 and a NiN4S2 octahedral coordination, respectively. The pair of monoprotic / neutral coordinating ligands

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(Z)-N,N-Dimethyl-2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioamide

Cited by 4 publications

References 10 publications

Structure–Activity Relationships of Di-2-pyridylketone, 2-Benzoylpyridine, and 2-Acetylpyridine Thiosemicarbazones for Overcoming Pgp-Mediated Drug Resistance

Structure–Activity Relationships of Di-2-pyridylketone, 2-Benzoylpyridine, and 2-Acetylpyridine Thiosemicarbazones for Overcoming Pgp-Mediated Drug Resistance

Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methylidene]-N-cyclohexylhydrazinecarbothioamide

Synthesis, characterization and antimicrobial activities of Co(III) and Ni(II) complexes with 5-methyl-3-formylpyrazole-N(4)-dihexylthiosemicarbazone (HMPzNHex2): X-ray crystallography and DFT calculations of [Co(MPzNHex2)2]ClO4·1.5H2O (I) and [Ni(HMPzNHex2)2]Cl2·2H2O (II)

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