4426-68-0Relevant academic research and scientific papers
A facile preparation of selenohydantoins using isoselenocyanate
Koketsu, Mamoru,Takahashi, Ayako,Ishihara, Hideharu
, p. 79 - 81 (2007)
(Chemical Equation Presented) Reactions of isoselenocyanate with methyl aminoacetate hydrochlorides in the presence of triethylamine afforded selenohydantoins, 2-selenoxoimidazolidin-4-ones, in high yields.
Room-Temperature Metal-Free Multicomponent Polymerizations of Elemental Selenium toward Stable Alicyclic Poly(oxaselenolane)s with High Refractive Index
Wu, Xiuying,He, Junxia,Hu, Rongrong,Tang, Ben Zhong
supporting information, p. 15723 - 15731 (2021/10/01)
Selenium-containing polymers are a group of fascinating functional polymers with unique structures, properties, and applications, which have been developed recently but only with limited examples. The challenges of developing selenium-containing polymers
Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas
Kuznetsov, Ya. P.,Rasskazova,Pitushkin,Eshtukov,Vasipov,Burmistrov,Butov
, p. 1036 - 1046 (2021/09/08)
Abstract: A series of N,N′-disubstituted selenoureas containing an adamantane fragmenthave been synthesized in 23–75% yields. Procedures for the isolation andpurification of aromatic isoselenocyanates have been improved. The chemicalshift of the C=Se carbon nucleus in the 13C NMRspectra of selenoureas has been refined. The synthesized selenoureas have beenfound to be promising as inhibitors of not only epoxide hydrolase (sEH-H) butalso phosphatase domains (sEH-P) of human soluble epoxide hydrolase.
Bis-Selenoureas for Anion Binding: A 1H NMR and Theoretical Study
Caltagirone, Claudia,Ciancaleoni, Gianluca,Lippolis, Vito,Mocci, Rita,Picci, Giacomo,Zielińska-B?ajet, Mariola
, p. 1389 - 1395 (2020/08/05)
The anion binding ability of a family of bis-selenoureas L1-L3 obtained by the reaction of 1,3-bis(aminomethyl)-benzene and phenylisoselenocyanate, p-methoxyphenylisoselenocyanate and naphtylisoselenocyanate, for L1, L2, and L3, respectively, has been tested and compared to that of previously described bis-urea analogues. Results suggest that the introduction of selenium leads to an increase in the acidity of the urea NH hydrogen atoms, and therefore to a stronger affinity (more than three-fold higher) towards anion species, in particular dihydrogen phosphate, in DMSO-d6. Theoretical calculations allowed for the optimization of the adducts receptors corroborating the experimental results.
The Importance of 1,5-Oxygen???Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis
Cockroft, Scott L.,Elmi, Alex,Frost, Aileen B.,Ling, Kenneth B.,McLaughlin, Calum,Morris, Rylie K.,Pascoe, Dominic J.,Slawin, Alexandra M. Z.,Smith, Andrew D.,Smith, Terry K.,Willoughby, Patrick H.,Woods, Andrew M.,Young, Claire M.,de la Houpliere, Alix
supporting information, p. 3705 - 3710 (2020/02/11)
The importance of 1,5-O???chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N-acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5-O???Ch interactions in enantioselective catalysis. Importantly, the selenium analogue demonstrates enhanced rate and selectivity profiles across a range of reaction processes including nitronate conjugate addition and formal [4+2] cycloadditions. A gram-scale synthesis of the most active selenium analogue was developed using a previously unreported seleno-Hugerschoff reaction, allowing the challenging kinetic resolutions of tertiary alcohols to be performed at 500 ppm catalyst loading. Density functional theory (DFT) and natural bond orbital (NBO) calculations support the role of orbital delocalization (occurring by intramolecular chalcogen bonding) in determining the conformation, equilibrium population, and reactivity of N-acylated intermediates.
Novel 1,3,4-Selenadiazole-Containing Kidney-Type Glutaminase Inhibitors Showed Improved Cellular Uptake and Antitumor Activity
Chen, Zhao,Li, Di,Xu, Ning,Fang, Jinzhang,Yu, Yan,Hou, Wei,Ruan, Haoqiang,Zhu, Panpan,Ma, Renchao,Lu, Shiying,Cao, Danhui,Wu, Rui,Ni, Mowei,Zhang, Wei,Su, Weike,Ruan, Benfang Helen
, p. 589 - 603 (2019/01/10)
Kidney-type glutaminase [KGA/isoenzyme glutaminase C (GAC)] is becoming an important tumor metabolism target in cancer chemotherapy. Its allosteric inhibitor, CB839, showed early promise in cancer therapeutics but limited efficacy in in vivo cancer models. To improve the in vivo activity, we explored a bioisostere replacement of the sulfur atom in bis-2-(5-phenylacetamido-1,2,4-thiadiazol)ethyl sulfide and CB839 analogues with selenium using a novel synthesis of the selenadiazole moiety from carboxylic acids or nitriles. The resulting selenadiazole compounds showed enhanced KGA inhibition, more potent induction of reactive oxygen species, improved inhibition of cancer cells, and higher cellular and tumor accumulation than the corresponding sulfur-containing molecules. However, both CB839 and its selenium analogues show incomplete inhibition of the tested cancer cells, and a partial reduction in tumor size was observed in both the glutamine-dependent HCT116 and aggressive H22 liver cancer xenograft models. Despite this, tumor tissue damage and prolonged survival were observed in animals treated with the selenium analogue of CB839.
Synthesis and leishmanicidal activity of novel urea, thiourea, and selenourea derivatives of diselenides
Díaz, Marta,de Lucio, Héctor,Moreno, Esther,Espuelas, Socorro,Aydillo, Carlos,Jiménez-Ruiz, Antonio,Toro, Miguel ángel,Gutiérrez, Killian Jesús,Martínez-Merino, Victor,Cornejo, Alfonso,Palop, Juan Antonio,Sanmartín, Carmen,Planoa, Daniel
, (2019/05/21)
A novel series of thirty-one N-substituted urea, thiourea, and selenourea derivatives containing diphenyldiselenide entities were synthesized, fully characterized by spectroscopic and analytical methods, and screened for their in vitro leishmanicidal activities. The cytotoxic activity of these derivatives was tested against Leishmania infantum axenic amastigotes, and selectivity was assessed in human THP-1 cells. Thirteen of the synthesized compounds showed a significant antileishmanial activity, with 50% effective concentration (EC50) values lower than that for the reference drug miltefosine (EC50, 2.84 M). In addition, the derivatives 9, 11, 42, and 47, with EC50 between 1.1 and 1.95 M, also displayed excellent selectivity (selectivity index ranged from 12.4 to 22.7) and were tested against infected macrophages. Compound 11, a derivative with a cyclohexyl chain, exhibited the highest activity against intracellular amastigotes, with EC50 values similar to those observed for the standard drug edelfosine. Structure-activity relationship analyses revealed that N-aliphatic substitution in urea and selenourea is recommended for the leishmanicidal activity of these analogs. Preliminary studies of the mechanism of action for the hit compounds was carried out by measuring their ability to inhibit trypanothione reductase. Even though the obtained results suggest that this enzyme is not the target for most of these derivatives, their activity comparable to that of the standards and lack of toxicity in THP-1 cells highlight the potential of these compounds to be optimized for leishmaniasis treatment.
A novel and convenient synthesis of 3-amino-2H-1,2,4-triazoles from isoselenocyanates and hydrazine hydrate
Li, Xue,Peng, Zhixiang,Zhang, Yuanyuan,Wang, Jiangwei,Gan, Bin,Xie, Yuanyuan
, p. 255 - 259 (2018/06/29)
A novel and convenient one-pot synthesis of 3-amino-2H-1,2,4-triazoles from two molecules of isoselenocyanates and hydrazine hydrate via cyclodeselenisation was developed. Various 3-amino-2H-1,2,4-triazoles were obtained in moderate to good yields (33-45%
Thermal stability and decomposition of urea, thiourea and selenourea analogous diselenide derivatives
Díaz, Marta,Palop, Juan Antonio,Sanmartín, Carmen,Lizarraga, Elena
, p. 1663 - 1674 (2017/02/10)
The fusion and thermal decomposition of thirty-three diselenide compounds with a urea, thiourea or selenourea group linked with different aliphatic or aromatic substituents have been studied by thermogravimetry, differential scanning calorimetry and mass spectrometry in order to perform comparative thermal stability studies among analogs. A relationship has been found between stability and a series of effects which occur in the compound structures. Analysis of the thermal data indicated that: (a) in general, compounds with a urea or selenourea group are more stable than those with a thiourea group; (b) no difference in stability exists when an aromatic or aliphatic group is linked to the thiourea group but when linked to the urea or selenourea groups, stability does differ; (c) selenourea compounds with aliphatic chain are the most unstable; and (d) the nature of the substituent located on the benzyl ring has no effects on thermal stability. Therefore, criteria for the selection of substituents can be established in order to improve the stability of these drugs. In addition, the mass spectral fragmentation in comparison with thermal analytical data helps in confirming the thermal behavior of the compounds.
Discovery of New Selenoureido Analogues of 4-(4-Fluorophenylureido)benzenesulfonamide as Carbonic Anhydrase Inhibitors
Angeli, Andrea,Tanini, Damiano,Peat, Thomas S.,Di Cesare Mannelli, Lorenzo,Bartolucci, Gianluca,Capperucci, Antonella,Ghelardini, Carla,Supuran, Claudiu T.,Carta, Fabrizio
, p. 963 - 968 (2017/09/22)
A series of benzenesulfonamides bearing selenourea moieties was obtained considering the ureido-sulfonamide SLC-0111, in Phase I clinical trials as antitumor agent, as a lead molecule. All compounds showed interesting inhibition potencies against the physiologically relevant human (h) carbonic anhydrase (hCAs, EC 4.2.1.1) isoforms I, II, IV, and IX. The most flexible analogues in the series 14-19 showed low nanomolar inhibition constants against hCA I, II, and IX. We assessed selected compounds on the in vitro antioxidant properties and binding modes and evaluated ex vivo human prostate (PC3), breast (MDA-MB-231), and colon-rectal (HT-29) cancer cell lines both in normoxic and hypoxic conditions.
