112700-37-5Relevant academic research and scientific papers
Expanding the scope of oligo-pyrrolinone-pyrrolidines as protein-protein interface mimics
Raghuraman, Arjun,Xin, Dongyue,Perez, Lisa M.,Burgess, Kevin
, p. 4823 - 4833 (2013/07/05)
Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains
Novel β-dicarbonyl derivatives as inhibitors of aminopeptidase N (APN)
Ma, Chunhua,Li, Xiaoguang,Liang, Xuewu,Jin, Kang,Cao, Jiangying,Xu, Wenfang
, p. 4948 - 4952 (2013/09/02)
Most zinc metalloproteases are over-expressed in tumor cells and play a critical role in the genesis, development, and metastasis of tumors. Novel zinc binding groups (ZBGs) represent a novel strategy to obtain optimal potency and selectivity for zinc metalloproteases inhibitors. Here we described the design, synthesis, and biological studies of novel β-dicarbonyl derivatives as aminopeptidase N (APN/CD13) inhibitors. The results demonstrated that some compounds exhibited moderate to good inhibitory activities against APN with compound 5c being the most potent, suggesting that 5c could serve as new lead for the future APN inhibitor development. The results further confirm our design rationale of β-dicarbonyl moiety as a new ZBG, which may provide a new direction for the design and discovery of zinc metalloproteases inhibitors as new anti-tumor agents.
A synthetic approach to diverse 3-acyltetramic acids via O- to C-acyl rearrangement and application to the total synthesis of penicillenol series
Sengoku, Tetsuya,Nagae, Yuta,Ujihara, Yasuaki,Takahashi, Masaki,Yoda, Hidemi
scheme or table, p. 4391 - 4401 (2012/06/18)
For the efficient approach to medicinally important α-branched 3-acyltetramic acids, the key reaction of O- to C- acyl rearrangement using α-amino-acid-derived 4-O-acyltetramic acids was extensively examined in the presence of various metal salts. Use of
Synthesis of N-substituted 3-ammomethylidenetetramic acids
Pirc, Samo,Bevk, David,Jakse, Renata,Recnik, Simon,Golic, Ljubo,Golobic, Amalija,Meden, Anton,Stanovnik, Branko,Svete, Jurij
, p. 2969 - 2988 (2007/10/03)
(S)-3-(Dimethylamino)methylidene-5-benzyltetramic acid derivatives 4a and 4b were prepared in three steps from N-protected (S)-3-phenylalanines 1a and 1b, respectively. Similarly, N-[N-(benzyloxycarbonyl)glycyl]grycine (1c) was transformed into the enamitione 4c. Acid-catalysed coupling of enaminones 4a-c with aliphatic, aromatic, and heteroaromatic primary amines 5-34 afforded the corresponding N(3′)-substituted 3-aminomethylidenetetramic acid derivatives 35-64 in 29-96% yields. Georg Thieme Verlag Stuttgart.
Synthesis of acylated active methylene compounds with N-boc-L-phenylalanine and their heterocyclization, both achieved enantioselectively
Hamilakis, Stylianos,Tsolomitis, Athanase
, p. 325 - 329 (2007/10/03)
Three active methylene compounds, malononitrile, methyl cyanoacetate and Meldrum's acid, have been found to be acylated effectively with N-Boc-L-phenylalanine using carbonyldiimidazole (CDI) activation conditions. Two of the aminoacetyl derivatives isolat
Design of potential new HIV protease inhibitors: Enantioconvergent synthesis of new pyrrolidin-3-ol, and pyrrolidin-3-one peptide conjugates
Courcambeck,Bihel,De Michelis,Quelever,Kraus
, p. 1421 - 1430 (2007/10/03)
Novel potential HIV protease inhibitors are obtained by an enantioconvergent synthesis of mimicking Phe-Pro dipeptides, achieved through the coupling between Boc(L)Phe or Boc(L)Tyr and both enantiomers of syn-2-benzylpyrrolidin-3-ol and their correspondin
Synthesis of Chiral Urethane N-Alkoxycarbonyl Tetramic Acids from Urethane N-Carboxyanhydrides (UNCAs)
Fehrentz, Jean-Alain,Bourdel, Elisabeth,Califano, Jean-Christophe,Chaloin, Oliveir,Devin, Chantal,et al.
, p. 1557 - 1560 (2007/10/02)
The synthesis of chiral N-protected tetramic acid derivatives which are precursors of β-hydroxy γ-amino acid under mild conditions is described.Reaction of urethane-N-carboxyanhydrides (UNCAs) with Meldrum's acid in the presence of a tertiary amine, follo
Stereospecific Synthesis of N-Protected Statine and Its Analogues via Chiral Tetramic Acid
Jouin, Patrick,Castro, Bertrand,Nisato, Dino
, p. 1177 - 1182 (2007/10/02)
The condensation of a chiral N-protected amino acid with Meldrum's acid in the presence of isopropenyl chloroformate (IPCF) and of 4-N,N-dimethylaminopyridine (DMAP) has been examined.The cyclisation of the reaction product, by heating in an organic solve
