6868-28-6Relevant academic research and scientific papers
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 of Ni(II) complexes bearing indole-based thiosemicarbazone ligands for interaction with biomolecules and some biological applications
Haribabu, Jebiti,Jeyalakshmi, Kumaramangalam,Arun, Yuvaraj,Bhuvanesh, Nattamai S. P.,Perumal, Paramasivan Thirumalai,Karvembu, Ramasamy
, p. 461 - 480 (2017)
Abstract: A series of new Ni(II) complexes containing indole-based thiosemicarbazone ligands was synthesized and characterized by elemental analyses, and UV–visible, FT-IR, 1H & 13C NMR and mass spectroscopic techniques. The Ni(II) c
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.
Aryl hydrazones linked thiazolyl coumarin hybrids as potential urease inhibitors
Salar, Uzma,Qureshi, Bakhtawer,Khan, Khalid Mohammed,Lodhi, Muhammad Arif,Ul?Haq, Zaheer,Khan, Farman Ali,Naz, Fouzia,Taha, Muhammad,Perveen, Shahnaz,Hussain, Shafqat
, p. 1221 - 1238 (2021/08/20)
Aryl hydrazones bearing thiazolyl coumarin hybrids 1–32 were prepared by following 'one-pot' two-steps reaction scheme. Various arylaldehydes were reacted to thiosemicarbazide under acidic condition to form aryl thiosemicarbazone intermediates which in turn treated with 3-bromoacetyl coumarin under basic condition to afford thiazolyl coumarin hybrids 1–32. All hybrids were recognized by EI- and HREI-MS and 1H- and 13C-NMR spectroscopic techniques. Compounds 1–32 were screened for in vitro inhibitory activity against urease enzyme and displayed good to moderate inhibitory potential in the ranges of IC50 = 16.29 ± 1.1–256.30 ± 1.4?μM. Worth stating that compound 21 (IC50 = 16.29 ± 1.1?μM) was identified as more potent urease inhibitor than the standard acetohydroxamic acid (IC50 = 27.0 ± 0.5?μM). Derivatives 19 (IC50 = 77.67 ± 1.5?μM) and 30 (IC50 = 71.21 ± 1.6?μM) were found to be moderately active. Structure–activity relationship revealed that -F, -Cl, -OH, and -OMe groups and their respective positions on aryl ring are playing important role in urease enzyme inhibition. Molecular docking studies identified important interaction between the ligand (active hybrids) and urease active site.
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.
Design and efficient synthesis of novel 4,5-dimethylthiazole-hydrazone derivatives and their anticancer activity
Evren, Asaf Evrim,Yurtta?, Leyla,Ekselli, Bü?ra,Aksoy, Onur,Akalin-?ift?i, Gül?en
, p. 372 - 386 (2021/06/17)
Background: Recently, researchers have been warning about the increased mortality of the various cancer types. Also, the lung adenocarcinoma and the glioma types are burning issues for world's health due to late or wrong diagnosis and/or insufficient treatment methods. For this purpose, our research group designed and synthesized novel 4,5-dimethyl thiazole-hydrazone derivatives which were tested against cancer and normal cell lines to understand the structure-activity relationship (SAR). Methods: The lead compounds were obtained by reacting 2-(substituted aryl-2-ylmethylene) hydrazin-1-carbothioamide with 3-chloro-2-butanone derivatives. The structural elucidation of the compounds was performed by1H-NMR,13C-NMR, and LC/MS-IT-TOF spectral and elemental analyses. The synthesized compounds were tested in vitro for the anticancer activity against A549 human lung adenocarcinoma and C6 rat glioma cells and investigated for which pathway to induce cell death. Also, the docking study of the active compounds was achieved to understand the SAR. Results: The targeted compounds (2a-2l) were synthesized successfully above 70% yields, and the analysis findings proved their purity. In general, the results of activity studies displayed significant effects against at least one cell line, except compounds 2e (indol-3-yl) and 2h (4-dimethylaminophenyl). Furthermore, compounds 2b and 2f displayed potential anticancer activity. With the help of molecular docking study, a potential selectivity of compound 2f was observed for type II protein kinase. On the other hand, compound 2b interacted with the active site nearly the same as Dasatinib. Therefore, these two compounds could be used as a base on developing selective anticancer drugs. Conclusion: Pyridin-2-yl (2b) derivative was found to be a favorable molecule with high anticancer potency against C6 and A549 cell lines. Additionally, 1-naphthyl (2f) derivative was a worthy compound for potential selectivity. In future studies, it will be our priority to focus on developing derivatives of these two compounds (2b and 2f) and elucidate their mechanisms.
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
Synthesis of hybrids thiazole-quinoline, thiazole-indole and their analogs:in vitroanti-proliferative effects on cancer cell lines, DNA binding properties and molecular modeling
Cavalcanti, Bruno C.,Figueiredo, Isis M.,Maciel, Thamilla Maria S.,Monteiro, Kadja Luana C.,Santos-Junior, Paulo Fernando da S.,da Silva, Edjan Carlos D.,de Abreu, Fabiane C.,de Aquino, Thiago,de Freitas, Johnnatan D.,de Lima Lins, Samaysa,Carinhanha C. Santos, Josué,Nascimento, Igor José dos S.,Pessoa, Claudia do ó,V. Neto, José de Brito,da Silva-Júnior, Edeildo F.,de Araújo-Júnior, Jo?o X.
, p. 13847 - 13859 (2021/08/16)
A convenient synthesis under ultrasound (US) irradiation of 4-thiazolidinone, thiazole, dihydrothiazole, and thiazine hybrid compounds containing quinoline and indole nucleus is described. All the title compounds were characterized by NMR and HRMS. The synthetic protocol affords highly selective conversions, short reaction times, simple work-up procedures, and good yields compared with conventional methods. All the synthesized compounds were tested forin vitrocytotoxic activity against glioblastoma (SF-295), leukemia (HL-60), and prostate cancer (PC-3) cell lines. Three compounds (4c-e) presented moderate to high activity against all cancer cell lines evaluated. Compound4cstood out with its promising cytotoxicity activity against the HL-60 cell line with an IC50value of 2.41 μM and an SI of 10.5. The electrochemical behavior of4cwas studied using differential pulse voltammetry (DPV) on a glassy carbon electrode modified with dsDNA and with ssDNA in the solution. As a result, the pre-concentration of the compound on the dsDNA biosensor surface and modification of the oxidation currents of guanosine and adenosine bases in ssDNA experiments demonstrated an interaction between4cand DNA. The affinity of4cwas evaluated against ctDNA by exploring spectroscopic techniques, showing that this compound acts preferentially as a groove binder. Molecular docking and dynamics simulations proposed that4cinteractsviagroove binding and intercalation, corroborating the experimental results. The dominating interactions were conventional hydrogen bonds and van der Waals forces. Finally, our findings suggest the4cderivative to be a potential anticancer prototype against HL-60.
New hydrazinothiazole derivatives of usnic acid as potent TDP1 inhibitors
Filimonov, Aleksander S.,Chepanova, Arina A.,Luzina, Olga A.,Zakharenko, Alexandra L.,Zakharova, Olga D.,Ilina, Ekaterina S.,Dyrkheeva, Nadezhda S.,Kuprushkin, Maxim S.,Kolotaev, Anton V.,Khachatryan, Derenik S.,Patel, Jinal,Leung, Ivanhoe K.H.,Chand, Raina,Ayine-Tora, Daniel M.,Reynisson, Johannes,Volcho, Konstantin P.,Salakhutdinov, Nariman F.,Lavrik, Olga I.
, (2019/10/28)
Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising therapeutic target in cancer therapy. Combination chemotherapy using Tdp1 inhibitors as a component can potentially improve therapeutic response to many chemotherapeutic regimes. A new set of usnic acid derivatives with hydrazonothiazole pharmacophore moieties were synthesized and evaluated as Tdp1 inhibitors. Most of these compounds were found to be potent inhibitors with IC50 values in the low nanomolar range. The activity of the compounds was verified by binding experiments and supported by molecular modeling. The ability of the most effective inhibitors, used at non-toxic concentrations, to sensitize tumors to the anticancer drug topotecan was also demonstrated. The order of administration of the inhibitor and topotecan on their synergistic effect was studied, suggesting that prior or simultaneous introduction of the inhibitor with topotecan is the most effective.
