- Synthesis, X-ray characterization, DFT calculations and Hirshfeld surface analysis of thiosemicarbazone complexes of Mn+ ions (n = 2, 3; M = Ni, Cd, Mn, Co and Cu)
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Two new pyridine-based heterocyclic thiosemicarbazone ligands and their Ni(ii), Cd(ii), Mn(ii), Co(iii) and Cu(ii) complexes have been synthesized and characterized by structural, analytical and spectroscopic methods. The monodeprotonated anionic forms of the ligands coordinate in a tridentate fashion via two nitrogen and one sulphur donor atoms to yield seven complexes in which metal centres vary from four-coordinated square planar to six-coordinated distorted octahedral geometries. Single-crystal X-ray crystallography showed that the molecular complexes can aggregate into larger entities depending on the anion coordinated to the metal centre. We have analysed the interesting supramolecular assemblies observed in the solid state of some complexes by means of DFT calculations. These assemblies are formed by a combination of several noncovalent interactions, including chelate ring-π, π-π, and chalcogen bonding interactions, that have been characterized using Bader's Theory of "atoms-in-molecules".
- Mahmoudi, Ghodrat,Casti?eiras, Alfonso,Garczarek, Piotr,Bauzá, Antonio,Rheingold, Arnold L.,Kinzhybalo, Vasyl,Frontera, Antonio
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Read Online
- Tin complex with 2-acetyl pyridine thiosemicarbazone as ligand and synthesis method thereof
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The invention discloses a tin complex taking 2-acetyl pyridine thiosemicarbazone as a ligand and a synthesis method thereof. The synthesis method comprises the following steps of: dissolving thiosemicarbazone in methanol, adding 2-acetyl pyridine dropwise
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Paragraph 0045-0048
(2020/02/14)
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- Palladium complex taking 2-acetylpyridine thiosemicarbazone as ligand and synthesis method of palladium complex
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The invention discloses a palladium complex taking 2-acetylpyridine thiosemicarbazone as a ligand and a synthesis method of the palladium complex. Five new palladium complexes are obtained by coordination of nitrogen heterocyclic ring-containing 2-acetylp
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Paragraph 0011; 0055-0058
(2020/12/30)
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- Rhodium complexes taking 2-acetylpyridine thiosemicarbazone as ligand and synthesis method thereof
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The invention discloses rhodium complexes taking 2-acetylpyridine thiosemicarbazone as a ligand and a synthesis method thereof. The three kinds of new rhodium complexes are obtained by coordination ofnitrogen heterocyclic ring-containing 2-acetylpyridine thiosemicarbazone and metal rhodium. According to the invention, in-vitro proliferation inhibition activity experiments are further carried outon the synthesized rhodium complexes, and results show that the synthesized rhodium complexes have generally better in-vitro activity than ligands thereof, show very good inhibition activity, have little toxic effect on human normal cells, and are suitable for preparation of high-efficiency and low-toxicity anti-tumor drugs.
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Paragraph 0043-0046
(2020/12/30)
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- Preparation, structural characterization, voltammetry and Hirshfeld surface analysis of homoleptic iron(III) thiosemicarbazone complexes
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Reactions of FeSO4 precursor with thiosemicarbazones Hatc-R, where R is ethyl (Et) or phenyl (Ph), led to the formation of homoleptic iron(III) complexes of the type [Fe(atc-R)2]HSO4. The characterization of the compounds was performed by spectroscopy techniques, such as FTIR, UV–Vis, besides elemental analysis, conductometry, voltammetry and magnetic susceptibility measurement. The crystalline structure of [Fe(atc-Ph)2]HSO4?H2O was determined by single-crystal X-ray diffraction and revealed the oxidation of the Fe(II) centre to Fe(III) upon complexation of the monoanionic N,N,S-tridentate thiosemicarbazonate ligands. The magnetic susceptibility results showed the paramagnetic property of the iron(III) complexes in the extension of 1 unpaired electron. The electrochemical analyses showed a nearly reversible process of the iron complex, which is slightly influenced by the peripheral substituent groups at the N(4) position of the atc-R1? ligands. Hirshfeld surface analysis revealed that the supramolecular structure of [Fe(atc-Ph)2]HSO4?H2O is stabilized mainly by H···H, C···H/H···C and O···H/H···O interactions.
- Costa, Waleska R. P.,Deflon, Victor M.,Oliveira, Carolina G.,Souza, Rafael A. C.
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p. 511 - 521
(2020/08/03)
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- Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents
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In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 μM, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial–mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer.
- Bo-Wang,He, Zhang-Xu,Li, Yi-Han,Liu, Hong-Min,Ma, Li-Ying,Ma, Qin,Tao, Yuan-Yuan,Wang, Hao-Jie,Wu, Hui-Pan,Zhang, Xin-Hui,Zhao, Bing
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- CHEMICAL ACTIVATORS OF NICOTINAMIDE MONONUCLEOTIDE ADENLYLY TRANSFERASE 2 (NMNAT2) AND USES THEREOF
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The present application relates to novel semicarbazones and thiosemicarbazones, to processes for preparing them, to pharmaceutical preparations comprising them, to the use of the novel semicarbazones and thiosemicarbazones for treatment and/or prophylaxis of diseases and to the use thereof for production of a medicament for treatment and/or prophylaxis of diseases, especially of neurodegeneration and age-associated diseases or conditions associated with NAD loss. The present application also provides a method for high throughput screening of NMNAT2 activators.
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Page/Page column 22-23; 25; 29
(2020/06/22)
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- IClick Reactions of Square-Planar Palladium(II) and Platinum(II) Azido Complexes with Electron-Poor Alkynes: Metal-Dependent Preference for N1 vs N2 Triazolate Coordination and Kinetic Studies with 1H and 19F NMR Spectroscopy
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Two square-planar palladium(II) and platinum(II) azido complexes [M(N3)(L)] with L = N-phenyl-2-[1-(2-pyridinyl)ethylidene]hydrazine carbothioamide reacted with four different electron-poor alkynes R-CC-R′ with R = R′ = COOCH3, COOEt, COOCH2CH2OCH3 or R = CF3, R′' = COOEt in a [3 + 2] cycloaddition "iClick" reaction. The resulting triazolate complexes [M(triazolateR,R')(L)] were isolated by simple precipitation and/or washing in high purity and good yield. Six out of the eight new compounds feature the triazolate ligand coordinated to the metal center via the N2 nitrogen atom, but fortuitous solubility properties allowed isolation of the N1 isomer in two cases from acetone. When the solvent was changed to DMSO, the N1 → N2 isomerization could be studied by NMR spectroscopy and took several days to complete. 19F NMR studies of the iClick reaction with F3C-CC-COOEt led to identification of a putative early linear intermediate in addition to the N1 and N2 isomers, however with the latter as the final product. Rate constants determined by 1H or 19F NMR spectroscopy increased in the order Pd > Pt and CF3/COOEt > COOR/COOR with R = CH3, Et, CH2CH2OCH3. The second-order rate constant k2 > 3.7 M-1 s-1 determined for the reaction of [Pd(N3)(L)] with F3C-CC-COOEt is the fastest observed for an iClick reaction so far and compares favorably with that of the most evolved strained alkynes reported for the SPAAC (strain-promoted azide-alkyne cycloaddition) to date. Selected title compounds were evaluated for their anticancer activity on the GaMG human glioblastoma brain cancer cell line and gave EC50 values in the low micromolar range (2-16 μM). The potency of the Pd(II) complexes increased with the chain length of the substituents in the 4- and 5-positions of the triazolate ligand.
- Peng, Kun,Mawamba, Viviane,Schulz, Ellina,L?hr, Mario,Hagemann, Carsten,Schatzschneider, Ulrich
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p. 11508 - 11521
(2019/08/26)
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- A thiourea structure unit including shrinking amino aromatic compound and its preparation method and application (by machine translation)
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The invention relates to the technical field of pharmaceutical chemistry, and in particular relates to a thiourea structure unit including shrinking amino aromatic compound and its preparation method and application. The present invention provides including shrinking amino thiourea structure unit of the aromatic heterocyclic compound with the gastric cancer cells through the inner metal ion chelating form stable complexes, thereby suppressing the MGC803 gastric cancer cell proliferation activity. The results of the embodiment of the display, and the compound 3 - AP compared with, the present invention provides including shrinking amino thiourea structure unit of the aromatic heterocyclic compound to stomach MGC803 has better proliferation inhibitory activity. (by machine translation)
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Paragraph 0119; 0124-0127; 0186-0190
(2019/07/10)
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- Synthesis of 2-acetylpyridine-N-substituted thiosemicarbazonates of copper(ii) with high antimicrobial activity against methicillin resistant S. aureus, K. pneumoniae 1 and C. albicans
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The basic interest in the present study pertains to developing metal based antimicrobial agents, as several microorganisms have built resistance to the conventional drugs. In this respect, reactions of 2-acetylpyridine-N1-substituted thiosemica
- Kaushal, Mani,Lobana, Tarlok S.,Nim, Lovedeep,Bala, Ritu,Arora, Daljit S.,Garcia-Santos, Isabel,Duff, Courtney E.,Jasinski, Jerry P.
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supporting information
p. 11727 - 11742
(2019/07/31)
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- Indium complex taking APT as ligand and having potential leaving group as well as synthesis method and application of the indium complex
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The invention discloses an indium complex taking APT as a ligand and having a potential leaving group as well as a synthesis method and application of the indium complex. The synthesis method comprises the following steps: dissolving 2-acetylpyridine in a
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Paragraph 0019; 0049-0051
(2019/12/02)
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- Synthesis, antiproliferative activity and mechanism of gallium(III)-thiosemicarbazone complexes as potential anti-breast cancer agents
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Five thiosemicarbazone ligands were synthesized and characterized by condensation with different aldehydes or ketones by 4-phenylthiosemicarbazone. The representative dichlorido[2-(Di-2-pyridinylmethylene)-Nphenylhydrazinecarbothioamide-N,N,S]-gallium(III
- Qi, Jinxu,Yao, Qian,Qian, Kun,Tian, Liang,Cheng, Zhen,Yang, Dongmei,Wang, Yihong
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- Desing and synthesis of potent anti-Trypanosoma cruzi agents new thiazoles derivatives which induce apoptotic parasite death
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Chagas disease, caused by the kinetoplastid protozoan parasite Trypanosoma cruzi, remains a relevant cause of illness and premature death and it is estimated that 6 million to 7 million people are infected worldwide. Although chemotherapy options are limited presenting serious problems, such as low efficacy and high toxicity. T. cruzi is susceptible to thiazoles, making this class of compounds appealing for drug development. Previously, thiazoles resulted in an increase in anti-T. cruzi activity in comparison to thiosemicarbazones. Here, we report the structural planning, synthesis and anti-T. cruzi evaluation of new thiazoles derivatives (3a-m and 4a-m), designed from molecular hybridization associated with non-classical bioisosterism. By varying substituents attached to the phenyl and thiazole rings, substituents were observed to retain, enhance or greatly increase their anti-T. cruzi activity, in comparison to the corresponding thiosemicarbazones. In most cases, electron-withdrawing substituents, such as bromine, 3,4-dichloro and nitro groups, greatly increased antiparasitic activity. Specifically, new thiazoles were identified that inhibit the epimastigote proliferation and were toxic for trypomastigotes without affecting macrophages viability. These compounds were also evaluated against cruzain. However, inhibition of this enzyme was not observed, suggesting that the compounds work through another mechanism. In addition, examination of T. cruzi cell death showed that these molecules induce apoptosis. In conclusion, except for compounds 3h and 3k, all thiazoles derivatives evaluated exhibited higher cytotoxic activity against the trypomastigote forms than the reference medicament benznidazole, without affecting macrophages viability. Compounds 4d and 4k were highlights, CC50 = 1.2 e 1.6 μM, respectively. Mechanistically, these compounds do not inhibit the cruzain, but induce T. cruzi cell death by an apoptotic process, being considered a good starting point for the development of new anti-Chagas drug candidates.
- da Silva, Elany Barbosa,Oliveira e Silva, Dayane Albuquerque,Oliveira, Arsênio Rodrigues,da Silva Mendes, Carlos Henrique,dos Santos, Thiago André Ramos,da Silva, Aline Caroline,de Castro, Maria Carolina Acioly,Ferreira, Rafaela Salgado,Moreira, Diogo Rodrigo Magalh?es,Cardoso, Marcos Veríssimo de Oliveira,de Simone, Carlos Alberto,Pereira, Valéria Rêgo Alves,Leite, Ana Cristina Lima
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- Improved cytotoxicity of pyridyl-substituted thiosemicarbazones against MCF-7 when used as metal ionophores
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Zinc is the second most abundant transition metal in the human body, between 3 and 10 % of human genes encoding for zinc binding proteins. We have investigated the interplay of reactive oxygen species and zinc homeostasis on the cytotoxicity of the thiose
- Akladios, Fady N.,Andrew, Scott D.,Parkinson, Christopher J.
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p. 157 - 170
(2016/02/14)
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- Synthesis, characterization and crystal structure of cobalt(III) complexes containing 2-acetylpyridine thiosemicarbazones: DNA/protein interaction, radical scavenging and cytotoxic activities
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The synthesis, structure and biological studies of cobalt(III) complexes supported by NNS-tridentate ligands are reported. Reactions of 2-acetylpyridine N-substituted thiosemicarbazone (HL1-3) with [CoCl 2(PPh3)2/sub
- Manikandan, Rajendran,Viswanathamurthi, Periasamy,Velmurugan, Krishnaswamy,Nandhakumar, Raju,Hashimoto, Takeshi,Endo, Akira
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p. 205 - 216
(2014/01/06)
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- Manganese(II) complexes with thiosemicarbazones as potential anti-Mycobacterium tuberculosis agents
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Through a systematic variation on the structure of a series of manganese complexes derived from 2-acetylpyridine-N(4)-R-thiosemicarbazones (Hatc-R), structural features have been investigated with the aim of obtaining complexes with potent anti-Mycobacter
- Oliveira, Carolina G.,Maia, Pedro Ivo Da S.,Souza, Paula C.,Pavan, Fernando R.,Leite, Clarice Q.F.,Viana, Rommel B.,Batista, Alzir A.,Nascimento, Otaciro R.,Deflon, Victor M.
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- Cobalt(III) complexes with thiosemicarbazones as potential anti-Mycobacterium tuberculosis agents
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CoIII complexes derived from 2-acetylpyridine N(4)-R thiosemicarbazone (Hatc-R, R = alkyl, aryl) have been characterized by elemental analysis, FTIR, UV-Visible and 1H NMR spectroscopies, cyclic voltammetry (CV), conductimetry measur
- Oliveira, Carolina G.,Maia, Pedro Ivo Da S.,Miyata, Marcelo,Pavan, Fernando R.,Leite, Clarice Q. F.,De Almeida, Eduardo Tonon,Deflon, Victor M.
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p. 1848 - 1856
(2016/10/12)
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- Inhibition of cast iron corrosion in acid, base, and neutral media using schiff base derivatives
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Three Schiff bases, 2-acetylpyridine thiosemicarbazone (I 1 ), 2-acetylpyridine-(4-methylthiosemicarbazone) (I 2 ), and 2-acetylpyridine-(4-phenylthiosemicarbazone) (I 3 ) were tested against corrosion of cast iron in aqueous solutions of HCl, NaOH, NH 4Cl, and NaCl by means of a mass loss method and electrochemical measurements. The inhibition efficiency is directly proportional to inhibitor concentration, while it decreases with prolonged immersion time and at low temperatures. In order to study the effect of an additive, synergism of KI was also studied. The adsorption of Schiff bases in corrosive media obeys Langmuir's isotherm, both in the presence and absence of KI. The UV-Vis, FT-IR, WAXD and SEM analyses were carried out to support the mechanism of corrosion inhibition. The ΔG ads values reveal that the inhibition was mainly due to physisorption of the inhibitor molecules on the surface of cast iron. The electrochemical polarization results showed the predominantly cathodic nature of the inhibitors.
- Rajeswari, Velayutham,Kesavan, Devarayan,Gopiraman, Mayakrishnan,Viswanathamurthi, Periasamy
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p. 571 - 580
(2013/07/26)
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- N4-Phenyl-substituted 2-acetylpyridine thiosemicarbazones: Cytotoxicity against human tumor cells, structure-activity relationship studies and investigation on the mechanism of action
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N4-Phenyl 2-acetylpyridine thiosemicarbazone (H2Ac4Ph; N-(phenyl)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide) and its N 4-ortho-, -meta- and -para-fluorophenyl (H2Ac4oFPh, H2Ac4mFPh, H2Ac4pFPh), N4-ortho-, -meta
- Soares, Marcella A.,Lessa, Josane A.,Mendes, Isolda C.,Da Silva, Jeferson G.,Dos Santos, Raquel G.,Salum, Lívia B.,Daghestani, Hikmat,Andricopulo, Adriano D.,Day, Billy W.,Vogt, Andreas,Pesquero, Jorge L.,Rocha, Willian R.,Beraldo, Heloisa
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scheme or table
p. 3396 - 3409
(2012/08/08)
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- Synthesis and structural studies of gallium(III) and indium(III) complexes of 2-acetylpyridine thiosemicarbazones
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Four 2-acetylpyridine 4N-alkyl thiosemicarbazones, and their Ga(III) and In(III) complexes have been prepared and characterised by fluorescence, UV-Vis, IR, 1H and 13C NMR spectroscopy, mass spectrometry and X-ray crystallographic analysis. Comparison of the crystal structures gave an insight into the nature of the complexes formed, demonstrating a preference for [ML2]+ type complexes with gallium and [MLX3] species with indium. Stability studies on two candidates indicated that complex [InL3Cl2MeOH] was stable to chemical degradation for prolonged periods in human serum, giving this complex potential for further biological evaluation.
- Chan, Jessica,Thompson, Amber L.,Jones, Michael W.,Peach, Josephine M.
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experimental part
p. 1140 - 1149
(2010/06/17)
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- 2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: Redox activity, iron complexation and characterization of their antitumor activity
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Through systematic structure-activity studies of the 2-benzoylpyridine thiosemicarbazone (HBpT), 2-(3- nitrobenzoyl)pyridine thiosemicarbazone (HNBpT) and dipyridylketone thiosemicarbazone (HDpT) series of iron (Fe) chelators, we identified structural fea
- Richardson, Des R.,Kalinowski, Danuta S.,Richardson, Vera,Sharpe, Philip C.,Lovejoy, David B.,Islam, Mohammad,Bernhardt, Paul V.
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supporting information; experimental part
p. 1459 - 1470
(2009/12/26)
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- Gold complexes with thiosemicarbazones: Reactions of bi- And tridentate thiosemicarbazones with dichloro2-(dimethylaminomethylphenyl-CilgoldCm), [Au(damp-C1A)Cl2]
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Dichloro[2-(A,A-dimethylaminomethyl)phenyl-C1,A]gold(iii), [Au(damp-C,A)Cl2] (1), reacts with salicylaldchyde thiosemicarbazone (H2saltsc), vanilline thiosemicarbaezone (Hvantsc), N-methylpyrrole aldehyde thiosemicarbazone (Hmepyrtsc), pyridoxal methylthiosemicarbazone (H2pydoxmetsc), 2-diphenylphosphinobenzaldehyde thiosemicarbazone (HPtsc) or variously substituted acetylpyridine thiosemicarbazones (HapRtsc; R = H, Me, Ph) with cleavage of the Au-N bond and protonation of the dimethylamino group. Compounds of general formulae [Au(Hdamp-C1)CI(L)f (L = Hsaltsc-, vantsc-, mepyrtsc1), [Au(Hdamp-C1)Cl(L)]2+ (L = H2pydoxmetsc) or [Au(Hdamp-C1)(L)]2+ (L = Ptsc-, apRtsc-, R = H, Me, Ph) have been isolated and characterized. The presence of the (T-bonded 2-(dimethylaminomethyl)phenyl ligand is mandatory to prevent reduction of the gold(in) centre. The crystal structures of [Au(Hdanip-C1)CI(HsaItsc)](PF6) (3a), [Au(Hdamp-C')Cl(mepyrtsc)]Cl (3c), [Au(Hdamp-C1)-CI(H2pydo.xtnetsc)]Cl2-MeOH (4), [Au(Hdamp-C1)(apPhtsc)]Cl2-2 MeOH (5c) and [Au(Hdamp-C')(Ptsc)]Cl2-1.5MeOH (6) have been elucidated, showing the gold atoms in distorted square-planar co-ordination environments. The potentially O,N,S-tridentate ligands H2saltsc and H2pydoxmetsc co-ordinate in a bidentate fashion and do not incorporate the OH groups in the chelating framework, whereas HapRtsc or HPtsc co-ordinate in a tridentate manner. Generally, one or more hydrogen atoms of the heterocyclic ligands and/or the NMe2H+ group form hydrogen bridges in the solid state structures. The preliminary results of antiproliferation tests on tumor cells demonstrate the considerable cytotoxicity of these new gold complexes. The Royal Society of Chemistry 2000.
- Abram, Ulrich,Ortner, Kirstin,Gusf, Ronald,Sommer, Klaus
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p. 735 - 744
(2007/10/03)
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- Antifungal and antibacterial activity of 2-acetylpyridine-(4-phenylthiosemicarbazone) and its metal (II) complexes
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2-Acetylpyridine-(4-phenylthiosemicarbazone) and its metal (II) complexes have been synthesized and characterized by chemical and spectral methods. They were studied for their antibacterial and antifungal activities in vitro. The ligand and its metal (II)
- Efanga Offiong,Martelli
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p. 1543 - 1554
(2007/10/02)
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- 2-Acetylpyridine thiosemicarbazones. 1. A new class of potential antimalarial agents
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Based on the antimalarial properties observed for 2-acetylpyridine 4-phenyl-3-thiosemicarbazone (1), an extensive series of related thiosemicarbazones was prepared and tested against Plasmodium berghei in mice. Screening results indicated that the presence of the 2-pyridylethylidene group was critical and that certain phenyl, benzyl, phenethyl, or cycloalkyl groups at N4 of the thiosemicarbazone moiety also contribute to antimalarial activity.
- Klayman,Bartosevich,Griffin,Mason,Scovill
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p. 855 - 862
(2007/10/04)
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