71639-13-9Relevant articles and documents
Synthesis and Biological Analysis of Anti-addiction Effect and Hepatotoxicity of Tow Baclofen Analogues Complexed with β-Cyclodextrin
Dib, Mohammed El Amine,El Ouar, Ibtissem,Keniche, Assia,Zeghina, Ibtissem
, p. 187 - 196 (2022/02/02)
Aim and Objective: The excessive consumption of alcohol and the installation of dependence is, in most cases, facilitated by favorable psychological factors that trigger and maintain the behavior of consumers. Examples more frequently encountered in individuals having difficulty with alcohol are, in particular: one or more anxiety disorders, deficits in the capacities to manage stress and anxiety. The main objective of this work was to study in vivo the anti-addiction effect and hepatotoxicity of tow baclofen analogues complexed with β-Cyclodextrin (βCD) on an alcohol-dependent rat model. Materials and Methods: The synthesis of two analogues, ABF1 and ABF2, close to baclofen was reported. The structural determination of the two compounds was confirmed by NMR and IR analysis. The complexation of analogues with β-Cyclodextrin (βCD) was performed in water at room temperature (25 °C). The interactions of ABF with β-Cyclodextrin, and the stability constant (Ka) of the inclusion complex formed between them were investigated by using UV-visible spectroscopy. The biological effects of baclofen and the two analogues on alcohol dependence were studied in wistar rats. The anti-addiction effect of the analogues was tested by measuring the alcohol intake and the variation of the animal behaviour. The toxicity of the compounds was also analysed on liver injury markers. Results: The amino-3-phenylbutanoic acid (ABF1) and 3,4,5-trihydroxy-N-(methyl-2-acetate) benzamide (ABF2) were synthesized. The complexation of both analogues of baclofen (BF) with β-cyclodextrin (βCD) (ABF-βCD) was realized and confirmed by the stability constant of the inclusion complex (Ka) and Job’s method. The evaluation of anti-addiction activity in vivo showed that ABF1-βCD inhibits the consumption of alcohol at doses equivalent to those of baclofen. Both baclofen analogues have shown an anxiolytic effect. Regarding the toxicity of the two compounds, our results showed that ABF1-βCD has less toxic effect than baclofen; it reduces the activity of ALT and AST enzymes. Histologically, ABF1-βCD has no effect on the liver structure and has a protective effect against lesions alcohol-induced liver disease. Conclusion: Therefore, it can be suggested that ABF1 analogue combined with β-Cyclodextrin can be used as a treatment for alcohol dependence. Further clinical works are needed to confirm its effectiveness.
Application of pentacoordinated spirophosphorane as a new organocatalyst for the Michael addition reaction
Wang, Peipei,Li, Wanjiao,Han, Kehui,Guo, Yanchun,Zhao, Yufen,Cao, Shuxia
, p. 936 - 947 (2021/07/09)
Pentacoordinated spirophosphorane as a simple, effective and novel organocatalyst for the Michael addition reaction has been investigated. The bisaminoacyl spirophosphorane that possessed a thiourea-like moiety and an amine group was applied to the Michae
Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles
Pirola, Margherita,Faverio, Chiara,Orlandi, Manuel,Benaglia, Maurizio
supporting information, p. 10247 - 10250 (2021/06/18)
A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).
Enantioselective Michael Addition Reaction Catalysed by Enantiopure Binuclear Nickel(II) Close-Ended Helicates
Arunachalam, Rajendran,Chinnaraja, Eswaran,Natarajan, Ramalingam,Samanta, Krishanu,Subramanian, Palani S.
, (2020/02/04)
The enantiopure Ni(II) helicates [Ni2L1RR.Cl2] (1), [Ni2L1SS.Cl2] (1′), [Ni2L2RR.Cl2] (2), [Ni2L2SS.Cl2] (2′) were synthesized by one-pot self-assembly technique from R-(+)- or S-(?)-1,1′-binaphthyl-2,2′-diamine, with 4-methyl-2,6-diformyl phenol or 4-tert-butyl-2,6-diformyl phenol and nickel salts. This binuclear double stranded Ni(II) helicates were characterized by ESI-MS, IR and single crystal X-ray structure wherever applicable. The extensive chiroptical studies suggest that the complexes are enantiopure in nature. The chirality transfer from ligand L1RR & L2RR to Ni(II) metal centre produced ΔΔ geometrical chirality, while their enantiomeric counterpart L1SS & L2SS produced ΛΛ chirality in their respective complexes.These enantiopure helicates were applied as catalysts in asymmetric Michael addition of 1,3-dicarbonyl compounds with β-nitrostyrene to produce nitroalkanes in good yield (96–98%) and ee (78–94%). (Figure presented.).
Tandem Ring Opening/Cyclization of trans-2-Aryl-3-nitrocyclopropane-1,1-dicarboxylates with 2-Aminopyridines: Access to Pyrido[1,2-a]pyrimidin-4-one Derivatives
Selvi, Subramani,Srinivasan, Kannupal
, p. 5644 - 5648 (2017/10/13)
A tandem ring-opening/cyclization reaction of trans-2-aryl-3-nitrocyclopropane-1,1-dicarboxylates with 2-aminopyridines was discovered. The reaction did not require the assistance of any catalyst and proceeded more efficiently in water than in organic solvents. This strategy afforded pyrido[1,2-a]pyrimidin-4-one derivatives having a carboxylate group at C3 in 62–90 % yields.
Supported and Unsupported Chiral Squaramides as Organocatalysts for Stereoselective Michael Additions: Synthesis of Enantiopure Chromenes and Spirochromanes
Andrés, José M.,Losada, Jorge,Maestro, Alicia,Rodríguez-Ferrer, Patricia,Pedrosa, Rafael
, p. 8444 - 8454 (2017/08/23)
Novel supported chiral bifunctional squaramides have been easily prepared starting from diamines derived from natural amino acids and commercially available aminoalkyl polystyrene resins. These squaramides behave as excellent stereoselective recoverable o
A thiourea-functionalized metal-organic macrocycle for the catalysis of Michael additions and prominent size-selective effect
Yang, Lu,Zhao, Liang,Zhou, Zhen,He, Cheng,Sun, Hui,Duan, Chunying
supporting information, p. 4086 - 4092 (2017/03/30)
A discrete tetranuclear thiourea-based metal-organic macrocycle (MOM) with a large size was constructed by a well-designed organic ligand and nickel(ii) ions via self-assembly. Incorporating thiourea groups as hydrogen-bond donors into a metal-organic com
Helical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C-C Bond-Forming Reactions
Bécart, Diane,Diemer, Vincent,Salaün, Arnaud,Oiarbide, Mikel,Nelli, Yella Reddy,Kauffmann, Brice,Fischer, Lucile,Palomo, Claudio,Guichard, Gilles
supporting information, p. 12524 - 12532 (2017/09/23)
Substantial progress has been made toward the development of metal-free catalysts of enantioselective transformations, yet the discovery of organic catalysts effective at low catalyst loadings remains a major challenge. Here we report a novel synergistic
Divergent Reactivity of Nitrocyclopropanes with Huisgen Zwitterions and Facile Syntheses of 3-Alkoxy Pyrazolines and Pyrazoles
Yang, Changjiang,Liu, Wei,He, Zijian,He, Zhengjie
supporting information, p. 4936 - 4939 (2016/10/18)
A novel annulation reaction of trans-2-substituted-3-nitrocyclopropane-1,1-carboxylates with in situ generated Huisgen zwitterions is reported, providing facile synthesis of 3-alkoxy pyrazolines in good yields and high diastereoselectivities. This reactio
Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions
Andrés, José M.,Ceballos, Miriam,Maestro, Alicia,Sanz, Isabel,Pedrosa, Rafael
, p. 628 - 635 (2016/07/06)
The catalytic activity of different supported bifunctional thioureas on sulfonylpolystyrene resins has been studied in the nitro-Michael addition of different nucleophiles to trans-β-nitrostyrene derivatives. The activity of the catalysts depends on the l
