14737-89-4Relevant articles and documents
Cinnamoyl-memantine hybrids: Synthesis, X-ray crystallography and biological activities
Chochkova, Maya,Jiang, Hailun,Kyoseva, Radoslava,Stoykova, Boyka,Tsvetanova, Elina,Alexandrova, Albena,Liu, Rui,Li, Zhuorong,Mitrev, Yavor,Dimitrova-Sbirkova, Hristina,?tícha, Martin,Shivachev, Boris
, (2021)
Herein, framework combinations of antioxidant substituted cinnamic acids and memantine (N-methyl-D-aspartate receptor antagonist) in a new multi-targeted chemical entity were described. The amide bond formation of the memantine hybrids 1–5 was performed by EDC/HOBt coupling reaction. The chemical structures of the synthesized compounds were confirmed by means of melting points, UV, IR, 1H NMR, 13C NMR, and HRMS. Additionally, the crystal structures of memantine hybrids (2–5) were also studied by single-crystal X-ray diffraction. The single-crystal X-ray analysis revealed that the compounds 2, 5 crystallize in a centrosymmetric manner both in monoclinic space group (SG) P21/c, (No 14) and in a non-centrosymmetric manner for compounds 3 and 4, SG R3, (No 146) and SG P212121, (No 19), respectively. Furthermore, preliminary in vitro screenings of their neuroprotective and radical scavenging activities were performed. The radical scavenging activity of synthesized memantine hybrids was measured against 1,1-diphenyl-2-picrylhydrazyl (DPPH●), hydroxyl (OH●) and superoxide (O2●?) radicals and compared with the standard antioxidants (ferulic and sinapic acids). Radical scavenging activity studies show that amongst the tested hybrids, N-sinapoyl amide of memantine (3) emerges as the most potent antioxidant in all tests. Moreover, in vitro evaluation of anti-Alzheimer effects showed that the obtained memantine hybrids displayed neuroprotection in the moderate levels. Generally, they possess a little weaker activity as compared to the positive control memantine. Taken together, our findings reveal that the N-sinapoylamide of memantine (3) can be considered as a promising neuroprotective agent for Alzheimer's disease, acting as well as a potent radical scavenger.
ARBORTRISTOSIDE A AND B, TWO IRIDOID GLUCOSIDES FROM NYCTANTHES ARBOR-TRISTIS
Purushothaman, Kozhiparambil K.,Venkatanarasimhan, Mathuram,Sarada, Ayyappath
, p. 773 - 776 (1985)
Two new iridioid glucosides, arbortristoside A and B have been isolated from the seeds of Nychtanthes arbortristis.The structures of the two new compounds were determined by spectroscopic methods and chemical reactions. - Key Word Index - Nyctanthes arbor-tristis; Oleaceae; iridoid glucosides; arbortristosides A and B.
Effect of solvent and hydrogen during selective hydrogenation
Maki, Shojiro,Harada, Yasuhiro,Matsui, Ryo,Okawa, Makiko,Hirano, Takashi,Niwa, Haruki,Koizumi, Megumi,Nishiki, Yoshinori,Furuta, Tsuneto,Inoue, Hiroshi,Iwakura, Chiaki
, p. 8323 - 8327 (2001)
Described is the solvent effect for the chemoselective hydrogenation of alkenes having a benzyloxy group (Bn-O-) using a hydrogenation system employing atomic hydrogen permeating through a Pd sheet electrode.
Oleanolic acid caffeate from the outer bark of Betula davurica
Odinokova, L. E.,Denisenko, V. A.,Pokhilo, N. D.,Uvarova, N. I.
, p. 255 - 256 (1985)
-
Covalent Inhibition of Bacterial Urease by Bifunctional Catechol-Based Phosphonates and Phosphinates
Pagoni, Aikaterini,Grabowiecka, Agnieszka,Tabor, Wojciech,Mucha, Artur,Vassiliou, Stamatia,Berlicki, ?ukasz
supporting information, p. 404 - 416 (2021/01/13)
In this study, a new class of bifunctional inhibitors of bacterial ureases, important molecular targets for antimicrobial therapies, was developed. The structures of the inhibitors consist of a combination of a phosphonate or (2-carboxyethyl)phosphinate functionality with a catechol-based fragment, which are designed for complexation of the catalytic nickel ions and covalent bonding with the thiol group of Cys322, respectively. Compounds with three types of frameworks, including β-3,4-dihydroxyphenyl-, α-3,4-dihydroxybenzyl-, and α-3,4-dihydroxybenzylidene-substituted derivatives, exhibited complex and varying structure-dependent kinetics of inhibition. Among irreversible binders, methyl β-(3,4-dihydroxyphenyl)-β-(2-carboxyethyl)phosphorylpropionate was observed to be a remarkably reactive inhibitor of Sporosarcina pasteurii urease (kinact/KI = 10 420 s-1 M-1). The high potential of this group of compounds was also confirmed in Proteus mirabilis whole-cell-based inhibition assays. Some compounds followed slow-binding and reversible kinetics, e.g., methyl β-(3,4-dihydroxyphenyl)-β-phosphonopropionate, with Ki? = 0.13 μM, and an atypical low dissociation rate (residence time τ = 205 min).
Novel anti-Alzheimer phenol-lipoyl hybrids: Synthesis, physico-chemical characterization, and biological evaluation
Pagoni, Aikaterini,Marinelli, Lisa,Di Stefano, Antonio,Ciulla, Michele,Turkez, Hasan,Mardinoglu, Adil,Vassiliou, Stamatia,Cacciatore, Ivana
, (2019/11/28)
To date, drugs that hit a single target are inadequate for the treatment of neurodegenerative diseases, such as Alzheimer's or Parkinson's diseases. The development of multitarget ligands, able to interact with the different pathways involved in the progession of these disorders, represents a great challenge for medicinal chemists. In this context, we report here the synthesis and biological evaluation of phenol-lipoyl hybrids (SV1-13), obtained via a linking strategy, to take advantage of the synergistic effect due to the antioxidant portions and anti-amyloid properties of the single constituents present in the hybrid molecule. Biological results showed that SV5 and SV10 possessed the best protective activity against Aβ1-42 induced neurotoxicity in differentiated SH-SY5Y cells. SV9 and SV10 showed remarkable antioxidant properties due to their ability to counteract the damage caused by H2O2 in SHSY-5Y-treated cells. Hovewer, SV5, showing moderate antioxidant and good neuroprotective activities, resulted the best candidate for further experiments since it also resulted stable both simulated and plasma fluids.