117490-34-3Relevant articles and documents
Iminophosphorane-Mediated Imidazole Ring Formation: A New and General Entry to Aplysinopsin-type Alkaloids of Marine Origin
Molina, Pedro,Almendros, Pedro,Fresneda, Pilar M.
, p. 2241 - 2254 (1994)
Aza Wittig-type reactions of iminophosphoranes 21, derived from ethyl α-azido-β-(3-indolyl)propenoates and triphenylphosphine, with methyl isocyanate, carbon dioxide or carbon disulfide provide the corresponding heterocumulenes 22, 25 and 28 which undergo
The indole-hydantoin derivative exhibits anti-inflammatory activity by preventing the transactivation of NF-κB through the inhibition of NF-κB p65 phosphorylation at Ser276
Lin, Xin,Tago, Kenji,Okazaki, Nozomi,So, Takanori,Takahashi, Kyoko,Mashino, Tadahiko,Tamura, Hiroomi,Funakoshi-Tago, Megumi
, (2021/09/02)
Indole- and hydantoin-based derivatives both exhibit anti-inflammatory activity, suggesting that the structures of indole and hydantoin are functional for this activity. In the present study, we synthesized two types of indole-hydantoin derivatives, IH-1 (5-(1H-indole-3-ylmethylene) imidazolidine-2,4-dione) and IH-2 (5-(1H-indole-3-ylmethyl) imidazolidine-2,4-dione) and examined their effects on LPS-induced inflammatory responses in murine macrophage-like RAW264.7 cells. LPS-induced inflammatory responses were not affected by indole, hydantoin, or IH-2. In contrast, IH-1 significantly inhibited the LPS-induced production of nitric oxide (NO) and secretion of CCL2 and CXCL1 by suppressing the mRNA expression of inducible NO synthase (iNOS), CCL2, and CXCL1. IH-1 markedly inhibited the LPS-induced activation of NF-κB without affecting the degradation of IκBα or nuclear translocation of NF-κB. IH-1 markedly attenuated the transcriptional activity of NF-κB by suppressing the LPS-induced phosphorylation of the NF-κB p65 subunit at Ser276. Furthermore, IH-1 prevented the LPS-induced interaction of NF-κB p65 subunit with a transcriptional coactivator, cAMP response element-binding protein (CBP). Collectively, these results revealed the potential of the novel indole-hydantoin derivative, IH-1 as an anti-inflammatory drug.
Hydantoin-based molecular photoswitches
Martínez-López, David,Yu, Meng-Long,García-Iriepa, Cristina,Campos, Pedro J.,Frutos, Luis Manuel,Golen, James A.,Rasapalli, Sivappa,Sampedro, Diego
, p. 3929 - 3939 (2015/05/05)
A new family of molecular photoswitches based on arylidenehydantoins is described together with their synthesis and photochemical and photophysical studies. A series of hydantoin derivatives have been prepared as single isomers using simple and versatile chemistry in good yields. Our studies show that the photostationary states of these compounds can be easily controlled by means of external factors, such as the light source or filters. Moreover, the detailed investigations proved that these switches are efficient (i.e., they make efficient use of the light energy, are high fatigue resistant, and are very photostable). In some cases, the switches can be completely turned on/off, a desirable feature for specific applications. A series of theoretical calculations have also been carried out to understand the photoisomerization mechanism at the molecular level.
Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry
Mendgen, Thomas,Steuer, Christian,Klein, Christian D.
supporting information; experimental part, p. 743 - 753 (2012/03/11)
Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.
Anticonvulsant Activity of Phenylmethylenehydantoins: A Structure-Activity Relationship Study
Thenmozhiyal, Jeyanthi Chinnappa,Wong, Peter Tsun-Hon,Chui, Wai-Keung
, p. 1527 - 1535 (2007/10/03)
Phenylmethylenehydantoins (PMHs) and their des-phenyl analogues were synthesized and evaluated for anticonvulsant activity using the maximal electroshock seizure (MES) assay. The phenyl rings of PMHs were substituted with a wide spectrum of groups, and th
A simple stereoselective synthesis of aplysinopsin analogs
Selic, Lovro,Jakse, Renata,Lampic, Kristina,Golic, Ljubo,Golic-Grdadolnik, Simona,Stanovnik, Branko
, p. 2802 - 2811 (2007/10/03)
Simple and stereoselective syntheses of aplysinopsins and their analogs from either methyl 2-[(2,2-disubstituted ethenyl)amino]-3-(dimethylamino)prop-2-enoates 11 or 5-[(dimethylamino)methylidene]imidazolidine-2,4-diones 20 are described. The structures of products are established by 1H- and 13C-NMR, and NOESY spectroscopy, and X-ray crystal-structure analysis.
cinnamamide analogs as inhibitors of protein tyrosine kinases
Buzzetti,Brasca,Crugnola,Fustinoni,Longo,Penco,Dalla Zonca,Comoglio
, p. 615 - 636 (2007/10/02)
Protein tyrosine kinases (PTK) arc important signal transducing enzymes involved in the modulation of normal cellular growth and differentiation and have been associated with the etiology of various human cancers. The development of properly designed inhibitors, which block their function by interfering with the substrate binding, may therefore offer an unique target for selective anticancer chemotherapy. Here we describe synthesis and biochemical testing of a novel series of non-peptide PTK inhibitors which have as characteristic active pharmacophore the cinnamamide moiety. For testing we used an exogenous substrate kinase assay based on the phosphorylation of (Val)-angiotensin II with radiolabelled ATP by the catalytic domain of the PTK encoded by the v-abl oncogene (p45 v-abl). The most potent compounds were found in the class of 3-arylidene-2-oxindoles (II) with IC50 values in the 1μM range. Among these the 2-tetralylmethylene-, 4-quinolylmethylene-, 5-quinolylmethylene- and 3-indolylmethylene-2-oxindole compounds of formulae 16, 20, 21 and 24 respectively were selected for further investigation.
TRIETHYLAMINE, ETHANOL- MEDIATED DISCIPLINED REACTIONS OF S-BENZYLISOTHIOURONIUM CHLORIDE WITH UNSATURATED 2-OXAZOLIN-5-ONES: SYNTHESIS OF (Z)-2-AMINO-4-ARYLMETHYLENE-2-IMIDAZOLIN-5-ONES, 5-BENZOYLAMINO-2-BENZYLTHIO-6-OXO-4,4-SPIROCYCLOHEXYL-1,4,5,6-TETRA
Mukerjee, Arya K.,Joseph, Kiran,Homami, Seyed-Saied,Tikdari, Ahmad M.
, p. 1317 - 1325 (2007/10/02)
Triethylamine-mediated condensation of S-benzylisothiouronium chloride with (Z)-4-arylmethylene-2-phenyl-2-oxazolin-5-ones (4) in ethanol gives (Z)-2-amino-4-arylmethylene-2-imidazolin-5-ones (7), whereas the similar reaction with 4-cyclohexylidene-2-phen
FACILE PREPARATION OF 5-(3-INDOLYLMETHYLENE)HYDANTOINS
Moriya, Tamon,Hagio, Katsuaki,Yoneda, Naoto
, p. 1891 - 1893 (2007/10/02)
A facile preparation of 5-(3-indolylmethylene)hydantoins, which are useful intermediates for syntheses of tryptophan and its derivatives, was achieved by condensation of hydantoin with 3-(aminomethylene)-3H-indoles formed in situ by the reaction of indoles with Vilsmeier-Haack reagent followed by neutralization with anhydrous bases.Keywords - tryptophan; hydantoin; 5-(3-indolylmethylene)hydantoin; 3-(aminomethylene)-3H-indole; Vilsmeier-haack reaction; condensation.
