- New bioactive Cu(I) thiourea derivatives with triphenylphosphine; synthesis, structure and molecular docking studies
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The synthesized thioureas, 1-(3-fluorobenzoyl))-3-(4-(diethyl aminophenyl) thiourea (I1), 1-benzoyl-3-(2-chlorophenyl) thiourea (I2) and 1-(2-fluorobenzoyl)-3-(2-chlorophenyl) thiourea (I3) along with triphenylphosphine were reacted with Cu(I) chloride in mole ratios 1:2:1 by using dry acetone as solvent under nitrogen to get 1–3. The synthesized thioureas and metal derivatives were characterized by spectroscopic techniques such as IR and multinuclear (1H, 13C) NMR. Compound 3 is analyzed by single crystal X-ray analysis and data reveal that the Cu is four coordinate having tetrahedral molecular geometry. The interaction of 1–3 with DNA is ascertained by cyclic voltammetry, determining binding constant, binding energy and diffusion coefficient. The findings suggest that the complexes interact with DNA in an electrostatic mode. The antioxidant activity data show that 3 has the highest free radical scavenging ability having Ic50 value of 10 μg/mL. The synthesized compounds were also screened against various bacterial strains and found some encouraging results. The binding interactions of the metal complexes with a specific protein were further validated by molecular docking studies and the results obtained show their strong interaction with amino acid residue in the binding pocket of the target protein.
- Hussain, Irfan,Hussain, Shabeeb,Hussain, Shazia,Imtiaz-ud-Din,Raheel, Ahmad,Tahir, Muhammad Nawaz
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- New supramolecular ferrocenyl phenylguanidines as potent antimicrobial and DNA-binding agents
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Six new ferrocenyl phenylguanidines have been synthesized and characterized by elemental analysis, FT-IR, multinuclear (1H and 13C) NMR, and single crystal analysis. The latter showed a supramolecular structure for 2 mediated by O H and π H interactions. A subsequent DNA-binding study of these complexes proved them to be good DNA binders with the binding constant varying in the range of 1.2-5.6×105M-1. These compounds were found to have moderate antibacterial and significant antifungal activities, especially for compounds having a chlorophenyl. These compounds may emerge as a new class of anticancer and antifungal agents alone or in combination with other drugs.
- Gul, Rukhsana,Khan, Azim,Badshah, Amin,Rauf, Muhammad Khawar,Shah, Afzal,-Rehman, Zia-Ur,Bano, Asghari,Naz, Rabia,Tahir, Muhammad Nawaz
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- Self-assembly of a benzothiazolone conjugate into panchromatic fluorescent fibres and their application in cellular imaging
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We report the synthesis and characterization of the structures formed by self-assembly of 4-chloro-2(3H)-benzothiazolone (CBT) into panchromatic fibres and their application in cellular imaging. The aggregation properties of the synthesized compound were studied extensively under different solvents and concentrations and their morphologies examined at a supramolecular level by various microscopic techniques such as atomic force microscopy (AFM), fluorescence microscopy, and optical microscopy. Interestingly, the self-assembled structures formed byCBTreveal panchromatic emission properties and show blue, green, and red fluorescence under different excitation wavelengths. The mechanism of structure formation of the self-assemblies was studied through different techniques such as concentration-dependent1H-NMR, ATR-FTIR, UV-visible spectroscopy, and fluorescence spectroscopy. Finally, the utility ofCBTfor cell imaging applications was demonstrated and it can be noted thatCBTwas efficiently taken up by mammalian cells and the cells revealed panchromatic emission in the blue, green, and red channels. The intensities of the fluorescence observed were blue > green > red and the dye interestingly does not exhibit any fluorescence quenching.
- Bhatia, Dhiraj,Gangrade, Ankit,Gour, Nidhi,Haque, Ashadul,Joshi, Khashti Ballabh,Koshti, Bharti,Kshtriya, Vivekshinh,Singh, Ramesh
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supporting information
p. 17211 - 17221
(2021/10/04)
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- Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
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Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect of a 3-bromophenylamino moiety in position 3 of the triazole for both series (compounds 2.6 and 4.6) on several cell lines tested. Moreover, our results point out an antiangiogenic activity of these compounds. Overall, the 5-aryl-3-phenylamino-1,2,4-triazole structure has promising dual anticancer activity.
- Benhida, Rachid,Demange, Luc,Dufies, Maeva,Grytsai, Oleksandr,Hagege, Anais,Martial, Sonia,Pagès, Gilles,Penco-Campillo, Manon,Ronco, Cyril,Valiashko, Oksana
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- Benzoylthioureas: Design, synthesis and antimycobacterial evaluation
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Background: New drugs and strategies to treat tuberculosis (TB) are urgently needed. In this context, thiourea derivatives have a wide range of biological activities, including anti-TB. This fact can be illustrated with the structure of isoxyl, an old anti-TB drug, which has a thiourea as a pharmacophore group. Objective: The aim of this study is to describe the synthesis and the antimycobacterial activity of fifty-nine benzoylthioureas derivatives. Methods: Benzoylthiourea derivatives have been synthesized and evaluated for their activity against Mycobacterium tuberculosis using the MABA assay. After that, a structure-activity relationship study of this series of compounds has been performed. Results and Discussion: Nineteen compounds exhibited antimycobacterial activity between 423.1 and 9.6 μM. In general, we observed that the presence of bromine, chlorine and t-Bu group at the para-position in benzene ring plays an important role in the antitubercular activity of Series A. These substituents were fixed at this position in benzene ring and other groups such as Cl, Br, NO2 and OMe were introduced in the benzoyl ring, leading to the derivatives of Series B. In general, Series B was less cytotoxic than Series A, which indicates that the presence of a substituent at benzoyl ring contributes to an improvement in both antimycobacterial activity and toxicity profiles. Conclusion: Compound 4c could be considered a good prototype to be submitted to further structural modifications in the search for new anti-TB drugs, since it is 1.8 times more active than the first line anti-TB drug ethambutol and 0.65 times less active than isoxyl.
- Abreu, Lethícia O.,Bispo, Marcelle L. F.,Brito, Tiago O.,Gomes, Karen M.,Louren?o, Maria C. S.,Macedo, Fernando,Pereira, Patricia M. L.,Tisher, Cesar A.,Yamada-Ogatta, Sueli F.,de Fátima, ?ngelo
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- Design, synthesis and algicides activities of thiourea derivatives as the novel scaffold aldolase inhibitors
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By using a new Fragment-Based Virtual Screen strategy, two series of novel FBA-II inhibitors (thiourea derivatives) were de novo discovered based on the active site of fructose-1, 6-bisphosphate aldolase from Cyanobacterial (CyFBA). In comparison, most of the N-(2-benzoylhydrazine-1-carbonothioyl) benzamide derivatives (L14~L22) exhibit higher CyFBA-II inhibitory activities compared to N-(phenylcarbamothioyl) benzamide derivatives (L1~L13). Especially, compound L14 not only shows higher CyFBA-II activity (Ki = 0.65 μM), but also exhibits most potent in vivo activity against Synechocystis sp. PCC 6803 (EC50 = 0.09 ppm), higher (7-fold) than that of our previous inhibitor (EC50 = 0.6 ppm). The binding modes of compound L14 and CyFBA-II were further elucidated by jointly using DOX computational protocol, MM-PBSA and site-directed mutagenesis assays. The positive results suggest that strategy adopted in this study was promising to rapidly discovery the potent inhibitors with novel scaffolds. The satisfactory algicide activities suggest that the thiourea derivatives is very likely to be a promising lead for the development of novel specific algicides to solve Cyanobacterial harmful algal blooms (CHABs).
- Xiao, Shan,Wei, Lin,Hong, Zongqin,Rao, Li,Ren, Yanliang,Wan, Jian,Feng, Lingling
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p. 805 - 812
(2019/02/03)
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- Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae
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A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).
- Wang, Rong,Hou, Shuang,Dong, Xiaojing,Chen, Daijie,Shao, Lei,Qian, Liujia,Li, Zhong,Xu, Xiaoyong
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p. 2060 - 2066
(2017/11/22)
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- Synthesis and antitumor evaluation of 5-(benzo[: D] [1,3]dioxol-5-ylmethyl)-4-(tert -butyl)- N -arylthiazol-2-amines
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A series of novel N-aryl-5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)thiazol-2-amines (C1-C31) were synthesized and evaluated for their antitumor activities against HeLa, A549 and MCF-7 cell lines. Some tested compounds showed potent growth inhibition properties with IC50 values generally below 5 μM against the three human cancer cells lines. Compound C27 showed potent activities against HeLa and A549 cell lines with IC50 values of 2.07 ± 0.88 μM and 3.52 ± 0.49 μM, respectively. Compound C7 (IC50 = 2.06 ± 0.09 μM) was the most active compound against A549 cell line, while compound C16 (IC50 = 2.55 ± 0.34 μM) showed the best inhibitory activity against the MCF-7 cell line. The preliminary mechanism of the inhibitory effect was investigated via further experiments, such as morphological analysis by dual AO/EB staining and Hoechst 33342 staining, and cell apoptosis and cycle assessment by FACS analysis. The results illustrated that compound C27 could induce apoptosis and cause both S-phase and G2/M-phase arrests in HeLa cell line. Therefore, compound C27 could be developed as a potential antitumor agent.
- Wu,Fang,Tang,Xiao,Ye,Li,Hu
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p. 1768 - 1774
(2016/09/28)
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- Synthesis and Cytotoxicity in Vitro of N-Aryl-4-(Tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine
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A series of novel N-aryl-4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amines were synthesized in a green way. H2O2-NaBr Brominating circulatory system was used in the synthesis of the key intermediate in a mild condition. All of the target compounds were confirmed by1H NMR and elemental analysis and tested for their cytotoxicity against two different human cancer cell lines. The cytotoxicity assay revealed that some of the title compounds showed moderate to strong cytotoxic activities. Compound 2i was the most potent compound with the IC50 values of 9 μMagainst Hela cells and 15 μMagainst Bel-7402 cells, respectively.
- Ye, Jiao,Xiao, Meng-Wu,Xie, Xuan-Qing,Qiu, Shen-Yi,Dai, Ming-Chong,Li, Wan,Shen, Fang,Hu, Ai-Xi
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p. 627 - 631
(2018/01/18)
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- Design, syntheses and evaluation of benzoylthioureas as urease inhibitors of agricultural interest
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Urea is one of the most used nitrogen fertilizers worldwide. However, occurrence of urea hydrolysis to ammonia and carbon dioxide on soil surface, catalyzed by soil ureases, considerably reduces nitrogen availability to crops. In this study, we describe the design, synthesis and screening of sixty five benzoylthioureas (BTUs) for their ability to inhibit purified jack bean and soil ureases. BTUs were readily obtained in one pot, two steps synthesis with no need of cumbersome procedures for product purification. In vitro assays revealed BTUs 11, 12, 14, 19-22 and 37 as the most active jack bean urease inhibitors. Such BTUs were found to be able to bind to both catalytic and allosteric sites of urease, acting therefore as mixed-type inhibitors. Out of 28 compounds that effectively inhibited soil ureases activity, BTUs 3, 6, 10, 12, 16, 19 and 22 were determined to be more potent than the reference inhibitor N-(butyl) thiophosphoric triamide (NBPT; 40%). The other 22 BTUs were as potent as NBPT on soil ureases. The temperature-tolerance of BTUs, along with their ability to inhibit soil ureases, makes of this class of compounds potential additive for urea-based fertilizers.
- Brito, Tiago O.,Souza, Aline X.,Mota, Yane C. C.,Morais, Vinicius S. S.,De Souza, Leandro T.,De Fátima, ?ngelo,Macedo, Fernando,Modolo, Luzia V.
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p. 44507 - 44515
(2015/06/02)
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- Solution-phase microwave assisted parallel synthesis of N,N′-disubstituted thioureas derived from benzoic acid: Biological evaluation and molecular docking studies
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An efficient and facile microwave-assisted solution phase parallel synthesis for a 26-member library of N,N′-disubstituted thiourea analogs were accomplished successfully. The reaction time for synthesis of analogs was drastically reduced from a reported 8-12 h to only 10 min. Compounds were more than 95% pure, as characterized by modern analytical techniques, i.e. 1H & 13C NMR and FT-IR. The solid phase structural analysis has also been performed by single crystal XRD analysis. Synthesized compounds were preliminary screened for their in vitro urease inhibition and antifungal activity. Most of the compounds were found to be potent inhibitors of urease. However, the most significant activity was found for 11 with IC 50 of 1.67 μM. The docking scores correlate with the IC 50 values of inhibitors.
- Rauf, Muhammad Khawar,Talib, Ammara,Badshah, Amin,Zaib, Sumera,Shoaib, Khurram,Shahid, Mohammad,Fl?rke, Ulrich,Imtiaz-Ud-Din,Iqbal, Jamshed
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p. 487 - 496
(2013/11/19)
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- Design and synthesis of N-Aryl isothioureas as a novel class of gastric H+/K+-ATPase inhibitors
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To find new H+/K+-ATPase inhibitors for the treatment of peptic ulcer disease, a series of novel N-aryl isothiourea derivatives were synthesized and their structures were identified by 1H NMR and GC-MS. The effects of these compounds on inhibiting gastric acid secretion were evaluated by the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. The results showed that, of the 37 N-aryl isothiourea compounds synthesized, 20 compounds have comparable or stronger gastric acid inhibitory activities than that of pantoprazole magnesium. The quantitative structure-activity relationships (QSARs) of the N-aryl isothiourea compounds were also studied by comparative molecular field analysis (CoMFA) computation, and the model structure that was supposed to give more powerful bioactivities was finally predicted. A series of novel N-aryl isothiourea derivatives were synthesized and evaluated for their effects of inhibiting gastric acid secretion using the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. Compounds 2c, 2e, and 2k have higher bioactivity. The quantitative structure-activity relationships also defined these structural requirements.
- Ma, Chao,Wu, Anhui,Wu, Yongqi,Ren, Xuhong,Cheng, Maosheng
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p. 891 - 900
(2014/01/06)
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- Antimicrobial activity and structural study of disubstituted Thiourea Derivatives
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The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included. Springer-Verlag 2007.
- Cunha, Silvio,MacEdo Jr., Fernando C.,Costa, Giselle A. N.,Rodrigues Jr., Manoel T.,Verde, Rosival B. V.,De Souza Neta, Lourdes C.,Vencato, Ivo,Lariucci, Carlito,Sa, Fernando P.
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p. 511 - 516
(2008/02/03)
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- A convenient and efficient method for the synthesis of mono- and N,N-disubstituted thioureas
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A convenient method for the synthesis of mono- and N,N-disubstituted thioureas by the debenzoylation of N-substituted- and N,N-disubstituted- N′-benzoylthioureas with hydrazine hydrate under solvent-free conditions has been developed. N-Substituted-N′-benzoylthioureas and hydrazine hydrate were mixed, and stirred at room temperature without a solvent to give the corresponding N-substituted thioureas in high yields.
- Kodomari, Mitsuo,Suzuki, Masato,Tanigawa, Keiko,Aoyama, Tadashi
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p. 5841 - 5843
(2007/10/03)
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- Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists
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A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC50 values of the most potent antagonists were ca. 0.050 μM in these assays.
- Xi, Ning,Bo, Yunxin,Doherty, Elizabeth M.,Fotsch, Christopher,Gavva, Narender R.,Han, Nianhe,Hungate, Randall W.,Klionsky, Lana,Liu, Qingyian,Tamir, Rami,Xu, Shimin,Treanor, James J.S.,Norman, Mark H.
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p. 5211 - 5217
(2007/10/03)
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- Microwave Promoted Efficient Synthesis of N-Aryl-N′-aroyl Thioureas under Solvent-Free and Phase Transfer Catalysis Conditions
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A simple, rapid and efficient method for the synthesis of N-aryl-N′-aroyl thioureas under phase transfer catalysis, microwave irradiation and solvent-free conditions is reported.
- Wei, Tai-Bao,Lin, Qi,Zhang, You-Ming,Wei, Wei
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p. 181 - 186
(2007/10/03)
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- A mild and efficient synthesis of N-aryl-N′-aroyl thioureas under phase transfer catalysis and solvent-free conditions
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A series of N-aryl-N′-aroyl thioureas 3a-m were synthesized in high yields (80.0-98.1%) by an environmentally benign, simple and efficient method under phase transfer catalysis and solvent-free conditions.
- Wei, Tai-Bao,Lin, Qi,Zhang, You-Ming,Wei, Wei
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p. 666 - 667
(2007/10/03)
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- Substituted N-phenylisothioureas: Potent inhibitors of human nitric oxide synthase with neuronal isoform selectivity
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S-Ethyl N-phenylisothiourea (4) has been found to be a potent inhibitor of both the human constitutive and inducible isoforms of nitric oxide synthase. A series of substituted N-phenylisothiourea analogues was synthesized to investigate the structure-activity relationship of this class of inhibitor. Each analogue was evaluated for human isoform selectivity. One analogue, S-ethyl N-[4-(trifluoromethyl)phenyl]isothiourea (39), exhibited 115-fold and 29-fold selectivity for the neuronal isoform versus the inducible and endothelial derived constitutive isoforms, respectively. Studies have shown the substituted N-phenylisothiourea 39 binds competitively with L,-arginine.
- Shearer, Barry G.,Lee, Shuliang,Oplinger, Jeffrey A.,Frick, Lloyd W.,Garvey, Edward P.,Furfine, Eric S.
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p. 1901 - 1905
(2007/10/03)
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- STUDIES ON THE MOESSBAUER SPECTRA OF SOME IRON(III) COMPLEXES WITH IMIDES AS PRIMARY AND SOME N-ARYL-N'-BENZOYLTHIOCARBAMIDES AS SECONDARY LIGANDS. EFFECT OF AMBIENT TEMPERATURE
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Ten new mixed ligand complexes of iron(III) of the type , where Im = deprotonated phthalimide or succinimide and STC = some N-aryl-N'-benzoylthiocarbamide derivativesN-(2-chlorophenyl)-N'-benzoylthiocarbamide, N-(3-methoxyphenyl)-N'-be
- Mishra, Virendra
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p. 155 - 161
(2007/10/02)
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- Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas
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An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N'-benzoylthioureas with 5percent aqueous sodium hydroxide.Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g. 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.
- Rasmussen, C. R.,Villani, F. J.,Weaner, L. E.,Reynolds, B. E.,Hood, A. R.,et al.
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p. 456 - 459
(2007/10/02)
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- CHARACTERIZATION OF THE COMPLEXES OF SOME BIOLOGICALLY ACTIVE N-ARYL-N'-BENZOYLTHIOCARBAMIDES WITH METAL(II) PHTHALIMIDES
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The mixed ligand complexes of Cu(II), Pd(II), Pt(II), Co(II) and Ni(II) with phthalimide as primary and N-aryl-N'-benzoylthiocarbamides as secondary ligands have been prepared and characterized on the basis of chemical analysis, conductance, magnetic meas
- Sharma, C. L.,Mishra, V. P.
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- Synthesis & Pharmacological Evaluation of Ethyl 3-Substituted-phenyl-2-methylmercapto/ phenyl/ methyl-4(3H)-pyrimidone-5-carboxylates
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A number of ethyl 3-substituted-phenyl-2-methylmercapto/ phenyl/ methyl-4(3H)-pyrimidone-5-carboxylates (V) have been prepared by the reaction of amidines (III) with diethyl ethoxymethylenemalonate.In order to confirm the structure (V), ethyl 3-(2'-methylphenyl)-2-methylmercapto-4(3H)pyrimidone-5-carboxylate (103) has been transformed into the earlier synthesised 3-(2'-methylphenyl)-2-methylmercapto-4(3H)-pyrimidone (115) by decarboxylation of 3-(2'-methylphenyl)-2-methylmercapto-4(3H)-pyrimidone-5-carboxylic acid (114), obtained by the alkaline hydrolysis of 103.Someof these compounds have shown antiinflammatory, diuretic and antipassive cutaneous anaphylaxis activities.
- Gupta, K. A.,Saxena, Anil K.,Jain, Padam C.
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p. 228 - 233
(2007/10/02)
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