- Organometallic ruthenium(II) complexes containing NS donor Schiff bases: Synthesis, structure, electrochemistry, DNA/BSA binding, DNA cleavage, radical scavenging and antibacterial activities
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Four new cyclopentadienylruthenium(II)-acetophenone-4(N)-substituted thiosemi-carbazone complexes, with the general formula [Ru(?5-C5H5)(H-Aptsc)PPh3].Cl (1), [Ru(?5-C5H5)(H-Apmt
- Devagi,Dallemer,Kalaivani,Prabhakaran
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- Synthesis and spectral characterization of acetophenone thiosemicarbazone-A nonlinear optical material
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Acetophenone thiosemicarbazone (APTSC) was synthesized. Solubility of APTSC was determined in ethanol and methanol at different temperatures. Single crystals were grown from ethanol by slow evaporation at room temperature. The grown crystal was subjected
- Santhakumari,Ramamurthi,Vasuki,Yamin, Bohari M.,Bhagavannarayana
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- Synthesis, characterization, alkaline phosphatase inhibition assay and molecular modeling studies of 1-benzylidene-2-(4-tert- butylthiazol-2-yl) hydrazines
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Alkaline phosphatases are homodimeric protein enzymes which removes phosphates from several types of molecules. These catalyze the hydrolysis of monoesters in phosphoric acid which in turn catalyze a transphosphorylation reaction. Thiazoles are a privileged class of heterocyclic compounds which may potentially serve as effective phosphatase inhibitors. In this regard, the present research paper reports the facile synthesis and characterization of substituted 1-benzylidene-2-(4-tert-butylthiazol-2-yl) hydrazines with excellent yields. The synthesized compounds were tested for inhibitory potential against alkaline phosphatases. The compound 1-(4-Hydroxy, 3-methoxybenzylidene)-2-(4-tert-butylthiazol-2-yl) hydrazine (5e) was found to be the most potent inhibitor of human tissue non-alkaline phosphatase in this group of molecules with an IC50 value of 1.09 ± 0.18 μM. The compound 1-(3,4-dimethoxybenzylidene)-2-(4-tert-butylthiazol-2-yl) hydrazine (5d) exhibited selectivity and potency for human intestinal alkaline phosphatase with an IC50 value of 0.71 ± 0.02 μM. In addition, structure activity relationship and molecular docking studies were performed to evaluate their binding modes with the target site of alkaline phosphatase. The docking analysis revealed that the most active inhibitors showed the important interactions within the binding pockets of human intestinal alkaline phosphatase and human tissue non-alkaline phosphatase and may be responsible for the inhibitory activity of the compound towards the enzymes. Therefore, the screened thiazole derivatives provided an outstanding platform for further development of alkaline phosphatase inhibitors.
- Aziz, Hamid,Mahmood, Abid,Zaib, Sumera,Saeed, Aamer,El-Seedi, Hesham R.,Pelletier, Julie,Sévigny, Jean,Iqbal, Jamshed
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p. 6140 - 6153
(2020/08/14)
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- The design, synthesis, and: In vitro trypanocidal and leishmanicidal activities of 1,3-thiazole and 4-thiazolidinone ester derivatives
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Chagas and leishmaniasis are both neglected tropical diseases, whose inefficient therapies have made them remain the cause for millions of deaths worldwide. Given this, we synthesized 27 novel 1,3-thiazoles and 4-thiazolidinones using bioisosteric and est
- Haroon, Muhammad,De Barros Dias, Mabilly Cox Holanda,Santos, Aline Caroline da Silva,Pereira, Valéria Rêgo Alves,Freitas, Luiz Alberto Barros,Balbinot, Rodolfo Bento,Kaplum, Vanessa,Nakamura, Celso Vataru,Alves, Luiz Carlos,Brayner, Fábio André,Leite, Ana Cristina Lima,Akhtar, Tashfeen
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p. 2487 - 2500
(2021/01/29)
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- Combined theoretical and experimental studies reveal the newly synthesized pyrimidinones as potential apoptotic agents
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Reaction of acetophenone thiosemicarbazones (5–8) and (2-methyl) diethyl malonate in absolute ethanol under reflux conditions furnished the corresponding pyrimidinone analogs (9–12) in good to excellent yields. The resulting pyrimidines were characterised
- Dar, Ayaz Mahmood,Mir, Shafia,Jan, Masrat,Nabi, Rizwan,Gatoo, Manzoor Ahmad,Shamsuzzaman
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- Expedient routes to 1,2,4-triazolinium salts
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Concomitant S-alkylation and ketazonation of thiosemicarbazide in acetone eventually led to unanticipated ring closure and formation of (3-alkylthio)-1,2,4-triazolinium salts. This initial finding was complemented by employing another three representative aldehydes and ketones. Supplementarily, some respective intermediates have been isolated by stepwise synthetic procedures. In addition to the usual spectroscopic characterization, the structures of six 1,2,4-triazolinium heterocycles, as well as two unexpected by-products thereof have been characterized by single-crystal X-ray diffraction.
- Fliri, Lukas,Partl, Gabriel,Gelbrich, Thomas,Nerdinger, Sven,Wurst, Klaus,Schottenberger, Herwig
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p. 593 - 610
(2020/01/31)
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- Synthesis, characterization, in vitro tissue-nonspecific alkaline phosphatase (TNAP) and intestinal alkaline phosphatase (IAP) inhibition studies and computational evaluation of novel thiazole derivatives
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Alkaline phosphatases (APs) are a class of homodimeric enzymes which physiologically possess the dephosphorylation ability. APs catalyzes the hydrolysis of monoesters into phosphoric acid which in turn catalyze a transphosphorylation reaction. Thiazoles are nitrogen and sulfur containing aromatic heterocycles considered as effective APs inhibitors. In this context, the current research paper presents the successful synthesis, spectroscopic characterization and in vitro alkaline phosphatase inhibitory potential of new thiazole derivatives. The structure activity relationship and molecular docking studies were performed to find out the binding modes of the screened compounds with the target site of tissue non-specific alkaline phosphatase (h-TNAP) as well as intestinal alkaline phosphatase (h-IAP). Compound 5e was found to be potent inhibitor of h-TNAP with IC50 value of 0.17 ± 0.01 μM. Additionally, compounds 5a and 5i were found to be highly selective toward h-TNAP with IC50 values of 0.25 ± 0.01 μM and 0.21 ± 0.02 μM, respectively. In case of h-IAP compound 5f was the most potent inhibitor with IC50 value of 1.33 ± 0.10 μM. The most active compounds were resort to molecular docking studies on h-TNAP and h-IAP to explore the possible binding interactions of enzyme-ligand complexes. Molecular dynamic simulations were carried out to investigate the overall stability of protein in apo and holo state.
- Aziz, Hamid,Iqbal, Jamshed,Mahmood, Abid,Pelletier, Julie,Sévigny, Jean,Saeed, Aamer,Shafiq, Zahid,Zaib, Sumera
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- Microwave-assisted Vilsmeier-Haack synthesis of Pyrazole-4-carbaldehydes
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The synthesis of 4-formylpyrazoles using Vilsmeier-Haack reagent is a common protocol in pyrazole chemistry. An efficient microwave-assisted synthesis of 4-formylpyrazoles by employing Vilsmeier-Haack reagent (OPC-VH) derived from phthaloyl dichloride/dimethylformamide has been described. This method offers the advantages of operational simplicity, avoiding the use of POCl3 as toxic reagents and reuse of the by-product in the preparation of phthaloyl dichloride.
- Kumari, Poonam,Sood, Sumit,Kumar, Anil,Singh, Karan
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p. 796 - 804
(2019/11/28)
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- Microwave-assisted synthesis and biological evaluation of pyrazole-4-carbonitriles as antimicrobial agents
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An efficient microwave-assisted method of synthesis of pyrazole-4-carbonitriles has been developed. Condensation of pyrazole-4-carbaldehydes with hydroxylamine hydrochloride followed by reaction of the resulting oximes with the Vilsmeier-Haack reagent pre-formed from phthaloyl dichloride and dimethylformamide under microwave irradiation afforded the corresponding pyrazole-4-carbonitriles in 73percent to 91percent yield. The operational simplicity, avoidance of toxic reagents such as POCl3, shorter reaction time, higher yield compared to the classical version, easy work up, and the use of the by-product in the regeneration of phthaloyl dichloride are the advantages of this methodology. All the target compounds were tested for antimicrobial activity against Gram-positive bacteria Bacillus cereus and Staphylococcus aureus; Gram-negative bacteria Escherichia coli and Yersinia enterocolitica, and the fungal species Candida albicans.
- Kumar, Anil,Kumari, Poonam,Singh, Karan,Sood, Sumit,Yadav, Ajar Nath
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- Design, synthesis and molecular docking studies of some thiazole clubbed heterocyclic compounds as possible anti-infective agents
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The present work describes synthesis of a series of 5-((1-(4-(4-chlorophenyl)thiazol-2-yl)-3- aryl-1H-pyrazol-4-yl)methylene)-2-(arylimino)thiazolidin-4-one derivatives and their molecular docking and biological evaluation as possible antimalarial, anthelmintic and antimicrobial agents. The synthesis of compounds has been accomplished by adopting suitable synthetic methods. Structures of newly synthesized compounds were characterized and authenticated by spectral methods such as IR, 1H-NMR and mass spectra. Synthesized compounds were screened for their in vitro antimicrobial activity against selected bacterial strains and fungal strains viz. B. subtilis, S. aureus, E. coli, P. fluorescens, C. albicans, C. glabrata and antimalarial studies against P. falciparum. Titled compounds were also tested against Pheretima posthuma (earthworm) for their anthelmintic activity. Molecular docking was done to study the binding modes of the potent compounds against Escherichia coli (PDB ID: 1AB4) and Candida P450DM (PDB ID: 1EA1) enzymes. The results revealed that all the compounds exhibited moderate to significant antimicrobial activities. Antimalarial activity screening revealed that one compound 8i showed significant antimalarial activity with of IC50; 0.59 μg/mL as compared to standard drugs chloroquine (IC50= 0.020 μg/mL) and quinine (IC50; 0.268 μg/mL). The most active compound exhibited the mean paralysis time of 19.2 ± 0.9 min and mean death time of 31.7 ± 2.5 min. It can be concluded that some of the synthesized compounds have remarkable antiinfective, antimalarial and anthelmintic activity and are suitable candidates for further scientific exploration.
- Sharma, Prabodh Chander,Saini, Anil,Bansal, Kushal Kumar,Sharma, Archana,Gupta, Girish Kumar
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p. 716 - 726
(2018/07/13)
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- Novel thiazole clubbed triazole derivatives as antimicrobial, antimalarial, and cytotoxic agents
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Thiazole is one of the most potential heterocyclic moieties in bioorganic chemistry and is major tool in drug design and discovery. The present work describes the synthesis of a series of N-{(1-(4-(4bromophenyl) thiazol-2-yl)-3-substitutedphenyl-1H-pyrazo
- Bansal, Kushal K.,Sharma, Diksha,Sharma, Archana,Rajak, Harish,Sharma, Prabodh C.
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p. 305 - 312
(2018/09/14)
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- Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity
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With reference to recent studies reporting on the various biological properties of the thiazolidinone scaffold, we synthesized more than a hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs (i.e. clotrimazole, fluconazole, ketoconazole, miconazole, tioconazole, amphotericin B). Compounds endowed with the lowest MICs underwent further testing in order to assess their cytotoxic effect (CC50) on Hep2 cells, which demonstrated their relative safety. Finally, QSAR and 3-D QSAR models were used to predict putative chemical modifications of the 1,3-thiazolidin-4-one scaffold in order to design new and potential more active compounds against Candida spp.
- Carradori, Simone,Bizzarri, Bruna,D'Ascenzio, Melissa,De Monte, Celeste,Grande, Rossella,Rivanera, Daniela,Zicari, Alessanda,Mari, Emanuela,Sabatino, Manuela,Patsilinakos, Alexandros,Ragno, Rino,Secci, Daniela
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p. 274 - 292
(2017/10/05)
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- Impact and correlation of p: K a and dn electrons of some selected thiosemicarbazone Schiff base metal Co, Ni, Cu complexes: A study of electrochemical behavior, excitation and optical energies
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The electron-transfer and coordination mechanism of Schiff bases with metal ions, correlation of the electrochemical and optical properties for their potential applications in various fields of chemistry and biochemistry are underexplored. Thus, detailed
- El-Shahawi,Ahmad,Mohammed,Moustafa,Al-Hazmi,El-Asmy
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p. 4853 - 4861
(2017/07/12)
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- Anti-Candida activity and cytotoxicity of a large library of new N-substituted-1,3-thiazolidin-4-one derivatives
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On the basis of the recent findings about the biological properties of thiazolidinones and taking into account the encouraging results about the antifungal activity of some (thiazol-2-yl)hydrazines, new N-substituted heterocyclic derivatives were designed combining the thiazolidinone nucleus with the hydrazonic portion. In details, 1,3-thiazolidin-4-ones bearing (cyclo)aliphatic or (hetero)aromatic moieties linked to the N1-hydrazine at C2 were synthesized and classified into three series according to the aromatic or bicyclic rings connected to the lactam nitrogen of the thiazolidinone. These molecules were assayed for their anti-Candida effects in reference to the biological activity of the conventional topic (clotrimazole, miconazole, tioconazole) and systemic drugs (fluconazole, ketoconazole, amphotericin B). Finally, we investigated the selectivity against fungal cells by testing the compounds endowed with the best MICs on Hep2 cells in order to assess their cell toxicity (CC50) and we noticed that two derivatives were less cytotoxic than the reference drug clotrimazole. Moreover, a preliminary molecular modelling approach has been performed against lanosterol 14-α demethylase (CYP51A1) to rationalize the activity of the tested compounds and to specify the target protein or enzyme.
- De Monte, Celeste,Carradori, Simone,Bizzarri, Bruna,Bolasco, Adriana,Caprara, Federica,Mollica, Adriano,Rivanera, Daniela,Mari, Emanuela,Zicari, Alessandra,Akdemir, Atilla,Secci, Daniela
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- Efficient "on water" green route heterocyclization of thiosemicarbazones with DMAD
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A simple, efficient, and eco-friendly procedure for the synthesis of thiazolidin-4-one derivatives in water from cyclocondensation reaction of thiosemicarbazone derivatives and dimethylacetylene dicarboxylate (DMAD) in good yield is reported. The regiochemistry of the cyclized products is established by elemental analysis, IR, NMR, and mass spectral data. A single crystal X-ray diffraction study of a representative compound, 3f, is reported.
- Singla, Rohit,Gautam, Deepika,Gautam, Poonam,Chaudhary
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p. 740 - 745
(2016/05/09)
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- Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma
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Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer.
- De Monte, Celeste,Carradori, Simone,Secci, Daniela,D'Ascenzio, Melissa,Guglielmi, Paolo,Mollica, Adriano,Morrone, Stefania,Scarpa, Susanna,Aglianò, Anna Maria,Giantulli, Sabrina,Silvestri, Ida
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p. 245 - 262
(2015/11/03)
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- In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives
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A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2- yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-{4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1, 3-thiazol-5-yl}ethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 μM and 0.648 μM respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl) thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 μM and 631.84 μM respectively.
- Makam, Parameshwar,Thakur, Prasoon Kumar,Kannan, Tharanikkarasu
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p. 138 - 145
(2014/01/06)
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- Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors
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Acetylation, which targets a broad range of histone and non-histone proteins, is a reversible mechanism and plays a critical role in eukaryotic genes activation/deactivation. Acetyltransferases are very well conserved through evolution. This allows the use of a simple model organism, such as budding yeast, for the study of their related processes and to discover specific inhibitors. Following a simple yeast-based chemogenetic approach, we have identified a novel HAT (histone acetyltransferase) inhibitor active both in vitro and in vivo. This new synthetic compound, 1-(4-(4-chlorophenyl)thiazol-2- yl)-2-(propan-2-ylidene)hydrazine, named BF1, showed substrate selectivity for histone H3 acetylation and inhibitory activity in vitro on recombinant HAT Gcn5 and p300. Finally, we tested BF1 on human cells, HeLa as control and two aggressive cancer cell lines: a neuroblastoma from neuronal tissue and glioblastoma from brain tumour. Both global acetylation of histone H3 and specific acetylation at lysine 18 (H3AcK18) were lowered by BF1 treatment. Collectively, our results show the efficacy of this novel HAT inhibitor and propose the utilization of BF1 as a new, promising tool for future pharmacological studies.
- Secci, Daniela,Carradori, Simone,Bizzarri, Bruna,Bolasco, Adriana,Ballario, Paola,Patramani, Zoi,Fragapane, Paola,Vernarecci, Stefano,Canzonetta, Claudia,Filetici, Patrizia
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p. 1680 - 1689
(2014/03/21)
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- Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies
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Recently we described some (thiazol-2-yl)hydrazones as antiprotozoal, antifungal and anti-MAO agents as well as Gcn5 HAT inhibitors. Among these last compounds, CPTH2 and CPTH6 showed HAT inhibition in cells and broad anticancer properties. With the aim to identify HAT inhibitors more potent than the two prototypes, we synthesized several new (thiazol-2-yl)hydrazones including some related thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis than CPTH6, and were more potent than CPTH6 in inducing cytodifferentiation (U937 cells).
- Carradori, Simone,Rotili, Dante,De Monte, Celeste,Lenoci, Alessia,D'Ascenzio, Melissa,Rodriguez, Veronica,Filetici, Patrizia,Miceli, Marco,Nebbioso, Angela,Altucci, Lucia,Secci, Daniela,Mai, Antonello
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p. 569 - 578
(2014/06/09)
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- Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii
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We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition.
- D'Ascenzio, Melissa,Bizzarri, Bruna,De Monte, Celeste,Carradori, Simone,Bolasco, Adriana,Secci, Daniela,Rivanera, Daniela,Faulhaber, Nathan,Bordón, Claudia,Jones-Brando, Lorraine
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- Structure-activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei
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To explore the structure-activity relationships of thiosemicarbazones on African trypanosome: Trypanosoma brucei brucei, a series of thirty-five thiosemicarbazones (1-35) have been synthesized and characterized by their 1H NMR, 13C NMR, and FT-IR spectra. All compounds were tested for trypanocidal activity using the method "Lilit alamar blue". The comparison of trypanocidal power of thiosemicarbazones was performed considering their structures. This study that was done using acetophenone thiosemicarbazone (1) as basic model, showed that: (a) the presence of lipophilic substituents in para position on benzene ring, (b) substitution of benzene ring and (c) substitution of hydrogen of thioamide function by a phenyl, strongly influence trypanocidal activity. The various modifications to basic structure (1) allowed the synthesis of 1-(4-chlorophenyl) ethylidene-4-phenyl- thiosemicarbazide (34). With a trypanocidal activity of 3.97 μM, this compound is the most active of the series.
- Fatondji, Houssou Raymond,Kpoviessi, Salome,Gbaguidi, Fernand,Bero, Joanne,Hannaert, Veronique,Quetin-Leclercq, Joelle,Poupaert, Jacques,Moudachirou, Mansourou,Accrombessi, Georges Coffi
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p. 2151 - 2162
(2013/07/26)
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- Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates
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The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Trypanosoma cruzi in in vitro assays (IC50 57 μM), and no mutagenic profile was observed in micronucleous tests. Although the in vitro inhibition test showed that 10-μM doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity.
- Blau, Lorena,Menegon, Renato Farina,Trossini, Gustavo H. G.,Molino, Jo?o Vitor Dutra,Vital, Drielli Gomes,Cicarelli, Regina Maria Barretto,Passerini, Gabriela Duó,Bosquesi, Priscila Longhin,Chin, Chung Man
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p. 142 - 151
(2013/10/01)
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- Synthesis, characterization, and anticancer activity of a series of ketone-N4-substituted thiosemicarbazones and their ruthenium(II) arene complexes
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A series of ketone-N4-substituted thiosemicarbazone (TSC) compounds (L1-L9) and their corresponding [(η6-p-cymene)Ru II(TSC)Cl]+/0 complexes (1-9) were synthesized and characterized by NMR, IR, elemental analysis, and HR-ESI-mass spectrometry. The molecular structures of L4, L9, 1-6, and 9 were determined by single-crystal X-ray diffraction analysis. The compounds were further evaluated for their in vitro antiproliferative activities against the SGC-7901 human gastric cancer, BEL-7404 human liver cancer, and HEK-293T noncancerous cell lines. Furthermore, the interactions of the compounds with DNA were followed by electrophoretic mobility spectrometry studies.
- Su, Wei,Qian, Quanquan,Li, Peiyuan,Lei, Xiaolin,Xiao, Qi,Huang, Shan,Huang, Chusheng,Cui, Jianguo
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p. 12440 - 12449
(2013/11/19)
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- Recent advances in the development of selective human MAO-B inhibitors: (Hetero)arylidene-(4-substituted-thiazol-2-yl)hydrazines
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A large series of (4-substituted-thiazol-2-yl)hydrazine derivatives was synthesized in good yield and assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity. Most of them showed inhibitory activity in the nanomolar range and hMAO-B selective inhibition higher than reference drugs, demonstrating our interest in this privileged scaffold. The structure-activity relationship of the different rings on the N1-hydrazine position indicated that a pyridine ring was preferred with the presence of electron-withdrawing substituents on the aryl group at C4 of the thiazole nucleus. The substituent on the α-carbon to the N1-hydrazine moiety (methyl or hydrogen) had a great influence on the activity and hMAO-B selectivity. Moreover, the reversibility of the enzyme inhibition for the best active compound was reported.
- Secci, Daniela,Bolasco, Adriana,Carradori, Simone,D'Ascenzio, Melissa,Nescatelli, Riccardo,Yá?ez, Matilde
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p. 405 - 417
(2013/02/21)
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- Ketonethiosemicarbazones: Structure-activity relationships for their melanogenesis inhibition
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A series of 2-(1-phenylalkylidene)hydrazinecarbothioamides 2, 2-(1-phenylalkyl)hydrazinecarbothioamides 3, 2-(3,4-dihydronaphthalen-1(2H)- ylidene)hydrazinecarbothioamide (4), and 2-(1-(thiophen-2-yl)ethylidene) hydrazinecarbothioamide (5) were synthesize
- Thanigaimalai, Pillaiyar,Lee, Ki-Cheul,Sharma, Vinay K.,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
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supporting information; experimental part
p. 3527 - 3530
(2011/07/31)
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- Synthesis and anti-Helicobacter pylori activity of 4-(coumarin-3-yl) thiazol-2-ylhydrazone derivatives
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A novel class of coumarin-thiazole conjugated systems (1-31) were synthesized by Hantzsch condensation between α-bromo-3-acetyl coumarin and several thiosemicarbazone intermediates. This scaffold was also evaluated for selective antibacterial activity against 20 isolates of H. pylori clinical strains, including four metronidazole resistant ones.
- Chimenti, Franco,Bizzarri, Bruna,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Granese, Arianna,Carradori, Simone,D'Ascenzio, Melissa,Scaltrito, M. Maddalena,Sisto, Francesca
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experimental part
p. 1269 - 1274
(2011/01/05)
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- Ruthenium(II) mediated C-H activation of substituted acetophenone thiosemicarbazones: Synthesis, structural characterization, luminescence and electrochemical properties
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Treatment of [RuHCl(CO)(AsPh3)3] with 4′-substituted acetophenone thiosemicarbazone derivatives in methanol under reflux afford a series of air stable new ruthenium(II) cyclometalated complexes containing thiosemicarbazone of general
- Prabhu, Rupesh Narayana,Pandiarajan, Devaraj,Ramesh, Rengan
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experimental part
p. 4170 - 4177
(2010/03/24)
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- 1-(1-Arylethylidene)thiosemicarbazide derivatives: A new class of tyrosinase inhibitors
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A series of 1-(1-arylethylidene)thiosemicarbazide compounds and their analogues were synthesized and characterized by 1H NMR, MS. Their tyrosinase inhibitory activities were investigated by an assay based on the catalyzing ability of tyrosinase
- Liu, Jinbing,Yi, Wei,Wan, Yiqian,Ma, Lin,Song, Huacan
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p. 1096 - 1102
(2008/09/18)
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- THIADIAZOLINE DERIVATIVES
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An antitumor agent comprising a thiadiazoline derivative represented by the general formula (I), or a pharmacologically acceptable salt thereof as an active ingredient: (wherein Z represents a sulfur atom and the like, R1 represents substituted or unsubstituted lower alkynyl and the like, R2 represents a hydrogen atom and the like, R3 represents substituted or unsubstituted lower alkyl and the like, and R4 represents substituted or unsubstituted aryl and the like), and the like are provided.
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- M-STAGE KINESIN INHIBITOR
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A mitotic kinesin Eg5 inhibitor which comprises a thiadiazoline derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient: [wherein R1 represents a hydrogen atom and the like, R2 represents a hydrogen atom, -C(=W)R6 (wherein W represents an oxygen atom or a sulfur atom, and R6 represents substituted or unsubstituted lower alkyl and the like) and the like, R3 represents -C(=Z)R19 (wherein Z represents an oxygen atom or a sulfur atom, and R19 represents substituted or unsubstituted lower alkyl and the like) and the like, R4 represents substituted or unsubstituted lower alkyl and the like, and R5 represents substituted or unsubstituted aryl and the like] and the like are provided.
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- Spectroscopic, thermal and electrochemical studies on some nickel(II) thiosemicarbazone complexes
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Several complexes of thiosemicarbazone derivatives with Ni(II) have been prepared. Structural investigation of the ligands and their complexes has been made based on elemental analysis, magnetic moment, spectral (UV-Vis, i.r., 1H NMR, ms), and
- El-Shazly,Al-Hazmi,Ghazy,El-Shahawi,El-Asmy
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p. 243 - 252
(2007/10/03)
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- THIADIAZOLINE DERIVATIVE
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(wherein R1 and R4 are the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkynyl, substituted or unsubstituted lower alkenyl, or the like; R5 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like; R2 represents -C(-W)R6 or the like; R3 represents a hydrogen atom, -C(=WA)R6A, or the like) Antitumor agents which comprises a thiadiazoline derivative represented by the aforementioned general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient are provided.
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- Evaluation of semicarbazones for anticonvulsant and sedative-hypnotic properties
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A series of semicarbazones and thiosemicarbazones were synthesized and evaluated for anti-convulsant activity. Some compounds provided significant protection against Maximal Electroshock (MES) and subcutaneous strychnine induced seizures. Compound 1 was the most active in the series with activity in a dose of 30 mg/kg in the strychnine seizure pattern test and an ED50 of 10 mg/kg in the MES test. Hence it could serve as a prototype molecule for future development. Also compounds with a p-nitrophenyl substitution in place of the amino hydrogen of semicarbazone moiety showed activity in a dose of 30 mg/kg and an ED50 of 83 mg/kg in the MES test.
- Pandeya,Aggarwal,Jain
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p. 300 - 302
(2007/10/03)
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- MULTINUCLEAR MAGNETIC RESONANCE AND RELATED STUDIES ON AZOMETHINE BORON COMPLEXES OF SEMICARBAZONES AND THIOSEMICARBAZONES
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Synthetic and stereochemical features of some interesting boron complexes have been described.These three and four coordinated complexes have been prepared by the interaction of 2-isopropoxy-1, 3,2-benzodioxaborole with semicarbazones and thiosemicarbazones having the donor sets NOH and NSH in unimolar ratio and with semicarbazones and thiosemicarbazones having the donor sets HONOH and OHNSH in 1:1 and 2:1 molar ratios.Depending on the stoichiometry of the reactions, different moles of isopropanol are liberated and a variety of new boron azomethine complexes are obtained.On the basis of IR, (1)H NMR, (11)B NMR and (13)C NMR data plausible geometries have been proposed for the resulting derivatives, X-ray powder diffraction studies of a representative compound have also been carried out and the results show that adopts 'orthorhombic' type of lattice with unit cell dimensions; a= 10.84 Angstroem, b= 24.12 Angstroem, and c= 28.74 Angstroem.
- Bhal, L.,Singh, R. V.,Tandon, J. P.
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p. 251 - 260
(2007/10/02)
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