5381-84-0Relevant academic research and scientific papers
Substrate and inhibitor selectivity, and biological activity of an epoxide hydrolase from Trichoderma reesei
de Oliveira, Gabriel S.,Adriani, Patricia P.,Wu, Hao,Morisseau, Christophe,Hammock, Bruce D.,Chambergo, Felipe S.
, p. 371 - 379 (2018/11/23)
Epoxide hydrolases (EHs) are present in all living organisms and catalyze the hydrolysis of epoxides to the corresponding vicinal diols. EH are involved in the metabolism of endogenous and exogenous epoxides, and thus have application in pharmacology and biotechnology. In this work, we describe the substrates and inhibitors selectivity of an epoxide hydrolase recently cloned from the filamentous fungus Trichoderma reesei QM9414 (TrEH). We also studied the TrEH urea-based inhibitors effects in the fungal growth. TrEH showed high activity on radioative and fluorescent surrogate and natural substrates, especially epoxides from docosahexaenoic acid. Using a fluorescent surrogate substrate, potent inhibitors of TrEH were identified. Interestingly, one of the best compounds inhibit up to 60% of T. reesei growth, indicating an endogenous role for TrEH. These data make TrEH very attractive for future studies about fungal metabolism of fatty acids and possible development of novel drugs for human diseases.
Synthesis of heterodinuclear hemisalen complexes on a hexaarylbenzene scaffold and their application for the cross-pinacol coupling reaction
Miyasaka, Akihiro,Amaya, Toru,Hirao, Toshikazu
, p. 1615 - 1621 (2014/03/21)
Intermolecular cross-pinacol coupling reaction between aliphatic and aromatic aldehydes by using heterodinuclear hemisalen complexes 1cis with vanadium(V) and titanium(IV) on a hexaarylbenzene scaffold is reported. Our ligand design is based on the individual activation of two aldehydes by vanadium and titanium, which are positioned with a suitable space on the rigid scaffold. Ligands such as 1cis were synthesized by Diels-Alder addition and decarbonylation reaction, followed by condensation of dialdehyde 3cis with various aminophenols. The influence of the substituents on the ligands on the pinacol coupling reaction was investigated. As a result, the reductive coupling reaction between aliphatic and aromatic aldehydes by using a catalytic amount of 1cis in the presence of Me3SiCl and Zn provided the corresponding cross-coupled 1,2-diol in good yields with high cross-selectivity. Working together: Dihemisalen ligands on a hexaaryl benzene scaffold were designed and the heterodinuclear complexes 1cis with vanadium(V) and titanium(IV) were synthesized from the corresponding disalicylaldehyde compound (see scheme). By using the heterodinuclear catalysts, the selective intermolecular cross-pinacol coupling reaction between aliphatic and aromatic aldehydes is demonstrated. Copyright
Reduction of carbonyl compounds to their corresponding of alcohols with [Zn(BH4)2(2-MeOpy)] & [Zn(BH4) 2(2-Mepy)] as new reducing agents (a comparison study)
Khezri, Behrooz,Ghadimi, Farnaz Najaf,Karashi, Chonur Nevisandeh,Setamdideh, Davood
, p. 623 - 629 (2013/11/06)
The reduction of a variety of carbonyl compounds was efficiently carried out with [Zn(BH4)2(2-MeOpy)] and [Zn(BH4) 2(2-Mepy)] as new reducing agents. The reduction reactions were performed to give the corresponding alcohols derivatives in perfect yields.
Zn(BH4)2/Al2O3: A new synthetic method for the efficient and convenient reduction of organic carbonyl compounds to their corresponding alcohols
Setamdideh, Davood,Khezri, Behrooz,Rahmatollahzadeh, Mehdi
, p. 1 - 13 (2013/08/25)
Zn(BH4)2 (0.5-2 mmol) in the presence of Al 2O3 (1 mmol) reduces a variety of organic carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α,β-unsaturated carbonyl compounds to their corresponding alcohols. The reduction reactions were realized in THF at room temperature affording high to excellent yields of the products. The chemoselective reduction of aldehydes over ketones was successfully accomplished with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was successfully accomplished.
Reduction of α-diketones and acyloins with Zn(BH4) 2/ZrCl4 to their corresponding vicinal diols
Kamari, Rasol,Setamdideh, Davood
, p. 497 - 499 (2013/11/06)
α-diketones and acyloins are reduced to the corresponding vicinal diols with Zn(BH4)2/ZrCl4 system in THF at room temperature.
Convenient reduction of carbonyl compounds to their corresponding alcohols with NaBH4/(NH4)2C2O4 system
Setamdideh, Davood,Ghahremani, Sahar
experimental part, p. 91 - 97 (2012/07/14)
Sodium borohydride (0.4-1.5 equivalents) in the presence of ammonium oxalate (0.2 equivalents) reduces varieties of organic carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α,β- unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in acetonitrile in high to excellent yields of products. The chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was achieved successfully with this reducing system.
Mild and efficient reduction of organic carbonyl compounds to their corresponding alcohols with Zn(BH4)2 under protic condition
Setamdideh, Davood,Khezri, Behrooz,Rahmatollahzadeh, Mehdi,Poramjad, Avat Ali
experimental part, p. 3591 - 3596 (2012/07/28)
Zn(BH4)2 (1-2 mmol) in wet THF or CH3CN reduces varieties of organic carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α, β-unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in wet THF at room temperature in high to excellent yields of products. The chemoselective reduction of aldehydes over ketones was accomplished successfully. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was accomplished successfully with this reducing system.
TiO2 as an efficient catalytic surface for reduction of carbonyl compounds with NaBH4 under solvent-free, solid-gel and microwave irradiation
Setamdideh, Davood,Karimi, Zahra,Rahimi, Fatemeh
experimental part, p. 1621 - 1634 (2012/06/16)
Structurally different carbonyl compounds such as aldehydes, ketones, α,β-unsaturated enals and enones, α-diketones and acyloins were reduced efficiently by NaBH4/TiO2 system under solvent-free, solid-gel and microwave irradiation. The chemoselective reduction of aldehydes over ketones was achieved successfully by NaBH4/TiO 2 system at solvent-free condition. In addition, regioselectivity and exclusive 1,2-reduction of Conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was accomplished successfully with this reducing system.
Wet SiO2 as a suitable media for fast and efficient reduction of carbonyl compounds with NABH3CN under solvent-free and acid-free conditions
Kouhkan, Mehri,Zeynizadeh, Behzad
experimental part, p. 2961 - 2966 (2012/04/17)
Reduction of carbonyl compounds such as aldehydes, ketones, α,β-unsaturated enals and enones, α-diketones and acyloins was carried out readily with NaBH3CN in the presence of wet SiO2 as a neutral media. The reactions were performed at solvent-free conditions in oil bath (70-80 °C) or under microwave irradiation (240 W) to give the product alcohols in high to excellent yields. Regioselective 1,2-reduction of conjugated carbonyl compounds took place in a perfect selectivity without any side product formation.
Modular asymmetric synthesis of 1,2-diols by single-pot allene diboration/hydroboration/cross-coupling
Pelz, Nicholas F.,Morken, James P.
, p. 4557 - 4559 (2007/10/03)
Chiral allyl vinyl boronates are generated by catalytic enantioselective diboration of prochiral allenes. They may then be reacted, in situ, with a hydroborating reagent to form a novel triboron intermediate. The least hindered and most reactive C-B bond
