56553-60-7Relevant articles and documents
Gribble, G. W.,Ferguson, D. C.
, (1975)
Synthesis from (+)-α-pinene of optically active macrocycles containing cyclobutane, ester, azine, or hydrazide groups
Ishmuratov,Mingaleeva,Shakhanova,Muslukhov,Yakovleva,Botsman,Tolstikov
, p. 210 - 214 (2011)
Optically active symmetric macrocyclic diesterazines and diesterdihydrazides were synthesized efficiently from the available natural monoterpene (+)-α-pinene (de 50%) using a [2+1]-reaction of 1'-[(1S,3S)-3-(2-hydroxyethyl)-2,2-dimethylcyclobutyl]ethanone and glutaric and adipic acid chlorides followed by [1+1]-condensation of the intermediate diketodiesters with hydrazine hydrate or glutaric acid dihydrazide.
Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction
Sridharan, Vellaisamy,Menendez, J. Carlos
, p. 4303 - 4306 (2008)
(Chemical Equation Presented) The cerium(IV) ammonium nitrate (CAN)-catalyzed sequential, one-pot reaction between alkylamines, β-ketoesters, and chalcones afforded cis-4,6-disubstituted 2-alkylaminocyclohexene-1-carboxylic esters with complete diastereoselectivity. The carbon-carbon double bond of these compounds was reduced with sodium triacetoxyborohydride, again with complete diastereoselectivity. This novel two-step route allows the transformation of very simple acyclic starting materials into tetrasubstituted cyclohexane derivatives bearing four functional groups, including a cis-β-aminoester moiety, and generates four stereocenters, three of which are adjacent and one of which is quaternary.
Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D
Mock, Elliot D.,Kotsogianni, Ioli,Driever, Wouter P. F.,Fonseca, Carmen S.,Vooijs, Jelle M.,Den Dulk, Hans,Van Boeckel, Constant A. A.,Van Der Stelt, Mario
, p. 481 - 515 (2021/02/05)
N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.
Low-cost method preparation for doxazosin mesylate controlled release tablets
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Paragraph 0017; 0018, (2019/07/01)
The invention relates to a preparation method of doxazosin mesylate controlled release tablets for treating urination disorder caused by prostatic hyperplasia, and belongs to the field of medicines. The invention provides a low-cost preparation method for doxazosin mesylate controlled release tablets.