676324-23-5Relevant academic research and scientific papers
New chiral amino alcohol ligands for catalytic enantioselective addition of diethylzincs to aldehydes
Sappino, Carla,Mari, Alessandra,Mantineo, Agnese,Moliterno, Mauro,Palagri, Matteo,Tatangelo, Chiara,Suber, Lorenza,Bovicelli, Paolo,Ricelli, Alessandra,Righi, Giuliana
, p. 1860 - 1870 (2018/03/23)
A study aimed at the synthesis and structure optimization of new, efficient, optically active β-amino alcohol ligands with a structure suitable for immobilization on magnetite nanoparticles has been carried out. The optimized homogeneous amino alcohol catalysts 13a and 13b, the chirality of which arises from the Sharpless epoxidation of suitable allyl alcohols, were tested by employing the well-established enantioselective amino alcohol-promoted addition of diethylzinc to benzaldehyde, giving the corresponding benzyl alcohol with nearly quantitative yield and ee = 95%. Then, their broad applicability as chiral catalysts was evaluated by carrying out the same reaction on a family of aldehydes, including variously substituted aromatic ones as well as an aliphatic analogue. The results have confirmed the validity of the fine-tuning process performed on ligands 13a and 13b. In fact, both exhibited excellent catalytic activity as demonstrated by the chemical yields and ee obtained from all the tested aldehydes, almost independent of the position and type of substitution in the aromatic ring.
Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate
Nishizawa, Rena,Nishiyama, Toshihiko,Hisaichi, Katsuya,Minamoto, Chiaki,Matsunaga, Naoki,Takaoka, Yoshikazu,Nakai, Hisao,Jenkinson, Stephen,Kazmierski, Wieslaw M.,Tada, Hideaki,Sagawa, Kenji,Shibayama, Shiro,Fukushima, Daikichi,Maeda, Kenji,Mitsuya, Hiroaki
, p. 1141 - 1145 (2011/04/16)
Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compo
Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5- dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist
Nishizawa, Rena,Nishiyama, Toshihiko,Hisaichi, Katsuya,Minamoto, Chiaki,Murota, Masayuki,Takaoka, Yoshikazu,Nakai, Hisao,Tada, Hideaki,Sagawa, Kenji,Shibayama, Shiro,Fukushima, Daikichi,Maeda, Kenji,Mitsuya, Hiroaki
, p. 4028 - 4042 (2011/08/21)
Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented.
Selective C-2 opening of 2,3-epoxyesters with HN3-amine system: A viable route to β-hdyroxy-α-amino acids
Saito,Takahashi,Ishikawa,Moriwake
, p. 667 - 670 (2007/10/02)
The combination of hydrogen azide with amines has proven to effect the C-2 opening of 2,3-epoxyester with high regioselectivity uniformly for trans-epoxyesters and depending on their structures for cis-2,3-epoxyesters.
