6868-28-6Relevant articles and documents
Photochromic behavior and mechanism of indole thiosemicarbazide derivates in amorphous powder, solution and nanofiber
Che, Yuanyuan,Liu, Lang,Zhao, Jianzhang,Yu, Yuming,Zhao, Xianmei
, p. 105 - 110 (2019)
A series of Schiff bases containing the indole group were synthesized. The compound 2-[(1-methyl-1H-indol-3-yl)methylene] hydrazinecarbothioamide (4) exhibits excellent reversible photochromic properties both in solid?solid state and solution. Moreover, t
Synthesis, spectroscopic studies and crystal structure of (E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone and (E)-2-[(1H-indol-3-yl)methylene]thiosemicarbazone
Yildiz, Mustafa,ünver, Hüseyin,Erdener, Di?dem,Kiraz, A?kin,Iskeleli, Nazan Ocak
, p. 227 - 234 (2009)
Thiosemicarbazone Schiff bases (1 and 2) derived from 2,4-dihydroxybenzaldehyde, indoline-3-carbaldehyde and thiosemicarbazone have been synthesized and their structures were elucidated by elemental analysis, FT-IR, 1H NMR, 13C NMR a
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
Haribabu, Jebiti,Sabapathi, Gopal,Tamizh, Manoharan Muthu,Balachandran, Chandrasekar,Bhuvanesh, Nattamai S. P.,Venuvanalingam, Ponnambalam,Karvembu, Ramasamy
, p. 1242 - 1257 (2018)
Indole thiosemicarbazone ligands were prepared from indole-3-carboxaldehyde and N-(un)substituted thiosemicarbazide. The Ru(η6-p-cymene) complexes [Ru(η6-p-cymene)(HL1)Cl]Cl (1) and [Ru(η6-p-cymene)(L2)]2Cl2 (2) were exclusively synthesized from thiosemicarbazone (TSC) ligands HL1 and HL2, and [RuCl2(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 five-membered 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 IC50 = 11.5 μM, which was lower than that of cisplatin against the A549 cancer cell line. The activity of the same complex (IC50 = 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.
Effect of N-benzyl group in indole scaffold of thiosemicarbazones on the biological activity of their Pd(II) complexes: DFT, biomolecular interactions, in silico docking, ADME and cytotoxicity studies
Balakrishnan, Nithya,Haribabu, Jebiti,Eshaghi Malekshah, Rahime,Swaminathan, Srividya,Balachandran, Chandrasekar,Bhuvanesh, Nattamai,Aoki, Shin,Karvembu, Ramasamy
, (2022/01/26)
A series of N-benzyl substituted indole-based thiosemicarbazone (TSC) ligands (L4-L6) and palladium(II) TSC complexes, [Pd(L)2] (1–6) (L = monoanionic bidentate un/N-substituted indole-based TSC ligand) have been synthesized and characterized using analytical and spectroscopic tools. The exact molecular structures of L4-L6 and the complexes (2–4 and 6) were ascertained by single-crystal X-ray diffraction (XRD) method. Spectroscopic and crystallographic studies indicated that Pd(II) ion was coordinated with TSCs as monobasic bidentate ligands, forming two five-membered rings with square planar geometry. The effect of N-benzyl substitution in indole scaffold of TSCs in the complexes was studied using DFT method, and structure–activity relationships (SAR) were explored. The in silico ADME properties of the ligands and their complexes were thoroughly analyzed with respect to their lipophilicity and oral bioavailability. The complexes (1–6) exhibited strong intercalation with calf thymus DNA (CT DNA), which was examined by absorption/emission spectroscopic titrations and viscosity measurements. Similarly, the interaction of bovine serum albumin (BSA) with complexes examined using spectroscopic methods showed a strong binding between them. A better picture of various possible interactions was acquired from the molecular docking of the complexes with the targets like DNA, BSA, DNA Topoisomerase II and CASP3. In addition, in vitro cytotoxicity of the complexes was screened against two cancer (HeLa-S3 and A549) and one normal (IMR-90) cell lines. It was learnt that the N-benzyl substitution in the indole system inactivated the whole molecule by diminishing its anticancer activity. The unsubstituted indole TSC complex (2) displayed significant activity towards HeLa-S3 cells, and the results were compared with those of cisplatin. Beneficially, the active complex showed less toxicity against IMR-90 normal cells. Further, the results of AO-EB staining studies indicated that the complexes induced cell death via apoptosis pathway. The steric influence of the substituted indole moiety, its limited electronic effects and lesser stability in aqueous systems retarded the Pd(II) complexes of N-benzyl substituted indole TSCs from exhibiting their biological activities.
Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones
Mashayekhi, Vida,Haj Mohammad Ebrahim Tehrani, Kamaleddin,Azerang, Parisa,Sardari, Soroush,Kobarfard, Farzad
, (2021/09/08)
Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two
