4921-82-8Relevant articles and documents
Sequential and cellular detection of copper and lactic acid by disaggregation and reaggregation of the fluorescent panchromatic fibres of an acylthiourea based sensor
Kshtriya, Vivekshinh,Koshti, Bharti,Pandey, Deepak K.,Kharbanda, Sumit,Chandra Kanth,Singh, Dheeraj K.,Bhatia, Dhiraj,Gour, Nidhi
, p. 4304 - 4316 (2021)
We report, for the first time, the self-assembly of an acyl-thiourea based sensor, N-{(6-methoxy-pyridine-2-yl) carbamothioyl}benzamide (NG1), with panchromatic fluorescent fibres and its dual-sensing properties for the sequential detection of Cu2+ ions and lactic acid. The panchromatic fibres formed by NG1 were disrupted in the presence of Cu2+ ions and this was accompanied by a visible colour change in the solution from colourless to yellow. The addition of lactic acid to the NG1 + Cu2+ solution, on the other hand, induced re-aggregation to fibrillar structures and the colour of the solution again changed to colourless. Hence, it may be surmised that the disaggregation and re-aggregation impart unique dual-sensing properties to NG1 for the sequential detection of Cu2+ ions and lactic acid. The application of NG1 as a selective sensor for Cu2+ ions and lactic acid has been assessed in detail by UV-visible and fluorescence spectroscopy. Furthermore, two structural variants of NG1, namely, NG2 and NG3, were synthesized, which suggest the crucial role of pyridine in imparting panchromatic emission properties and of both pyridine and acyl-thiourea side chain in the binding of Cu2+ ions. The O-methoxy group plays an important part in making NG1 the most sensitive probe of its structural analogs. Finally, the utility of NG1 for the sequential and cellular detection of Cu2+ ions and lactic acid was studied in human RPE cells. The experimental results of the interaction of NG1 with Cu2+ ions and lactic acid have also been validated theoretically by using quantum chemical calculations based on density functional theory (DFT). To the best of our knowledge, this is the first report wherein a dual sensor for Cu2+ ions and lactate ions is synthesized. More importantly, the aggregation properties of the sensor have been studied extensively and an interesting correlation of the photophysical properties of the probe with its self-assembling behavior has been elucidated.
Coordination polymers and molecular structures among complexes of mercury(II) halides with selected 1-benzoylthioureas
Okuniewski, Andrzej,Rosiak, Damian,Chojnacki, Jaros?aw,Becker, Barbara
, p. 47 - 57 (2015)
Six new 1-benzoyl-3-phenylthiourea and 1-benzoyl-3-(2-methylphenyl)thiourea complexes of mercury(II) were obtained in the reactions of the ligands with HgX2 in methanol (X = Cl, Br, I). Their structures, determined by single-crystal X-ray diffr
Colorimetric detection of fluoride ions in aqueous medium using thiourea derivatives: A transition metal ion assisted approach
Choudhury, Diganta,Das, Rituraj,Kuilya, Hemrupa,Mahanta, Sanjeev P.,Sarma, Plaban J.,Talukdar, Dhrubajyoti,Thakuria, Ranjit
supporting information, p. 15287 - 15295 (2021/11/17)
This work explores the position of the hydroxyl moiety and its participation in intramolecular H-bonding towards dictating the fluoride selective colorimetric response in functionalized thiourea derivatives. The study reveals the pivotal aspect of the hyd
Synthesis, crystal structure and Hirshfeld Surface analysis of benzamide derivatives of thiourea as potent inhibitors of α-glucosidase in-vitro
Akhter, Sidra,Ullah, Saeed,Yousuf, Sammer,Atia-tul-Wahab,Siddiqui, Hina,Choudhary, M. Iqbal
, (2020/12/25)
Benzamide based structural analogues 1–15 were synthesized, and evaluated for α-glucosidase inhibition activity in vitro for the first time. Compounds 1–9 were found to be known, while compounds 10–15 were found to be new. However, to the best of our knowledge we are reporting α-glucosidase inhibitory activity of these bezamide derivatives of thiourea for the first time. Compounds 1, 3, 6–8, 10–14 were found to be potent inhibitors of α-glucosidase within IC50 range of 20.44–333.41 μM, in comparison to the standard inhibitor, acarbose (IC50 = 875.75 ± 2.08 μM). Mode of the enzyme inhibition was determined on the basis of kinetic studies which demonstrated that compounds 8, and 10 were non-competitive and competitive inhibitors of α-glucosidase enzyme, respectively. These compounds were also evaluated for their DPPH radical scavenging activity, and cytotoxicity against 3T3 mouse fibroblast cell lines. All synthesized compounds showed a significant to moderate DPPH radical scavenging activity and appeared to be non-cytotoxic except compound 9 which showed cytotoxicity against 3T3 normal mouse fibroblast cell lines. A single crystal X-ray and Hirshfeld Surface analysis of a representative compound is also presented.
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.
Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
Benhida, Rachid,Demange, Luc,Dufies, Maeva,Grytsai, Oleksandr,Hagege, Anais,Martial, Sonia,Pagès, Gilles,Penco-Campillo, Manon,Ronco, Cyril,Valiashko, Oksana
, (2020/10/02)
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.
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.
Strategy and validation of a structure-based method for the discovery of selective inhibitors of PAK isoforms and the evaluation of their anti-cancer activity
Song, Pei-Lu,Wang, Gang,Su, Yuan,Wang, Han-Xun,Wang, Jian,Li, Feng,Cheng, Mao-Sheng
, (2019/08/12)
p21 activated kinase 4 (PAK4), which belongs to the serine/threonine (Ser/Thr) protein kinase family, is a representative member of the PAK family and plays a significant role in multiple processes associated with cancer development. In this study, structure-based virtual screening was performed to discover novel and selective small molecule scaffolds, and a 6-hydroxy-2-mercapto-3-phenylpyrimidin-4(3H)-one-based compound (SPU-106, 14No.) was identified as an effective PAK4 inhibitor. By combining both a molecular docking study and molecular dynamics (MD) simulation strategies, the binding mode was determined in the PAK4 site. The SPU-106 compound could efficiently and selectively bind to the PAK4 kinase domain at an IC50 of 21.36 μM according to the kinase analysis. The designed molecular probe demonstrated that SPU-106 binds to the kinase domain in the C-terminus of PAK4. Further investigation revealed that the SPU-106 had a strong inhibitory effect on the invasion of SGC7901 cells but without any cytotoxicity. The western blot analysis indicated that the compound potently inhibited the PAK4/LIMK1/cofilin and PAK4/SCG10 signaling pathways. Thus, our work shows the successful application of computational strategies for the discovery of selective hits, and SPU-106 may be an effective PAK4 inhibitor for further development as an antitumor agent.
Synthesis, characterization and chemosensitivity studies of half-sandwich ruthenium, rhodium and iridium complexes containing к1(S) and к2(N,S) aroylthiourea ligands
Lapasam, Agreeda,Hussain, Omar,Phillips, Roger M.,Kaminsky, Werner,Kollipara, Mohan Rao
, p. 272 - 280 (2018/11/26)
The reaction of [(p-cymene)RuCl2]2 and [Cp*MCl2]2 (M = Rh/Ir) metal precursors with aroylthiourea ligands (L1-L3) yielded a series of neutral mono-dentate complexes 1–9. The neutral mono-dentate coordination of aroylthiourea with metals via S atom was confirmed by single crystal X-ray diffraction study. Further reaction of mono-dentate complexes 1–9 with excess NaN3 in polar solvent resulted in the formation of highly strained four member ring к2(N,S) azido complexes 10–18. Further these complexes were treated with activated alkynes to isolate triazole complexes, but unfortunately the reaction was unsuccessful. All these complexes were fully characterized by various spectroscopic techniques. The molecular structures of the representative complexes have been determined by single crystal X-ray diffraction studies. The molecular structures of the complexes revealed typical piano stool geometry around the metal center. The chemosensitivity activities of the complexes 1–9 evaluated against the cancer cell line HCT-116 (human colorectal carcinoma) and ARPE-19 (human retinal epithelial cells) cell line. Of these, complex 3 was the most potent and whilst its potency was less than cisplatin, its selectivity for cancer as opposed to non-cancer cell lines in vitro was comparable to cisplatin.
N, N′ N″-trisubstituted guanidines: Synthesis, characterization and evaluation of their leishmanicidal activity
do Espírito Santo, Rafael Dias,Velásquez, ángela María Arenas,Passianoto, Luana Vitorino Gushiken,Sepulveda, Alex Arbey Lopera,da Costa Clementino, Leandro,Assis, Renata Pires,Baviera, Amanda Martins,Kalaba, Predrag,dos Santos, Fábio Neves,éberlin, Marcos Nogueira,da Silva, Gil Valdo José,Zehl, Martin,Lubec, Gert,Graminha, Márcia Aparecida Silva,González, Eduardo René Pérez
, p. 116 - 128 (2019/03/26)
Leishmaniasis is a group of diseases caused by protozoan parasites from the genus Leishmania. There are estimated 1.3 million new cases annually with a mortality of 20,000–30,000 per year, when patients are left untreated. Current chemotherapeutic drugs available present high toxicity and low efficacy, the latter mainly due to the emergence of drug-resistant parasites, which makes discovery of novel, safe, and efficacious antileishmanial drugs mandatory. The present work reports the synthesis, characterization by ESI-MS, 1H and 13C NMR, and FTIR techniques as well as in vitro and in vivo evaluation of leishmanicidal activity of guanidines derivatives presenting lower toxicity. Among ten investigated compounds, all being guanidines containing a benzoyl, a benzyl, and a substituted phenyl moiety, LQOF-G2 (IC50-ama 5.6 μM; SI = 131.8) and LQOF-G7 (IC50-ama 7.1 μM; SI = 87.1) were the most active against L. amazonensis intracellular amastigote, showing low cytotoxicity to the host cells according to their selectivity index. The most promising compound, LQOF-G2, was further evaluated in an in vivo model and was able to decrease 60% of the parasite load in foot lesions at a dose of 0.25 mg/kg/day. Moreover, this guanidine derivative demonstrated reduced hepatotoxicity compared to other leishmanicidal compounds and did not show nephrotoxicity, as determined by the analyses of biomarkers of hepatic damage and renal function, which make this compound a potential new hit for therapy against leishmaniasis.
