6006-82-2Relevant articles and documents
Synthesis and structure–activity relationships of novel arylpiperazines as potent antagonists of α1-adrenoceptor
Silva, Renata Oliveira,de Oliveira, Andressa Souza,Nunes Lemes, Laís Flávia,de Camargo Nascente, Luciana,Coelho do Nascimento Nogueira, Patrícia,Silveira, Edilberto R.,Brand, Guilherme D.,Vistoli, Giulio,Cilia, Antonio,Poggesi, Elena,Buccioni, Michela,Marucci, Gabriella,Bolognesi, Maria Laura,Romeiro, Luiz Antonio Soares
, p. 601 - 610 (2016)
Arylpiperazines 2–11 were synthesized, and their biological profiles at α1-adrenergic receptors (α1-ARs) assessed by binding assays in CHO cells expressing human cloned subtypes and by functional experiments in isolated rat vas deferens (α1A), spleen (α1B
A simple, efficient access to functionalized pyrrolobenzazepines related to the BBC core of cephalotaxine
De Oliveira, Eduardo R.,Dumas, Francoise,D'Angelo, Jean
, p. 3723 - 3726 (1997)
Tetracyclic nitrile 19a and ester 19b, exhibiting the ABC core of cephalotaxine 1a, were prepared through K-H-induced cyclization of thioimides 14a and 14b, respectively. This new ring-closure methodology proved to he particularly efficient: thus nitrile 19a was obtained in only 7 steps with a 17 % overall yield from commercially available, inexpensive safrole 2.
An unexpected pentacarbonyl chromium complexation of a cyano group of the ABC core of cephalotaxine
Quteishat, Laith,Panossian, Armen,Le Bideau, Franck,Alsalim, Rana,Retailleau, Pascal,Troufflard, Claire,Rose, Eric,Dumas, Fran?oise
, p. 35 - 42 (2015)
A new penta-carbonyl chromium(0) complex of the type [Cr(CO)5(L)] (L = tetracyclic pyrrolobenzazepine unit 3) was surprisingly obtained by reacting [Cr(CO)3(naphthalene)] or [Cr(CO)3(tmtach)] with the tetracyclic pyrrolobenzazepine unit 3 in octane-ether/THF-solvent mixtures or acetone under ambient temperature or reflux. The new complex 13 has been characterized by spectral analysis including IR, 1H and 13C NMR data. For comparison purposes, the safrole-tricarbonyl chromium(0) complex 12 was prepared and characterized. X-ray diffraction analyses of both complexes were determined. Based on the above data, an octahedral structure has been assigned to the new complex 13.
Straightforward access to novel mitochondriotropics derived from 2-arylethanol as potent and selective antiproliferative agents
Hicke, Francisco J.,Puerta, Adrián,Dini?, Jelena,Pe?i?, Milica,Padrón, José M.,López, óscar,Fernández-Bola?os, José G.
, (2021/12/01)
The necessity for developing novel cytostatic agents with improved activities and reduced side-effects to tackle cancer prompted us to investigate mitochondria-targeted compounds, an approach that is gaining attention for the selective transportation of cytotoxic agents. We envisioned the possibility of conjugating a phenethyl alcohol motif, decorated with a series of phenol-based substituents on the aryl moiety, with a triphenyl phosphonium scaffold (a mitochondria-directed vector), through a hydrocarbon chain of different lengths. Thus, such compounds that incorporate the phenethyl skeleton can be considered as masked phenolic compounds derived from relevant natural counterparts found in olive tree (e.g. tyrosol, hydroxytyrosol). Title compounds exhibited very strong in vitro antiproliferative activities against the panel of six human tumor cell lines tested, with GI50 values ranging from the nanomolar (0.026 ± 0.010 μM for 36) to the submicromolar range in most of the cases; this represents an improvement of up to 350-fold compared to classical chemotherapeutic agents, like 5-fluorouracil or cisplatin. Interestingly, decrease in the linker length led to an increase of GI50 values against non-tumor cells, thus allowing a remarkable improvement of selectivity (SI up to 269). The very promising antiproliferative activities prompted us to further investigate their behaviour against multidrug resistant cell lines (MDR). The results indicated a reduced sensitivity of the multidrug resistant cells to compounds, probably due to P-gp-mediated efflux of these antiproliferative agents. Interestingly, activities were completely restored to the same levels by co-administration of tariquidar, a well-known inhibitor of P-gp. Flow cytometry analysis on sensitive cell lines revealed a decrease in the percentage of cells in G1 phase accompanied by increase in S and G2/M phases. In addition, a significant increase in subG1 area, was observed. These results are compatible with the necrotic and apoptotic cell death detected in the Annexin V assay, and with the depolarization of the mitochondria membrane. Thus, the new mitochondriotropic agents reported herein can be considered as promising antiproliferative agents, endowed with remarkable potency and selectivity, including MDR cells, upon co-administration with a pump-efflux inhibitor.
Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors
Ahuja-Casarín, Ana I.,Merino-Montiel, Penélope,Vega-Baez, José Luis,Montiel-Smith, Sara,Fernandes, Miguel X.,Lagunes, Irene,Maya, Inés,Padrón, José M.,López, óscar,Fernández-Bola?os, José G.
, p. 138 - 146 (2020/11/27)
We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (
The total synthesis of berberine and selected analogues, and their evaluation as amyloid beta aggregation inhibitors
Tajiri, Misato,Yamada, Ryo,Hotsumi, Mayumi,Makabe, Koki,Konno, Hiroyuki
, (2021/02/26)
The total synthesis of berberine and selected analogues. And their evaluation as amyloid β (Aβ) aggregation inhibitors is described. The key step in the synthesis, the assembly of the berberine framework, was accomplished using an intermolecular Heck reaction. Berberine analog 17 incorporating a tertiary amine moiety showed good anti Aβ aggregation activity, water solubility, and almost no toxicity to nerve cells.
Process for preparing hydroxytyrosol
-
Paragraph 0050; 0075-0089, (2021/08/19)
The invention discloses a process for preparing hydroxytyrosol. According to the process, benzodioxole is used as a starting material, firstly, benzodioxole and ethylene oxide are subjected to a Friedel-Crafts alkylation reaction to prepare pepper ethanol, and then the pepper ethanol is subjected to a catalytic hydrolysis reaction to prepare hydroxytyrosol. The hydroxytyrosol preparation process disclosed by the invention has the characteristics of easily available and cheap raw materials, simple operation process, safety, environmental protection and the like.
Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides
Fang, Ping,Jiao, Ke-Jin,Liu, Dong,Ma, Hong-Xing,Mei, Tian-Sheng,Qiu, Hui
supporting information, p. 6520 - 6524 (2020/01/24)
A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which pro
Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids
Nishimoto, Saeko,Nakahashi, Hiromichi,Toyota, Masahiro
supporting information, (2020/11/13)
A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.
Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles
Xu, Xiaoming,Zhong, Ying,Xing, Qingzhao,Gao, Ziwei,Gou, Jing,Yu, Binxun
supporting information, p. 5176 - 5181 (2020/07/14)
The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)3 and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.
