1<i>H</i>-Indole-3-carbaldehyde thiosemicarbazone

Razali, Mohd. R.; Ali, Hapipah Mohd; Ng, Seik Weng

doi:10.1107/s1600536808011082

Cited by 3 publications

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“…A previous study reports the structure of 1H-indole-3-carboxaldehyde thiosemicarbazone (Rizal et al, 2008). The compound in its deprotonated form can function as a bidentate chelate, and this is confirmed in the present nickel(II) derivative (Scheme I, Fig.…”

Section: S1 Commentsupporting

confidence: 74%

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trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ²N¹,S)nickel(II)

Razali

Ali

2008

Acta Cryst E

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Section: S1 Commentsupporting

confidence: 74%

“…For the structure of the neutral Schiff base, see: Rizal et al (2008). For background literature on the medicinal activity of metal complexes of the Schiff base and related compounds, see: Husain et al (2007); Wilson et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ²N¹,S)nickel(II)

Razali

Ali

2008

Acta Cryst E

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“…The preparation of these receptors 1-3 in the form of their metal complexes is reported, and their magnetic and spectral properties are studied. [30][31][32] Thiosemicarbazone is a well known tridentate ligand and provides various binding sites such as -NH, CH]N and C]S for the formation of metal complexes in inorganic chemistry. Literature reports are available detailing the synthesis of various metal complexes with different kinds of thiosemicarbazone ligand.…”

Section: Introductionmentioning

confidence: 99%

Heterocyclic thiosemicarbazones as fluorescent sensors for the selective recognition of cations in the aqueous phase

2013

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Highly sensitive and selective fluorescent cation sensors 1-3, based on heterocyclic derivatives, have been synthesized from the condensation reaction between their corresponding heterocyclic aldehydes and thiosemicarbazide. All of the receptors 1-3 can act as optical sensors for the detection of Cu 2+ and Hg 2+ ions, and as fluorescent sensors for the Cr 3+ ion, via a chelation enhanced fluorescence effect in an aqueous environment. The structures of the receptors 1-3 were well characterized by IR, 1 H NMR, 13 C NMR and HRMS techniques and their cation sensing abilities were studied by UV-vis and fluorescence spectroscopy.

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Water-Soluble Mono- and Binuclear Ru(η⁶-p-cymene) Complexes Containing Indole Thiosemicarbazones: Synthesis, DFT Modeling, Biomolecular Interactions, and In Vitro Anticancer Activity through Apoptosis

et al. 2018

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Indole thiosemicarbazone ligands were prepared from indole-3-carboxaldehyde and N-(un)substituted thiosemicarbazide. The Ru(η 6 -p-cymene) complexes [Ru(η 6 -pcymene)(HL1)Cl]Cl (1) and [Ru(η 6 -p-cymene)(L2)] 2 Cl 2 (2*) were exclusively synthesized from thiosemicarbazone (TSC) ligands HL1 and HL2, and [RuCl 2 (p-cymene)] 2 . The compounds were characterized by analytical and various spectroscopic (electronic, FT-IR, 1D/2D NMR, and mass) tools. The exact structures of the compounds (HL1, HL2, 1, and 2*) were confirmed by single-crystal X-ray diffraction technique. In complexes 1 and 2*, the ligand coordinated in a bidentate neutral (1)/monobasic (2*) fashion to form a fivemembered ring. The complexes showed a piano-stool geometry around the Ru ion. While 2* existed as a dimer, 1 existed as a monomer, and this was well explained through free energy, bond parameter, and charge values computed at the B3LYP/SDD level. The intercalative binding mode of the complexes with calf thymus DNA (CT DNA) was revealed by spectroscopic and viscometric studies. The DNA (pUC19 and pBR322 DNA) cleavage ability of these complexes evaluated by an agarose gel electrophoresis method confirmed significant DNA cleavage activity. Further, the interaction of the complexes with bovine serum albumin (BSA) was investigated using spectroscopic methods, which disclosed that the complexes could bind strongly with BSA. A hemolysis study with human erythrocytes revealed blood biocompatibility of the complexes. The in vitro anticancer activity of the compounds (HL1, HL2, 1, and 2*) was screened against two cancer cell lines (A549 and HepG-2) and one normal cell line (L929). Interestingly, the binuclear complex 2* showed superior activity with IC 50 = 11.5 μM, which was lower than that of cisplatin against the A549 cancer cell line. The activity of the same complex (IC 50 = 35.3 μM) was inferior to that of cisplatin in the HepG-2 cancer cell line. Further, the apoptosis mode of cell death in the cancer cell line was confirmed by using confocal microscopy and DNA fragmentation analysis.

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1H-Indole-3-carbaldehyde thiosemicarbazone

Abstract: The molecules of the title compound, C10H10N4S, are linked by N—Hindole⋯S hydrogen bonds to form a linear hydrogen-bonded chain. There are two independent molecules in the asymmetric unit.

Cited by 3 publications

References 21 publications

trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ²N¹,S)nickel(II)

trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ²N¹,S)nickel(II)

Heterocyclic thiosemicarbazones as fluorescent sensors for the selective recognition of cations in the aqueous phase

Water-Soluble Mono- and Binuclear Ru(η⁶-p-cymene) Complexes Containing Indole Thiosemicarbazones: Synthesis, DFT Modeling, Biomolecular Interactions, and In Vitro Anticancer Activity through Apoptosis

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1H-Indole-3-carbaldehyde thiosemicarbazone

Abstract: The mol­ecules of the title compound, C10H10N4S, are linked by N—Hindole⋯S hydrogen bonds to form a linear hydrogen-bonded chain. There are two independent mol­ecules in the asymmetric unit.

Cited by 3 publications

References 21 publications

trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ2N1,S)nickel(II)

trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ2N1,S)nickel(II)

Heterocyclic thiosemicarbazones as fluorescent sensors for the selective recognition of cations in the aqueous phase

Water-Soluble Mono- and Binuclear Ru(η6-p-cymene) Complexes Containing Indole Thiosemicarbazones: Synthesis, DFT Modeling, Biomolecular Interactions, and In Vitro Anticancer Activity through Apoptosis

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Abstract: The molecules of the title compound, C10H10N4S, are linked by N—Hindole⋯S hydrogen bonds to form a linear hydrogen-bonded chain. There are two independent molecules in the asymmetric unit.

trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ²N¹,S)nickel(II)

trans-Bis(1H-indole-3-carbaldehyde thiosemicarbazonato-κ²N¹,S)nickel(II)

Water-Soluble Mono- and Binuclear Ru(η⁶-p-cymene) Complexes Containing Indole Thiosemicarbazones: Synthesis, DFT Modeling, Biomolecular Interactions, and In Vitro Anticancer Activity through Apoptosis