- Inhibition kinetics of chlorobenzaldehyde thiosemicarbazones on mushroom tyrosinase
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2-Chlorobenzaldehyde thiosemicarbazone (2-Cl-BT) and 4-chlorobenzaldehyde thiosemicarbazone (4-Cl-BT) were synthesized, and their inhibitory kinetics on the activity of mushroom tyrosinase were investigated. Results showed that these compounds exhibited s
- Li, Zhi-Cong,Chen, Liang-Hua,Yu, Xiao-Jie,Hu, Yong-Hua,Song, Kang-Kang,Zhou, Xing-Wang,Chen, Qing-Xi
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- Effect of organic solvents on solvatochromic, fluorescence, and electrochemical properties of synthesized thiazolylcoumarin derivatives
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In this present investigation, thiazolylcoumarin derivatives (5a–5k) were synthesized from thiosemicarbazide, ethyl acetoacetate, and naphthaldehyde through a multistep route. The formation of thiazolylcoumarin derivatives with bioactive scaffolds was con
- Bahadur, Ali,Iqbal, Shahid,Ujan, Rabail,Channar, Pervaiz Ali,AL-Anazy, Murefah Mana,Saeed, Aamer,Mahmood, Qaiser,Shoaib, Muhammad,Shah, Mazloom,Arshad, Ifzan,Shabir, Ghulam,Saifullah, Muhammad,Liu, Guocong,Qayyum, Muhammad Abdul
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p. 1189 - 1197
(2021/04/16)
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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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- Assessment of Thiosemicarbazone-Containing Compounds as Potential Antileukemia Agents against P-gp Overexpressing Drug Resistant K562/A02 Cells
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P-Glycoprotein (P-gp) overexpression is considered to be the leading cause of multidrug resistance (MDR) and failure of chemotherapy for leukemia. In this study, seventeen thiosemicarbazone-containing compounds were prepared and evaluated as potential ant
- Gu, Xiaoke,Guan, Mingyu,Jiang, Chunyu,Song, Qinghua,Li, Xin,Sun, Nan,Chen, Jing,Qiu, Jingying
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- Thiosemicarbazones exhibit inhibitory efficacy against New Delhi metallo-β-lactamase-1 (NDM-1)
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The superbug infection caused by metallo-β-lactamases (MβLs) carrying drug-resistant bacteria, specifically, New Delhi metallo-β-lactamase (NDM-1) has become an emerging threat. In an effort to develop novel inhibitors of NDM-1, thirteen thiosemicarbazones (1a-1m) were synthesized and assayed. The obtained molecules specifically inhibited NDM-1, with an IC50 in the range of 0.88–20.2 μM, and 1a and 1f were found to be the potent inhibitors (IC50 = 1.79 and 0.88 μM) using cefazolin as substrate. ITC and kinetic assays indicated that 1a irreversibly and non-competitively inhibited NDM-1 in vitro. Importantly, MIC assays revealed that these molecules by themselves can sterilize NDM-producing clinical isolates EC01 and EC08, exhibited 78-312-fold stronger activities than the cefazolin. MIC assays suggest that 1a (16 μg ml?1) has synergistic antimicrobial effect with ampicillin, cefazolin and meropenem on E. coli producing NDM-1, resulting in MICs of 4-32-, 4-32-, and 4-8-fold decrease, respectively. These studies indicate that the thiosemicarbazide is a valuable scaffold for the development of inhibitors of NDM-1 and NDM-1 carrying drug-resistant bacteria.
- Ge, Ying,Kang, Peng-Wei,Li, Jia-Qi,Gao, Han,Zhai, Le,Sun, Le-Yun,Chen, Cheng,Yang, Ke-Wu
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p. 574 - 579
(2021/07/17)
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- Intrabacterial Metabolism Obscures the Successful Prediction of an InhA Inhibitor of Mycobacterium tuberculosis
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Tuberculosis, caused by Mycobacterium tuberculosis (M. tuberculosis), kills 1.6 million people annually. To bridge the gap between structure- A nd cell-based drug discovery strategies, we are pioneering a computer-aided discovery paradigm that merges stru
- Wang, Xin,Perryman, Alexander L.,Li, Shao-Gang,Paget, Steve D.,Stratton, Thomas P.,Lemenze, Alex,Olson, Arthur J.,Ekins, Sean,Kumar, Pradeep,Freundlich, Joel S.
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p. 2148 - 2163
(2019/11/19)
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- Synthesis and comparison of antileishmanial and cytotoxic activities of S-(?)-limonene benzaldehyde thiosemicarbazones with their R-(+)-analogues
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In this study, we explore a series of novel potential antiprotozoal S-(?)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(?)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis.
- Almeida Batista, Sabrina A.,Vandresen, Fábio,Falzirolli, Hugo,Britta, Elizandra,de Oliveira, Diogo N.,Catharino, Rodrigo R.,Gon?alves, Mateus A.,Ramalho, Teodorico C.,La Porta, Felipe A.,Nakamura, Celso V.,da Silva, Cleuza C.
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p. 252 - 262
(2018/11/24)
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- Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents
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A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16–25 were synthesized by reacting the correspondin
- Demirci, Asl?,Karayel, Kaan G?k?e,Tatar, Esra,Okullu, Sinem ?KTEM,Unübol, Nihan,Ta?li, Pakize Neslihan,Kocag?z, Zühtü Tan?l,Sahin, Fikrettin,Kü?ükgüzel, Ilkay
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p. 839 - 858
(2018/06/07)
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- Microwave Assisted Synthesis and Biological Activity of Novel Bis{2-[2-(substituted benzylidene)hydrazinyl]thiazole} Derivatives
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Abstract—New 4,4'-(4,6-dimethoxy-1,3-phenylene)bis{2-[2-(substituted benzylidene)hydrazinyl]thiazole} derivatives (5a–5j) have been synthesized from the corresponding 1,1'-(4,6-dimethoxy-1,3-phenylene)bis(2,2- dibromoethanone) and substituted thiosemicarbazones by the conventional method and under microwave irradiation. Structures of the synthesized compounds were characterized by FT-IR, 1H, and 13C NMR and Mass spectra. The products were evaluated for their in vitro antibacterial activity against Gram-positive and Gramnegative stains. Some of the compounds 5b, 5f, 5h demonstrated high activity against B. subtilis (+ve), compound 5c exhibited high activity against E. coli (–ve) and P. aeruginosa (–ve) stains. Among the titled compounds also evaluated for their in vitro antimycobacterial activity, the product 5b demonstrated pronounced antimycobacterial activity against M. bovis stain.
- Kumar Baba,Ashok,Rao, Boddu Ananda,Sarasija, Madderla,Murthy
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p. 580 - 586
(2018/04/24)
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- One PotTwo Step Synthesis of 2-Arylidenehydrazinyl-4-arylthiazole
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An efficient, simple one pot, two step procedure has been developed for the synthesis of 2-arylidenehydrazinyl-4-arylthiazole. The reaction of aromatic aldehyde, thiosemicarbazide and phenacyl bromide gave the desired products in good yield. The first reaction product thiosemicarbazone was obtained on reaction with aromatic aldehyde and thiosemicarbazide; without isolating this directly treated with phenacyl bromide in presence of acidic buffer at room temperature desired product was obtained with simple workup procedure.
- Tatyaram Tryambake, Pravin
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p. 1646 - 1652
(2018/07/10)
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- PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles
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A highly efficient method for the synthesis of thiadiazole derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields. Graphical Abstract: A highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling of thiosemicarbazide has been developed.
- Han, Yingzhi,Sun, Yadong,Abdukader, Ablimit,Liu, Bifu,Wang, Duozhi
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p. 3486 - 3491
(2018/09/27)
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- Cyclization–oxidation of Benzylidenehydrazinecarbothioamides by FeCl3.6H2O or ZnCl2.6H2O Catalysts and Synthesis of New 1,3,4-Thiadiazolo-[3,2- α]Pyrimidines
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We report new method for preparation of 2-amino-5-aryl-1,3,4-thiadiazoles by reaction of arylaldehyde with thiosemicarbazide and in the next step via cyclization of 2-aryl hydrazinecarbothioamide in the presence of ZnCl2.6H2O or FeCl3.6H2O. Also, in this research, new substituted 1,3,4-thiadiazolo-[3,2-α]pyrimidines were synthesized by the reaction of 2-amino-5-aryl-1,3,4-thiadiazoles derivatives with DMAD or DEAD in the presence of K2CO3 under reflux conditions. The FT-IR, 1H-NMR, 13C-NMR, elemental analysis and single- crystal X-ray analysis confirm the structures of the products.
- Darehkordi, Ali,Zarezadeh Abarqouei, Behnam,Rahmani, Fariba
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p. 1872 - 1879
(2017/05/29)
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- Synthesis and antimicrobial evaluation of novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones and their 2-thioxo analogues
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The preparation of some novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones 8(i–xiv) and 3-(arylideneamino)-3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-ones 9(i–xiv) have been reported through one-pot catalyst-free reaction of aldehydes, semicarbazide hydrochloride/thiosemicarbazide with ninhydrin. All the synthesized compounds have been screened for antimicrobial activity and some of them were observed to possess broad spectrum antibacterial potential as well as significant antagonistic potential against fungal pathogens.
- Saini, Yeshwinder,Khajuria, Rajni,Kaur, Ramneet,Kaul, Sanjana,Sharma, Tanwi,Gupta, Suruchi,Gupta, Vivek K.,Kant, Rajni,Kapoor, Kamal K.
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supporting information
p. 1159 - 1168
(2017/06/09)
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- Novel 4-thiazolidinones as non-nucleoside inhibitors of hepatitis C virus NS5B RNA-dependent RNA polymerase
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In continuation of our efforts to develop new derivatives as hepatitis C virus (HCV) NS5B inhibitors, we synthesized novel 5-arylidene-4-thiazolidinones. The novel compounds 29-42, together with their synthetic precursors 22-28, were tested for HCV NS5B inhibitory activity; 12 of these compounds displayed IC50 values between 25.3 and 54.1 μM. Compound 33, an arylidene derivative, was found to be the most active compound in this series with an IC50 value of 25.3 μM. Molecular docking studies were performed on the thumb pocket-II of NS5B to postulate the binding mode for these compounds.
- akir, Gizem,Kücükgüzel, Ilkay,Guhamazumder, Rupa,Tatar, Esra,Manvar, Dinesh,Basu, Amartya,Patel, Bhargav A.,Zia, Javairia,Talele, Tanaji T.,Kaushik-Basu, Neerja
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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, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents
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Since the first histone deacetylase (HDAC) inhibitor (Zolinza, widely known as suberoylanilide hydroxamic acid; SAHA) was approved by the Food and Drug Administration for the treatment of T-cell lymphoma in 2006, the search for newer HDAC inhibitors has attracted a great deal of interest of medicinal chemists worldwide. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. A number of compounds in this series, for example, N1-hydroxy-N8-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5b), N1-hydroxy-N8-(5-(3-chlorophenyl-1,3,4-thiadiazol-2-yl)octandiamide (5c) and N1-hydroxy-N8-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5d), were found to possess potent anticancer cytotoxicity and HDAC inhibition effects. Compounds 5b-d were generally two- to five-fold more potent in terms of cytotoxicity compared to SAHA against five cancer cell lines tested. Docking studies revealed that these hydroxamic acid displayed higher affinities than SAHA toward HDAC8.
- Nam, Nguyen-Hai,Huong, Tran Lan,Dung, Do Thi Mai,Dung, Phan Thi Phuong,Oanh, Dao Thi Kim,Park, Sang Ho,Kim, Kyungrok,Han, Byung Woo,Yun, Jieun,Kang, Jong Soon,Kim, Youngsoo,Han, Sang-Bae
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p. 611 - 618
(2015/02/18)
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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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- 2,5-Disubstituted-1,3,4-oxadiazoles/thiadiazole as surface recognition moiety: Design and synthesis of novel hydroxamic acid based histone deacetylase inhibitors
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The enzymatic inhibition of histone deacetylase activity has come out as a novel and effectual means for the treatment of cancer. Two novel series of 2-[5-(4-substitutedphenyl)-[1,3,4]-oxadiazol/thiadiazol-2-ylamino] -pyrimidine-5-carboxylic acid (tetrahydro-pyran-2-yloxy)-amides were designed and synthesized as novel hydroxamic acid based histone deacetylase inhibitors. The antiproliferative activities of the compounds were investigated in vitro using histone deacetylase inhibitory assay and MTT assay. The synthesized compounds were also tested for antitumor activity against Ehrlich ascites carcinoma cells in Swiss albino mice. The efforts were also made to establish structure-activity relationships among synthesized compounds. The results of the present studying indicates 2,5-disubstituted 1,3,4-oxadiazole/thiadiazole as promising surface recognition moiety for development of newer hydroxamic acid based histone deacetylase inhibitor.
- Rajak, Harish,Agarawal, Avantika,Parmar, Poonam,Thakur, Bhupendra Singh,Veerasamy, Ravichandran,Sharma, Prabodh Chander,Kharya, Murli Dhar
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supporting information; scheme or table
p. 5735 - 5738
(2011/10/09)
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- Synthesis, antibacterial activity and quantum-chemical studies of novel 2-arylidenehydrazinyl-4-arylthiazole analogues
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A new series of 2-arylidenehydrazinyl-4-arylthiazole derivatives (2a-k) was designed and synthesized through a rapid, simple, and efficient methodology in excellent isolated yield. These compounds were screened for in vitro antimicrobial activities against eight bacteria, e.g. Bacillus cereus, Staphylococcus aureus, Bacillus subtilis, Bacillus megaterium, Pseudomonas aeruginosa, Shigella dysenteriae, Salmonella typhi, Escherichia coli, and three fungi e.g. Aspergillus oryzae, Candida albicans, and Saccharomyces cerevis. The results indicate that some of the compounds exhibit strong antibacterial activity, depending on the bacterial strain, but show virtually no antifungal activity. The structure-antibacterial activity relationships were studied using some physicochemical and quantum-chemical parameters with the ab initio Hartree-Fock model at the RHF/6-31G level of theory. A good qualitative correlation between predicted lipophilic parameters and antibacterial activity has been found.
- Alam, Mohammad Sayed,Liu, Lijun,Lee, Yong-Eok,Lee, Dong-Ung
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experimental part
p. 568 - 573
(2011/06/24)
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- Synthesis of Biologically Active [4-(4-Bromophenyl)-2-thiazolyl]hydrazones and their D-Galactose Derivatives
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Benzaldehyde [4-(4-bromophenyl)thiazol-2-yl]hydrazones 5a-5d were prepared by reacting the thiosemicarbazones 2a-2d with 2,4'-dibromoacetophenone (1) in absolute ethanol. Acetylation of 5a and 5b with Ac2O/Py at room temperature gave the N-acetyl derivatives 6a and 6b. 4-Methyl-2-pentanone/cyclopentanone [4-(4-bromophenyl) thiazol-2-yl]hydrazones (8a) and (8b) were similarly obtained from the reaction of 1 with the thiosemicarbazones 7a and 7b, respectively. Cyclization of D-galactose thiosemicarbazone (9) and its tautomers 10 and 11 with 1 afforded an equilibrium mixture of the acyclic 2-thiazolylhydrazone 12, together with its respective cyclic galactosyl derivatives 13 and 14, whose structures were studied by using 1H and 13C NMR spectra. The antimicrobial activity of the synthesized thiazole derivatives was evaluated in vitro by using an agar diffusion technique, and some of these compounds showed potential activity against Candida albicans.
- Ramadan, El Sayed
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experimental part
p. 594 - 600
(2010/10/04)
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- Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis
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A series of thiosemicarbazones 2(e-s) have been synthesized and studied their structure-activity relationship as melanogenesis inhibitor. Among them, (Z)-2-(naphthalen-1-ylmethylene)hydrazinecarbothioamide (2q, >100% inhibition at 10 μM, IC50 = 1.1 μM, C log P = 3.039) showed the strongest inhibitory activity. Regarding their structure-activity relationship, the hydrophobic substituents regardless the position on phenyl ring of benzaldehyde thiosemicarbazones enhance the inhibitory activity. Furthermore, the aromatic group of benzaldehydethiosemicarbazones can be replaced with sterically bulky cyclohexyl. Thus, hydrophobicity of the aryl or alkyl group on hydrazine of thiosemicarbazones is determinant factor for their inhibitory activity in melanogenesis rather than planarity.
- Lee, Ki-Cheul,Thanigaimalai, Pillaiyar,Sharma, Vinay K.,Kim, Min-Seok,Roh, Eunmiri,Hwang, Bang-Yeon,Kim, Youngsoo,Jung, Sang-Hun
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supporting information; experimental part
p. 6794 - 6796
(2011/01/04)
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- Design, synthesis and biological evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones as a new class of antimicrobial agents
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New series of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (9-16) obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones (1-8) upon cyclization with ethylbromoacetate in the presence of sodium acetate-acetic acid buffer afforded novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones (17-24). The synthesized compounds have been characterized by their elemental, analytical and spectral studies. Besides, the reported compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 11/18/20/23 against Staphylococcus aureus, 19/20/24 against Salmonella typhi show maximum inhibition potency at low concentration (6.25 μg/ml) whereas 18/19 against Candida albicans and 19/20/21 against Rhizopus sp. showed beneficial antifungal activity at minimum concentration.
- Ramachandran,Rani,Kabilan
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supporting information; experimental part
p. 2819 - 2823
(2009/12/31)
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- Synthesis, anticancer, and cytotoxic activities of some mononuclear Ru(II) compounds
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The synthesis and characterization of ruthenium compounds (Ru1-Ru12) of the type [Ru(S)2(K)], (where S = 1,10-phenanthroline/2,2′-bipyridine and K = itsz, MeO-btsz, 4-Cl-btsz, 2-Cl-btsz, 2-F-btsz, hfc and itsz = isatin-3-thiosemicarbazone, MeO-btsz = 1-(4′-methoxy-benzyl)-thiosemicarbazone, hfc = 2-{[3-chloro-4-fluoro-phenylimino]methyl}phenol, 4-Cl-btsz = 1-(4′-chlorobenzyl)-thiosemicarbazone, 2-Cl-btsz = 1-(2′-chloro benzyl)-thiosemicarbazone, 2-F-btsz = 1-(2′-fluorobenzyl)-thiosemicarbazone) are described. These ligands form bidentate octahedral ruthenium compounds. The title compounds were subjected to in vivo anticancer activity against a transplantable murine tumor cell line Ehrlich's Ascites Carcinoma (EAC) and in vitro cytotoxic activity against human cancer cell line Molt 4/C8, CEM and murine tumor cell line L1210. Ruthenium compounds (Ru1-Ru12) showed promising biological activity especially in decreasing tumor volume and viable ascites cell counts. Treatment with these compounds prolonged the life span of mice bearing EAC tumor by 10-43%. In vitro evaluation of these ruthenium compounds revealed cytotoxic activity from 0.24 to 27 μM against Molt 4/C8, 0.27 to 48 μM against CEM, and 0.94 to 248 μM against L1210. Their ligands alone failed to show cytotoxic activity at the concentrations tested (68-405 μM).
- Karki, Subhas S.,Thota, Sreekanth,Darj, Satyanarayana Y.,Balzarini, Jan,De Clercq, Erik
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p. 6632 - 6641
(2008/03/27)
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- Polyazanaphthalenes, I. The Reaction of Ethyl 6-Amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylate with Nucleophilic Reagents
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Ethyl 6-amino-5-cyano-4-aryl-2-methyl-4H-pyran-3-carboxylates 4 could be converted into 1,6-diazanaphthalene, pyranopyrazole, isoxazolopyridine, pyranopyridine, 1,8-diazanaphthalene, and pyranopyridine derivatives on treatment
- Harb, Abdel-Fattah A.,Hesien, Abdel-Haleem M.,Metwally, Saoud A.,Elnagdi, Mohamed Hilmy
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p. 585 - 588
(2007/10/02)
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