14737-89-4Relevant academic research and scientific papers
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.
Synthesis, structure, and biological evaluation of three Cu(II) and Ni(II) (E)-3-(3,4-dimethoxyphenyl)acrylate complexes with organic diamines as potential urease inhibitors
Zhu, Hui,Wang, Zi-Zhen,Qi, Bing,Huang, Tao,Zhu, Hai-Liang
, p. 2980 - 2991 (2013)
Three new complexes (1-3) have been synthesized and characterized by X-ray single crystal determination and evaluated for inhibitory activity on jack bean urease. All the complexes contained a new cinnamic acid derivative as the ligand (C11H12O4), (E)-3-(3,4-dimethoxyphenyl)acrylic acid, and crystallized in monoclinic C2/c space group. Complex 1 (C1 1H11O4)4(C3N 2H8)2Cu2 (C3N 2H8 = 1,2-diaminopropane) was obtained with a = 20.488(2), b = 19.596(2), c = 15.2500(13), β = 93.502(2)°, V = 6111.2(10) A3, Z = 4, R1 = 0.0616, and wR2 = 0.2059. Complex 2 (C11H11O4)4(C 3N2H8)2Cu2 (C 3N2H8=1,3-diaminopropane) was obtained with a = 20.2494(12), b = 19.5732(12), c = 14.8940(8), β = 96.884(2)°, V = 5860.6(6) A3, Z = 4, R1 = 0.0409, and wR2 = 0.1107. Complex 3 (C11H11O4) 2(C2N2H6)2Ni 2·H2O (C2N2H6 = ethylenediamine) was obtained with a = 28.359(2), b = 6.5422(5), c = 16.8587(14), β = 101.359(2)°, V = 3066.5(4) A3, Z = 4, R1 = 0.0422, and wR2 = 0.1190. It was found that copper(II) complexes 1 [IC50 = 4.71 M] and 2 [IC50 = 3.15 M] showed strong inhibitory activity against jack bean urease compared with acetohydroxamic acid [IC50 = 10.01 M] as a positive reference. Unfortunately, 3 exhibited no inhibitory activity. 102013
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.
Hydrogenolysis-free hydrogenation by Pd black powder catalyst
Maki,Okawa,Matsui,Hirano,Niwa
, p. 1590 - 1592 (2001)
A new general method of hydrogenolysis-free hydrogenation using a commercially available Pd black powder catalyst has developed.
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.
Cinnamoylated chloroquine analogues: A new structural class of antimalarial agents
Gayam, Venkatareddy,Ravi, Subban
, p. 382 - 391 (2017)
A novel series of cinnamoylated chloroquine hybrid analogues were synthesized and evaluated as antimalarial agents. The trans cinnamic acid derivatives (3–8) were synthesized by utilizing substituted aldehydes and malanoic acid in DMF catalysed by DABCO. The final cinnamoylated chloroquine analogues (9–14) were synthesized by utilizing DCC coupling reagent. The amido chloroquine (17) was prepared from acid (16) and compound 2 in benzene using SOCl2 as chlorinating agent. The corresponding ester (15) was prepared from 2-hydroxy acetophenone and 2-bromoacetates in actonitrile in presence of K2CO3?as?base followed by basic hydrolysis. The preparation of amide based chloroquine-chalcone analogues (18–22), were obtained by the combination of amido chloroquine (17) and aldehydes in 10% aq. KOH in methanol at room temperature. Further we prepared epichlorohydrin based chloroquine-chalcone analogues (25–28), by reacting the epoxide (24a, 24b and 24c) with 2 and methelenedioxy aniline. In?vitro antimalarial activity against chloroquine sensitive strain 3D7, chloroquine resistant strain K1 of P.?falciparum and in?vitro cytotoxicity of compounds using VERO cell line was carried out. The synthesized molecules showed significant in?vitro antimalarial activity especially against CQ resistant strain (K1). Among tested compounds, 13, 9 and 10 were found to be the most potent compounds of the series with IC50 value of 44.06, 48.04 and 59.37?nM against chloroquine resistant K1 strain.
PHENYLPROPANOID GLYCOSIDES ISOLATED FROM SCROPHULARIA SCOPOLI
Calis, Ihsan,Gross, Gian-Andrea,Sticher, Otto
, p. 2057 - 2062 (1987)
Key Word Index - Scrophularia scopolii var. scopolii; Scrophulariaceae; phenylpropanoid glycosides; acteoside; verbascoside; angoroside A; deacyl angoroside A dimethyl ether; deacyl acteoside dimethyl ether. A new phenylpropanoid glycoside, angoroside A, and a known glycoside, acteoside, were isolated from the roots of Scrophularia scopolii var. scopolii.On the basis of chemical and spectral evidence, angoroside A was shown to be 3,4-dihydroxy-β-phenylethoxy-O-α-L-arabinopyranosyl-(1->6)-α-L-rhamnopyranosyl-(1->3)-4-O-caffeoyl-β-D-glucopyranoside.
Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum
Baruch, Yifat,Gopas, Jacob,Kadosh, Yael,Kumar, Rajendran Saravana,Kushmaro, Ariel,Muthuraman, Subramani,Yaniv, Karin
supporting information, (2021/05/28)
Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.
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).
Design, synthesis, and evaluation of novel cinnamic acid-tryptamine hybrid for inhibition of acetylcholinesterase and butyrylcholinesterase
Ghafary, Shahrzad,Ghobadian, Roshanak,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Akbarzadeh, Tahmineh,Najafi, Zahra,Sharifzadeh, Mohammad,Edraki, Najmeh,Moghadam, Farshad Homayouni,Amini, Mohsen
, p. 463 - 477 (2020/05/25)
Background: Acetylcholine deficiencies in hippocampus and cortex, aggregation of β-amyloid, and β-secretase over activity have been introduced as main reasons in pathogenesis of Alzheimer’s disease. Methods: Colorimetric Ellman’s method was used for determination of IC50 value in AChE and BChE inhibitory activity. The kinetic studies, neuroprotective and β-secretase inhibitory activities, evaluation of inhibitory potency on β-amyloid (Aβ) aggregations induced by AChE, and docking study were performed for prediction of the mechanism of action. Result and discussion: A new series of cinnamic acids-tryptamine hybrid was designed, synthesized, and evaluated as dual cholinesterase inhibitors. These compounds demonstrated in-vitro inhibitory activities against acetyl cholinesterase (AChE) and butyryl cholinesterase (BChE). Among of these synthesized compounds, (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide (5q) demonstrated the most potent AChE inhibitory activity (IC50 = 11.51?μM) and (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(2-chlorophenyl)acrylamide (5b) were the best anti-BChE (IC50 = 1.95?μM) compounds. In addition, the molecular modeling and kinetic studies depicted 5q and 5b were mixed type inhibitor and bound with both the peripheral anionic site (PAS) and catalytic sites (CAS) of AChE and BChE. Moreover, compound 5q showed mild neuroprotective in PC12 cell line and weak β-secretase inhibitory activities. This compound also inhibited aggregation of β-amyloid (Aβ) in self-induced peptide aggregation test at concentration of 10?μM. Conclusion: It is worth noting that both the kinetic study and the molecular modeling of 5q and 5b depicted that these compounds simultaneously interacted with both the catalytic active site and the peripheral anionic site of AChE and BChE. These findings match with those resulted data from the enzyme inhibition assay. [Figure not available: see fulltext.]
