14328-63-3Relevant articles and documents
Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates
Bischoff, Amanda J.,Nelson, Brandon M.,Niemeyer, Zachary L.,Sigman, Matthew S.,Movassaghi, Mohammad
, p. 15539 - 15547 (2017)
The bis(pyridine)silver(I) permanganate promoted hydroxylation of diketopiperazines has served as a pivotal transformation in the synthesis of complex epipolythiodiketopiperazine alkaloids. This late-stage C-H oxidation chemistry is strategically critical to access N-acyl iminium ion intermediates necessary for nucleophilic thiolation of advanced diketopiperazines en route to potent epipolythiodiketopiperazine anticancer compounds. In this study, we develop an informative mathematical model using hydantoin derivatives as a training set of substrates by relating the relative rates of oxidation to various calculated molecular descriptors. The model prioritizes Hammett values and percent buried volume as key contributing factors in the hydantoin series while correctly predicting the experimentally observed oxidation sites in various complex diketopiperazine case studies. Thus, a method is presented by which to use simplified training molecules and resulting correlations to explain and predict reaction behavior for more complex substrates.
A class of nitrogen-containing heterocyclic butane framework of non-natural amino acid derivative and its synthesis method (by machine translation)
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Paragraph 0043-0045, (2019/03/26)
The invention belongs to the technical field of chemical synthesis, in particular discloses a containing azetidine skeleton of the synthesis method of the non-natural amino acid derivatives, its target product non-natural amino acid derivatives of the formula such as the specification of the Chinese (I), (II), (III), (IV) and (V) as shown in the, in the formula compound is a nitrogen-containing heterocyclic butane framework of non-naturalα-,β- Andγ- Amino acid derivatives, nitrogen atom are 2 - pyridine carboxylic acid protection; carboxyl methyl esterification; formula (I) in order to contain the azetidine framework of non-naturalα- Amino acid derivatives; (II) for the formula containing azetidine bridge ring skeleton of non-naturalα- Amino acid derivatives, wherein n=1 or 2; type (III) is a nitrogen-containing heterocyclic butane and ring skeleton of non-naturalα- Amino acid derivatives; formula (IV) is a nitrogen-containing heterocyclic butane bridge ring skeleton of non-naturalβ- Amino acid derivatives; type (V) is a nitrogen-containing heterocyclic butane and ring skeleton of non-naturalγ- Amino acid derivatives. The experiment of this invention result proves that: the compounds have potential hypolipidemic activity. (by machine translation)
Structure-guided design and optimization of dipeptidyl inhibitors of norovirus 3CL protease. Structure-activity relationships and biochemical, X-ray crystallographic, cell-based, and in vivo studies
Galasiti Kankanamalage, Anushka C.,Kim, Yunjeong,Weerawarna, Pathum M.,Uy, Roxanne Adeline Z.,Damalanka, Vishnu C.,Mandadapu, Sivakoteswara Rao,Alliston, Kevin R.,Mehzabeen, Nurjahan,Battaile, Kevin P.,Lovell, Scott,Chang, Kyeong-Ok,Groutas, William C.
, p. 3144 - 3155 (2015/04/27)
Norovirus infection constitutes the primary cause of acute viral gastroenteritis. There are currently no vaccines or norovirus-specific antiviral therapeutics available for the management of norovirus infection. Norovirus 3C-like protease is essential for viral replication, consequently, inhibition of this enzyme is a fruitful avenue of investigation that may lead to the emergence of antinorovirus therapeutics. We describe herein the optimization of dipeptidyl inhibitors of norovirus 3C-like protease using iterative SAR, X-ray crystallographic, and enzyme and cell-based studies. We also demonstrate herein in vivo efficacy of an inhibitor using the murine model of norovirus infection.
