- Vibrational spectra, molecular structure, natural bond orbital, first order hyperpolarizability, thermodynamic analysis and normal coordinate analysis of Salicylaldehyde p-methylphenylthiosemicarbazone by density functional method
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The thiosemicarbazone compound, Salicylaldehyde p- methylphenylthiosemicarbazone (abbreviated as SMPTSC) was synthesized and characterized by FTIR, FT-Raman and UV. Density functional (DFT) calculations have been carried out for the title compound by perf
- Porchelvi, E. Elamurugu,Muthu
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- Thiosemicarbazones and 4-thiazolidinones indole-based derivatives: Synthesis, evaluation of antiproliferative activity, cell death mechanisms and topoisomerase inhibition assay
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In this study, we report the synthesis and structural characterization of a series of thiosemicarbazone and 4-thiazolidinones derivatives, as well as their in?vitro antiproliferative activity against eight human tumor cell lines. For the most potent compo
- de Oliveira, Jamerson Ferreira,Lima, Talitha Santos,Vendramini-Costa, Débora Barbosa,de Lacerda Pedrosa, Sybelle Christianne Batista,Lafayette, Elizabeth Almeida,da Silva, Rosali Maria Ferreira,de Almeida, Sinara Monica Vitalino,de Moura, Ricardo Olímpio,Ruiz, Ana Lúcia Tasca Gois,de Carvalho, Jo?o Ernesto,de Lima, Maria do Carmo Alves
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- Novel indol-3-yl-thiosemicarbazone derivatives: Obtaining, evaluation of in vitro leishmanicidal activity and ultrastructural studies
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Parasitic diseases still represent serious public health problems, since the high and steady emergence of resistant strains is evident. Because parasitic infections are distributed predominantly in developing countries, less toxic, more efficient, safer and more accessible drugs have become desirable in the treatment of the infected population. This is the case of leishmaniasis, an infectious disease caused by a protozoan of the genus Leishmania sp., responsible for triggering pathological processes from the simplest to the most severe forms leading to high rates of morbidity and mortality throughout the world. In the search for new leishmanicidal drugs, the thiosemicarbazones and the indole fragments have been identified as promising structures for leishmanicidal activity. The present study proposes the synthesis and structural characterization of new indole-thiosemicarbazone derivatives (2a-j), in addition to performing in vitro evaluations through cytotoxicity assays using macrophages (J774) activity against forms of Leishmania infantum and Leishmania amazonensis promastigote as well as ultrastructural analyzes in promastigotes of L. infantum. Results show that the indole-thiosemicarbazone derivatives were obtained with yield values varying from 32.09 to 94.64%. In the evaluation of cytotoxicity, the indole-thiosemicarbazone compounds presented CC50 values between 53.23 and 357.97 μM. Concerning the evaluation against L. amazonensis promastigote forms, IC50 values ranged between 12.31 and > 481.52 μM, while the activity against L. infantum promastigotes obtained IC50 values between 4.36 and 23.35 μM. The compounds 2d and 2i tested against L. infantum were the most promising in the series, as they showed the lowest IC50 values: 5.60 and 4.36 respectively. The parasites treated with the compounds 2d and 2i showed several structural alterations, such as shrinkage of the cell body, shortening and loss of the flagellum, intense mitochondrial swelling and vacuolization of the cytoplasm leading the parasite to cellular unviability. Therefore, the indole-thiosemicarbazone compounds are promising because they yield considerable synthesis, have low cytotoxicity to mammalian cells and act as leishmanicidal agents.
- da Silva, Paula Roberta,de Oliveira, Jamerson Ferreira,da Silva, Anekécia Lauro,Queiroz, Camila Marques,Feitosa, Ana Paula Sampaio,Duarte, Denise Maria Figueiredo Araújo,da Silva, Aline Caroline,de Castro, Maria Carolina Accioly Brelaz,Pereira, Valéria Rêgo Alves,da Silva, Rosali Maria Ferreira,Alves, Luiz Carlos,dos Santos, Fábio André Brayner,de Lima, Maria do Carmo Alves
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- Synthesis and spectral studies of platinum complexes of para-substituted 4-phenylthiosemicarbazides
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Platinum(II) complexes of para-substituted 4-phenylthiosemicarbazides, RPhNHCSNHNH2 (R = H, CH3, Br, F and NO2) have been prepared and characterised by infrared and multinuclear NMR spectroscopy. The thiosemicarbazides act as bidentate ligands bonding through the sulphur and hydrazinic nitrogen atoms to form mixtures of cis- and trans-isomers of square planar complexes. 1H and 195Pt NMR spectroscopy suggest that the trans-isomer predominates in solution and that the relative ratio of trans: cis increases with increasing temperature of synthesis. 15N NMR spectroscopy has also been used to assign the cis- and trans-isomers of platinum complexes of 15N enriched 4-(4′-bromophenyl)thiosemicarbazide using 15N chemical shifts and |1J 195Pt-15N| values. The magnitude of the coupling constant |1J 195Pt-15N| of 238 Hz compares favourably with other platinum(II) complexes in which the 15N donor atom is trans to 15N and thus confirms the assignment of the trans-isomer as the predominant one in solution.
- Arendse, Malcolm J.,Green, Ivan R.,Koch
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- Two Different Thiosemicarbazone Tauto-Conformers Coordinate to Palladium (II). Stability and Biological Studies of the Final Complexes
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Thiosemicarbazone moiety is a valuable scaffold for the synthesis of metallic complexes with anticancer purposes, when bearing N-heterocyclic the final compounds possess diverse biological activities. Using thiazole as bioisosteres, the resulting thiosemi
- Fabra, David,Matesanz, Ana I.,Herrero, Jorge M.,Alvarez, Cristina,Balsa, Lucia M.,Leon, Ignacio E.,Quiroga, Adoracion G.
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- Synthesis, cytotoxicity, and in vivo antitumor activity study of parthenolide semicarbazones and thiosemicarbazones
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Parthenolide is an important sesquiterpene lactone with potent anticancer activities. In order to further improve its biological activity, a series of parthenolide semicarbazone or thiosemicarbazone derivatives was synthesized and evaluated for their anti
- Du, Guohua,Jia, Xinxin,Li, Yan,Liu, Qi,Wang, Shiyi,Zeng, Binglin,Zhang, Chen
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- Novel 4-quinoline-thiosemicarbazone derivatives: Synthesis, antiproliferative activity, in vitro and in silico biomacromolecule interaction studies and topoisomerase inhibition
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Twelve 2-(quinolin-4-ylmethylene) hydrazinecarbothioamide derivatives were synthetized and their biological properties were investigated, among which, the ability to interact with DNA and BSA through UV–Vis absorption, fluorescence, Circular Dichroism, molecular docking and relative viscosity, antiproliferative activity against MCF-7 and T-47D mammary tumor cells and RAW-264.7 macrophages and inhibitory capacity of the enzyme topoisomerase IIα. In the binding study with DNA and BSA, all the compounds displayed affinity for interaction with both biomolecules, especially JF-92 (p-ethyl-substituted), with binding constant of 1.62 × 106 and 1.43 × 105, respectively, and DNA binding mode by intercalation. The IC50 values were obtained between 0.81 and 1.48 μM and topoisomerase inhibition results in 10 μM. Thus, we conclude that the reduction of the acridine to quinoline ring did not disrupt the antitumor action and that substitution patterns are important for biomolecule interaction affinity as they demonstrate the potential of these compounds for anticancer therapy.
- Ribeiro, Amélia Galdino,Almeida, Sinara M?nica Vitalino de,de Oliveira, Jamerson Ferreira,Souza, Tulio Ricardo Couto de Lima,Santos, Keriolaine Lima dos,Albuquerque, Amanda Pinheiro de Barros,Nogueira, Mariane Cajuba de Britto Lira,Carvalho Junior, Luiz Bezerra de,Moura, Ricardo Olímpio de,da Silva, Aline Caroline,Pereira, Valéria Rêgo Alves,Castro, Maria Carolina Accioly Brelaz de,Lima, Maria do Carmo Alves de
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- Synthesis and antitumor activity of new thiosemicarbazones of 2-acetylimidazo[4,5-b]pyridine
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A number of thiosemicarbazones of 2-acetyl-imidazo[4,5-b]pyridine were prepared in order to investigate their in vitro antineoplastic activities. Three compounds: (i) 2-acetylimidazo[4,5-b]pyridin-4-tert-butyl-3-thiosemicarbazone [(A7), NSC674098], (ii) 2-acetylimidazo[4,5-e]pyridin-4-tert-butyl-3- thiosemicarbazone [(A9), NSC674099], (iii) 2-acetylimidazo[4,5-i] pyridin-4-cyclohexyl-3-thiosemicarbozone [(A11), NSC674101] showed remarkable activity against some of the cell lines tested. The Biological Evaluation Committee of N.C.I, determined that further secondary testing should be carried out (these compounds were tested against prostate cancer).
- Mylonas, Stavros,Mamalis, Athanasios
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- Design, synthesis and anticancer activity of dihydropyrimidinone-semicarbazone hybrids as potential human DNA ligase 1 inhibitors
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A series of new dihydropyrimidinone-semicarbazone hybrids were successfully synthesised by integrating regioselective multicomponent reaction with the pharmacophore hybridization approach. All the synthesised compounds were evaluated for their hLig1 inhibition potency and most of them were found to be good to moderately active. Out of the tested derivatives, compound 6f showed selective anti-proliferative activity against HepG2 cells in a dose-dependent manner with an IC50 value of 10.07 ± 1.2. It also reduced cell survival at ≤20 μM concentration. Further, analysis of treated HepG2 cell lysates by western blot assay showed increased γ-H2AX levels and upregulation of p53, leading to apoptosis. In silico docking results explain the binding modes of compound 6f to the DNA-binding domain of hLig1 enzyme thereby preventing its nick sealing activity. In addition, the favourable pharmacokinetic properties suggest that this new class of hLig1 inhibitors could be promising leads for further drug development.
- Sashidhara, Koneni V.,Singh, L. Ravithej,Shameem, Mohammad,Shakya, Sarika,Kumar, Anoop,Laxman, Tulsankar Sachin,Krishna, Shagun,Siddiqi, Mohammad Imran,Bhatta, Rabi S.,Banerjee, Dibyendu
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- Synthesis and antibacterial activity of novel Schiff bases of thiosemicarbazone derivatives with adamantane moiety
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Increased bacterial resistance to antibiotics is a major threat to human health, and it is particularly important to develop novel antibiotic drugs. Here, we designed a series of Schiff base thiosemicarbazone derivatives containing an adamantane moiety, and carried out the structural characterization of the compounds and in vitro antibacterial activity tests. Compound 7e was as effective as the commonly used antibiotic ampicillin against the Gram-negative bacterium Escherichia coli, and compound 7g had a good inhibitory effect against Gram-positive Bacillus subtilis. These findings provide data for the development of better thiosemicarbazone antibacterial agents.
- Zhu, Jiahui,Teng, Guosheng,Li, Dongfeng,Hou, Ruibin,Xia, Yan
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- Efficient synthesis of 1,3,4-thiadiazoles using hydrogen bond donor (thio)urea derivatives as organocatalysts
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(Chemical Equation Presented) A simple and efficient procedure for the synthesis of 1,3,4-thiadiazoles has been achieved using thiourea as organocatalyst. In this study, the steric and electronic effects using structurally different derivatives of urea and thiourea in different solvents were evaluated. The best yields and the rate of the reactions were obtained using 30 mol % of thiourea as catalyst in acetonitrile at room temperature. The molecular structures of the products were established by 1H and 13C NMR spectral data.
- Rostamizadeh, Shahnaz,Aryan, Reza,Ghaieni, Hamid Reza,Amani, Ali Mohammad
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- CERTAIN NEW 4-(2-((5-(SUBSTITUTEDAMINO)-1,3,4-THIADIAZOLE-2-YL)THIO)ACETYL)BENZENESULPHONEAMIDE DERIVATIVES AND A METHOD FOR THE SYNTHESIS OF SAID DERIVATIVES
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The invention relates to a certain new 4-(2-((5-(substitutedamino)-1,3,4-thiadiazole-2-yl)thio)acetyl)benzenesulphonamide derivatives for use in pharmaceutics, chemical and pharmaceutical industry, and to a method for the synthesis of said derivatives.
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(2022/04/02)
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- Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors
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The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.
- Li, Jia-Qi,Sun, Le-Yun,Jiang, Zhihui,Chen, Cheng,Gao, Han,Chigan, Jia-Zhu,Ding, Huan-Huan,Yang, Ke-Wu
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- Synthesis and Antiproliferative Activity of New Thiosemicarboxamide Derivatives
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To discover new anticancer agents, two series of thiosemicarboxamide derivatives were synthesized and evaluated for their antiproliferative activity against human cancer cells in vitro. Most target compounds (especially 3f, 3g, and 3h) exhibit potent antiproliferative activity against HeLa cells. Importantly, compound 3h, bearing a 4-methylphenyl substituent at N position of thiourea moiety, has significant and broad-spectrum inhibitory activities against cancer cells (HepG2, HeLa, MDA-MB231, A875, and H460 cells) with low IC50 values (5.0 μM) and shows low toxicity to normal LO2 and MRC-5 cells. Further studies show that compound 3h exerts high inhibitory activity in cancer cells by inducing the G2/M-phase arrest of cancer cells. Collectively, this study presents compound 3h as a new entity for the development of cell cycle arrest inducers for the treatment of cancer.
- Chen, Jun,Fang, Meijuan,Guo, Yafei,Hu, Hongyu,Hu, Sangsang,Sun, Ke,Wu, Jun,Xue, Yuhua
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- Synthesis, characterization, antibacterial, antifungal and antimalarial study of mixed ligand metal complexes derived from azo quinoline with thiosemicarbazone
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Mixed ligand metal complexes of azo quinoline and thiosemicarbazone with Mn(II), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) metal ions were synthesized. The structure and possible geometry of all the metal(II) complexes were analyzed and supported by IR, m
- Borhade,Tryambake
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p. 885 - 891
(2021/04/09)
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- Preparation and application of thiosemicarbazone compound
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The invention discloses a thiosemicarbazone compound, and biological activity analysis is carried out on the thiosemicarbazone compound. The invention also discloses application of the thiosemicarbazone compound in preparation of antibacterial drugs. According to the invention, important intermediates 6a-6h are synthesized from hydrazine hydrate and react with adamantane benzaldehyde respectivelyto synthesize eight adamantane aromatic aldehyde thiosemicarbazone compounds, the structures of the compounds can be confirmed by infrared, nuclear magnetic hydrogen spectrum, carbon spectrum and massspectrum methods, and the antibacterial activity of the compounds is tested in vitro. The result shows that the compound has a good antibacterial effect on escherichia coli and bacillus subtilis.
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Paragraph 0010; 0014; 0015
(2021/02/20)
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- Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety
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A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.
- Qin, Junhu,Zhu, Mei,Zhu, Hongmei,Zhang, Liqiong,Fu, Yihong,Liu, Jiamin,Wang, Zhenchao,OuYang, Guiping
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p. 592 - 599
(2020/03/16)
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- Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents
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Cancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities, including anticancer activities. The aim of this study was to determine the capacity of newly synthesized 1,3,4-thiadiazole compounds as chemotherapeutic agents. The structures of the obtained compounds were elucidated using 1H-NMR, 13C-NMR and mass spectrometry. Although the thiadiazole derivatives did not prove to be significantly cytotoxic to the tumour tissue cultures, compound 4i showed activity against the C6 rat brain cancer cell line (IC50 0.097 mM) at the tested concentrations.
- ?evik, Ulviye Acar,Osmaniye, Derya,Levent, Serkan,Sa?lik, Begüm Nurpelin,?avu?o?lu, Betül Kaya,?zkay, Yusuf,Kaplancikl, Zafer Aslm
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- Synthesis of novel quinoline-thiosemicarbazide hybrids and evaluation of their biological activities, molecular docking, molecular dynamics, pharmacophore model studies, and ADME-Tox properties
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In the present study, a novel series of N-((substituted)carbamothioyl)-2,4-dimethylquinoline-3-carboxamide (7a-7s) was synthesized by microwave-assisted method. Structure of these derivatives was examined by spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR, and ESI-MS. Further, the novel synthesized compounds were evaluated for their in-vitro biological activities against antibacterial, antifungal, antimalarial, and antituberculosis activity as well as for in-silico study. The antimalarial results demonstrated that compounds 7c and 7q (0.02 μg/mL) have notable potency against Plasmodium falciparum compared with chloroquine (0.02 μg/mL); compounds 7l (0.10 μg/mL), 7e, 7s (0.19 μg/mL), 7b, 7p (0.15 μg/mL), 7a, 7f, and 7f (0.25 μg/mL) also exhibited good activity against P. falciparum compared with quinine (0.26 μg/mL) as standard drug. Docking was performed on PFDHFR-TS, given the effect of compounds against the P. falciparum strain was excellent in comparison with standard drug. Molecular docking suggested that compounds 7b, 7i and 7c, 7e, and 7l closely bind with the active site of protein 3JSU and 4DP3, respectively, and compared with biological activity. We have also carried out molecular dynamics simulation on the best dock compound 7e complex with PDB: 3JSU to check the stability of docked complex and their molecular interaction. The calculated ADME-Tox descriptors for the synthesized compounds validated good pharmacokinetics properties, suggesting that these compounds could be used as hit for the development of the new active agents.
- Darji, Drashti G.,Patel, Dhaval B.,Patel, Hitesh D.,Patel, Krupa R.,Rajani, Dhanji P.,Rajani, Smita D.
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- Isatin based thiosemicarbazide derivatives as potential inhibitor of α-glucosidase, synthesis and their molecular docking study
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A new series of isatin based thiosemicarbazide derivatives 1–15 were synthesized and characterized by 1H NMR, 13C NMR and HR-EIMS. The synthetic derivatives were evaluated for α-glucosidase inhibitory potential. All compounds showed
- Hayat, Shawkat,Iqbal, Naveed,Khan, Khalid Mohammed,Nawaz, Muhammad,Qureshi, Faiza,Rab, Abdur,Rahim, Fazal,Shah, Syed Adnan Ali,Taha, Muhammad,Uddin, Imad,Uddin, Nizam,Wadood, Abdul,Zaman, Khalid
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- Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1H-indole-2,3-dione 3-thiosemicarbazones
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In this work, novel 5-fluoro-1-methyl/ethyl-1H-indole-2,3-dione 3-[4-(substituted phenyl)-thiosemicarbazones] 6a-n and 7a-n were synthesized. The antiviral effects of the compounds were tested against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV in HEL cell cultures using acyclovir and ganciclovir as standards, and Coxsackie B4 virus in Vero cell cultures using ribavirin and mycophenolic acid as standards. R2 ethyl substituted 7 derivatives were found effective against viruses tested. R1 4-CF3 substituted 7d, R1 4-OCH3 substituted 7 g and R1 3-Cl substituted 7 l showed activity against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV. Whereas only R1 4-Br substituted 7n has selective activity against coxsackie B4 virus. Molecular modeling studies of 7d and 7l were performed to determine binding side on HSV-1 glycoprotein B and D, HSV-2 glycoprotein B structures.
- ?zbil, Mehmet,Duran, Gizem Nur,Karal?, Nilgün,Sevin?li, Zekiye ?eyma
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- Novel 1,3,4-thiadiazole compounds as potential MAO-A inhibitors-design, synthesis, biological evaluation and molecular modelling
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Monoamine oxidases (MAOs) are important drug targets for the management of neurological disorders. Herein, a series of new 1,3,4-thiadiazole derivatives bearing various alkyl/arylamine moieties as MAO inhibitors were designed and synthesized. All of the compounds were more selective against hMAO-A than hMAO-B. The half maximal inhibitory concentration (IC50) values of most of the compounds were lower than that of the common drug moclobemide (IC50 = 4.664 μM) and compound 6b was proven to be the most active compound (IC50 = 0.060 μM). Moreover, it was seen that compound 6b showed a similar inhibition profile to that of clorgyline (IC50 = 0.048 μM). The inhibition profile was found to be reversible and competitive for compound 6b with MAO-A selectivity. Molecular modelling studies aided in the understanding of the interaction modes between compound 6b and MAO-A. Furthermore, this compound was predicted to have a good pharmacokinetic profile and high BBB penetration. Therefore, such compounds are of interest towards developing new MAO inhibitors.
- Kaplancikli, Zafer Asim,Levent, Serkan,Osmaniye, Derya,?zkay, Yusuf,Acar ?evik, Ulviye,Kaya ?avu?o?lu, Betül,Sa?lik, Begüm Nurpelin
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p. 1063 - 1074
(2020/10/06)
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- Functionalized Oxoindolin Hydrazine Carbothioamide Derivatives as Highly Potent Inhibitors of Nucleoside Triphosphate Diphosphohydrolases
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Ectonucleoside triphosphate diphosphohydrolases (NTPDases) are ectoenzymes that play an important role in the hydrolysis of nucleoside triphosphate and diphosphate to nucleoside monophosphate. NTPDase1, -2, -3 and -8 are the membrane bound members of this enzyme family that are responsible for regulating the levels of nucleotides in extracellular environment. However, the pathophysiological functions of these enzymes are not fully understood due to lack of potent and selective NTPDase inhibitors. Herein, a series of oxoindolin hydrazine carbothioamide derivatives is synthesized and screened for NTPDase inhibitory activity. Four compounds were identified as selective inhibitors of h-NTPDase1 having IC50 values in lower micromolar range, these include compounds 8b (IC50 = 0.29 ± 0.02 μM), 8e (IC50 = 0.15 ± 0.009 μM), 8f (IC50 = 0.24 ± 0.01 μM) and 8l (IC50 = 0.30 ± 0.03 μM). Similarly, compound 8k (IC50 = 0.16 ± 0.01 μM) was found to be a selective h-NTPDase2 inhibitor. In case of h-NTPDase3, most potent inhibitors were compounds 8c (IC50 = 0.19 ± 0.02 μM) and 8m (IC50 = 0.38 ± 0.03 μM). Since NTPDase3 has been reported to be associated with the regulation of insulin secretion, we evaluated our synthesized NTPDase3 inhibitors for their ability to stimulate insulin secretion in isolated mice islets. Promising results were obtained showing that compound 8m potently stimulated insulin secretion without affecting the NTPDase3 gene expression. Molecular docking studies of the most potent compounds were also carried out to rationalize binding site interactions. Hence, these compounds are useful tools to study the role of NTPDase3 in insulin secretion.
- Afzal, Saira,Hameed, Abdul,Iqbal, Jamshed,Pelletier, Julie,Sévigny, Jean,al-Rashida, Mariya
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- Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents
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A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity against five pathogenic strains. In comparison with precursor selenochroman-4-ones, the hybrid molecules in this study showed significant improvement in antifungal activities. Notably, compound B8 showed significant antifungal activity against other strains excluding Aspergillus fumigatus (0.25 μg/mL on Candida albicans, 2 μg/mL on Cryptococcus neoformans, 8 μg/mL on Candida zeylanoides and 2 μg/mL on fluconazole-sensitive strains of Candida albicans). Moreover, compounds B8, B9 and C2 also displayed most potent activities against four fluconazole-resistance strains. Especially the MIC values of the hybrid molecule B8 against fluconazole-resistant strains were in the range of 0.5–2 μg/mL. Therefore, the molecular hybridization approach in this study provided new ideas for the development of antifungal drug.
- Xu, Hang,Su, Xin,Liu, Xiao-qian,Zhang, Kai-peng,Hou, Zhuang,Guo, Chun
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- Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives
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Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630?μM, comparable to the standard ascorbic acid (0.655?μM).
- Bakherad, Zohreh,Safavi, Maliheh,Fassihi, Afshin,Sadeghi-Aliabadi, Hojjat,Bakherad, Mohammad,Rastegar, Hossein,Ghasemi, Jahan B.,Sepehri, Saghi,Saghaie, Lotfollah,Mahdavi, Mohammad
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p. 2827 - 2854
(2019/03/13)
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- Synthesis of novel triazinoindole-based thiourea hybrid: A study on α-glucosidase inhibitors and their molecular docking
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A new class of triazinoindole-bearing thiosemicarbazides (1-25) was synthesized and evaluated for α-glucosidase inhibitory potential. All synthesized analogs exhibited excellent inhibitory potential, with IC50 values ranging from 1.30 ± 0.01 to 35.80 ± 0.80 μM when compared to standard acarbose (an IC50 value of 38.60 ± 0.20 μM). Among the series, analogs 1 and 23 were found to be the most potent, with IC50 values of 1.30 ± 0.05 and 1.30 ± 0.01 μM, respectively. The structure- activity relationship (SAR) was mainly based upon bringing about different substituents on the phenyl rings. To confirm the binding interactions, a molecular docking study was performed.
- Taha, Muhammad,Alshamrani, Foziah J.,Rahim, Fazal,Hayat, Shawkat,Ullah, Hayat,Zaman, Khalid,Imran, Syahrul,Khan, Khalid Mohammed,Naz, Farzana
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- Containing trifluoromethyl and piperazine triazole Mannich alkali compound and its preparation and use
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The invention belongs to the field of agricultural bactericides and herbicides, and particularly discloses triazole Mannich base compounds containing trifluoromethyl and piperazine, as well as preparation methods and application of the triazole Mannich ba
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Paragraph 0024-0028
(2019/03/21)
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- Thiazolyl-thiadiazines as Beta Site Amyloid Precursor Protein Cleaving Enzyme-1 (BACE-1) Inhibitors and Anti-inflammatory Agents: Multitarget-Directed Ligands for the Efficient Management of Alzheimer's Disease
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Alzheimer's disease (AD) is associated with multiple neuropathological events including β-site amyloid precursor protein cleaving enzyme-1 (BACE-1) inhibition and neuronal inflammation, ensuing degeneracy, and death to neuronal cells. Targeting such a complex disease via a single target directed treatment was found to be inefficacious. Hence, with an intention to incorporate multiple therapeutic effects within a single molecule, multitarget-directed ligands (MTDLs) have been evolved. Herein, for the first time, we report the discovery of novel thiazolyl-thiadiazines that can serve as MTDLs as evident from the in vitro and in vivo studies. These MTDLs exhibited BACE-1 inhibition down to micromolar range, and results from the in vivo studies demonstrated efficient anti-inflammatory activity with inherent gastrointestinal safety. Moreover, compound 6d unveiled noteworthy antioxidant, antiamyloid, neuroprotective, and antiamnesic properties. Overall, results of the present study manifest the potential outcome of thiazolyl-thiadiazines for AD treatment.
- Sagar, Sneha R.,Singh, Devendra Pratap,Panchal, Nirupa B.,Das, Rajesh D.,Pandya, Dhaivat H.,Sudarsanam, Vasudevan,Nivsarkar, Manish,Vasu, Kamala K.
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p. 1663 - 1679
(2018/05/14)
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- Synthetic thiosemicarbazones as a new class of Mycobacterium tuberculosis protein tyrosine phosphatase A inhibitors
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Mycobacterium tuberculosis secretes two protein tyrosine phosphatases as virulence factors, PtpA and PtpB. Inhibition studies of these enzymes have shown significant attenuation of the M. tuberculosis growth in vivo. As PtpA mediates many effects on the r
- Sens, Larissa,de Souza, Ana Caroline Arruda,Pacheco, Lucas Antonio,Menegatti, Angela Camila Orbem,Mori, Mattia,Mascarello, Alessandra,Nunes, Ricardo José,Terenzi, Hernán
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p. 5742 - 5750
(2018/11/03)
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- Synthesis of thiazol, thiazinan, thiadiazin, thiazolidin, triazine, thioxo-pyrimidin and thioxo-imidazolidine by inter-intra molecular cyclization
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Syntheses of five and six membered heterocyclic derivatives by the reaction of disubstituted thiocarbamides with interintramolecular cyclizations in catalyst free condition have been reported. The simple product isolation without column, good yields under mild condition, and applicable green matrix are the advantages of present protocol.
- Zade, Mangesh N.,Katiya, Manish M.,Deotale, Vinod D.,Sontakke, Madhuri M.,Dhonde, Madhukar G.,Berad, Baliram N.
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p. 1493 - 1500
(2019/05/21)
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- Design, synthesis and biological evaluation of thiosemicarbazones, hydrazinobenzothiazoles and arylhydrazones as anticancer agents with a potential to overcome multidrug resistance
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There is a constant need for new therapies against multidrug resistant (MDR) cancer. An attractive strategy is to develop chelators that display significant antitumor activity in multidrug resistant cancer cell lines overexpressing the drug efflux pump P-glycoprotein. In this study we used a panel of sensitive and MDR cancer cell lines to evaluate the toxicity of picolinylidene and salicylidene thiosemicarbazone, arylhydrazone, as well as picolinylidene and salicylidene hydrazino-benzothiazole derivatives. Our results confirm the collateral sensitivity of MDR cells to isatin-β-thiosemicarbazones, and identify several chelator scaffolds with a potential to overcome multidrug resistance. Analysis of structure-activity-relationships within the investigated compound library indicates that NNS and NNN donor chelators show superior toxicity as compared to ONS derivatives regardless of the resistance status of the cells.
- Pape, Veronika F.S.,Tóth, Szilárd,Füredi, András,Szebényi, Kornélia,Lovrics, Anna,Szabó, Pál,Wiese, Michael,Szakács, Gergely
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p. 335 - 354
(2016/05/19)
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- Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities
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A series of thiophene-2-thiosemicarbazones derivatives (5-14) was synthesized, characterized and evaluated for their antitumor activity. They were tested in vitro against human tumor cell lines through the colorimetric method. The results revealed that compounds 7 and 9 were the most effective in inhibiting 50% of the cell growth after 48 h of treatment. As compound 7 showed a potent antiproliferative profile, it has been chosen for further studies in 786-0 cell line by flow cytometry. Treatments with compound 7 (50 μM) induced early phosphatidylserine exposure after 18 h of exposure and this process progressed phosphatidylserine exposure with loss of cell membrane integrity after 24 h of treatment, suggesting a time-dependent cell death process. Regarding the cell cycle profile, no changes were observed after treatment with compound 7 (25 μM), suggesting a mechanism of cell death independent on the cell cycle. The in vivo studies show that compound 7 possess low acute toxicity, being the doses of 30-300 mgKg-1 chosen for studies in Ehrlich solid tumor model in mice. All doses were able to inhibit tumor development being the lowest one the most effective. Our findings highlight thiophene-2-thiosemicarbazones as a promising class of compounds for further studies concerning new anticancer therapies.
- De Oliveira, Jamerson Ferreira,Da Silva, Anekécia Lauro,Vendramini-Costa, Débora Barbosa,Da Cruz Amorim, Cezar Augusto,Campos, Júlia Furtado,Ribeiro, Amélia Galdino,De Moura, Ricardo Olímpio,Neves, Jorge Luiz,Ruiz, Ana Lúcia Tasca Gois,De Carvalho, Jo?o Ernesto,Alves De Lima, Maria Do Carmo
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p. 148 - 156
(2015/10/29)
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- Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties
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With the aim to explore the interest of the thiosemicarbazide scaffold for the inhibition of the indoleamine 2,3-dioxygenase (IDO), a promising therapeutic target for anticancer immunotherapy, a series of 32 phenylthiosemicarbazide derivatives was prepared and their IDO inhibition evaluated. Our study demonstrated that among these derivatives, compound 14 characterized with a 4-cyanophenyl group on the thiosemicarbazide was the more potent IDO inhibitor in this series being endowed with an IC50 of 1.2 μM. The SAR depicted showed that substitution in the 3- and 4-position relative to the phenylthiosemicarbazide are very promising whereas substitution in the 2-position always leads to less potent or inactive derivatives. In fact the study highlighted a novel interesting scaffold for IDO inhibition for further development.
- Serra, Silvia,Moineaux, Laurence,Vancraeynest, Christelle,Masereel, Bernard,Wouters, Johan,Pochet, Lionel,Frédérick, Rapha?l
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- Synthesis and fungicidal activities of some 2-substituted arylamino-5-(2′-furyl)-1,3,4-thiadiazolo[3,2-c]thiazoles and 5-substituted aryl-2-substituted arylamino-1,3,4-thiadiazolo[3,2-c]thiazoles
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Several 2-substituted arylamino-5-(2′-furyl)-1,3,4-thiadiazolo[3,2-c] thiazoles have been synthesised by cyclisation of 3-substituted aryl thiocarbanilido-2-(2′-furyl)thiazolidin-4-ones with cone. H 2SO4 with constant stirring in cold and 5-substituted aryl-2-substituted arylamino-1,3,4-thiadiazolo[3,2-c]thiazoles have been synthesised by the cyclisation of 2-substituted aryl-3-substituted arylthiourido-thiazolidin-4-ones with cone. H2SO4 with constant stirring in cold and screened for their antifungal activities against Helminthosporium oryzae and Cephalosporium sacchari.
- Tiwari, Shailendra,Nizamuddin
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p. 679 - 683
(2013/07/26)
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- Augmentation of GABAergic neurotransmission by novel N-(substituted)-2-[4- (substituted)benzylidene]hydrazinecarbothioamides - A potential anticonvulsant approach
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New N-(substituted)-2-[4-(substituted)benzylidene]hydrazinecarbothioamides were designed, synthesized and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity was established in three seizure models i.e. MES, scMET and 6 Hz model. The most active compound was N-(4-methoxyphenyl)-2-[4-(4-methylphenoxy) benzylidene]hydrazinecarbothioamide PT 30 which showed 100% protection in both MES and 6 Hz test. Compound PT 30 showed protection at three different time points in 6 Hz test at a dose of 100 mg/kg. Compound 2-[4-(4-Chlorophenoxy)benzylidene]-N-cyclohexylhydrazine carbothioamide PT 4 was also found to be active in both MES and 6 Hz test. Titled compounds exhibited good binding properties with epilepsy molecular targets GABA (A) delta and GABA (A) alpha-1 receptors, in LGA based flexible docking studies. Compounds PT 30 and PT 4 were found to elevate γ-aminobutyric acid (GABA) levels in the midbrain and medulla oblongata regions of rat brain. A computational study was carried out for calculation of pharmacophore pattern and prediction of pharmacokinetic properties.
- Tripathi, Laxmi,Kumar, Praveen
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p. 477 - 487
(2013/07/19)
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- Synthesis and biological activities of novel artemisinin derivatives as cysteine protease falcipain-2 inhibitors
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A series of novel artemisinin derivatives were synthesized from artemisinin and different anilines. All compounds were obtained as β-isomers. The target compounds were evaluated for inhibition activity against Plasmodium falciparum falcipain-2 in vitro, and most of them exhibited potent inhibition in the low micromolar range and proved to be new types of falcipain-2 inhibitors.
- Liu, Yang,Lu, Wei-Qiang,Cui, Kun-Qiang,Luo, Wei,Wang, Jian,Guo, Chun
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p. 1525 - 1531
(2013/03/14)
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- Synthesis, anticonvulsant and toxicity screening of thiazolyl-thiadiazole derivatives
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Various thiazole-substituted thiadiazole derivatives (7a-t) were designed and synthesized using substituted acetophenones and substituted anilines as starting materials. Thiazole and thiadiazole moieties being anticonvulsants were clubbed together to get the titled compounds and their in vivo anticonvulsant screening were performed by two most adopted seizure models, maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ). Three compounds 7i, 7l and 7n were found to be potent in both the screens with comparable ED50 and better TD50 values than some standard drugs. These compounds were also found to exert lesser toxic effects on liver.
- Siddiqui, Nadeem,Ahsan, Waquar
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experimental part
p. 261 - 268
(2012/02/13)
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- Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors
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A series of isatin-β-thiosemicarbazones have been designed and evaluated for antiviral activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in a plaque reduction assay. Their cytotoxicity was examined using human rhabdomyosarcoma cells (RD cells). Several derivatives of isatin-β-thiosemicarbazone exhibited significant and selective antiviral activity with low cytotoxicity. It was found that the thiourea group at thiosemicarbazone and the NH functionality at isatin were essential for their antiherpetic activity. The synthesis and structure-activity relationship studies are presented.
- Kang, Iou-Jiun,Wang, Li-Wen,Hsu, Tsu-An,Yueh, Andrew,Lee, Chung-Chi,Lee, Yen-Chun,Lee, Ching-Yin,Chao, Yu-Sheng,Shih, Shin-Ru,Chern, Jyh-Haur
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scheme or table
p. 1948 - 1952
(2011/05/04)
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- Novel bis(thiosemicarbazones) of the 3,5-diacetyl-1,2,4-triazol series and their platinum(ii) complexes: chemistry, antiproliferative activity and preliminary nephrotoxicity studies
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The preparation and characterization of three novel 4N- monosubstituted bis(thiosemicarbazone) ligands of 3,5-diacetyl-1,2,4-triazol series and their dinuclear platinum complexes are described. The crystal and molecular structure of the [Pt(μ-H
- Matesanz, Ana I.,Hernandez, Carolina,Rodriguez, Ana,Souza, Pilar
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experimental part
p. 5738 - 5745
(2011/08/04)
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- Synthesis and anticonvulsant evaluation of some novel (thio)semicarbazone derivatives of arylalkylimidazole
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A number of novel 2-(1H-imidazole-1-yl)-1-aryl-substituted ethane-1-one N-substituted phenyl(thio)semicarbazones (1-14) were synthesized to test for their anticonvulsant activity against the two seizure models, maximal electroshock (MES) and subcutaneous
- Calis, Uensal,Septioglu, Ebubekir,Aytemir, Mutlu Dilsiz
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experimental part
p. 327 - 334
(2012/02/02)
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- Microwave-assisted synthesis and antibacterial activity of novel chenodeoxycholic acid thiosemicarbazone derivatives
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A rapid and efficient method for the synthesis of novel chenodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave irradiation is reported. Ten novel compounds have been synthesised in good yields. Their structures were elucidated by 1H NMR, IR, ESI-MS spectra and elemental analysis. Preliminary results showed that some of these compounds possess inhibitory effects against S. typhimurium and E. coli.
- Qiu, Liying,Shi, Zhichuan,Mei, Qinggang,Zhao, Zhigang
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experimental part
p. 456 - 459
(2011/11/06)
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- Synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave
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An efficient and simple method for synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave has been developed. Its main advantages are short reaction times, good conversions and the environmentally friendly nature of the process. The preliminary results indicate that some of these compounds possess inhibitory effects against E. coli.
- Shi, Zhi Chuan,Zhao, Zhi Gang,Liu, Xing Li,Chen, Yu
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experimental part
p. 405 - 408
(2012/01/05)
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- 3-(1,3,4-Thiadiazole-2-yl)quinoline derivatives: Synthesis, characterization and anti-microbial activity
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A new series of thiadiazoles and intermediate thiosemicarbazones were synthesized from the chloroquinone molecule, with an aim to explore their effect on in vitro growth of microorganisms causing microbial infection. The chemical structures of the compound were elucidated by elemental analysis, FTIR, 1H and 13C NMR and ESI-MS spectral data. In vitro anti-microbial activity was performed against Staphylococcusaureus, Streptococcuspyogenes, Salmonellatyphimurium, and Escherichiacoli. The MIC was detected using the double dilution method. The results were compared by calculating percent inhibit area/μg of the compounds and the standard "amoxicillin". The selected compounds were tested for cytotoxic results using MTT assay H9c2 cardiac myoblasts cell line and the results showed that all the compounds offered remarkable >80% viability to a concentration of 200 μg/mL.
- Bhat, Abdul R.,Tazeem,Azam, Amir,Choi, Inho,Athar, Fareeda
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p. 3158 - 3166
(2011/06/26)
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- Triazole incorporated thiazoles as a new class of anticonvulsants: Design, synthesis and in vivo screening
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Various 3-[4-(substituted phenyl)-1,3-thiazol-2-ylamino]-4-(substituted phenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thiones (7a-t) were designed keeping in view the structural requirements suggested in the pharmacophore model for anticonvulsant activity. Thiazole and triazole moieties being anticonvulsants were clubbed together to get the titled compounds and their in vivo anticonvulsant screening were performed by two most adopted seizure models, maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (scPTZ). Two compounds 7d and 7f showed significant anticonvulsant activity in both the screens with ED50 values 23.9?mg/kg and 13.4?mg/kg respectively in MES screen and 178.6?mg/kg and 81.6?mg/kg respectively in scPTZ test. They displayed a wide margin of safety with Protective index (PI), median hypnotic dose (HD50) and median lethal dose (LD50) much higher than the standard drugs.
- Siddiqui, Nadeem,Ahsan, Waquar
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experimental part
p. 1536 - 1543
(2010/06/16)
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- A series of α-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIα catalytic activity
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A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase IIα catalytic inhibitor. Its inhibition on topoisomerase IIα was due to direct interaction with the ATPase domain of topoisomerase IIα which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase IIα.
- Huang, He,Chen, Qin,Ku, Xin,Meng, Linghua,Lin, Liping,Wang, Xiang,Zhu, Caihua,Wang, Yi,Chen, Zhi,Li, Ming,Jiang, Hualiang,Chen, Kaixian,Ding, Jian,Liu, Hong
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experimental part
p. 3048 - 3064
(2010/09/05)
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- Microwave-assisted synthesis of new steroidal thiosemicarbazones derived from methyl 3-oxocholanate under solvent-free conditions
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A series of novel steroidal thiosemicarbazones derived from methyl 3-oxocholanate were synthesised in good yields via microwave irradiation under solvent-free conditions. The structures of the compounds were confirmed by spectroscopic data. Compared to the conventional method, microwave irradiation was a fast and simple method. These compounds were tested for antibacterial activity against S. aureus, S. pyogenes, and E. coli bacteria.
- Zhao, Zhigang,Liu, Xingli,Liu, Lingling,Li, Guohua
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experimental part
p. 455 - 458
(2010/12/24)
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- Synthesis of novel alkoxycarbonyl thiosemicarbazide molecular tweezers derived from deoxycholic acid under microwave irradiation
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A series of novel 12α-alkoxycarbonyl thiosemicarbazide molecular tweezers based on 3α-(1-naphthoyl) deoxycholic acid methyl ester were synthesised under microwave irradiation. Their structures were characterised by 1H NMR, IR, MS spectra and elemental analysis. Their chiral recognition properties for the methyl esters of amino acids were investigated. The preliminary results showed that these molecular tweezers have good enantioselective recognition for D/L-amino acid methyl esters.
- Chen, Yu,Zhao, Zhi Gang,Liu, Xing Li,Shi, Zhi Chuan
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scheme or table
p. 416 - 420
(2010/12/19)
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- Synthesis, characterization and spectral evaluation of some new substituted thiosemicarbazides and thiosemicarbazones
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A new series of substituted thiosemicarbazides and substituted thiosemicarbazones containing different functional groups, thiosemicarbazones have been synthesized by the condensation reaction between newly synthesized substituted thiosemicarbazides with s
- Pareek, Alok K.,Joseph,Seth, Daya S.
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experimental part
p. 1549 - 1552
(2011/10/12)
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- N-(Acetamido)thiourea based simple neutral hydrogen-bonding receptors for anions
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N-(Acetamido)-N′-phenylthioureas (4-6) were found to be efficient anion receptors with higher anion affinity than their N-benzamido-N′- phenylthiourea counterparts (1 and 2). The N′-phenylthiourea moiety in 4-6 was shown to be the chromophore with an absorption maximum at ca. 270 nm. It was found that, in the presence of anions, the absorption at ca. 270 nm of 4-6 (except 5f) in acetonitrile (MeCN) was blue shifted and enhanced while a red-shifted shoulder appeared at ca. 295 nm, together with an isosbestic point at ca. 240 nm. The 1:1 anion binding constants of 4-6, for example at 10 6-107 M-1 order of magnitude for AcO - in MeCN, were found to be higher than those of 1 and 2, although the acidity of the thioureido -NH protons in 4-6 is lower than that in 1 and 2. 1H NMR data indicates that the N-N single bond in 4-6 is twisted but less than that in 1 and 2. A conformation change at the N-N single bond of 4-6 was suggested to occur upon anion binding which leads to a planar hydrogen-bonding network in the anion binding complex in which a charge transfer takes place with the N-acyl moiety being the electron acceptor. Variations in the CD signals of a proline derivative 6 bearing a chiral center in the N-amido moiety provide direct evidence for this conformation change upon its binding with anions in MeCN. The amplified effect of substituent X at the N′-phenyl ring of 5 on the anion binding constant supports the conclusion of anion-binding switched charge transfer in the anion binding complex. 1H NMR and absorption titrations for 5 indicated that the anion-receptor interaction was of a hydrogen-bonding nature until the N′-phenyl substituent X is as electron-withdrawing as m-CF3 (5e). With X being the more electron-withdrawing p-NO2 (5f), deprotonation of the thioureido -NH occurs in the presence of anion. Results reported here confirm that N-amidothioureas derived from both N-aliphatic and N-aromatic amides can in general be a family of efficient hydrogen-bonding receptors, with the aliphatic N-amido derivatives being more efficient. This provides a wider structural diversity for designing thiourea-based functional molecules such as anion receptors and organocatalysts. Preliminary experiments confirm that 6 could catalyse efficiently the reduction of nitrostyrene in CH2Cl2 and MeCN.
- Liu, Wen-Xia,Yang, Rui,Li, Ai-Fang,Li, Zhao,Gao, Yu-Feng,Luo, Xing-Xing,Ruan, Yi-Bin,Jiang, Yun-Bao
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experimental part
p. 4021 - 4028
(2009/12/06)
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- 5-Nitrofuran-2-yl derivatives: Synthesis and inhibitory activities against growing and dormant mycobacterium species
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Eighteen 5-nitrofuran-2-yl derivatives were prepared by reacting 5-nitro-2-furfural with various (sub)phenyl/pyridyl thiosemicarbazide using microwave irradiation. The compounds were tested for their in vitro activity against tubercular and various non-tubercular mycobacterium species in log-phase and 6-week-starved cultures. Compound N-(3,5-dibromopyridin-2-yl)-2-((5-nitrofuran-2-yl)methylene)hydrazinecarbothioamide (4r) was found to be the most potent compound (MIC: 0.22 μM) and was 3 times more active than standard isoniazid (INH) and equally active as rifampicin (RIF) in log-phase culture of Mycobacterium tuberculosis H37Rv. In starved M. tuberculosis H37Rv, 4r inhibited with MIC of 13.9 μM and was found to be 50 times more active than INH and slightly more active than RIF.
- Sriram, Dharmarajan,Yogeeswari, Perumal,Dhakla, Prathiba,Senthilkumar, Palaniappan,Banerjee, Debjani,Manjashetty, Thimmappa H.
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body text
p. 1152 - 1154
(2009/08/07)
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- Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines
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Thirty new pyrazoline derivatives were synthesized by cyclization of Mannich bases with thiosemicarbazides being substituted by different cyclic and aromatic amines. The structures of the compounds were elucidated by elemental analyses, UV, IR, 1H and 13C NMR and ESI-MS spectral data. The in vitro antiamoebic activity was evaluated against Entamoeba histolytica in comparison with metronidazole used as reference substance. Out of the 30 compounds screened for antiamoebic activity, 10 (5, 6, 15, 18, 25-30) were found to be better inhibitors of E. histolytica since they showed lesser IC50 values than metronidazole. The preliminary results indicated that the presence of 3-chloro or 3-bromo substituent on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. The study suggests that the preliminary activity of these compounds may further be explored for the development of new targets for amoebiasis.
- Abid, Mohammad,Bhat, Abdul Roouf,Athar, Fareeda,Azam, Amir
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scheme or table
p. 417 - 425
(2009/04/18)
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