- Structural Effect of Pincer Pd(II)–ONO Complexes Modified with Acylthiourea on Sizes of the In Situ Generated Pd Nanoparticles During Heck Coupling Reaction
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Abstract: The Pd nanoparticles generated in situ from Pd–pincer complexes catalyzed Heck coupling reaction. For this purpose, new Pd(II)–ONO pincer complexes (1–4) containing acylthiourea ancillary ligand were obtained by treating [Pd(ONO)(CH3CN)] with the respective N-substituted carbamothioyl benzamide ligand (L1–L4). Formation of these complexes was confirmed by UV–Visible, FT-IR, NMR and mass spectroscopic techniques. The sizes of in situ formed Pd nanoparticles were greatly affected by the substituent in ancillary ligand, which in turn influenced their catalytic activity towards Heck coupling reaction. The in situ formed Pd nanoparticles during Heck reaction were removed from the reaction medium and analyzed using HR-TEM to estimate the sizes of the Pd nanoparticles. Complex [Pd(ONO)((N-benzylcarbamothioyl)benzamide)] (1) which does not possess any substituent on the benzyl moiety of acylthiourea produced the smallest Pd nanoparticles with the average particle size of 3.7?nm. Hence, complex 1 showed the utmost catalytic activity. With complex 1, 51–99% of conversion was observed during Heck coupling reaction of styrene with various aryl halides. XPS results confirmed that the recovered black particles were Pd(0). A reasonable recyclability results were achieved by these in situ generated Pd nanoparticles. Graphic Abstract: [Figure not available: see fulltext.]
- Jerome,Babu, S. Ganesh,Karvembu
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p. 1633 - 1645
(2020/10/15)
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- Iodine-mediated multi-component reactions: Readily access to tetrazoles and guanidines
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Environmentally benign syntheses of One-pot sequential reactions of benzoyl chloride with amines followed by the treatment of molecular I2 reagent under basic conditions provide benzoyl tetrazoles and guanidines in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, high yields, using cheap and readily available reagent molecular Iodine. In addition, functional group tolerance has been explored.
- Kammela, Prasad Rao,Seelam, Mohan,Shaik, Bajivali,Tamminana, Ramana
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p. 382 - 388
(2021/09/07)
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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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- ANTIVIRAL COMPOUNDS AND USE THEREOF
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The present invention relates to compounds of formula (I), their use as medicaments, in particular as broad spectrum antiviral agents, their combination with a further antiviral agent and relative pharmaceutical compositions. In particular, the compounds of the invention are useful in the treatment of a disease caused by an enveloped virus.
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Page/Page column 36-37
(2019/10/04)
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- Novel broad spectrum virucidal molecules against enveloped viruses
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Viral infections are an important cause of death worldwide. Unfortunately, there is still a lack of antiviral drugs or vaccines for a large number of viruses, and this represents a remarkable challenge particularly for emerging and re-emerging viruses. For this reason, the identification of broad spectrum antiviral compounds provides a valuable opportunity for developing efficient antiviral therapies. Here we report on a class of rhodanine and thiobarbituric derivatives displaying a broad spectrum antiviral activity against seven different enveloped viruses including an HSV-2 acyclovir resistant strain with favorable selectivity indexes. Due to their selective action on enveloped viruses and to their lipid oxidation ability, we hypothesize a mechanism on the viral envelope that affects the fluidity of the lipid bilayer, thus compromising the efficiency of virus-cell fusion and preventing viral entry.
- Cagno, Valeria,Tintori, Cristina,Civra, Andrea,Cavalli, Roberta,Tiberi, Marika,Botta, Lorenzo,Brai, Annalaura,Poli, Giulio,Tapparel, Caroline,Lembo, David,Botta, Maurizio
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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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- A simple one-pot methodology for the synthesis of substituted benzoylguanidines from benzoylthioureas using tert-butyl hydroperoxide
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The potential of tert-butyl hydroperoxide as a reagent in the guanylation of benzoylthioureas in the presence of amines has been evaluated in a systematic study involving substrates bearing N2-substituents with different electronic properties. The results show that tBuOOH is a suitable and robust reagent for the synthesis of either N1,N2,N3-tri- and tetrasubstituted or N1,N2-disubstituted guanidines from N2-substituted N1-benzoylthioureas and N1-benzoylthioureas, respectively. The recrystallised guanylation adducts were readily obtained in good yields and at high purity levels after a simple one-pot reaction procedure. The crystal structures of two novel benzoylguanidines are provided.
- Esteves, Henrique,De Fátima, ?ngelo,Castro, Rosane De P.,Sabino, José R.,MacEdo, Fernando,Brito, Tiago Oliveira
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supporting information
p. 6872 - 6874
(2015/11/27)
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- Antitubercular activities of the novel synthesized 1,2,4-triazole derivatives
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1,2,4-Triazoles exert antimycobacterial activity by inhibiting the cell wall biosynthesis. In an attempt to developing lead compounds exhibiting antitubercular activities, a series of 1,2,4-triazole derivatives were synthesized by introducing various substitutes into a scaffold and the antitubercular activity was evaluated. The most potent compounds 3e and 8d showed their minimum inhibitory concentrations against Mycobacterium tuberculosis as 12.5 ??M. The results indicate that those compounds can be considered as leads for further development of new 1,2,4-triazole type candidates with high antitubercular activities.
- Oh, Taegwon,Hayat, Aisal,Yoo, Euna,Cho, Sang-Nae,Sheen, Yhun Yhung,Kim, Dae-Kee,Choo, Hea-Young Park
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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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- Histone deacetylase activators: N-acetylthioureas serve as highly potent and isozyme selective activators for human histone deacetylase-8 on a fluorescent substrate
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We report, for the first time, that certain N-acetylthiourea derivatives serve as highly potent and isozyme selective activators for the recombinant form of human histone deacetylase-8 in the assay system containing Fluor-de-Lys as a fluorescent substrate. The experimental data reveals that such activating feature is manifested via decrease in the Km value of the enzyme's substrate and increase in the catalytic turnover rate of the enzyme.
- Singh, Raushan K.,Mandal, Tanmay,Balsubramanian, Narayanaganesh,Viaene, Tajae,Leedahl, Travis,Sule, Nitesh,Cook, Gregory,Srivastava
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supporting information; experimental part
p. 5920 - 5923
(2011/10/18)
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- Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B 16 cells
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In order to define the structural requirements of phenylthiourea (PTU), a series of thiourea and thiosemicarbazone analogs were prepared and evaluated as inhibitors of melanogenesis in melanoma B16 cells. The most potent analog was 2-(4-tert-butylbenzylidene)hydrazinecarbothioamide (1u) with an IC50 value of 2.7 μM in inhibition of melanogenesis. The structure for potent inhibitory activity of these derivatives are required with the direct connection of π-planar structure to thiourea without steric hinderance in PTU derivatives and the hydrophobic substituent at para position in case of semicarbazones.
- Thanigaimalai,Le Hoang, Tuan Anh,Lee, Ki-Cheul,Bang, Seong-Cheol,Sharma, Vinay K.,Yun, Cheong-Yong,Roh, Eunmiri,Hwang, Bang-Yeon,Kim, Youngsoo,Jung, Sang-Hun
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supporting information; experimental part
p. 2991 - 2993
(2010/08/06)
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- Clobenpropit analogs as dual activity ligands for the histamine H3 and H4 receptors: Synthesis, pharmacological evaluation, and cross-target QSAR studies
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Previous studies have demonstrated that clobenpropit (N-(4-chlorobenzyl)-S-[3-(4(5)-imidazolyl)propyl]isothiourea) binds to both the human histamine H3 receptor (H3R) and H4 receptor (H4R). In this paper, we describe the synthesis and pharmacological characterization of a series of clobenpropit analogs, which vary in the functional group adjacent to the isothiourea moiety in order to study structural requirements for H3R and H4R ligands. The compounds show moderate to high affinity for both the human H3R and H4R. Furthermore, the changes in the functional group attached to the isothiourea moiety modulate the intrinsic activity of the ligands at the H4R, ranging from neutral antagonism to full agonism. QSAR models have been generated in order to explain the H3R and H4R affinities.
- Lim, Herman D.,Istyastono, Enade P.,van de Stolpe, Andrea,Romeo, Giuseppe,Gobbi, Silvia,Schepers, Marjo,Lahaye, Roger,Menge, Wiro M.B.P.,Zuiderveld, Obbe P.,Jongejan, Aldo,Smits, Rogier A.,Bakker, Remko A.,Haaksma, Eric E.J.,Leurs, Rob,de Esch, Iwan J.P.
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experimental part
p. 3987 - 3994
(2009/10/02)
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- Bismuth chloride mediated synthesis, antimicrobial, and anti-inflammatory activities of new 4-aryl-2-amino thiazoles
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Synthesis of 4-aryl-2-Amino thiazoles (3a-u), (4a-c), and (5a-c) was achieved from the reaction of 4-butyl phenacyl chlorides (2a-c) with N-substituted thioureas, in the presence of Bismuth Chloride. The antimicrobial and anti-inflammatory activities of the final products were also studied. Copyright Taylor & Francis Group, LLC.
- Giridhar,Reddy, R. Buchi,Kumar, A. Sunil,Chandra Mouli
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scheme or table
p. 2058 - 2072
(2009/07/18)
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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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- Aromatic nucleophilic substitution or CuI-catalyzed coupling route to martinellic acid
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Condensation of β-amino ester 8b with triflate 7 gives N-aryl amino ester 11, which is converted into 2-substituted 4-oxoquinoline 4 using an intramolecular Dieckmann reaction as the key step. CuI-mediated coupling of β-amino ester 8a with 1,4-diiodobenzene followed by an intramolecular acylation and Pd-catalyzed carbonylation provide another manner to 4. Alkylation of 4 and subsequent reductive amination deliver the cyclic imine 14, which is transformed into triamine 3 by ordinary operations. Guanylation of 3 under mild condition followed by deprotection results in the synthesis of martinellic acid 1.
- Ma, Dawei,Xia, Chengfeng,Jiang, Jiqing,Zhang, Jianhua,Tang, Wenjun
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p. 442 - 451
(2007/10/03)
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- Synthesis of 1-benzoyl-3-alkylthioureas by transamidation under microwave in dry media
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1-Benzoyl-3,3-diethylthiourea was transamidated with several amines to the corresponding 1-benzoyl-3-alkylthioureas in open vessels under microwave irradiation using a domestic oven. The syntheses were performed in solvent- free conditions on potassium fluoride impregnated alumina. Yields were dramatically improved in comparison with classical heating under the same conditions. (C) 2000 Published by Elsevier Science Ltd.
- Márquez, Heiddy,Pérez, Eduardo R.,Plutín, Ana M.,Morales, Margarita,Loupy, André
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p. 1753 - 1756
(2007/10/03)
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- Isothiourea analogues of histamine as potent agonists or antagonists of the histamine H3-receptor
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The synthesis and H3-activity of a series of isothiourea analogues of histamine have been described. It has been shown that S-[2-(4(5)-imidazolyl)ethylisothiourea (VUF 8325) is a potent H3-agonist measured as the electrically evoked contraction of the guinea-pig ileum. Upon methylation of the imidazole system or the isothiourea moiety a decrease in affinity was observed leading to either weak agonists or weak antagonists. Introduction of N-(phenylalkyl) substituents at the isothiourea part gives rise to highly potent H3-antagonists. Particularly the 4-chlorobenzyl group appeared to be favourable in the series described resulting in a histamine H3-antagonist with a pA2-value of 9.9.
- Van der Goot,Schepers,Sterk,Timmerman
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p. 511 - 517
(2007/10/02)
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- Reaction of β-Nitro Enamines with Isocyanates, Isothiocyanates and Dimethyl Acetylenedicarboxylate
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β-Nitro enamines (1) reacted with isocyanates and isothiocyanates to give β-(substituted carbamoyl) and β-(substituted thiocarbamoyl) β-nitro enamines, respectively.The reaction of 1 with benzoyl isothiocyanate gave β-(benzoylthiocarbamoyl) β-nitro enamines (8) and/or a mixture of 8 and 4(1H)-pyrimidinethione derivatives (9), which were cyclization products of 8.The isolated 8 afforded the corresponding 9 in high yields upon heating in DMF.The reaction of 1 with dimethyl acetylenedicarboxylate gave cycloadducts (12) and/or a mixture of 12 and δ-nitro dienamino diesters (13) which were ring cleavage products of 12.Compounds 12 afforded 13 upon heating in toluene or xylene.
- Tokumitsu, Takao
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p. 3871 - 3876
(2007/10/02)
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- Reactions of benzoyl isothiocyanates with azomethines
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Preparation of substituted 1,3,5-oxadiazine-4-thiones and s-triazines by reacting benzoyl isothiocyanates with azomethines, and hydrolysis of the obtained oxadiazinethiones is described.The observed, IR, Raman,UV and 1H-NMR spectral characteristics of the
- Uher, Michal,Kovac, Stefan,Ilias, Peter,Floch, Lubomir,Martvon, Augustin
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p. 2254 - 2259
(2007/10/02)
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