4921-92-0Relevant articles and documents
Iodine-mediated multi-component reactions: Readily access to tetrazoles and guanidines
Kammela, Prasad Rao,Seelam, Mohan,Shaik, Bajivali,Tamminana, Ramana
supporting information, p. 382 - 388 (2021/09/07)
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.
In vitro evaluation of antitrypanosomal activity and molecular docking of benzoylthioureas
Pereira, Patricia M.L.,Camargo, Priscila G.,Fernandes, Bruna T.,Flores-Junior, Luiz A.P.,Dias, Luiza R.S.,Lima, Camilo H.S.,Pinge-Filho, Phileno,Lioni, Lucy M.Y.,Yamada-Ogatta, Sueli F.,Bispo, Marcelle L.F.,Macedo Jr, Fernando
, (2020/11/23)
A series of sixteen benzoylthioureas derivatives were initially evaluated in vitro against the epimastigote form of Trypanosoma cruzi. All of the tested compounds inhibited the growth of this form of the parasite, and due to the promising anti-epimastigot
Benzoylthioureas: Design, synthesis and antimycobacterial evaluation
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
, p. 93 - 103 (2020/02/04)
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.
Multitarget CFTR Modulators Endowed with Multiple Beneficial Side Effects for Cystic Fibrosis Patients: Toward a Simplified Therapeutic Approach ?
Tassini, Sabrina,Langron, Emily,Delang, Leen,Mirabelli, Carmen,Lanko, Kristina,Crespan, Emmanuele,Kissova, Miroslava,Tagliavini, Giulia,Fontò, Greta,Bertoni, Simona,Palese, Simone,Giorgio, Carmine,Ravanetti, Francesca,Ragionieri, Luisa,Zamperini, Claudio,Mancini, Arianna,Dreassi, Elena,Maga, Giovanni,Vergani, Paola,Neyts, Johan,Radi, Marco
supporting information, p. 10833 - 10847 (2019/12/25)
Cystic fibrosis (CF) is a multiorgan disease caused by mutations of the cystic fibrosis transmembrane conductance regulator (CFTR). In addition to respiratory impairment due to mucus accumulation, viruses and bacteria trigger acute pulmonary exacerbations, accelerating disease progression and mortality rate. Treatment complexity increases with patients' age, and simplifying the therapeutic regimen represents one of the key priorities in CF. We have recently reported the discovery of multitarget compounds able to "kill two birds with one stone" by targeting F508del-CFTR and PI4KIIIβ and thus acting simultaneously as CFTR correctors and broad-spectrum enterovirus (EV) inhibitors. Starting from these preliminary results, we report herein a hit-to-lead optimization and multidimensional structure-activity relationship (SAR) study that led to compound 23a. This compound showed good antiviral and F508del-CFTR correction potency, additivity/synergy with lumacaftor, and a promising in vitro absorption, distribution, metabolism, and excretion (ADME) profile. It was well tolerated in vivo with no sign of acute toxicity and histological alterations in key biodistribution organs.
Mononuclear copper(I) complexes with triphenylphosphine and N,N′-disubstituted thioureas: synthesis, characterization, and biological evaluation
Khan, Syed Ishtiaq,Ali Khan, Inayat,Badshah, Amin,Perveen Malik, Fouzia,Tabassum, Saira,Ullah, Ikram,Zargarian, Davit,Khawar Rauf, Muhammad
, p. 4086 - 4108 (2018/12/04)
Twelve new complexes, of the general formula CuCl(TPP)2Tu1–12 (Tu = thiourea), were synthesized by the reaction of CuCl(TPP)3 (TPP = triphenylphosphine) and various N,N′-disubstituted thioureas. The structures of the synthesized complexes were characterized by different techniques such as Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy (1H, 13C, 31P, and 19F), and the representative complexes (1, 2 and 12) were analyzed via single crystal X-ray diffraction. The single crystal X-ray analysis revealed that copper(I) is coordinated with chlorine, two TPP, and the thiourea ligands through the sulfur atom in a mononuclear distorted tetrahedral mode. The compounds were tested for antibacterial, antifungal, cytotoxicity, antileishmanial, and antioxidant activities. The results showed that the synthesized complexes are significantly more active than the free ligands and the commercial reference compounds. The high biological activities of the complexes versus free ligands can be attributed to the copper(I) chloride complexation with thiourea ligands. The synthesized complexes were also evaluated, both experimentally and theoretically, for DNA binding studies. The UV-visible spectroscopic and molecular docking studies demonstrated that the complexes are conjugating with DNA through a groove binding mode.
Synthesis of new 2-aminoimidazolones with antiproliferative activity via base promoted amino-β-lactam rearrangement
Dra?i?, Tonko,Vazdar, Katarina,Vazdar, Mario,Crossed D Signakovi?, Marijana,Mikecin, Ana-Matea,Kralj, Marijeta,Malnar, Martina,He?imovi?, Silva,Habu?, Ivan
, p. 9202 - 9215 (2015/11/27)
A facile and efficient transformation of amino-β-lactam guanidines to 2-aminoimidazolones is described. The base-promoted transformation proceeds in two steps, with the rearrangement of four-membered β-lactam ring to five-membered imidazolone and subsequent E1cB elimination and formation of double bond at the 4-position of imidazolone ring, which is supported with quantum chemical calculations. The benzoylaminoimidazolone and 2-aminoimidazolone products are obtained in high yields. The benzoylaminoimidazolone products show antiproliferative activity in HCT116 (colon carcinoma) and H460 (lung carcinoma) cell lines.
Design, syntheses and evaluation of benzoylthioureas as urease inhibitors of agricultural interest
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.
, p. 44507 - 44515 (2015/06/02)
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.
A simple one-pot methodology for the synthesis of substituted benzoylguanidines from benzoylthioureas using tert-butyl hydroperoxide
Esteves, Henrique,De Fátima, ?ngelo,Castro, Rosane De P.,Sabino, José R.,MacEdo, Fernando,Brito, Tiago Oliveira
supporting information, p. 6872 - 6874 (2015/11/27)
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.
Evaluation of aminohydantoins as a novel class of antimalarial agents
Meyers, Marvin J.,Tortorella, Micky D.,Xu, Jing,Qin, Limei,He, Zhengxiang,Lang, Xingfen,Zeng, Wentian,Xu, Wanwan,Qin, Li,Prinsen, Michael J.,Sverdrup, Francis M.,Eickhoff, Christopher S.,Griggs, David W.,Oliva, Jonathan,Ruminski, Peter G.,Jacobsen, E. Jon,Campbell, Mary A.,Wood, David C.,Goldberg, Daniel E.,Liu, Xiaorong,Lu, Yongzhi,Lu, Xin,Tu, Zhengchao,Lu, Xiaoyun,Ding, Ke,Chen, Xiaoping
supporting information, p. 89 - 93 (2014/02/14)
Given the threat of drug resistance, there is an acute need for new classes of antimalarial agents that act via a unique mechanism of action relative to currently used drugs. We have identified a set of druglike compounds within the Tres Cantos Anti-Malar
ACCELERATORS FOR CURABLE COMPOSITIONS
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Paragraph 0055, (2014/01/17)
Benzoylthiourea or benzoylthiourethane derivatives as cure accelerators for curable compositions are provided.
