99281-90-0Relevant academic research and scientific papers
Design, synthesis and cytotoxic evaluation of a library of oxadiazole-containing hybrids
Barrionuevo, Elizabeth,Bellizzi, Yanina,Blank, Viviana C.,Boggián, Dora B.,Camacho, Cristián M.,Mata, Ernesto G.,Pizzio, Marianela G.,Roces, David L.,Roguin, Leonor P.
, p. 29741 - 29751 (2021/10/07)
The development of hybrid compounds led to the discovery of new pharmacologically active agents for some of the most critical diseases, including cancer. Herein, we describe a new series of oxadiazole-containing structures designed by a molecular hybridiz
Dehydration of Chiral α-Amides to Chiral α-Nitriles Under the Appel Reaction Conditions
Shekharappa,Roopesh Kumar,Srinivasulu,Sureshbabu, Vommina V.
, p. 497 - 502 (2020/07/30)
An efficient synthesis of Nα-protected amino nitriles from Nα-protected amino acid amides employing Ph3P, I2 and NMM was described. Various amino acid amides, protected by Fmoc, Z and Boc were conveniently conve
Optimization strategy of single-digit nanomolar cross-class inhibitors of mammalian and protozoa cysteine proteases
Cianni, Lorenzo,Rocho, Fernanda dos Reis,Rosini, Fabiana,Bonatto, Vinícius,Ribeiro, Jean F.R.,Lameira, Jer?nimo,Leit?o, Andrei,Shamim, Anwar,Montanari, Carlos A.
, (2020/07/07)
Cysteine proteases (CPs) are involved in a myriad of actions that include not only protein degradation, but also play an essential biological role in infectious and systemic diseases such as cancer. CPs also act as biomarkers and can be reached by active-
N-Sulfonyl dipeptide nitriles as inhibitors of human cathepsin S: In silico design, synthesis and biochemical characterization
Lemke, Carina,Cianni, Lorenzo,Feldmann, Christian,Gilberg, Erik,Yin, Jiafei,dos Reis Rocho, Fernanda,de Vita, Daniela,Bartz, Ulrike,Bajorath, Jürgen,Montanari, Carlos A.,Gütschow, Michael
, (2020/08/07)
A library of cathepsin S inhibitors of the dipeptide nitrile chemotype, bearing a bioisosteric sulfonamide moiety, was synthesized. Kinetic investigations were performed at four human cysteine proteases, i.e. cathepsins S, B, K and L. Compound 12 with a t
Synthesis and structure-activity relationship of nitrile-based cruzain inhibitors incorporating a trifluoroethylamine-based P2 amide replacement
Gomes, Juliana C.,Cianni, Lorenzo,Ribeiro, Jean,dos Reis Rocho, Fernanda,da Costa Martins Silva, Samelyn,Batista, Pedro Henrique Jatai,Moraes, Carolina Borsoi,Franco, Caio Haddad,Freitas-Junior, Lucio H.G.,Kenny, Peter W.,Leit?o, Andrei,Burtoloso, Antonio C.B.,de Vita, Daniela,Montanari, Carlos A.
, (2019/09/30)
The structure-activity relationship for nitrile-based cruzain inhibitors incorporating a P2 amide replacement based on trifluoroethylamine was explored by deconstruction of a published series of inhibitors. It was demonstrated that the P3 biphenyl substituent present in the published inhibitor structures could be truncated to phenyl with only a small loss of affinity. The effects of inverting the configuration of the P2 amide replacement and linking a benzyl substituent at P1 were observed to be strongly nonadditive. We show that plotting affinity against molecular size provides a means to visualize both the molecular size efficiency of structural transformations and the nonadditivity in the structure-activity relationship. We also show how the relationship between affinity and lipophilicity, measured by high-performance liquid chromatography with an immobilized artificial membrane stationary phase, may be used to normalize affinity with respect to lipophilicity.
METHOD FOR PRODUCING CHIRAL AMINONITRILES
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Paragraph 0091; 0092, (2019/07/03)
The invention relates to a method for preparing an N-acyl- or N-sulfonyl-α-aminonitrile, comprising the following steps: a) condensation of an N-acyl- or N-sulfonyl-α-aminoaldehyde with hydroxylamine to give an aldoxime, and b) dehydration of the aldoxime
Total Synthesis of the Cyclic Dodecapeptides Wewakazole and Wewakazole B
Inman, Martyn,Dexter, Hannah L.,Moody, Christopher J.
, p. 3454 - 3457 (2017/07/15)
The cyclic dodecapeptides wewakazole and wewakazole B have been synthesized by a divergent strategy via a common tris-proline containing oxazole octapeptide and two separate bis-oxazole containing tetrapeptide units, followed by peptide coupling and macro
One-pot conversion of aldehydes to nitriles mediated by TiCl4
Leggio, Antonella,Belsito, Emilia Lucia,Gallo, Sonia,Liguori, Angelo
supporting information, p. 1512 - 1514 (2017/03/23)
A simple and convenient one-pot synthesis of nitriles from the corresponding aliphatic and aromatic aldehydes has been developed. The titanium tetrachloride assisted reaction was conducted in pyridine under mild conditions using various types of aldehyde precursors and gave the corresponding nitriles in excellent yields. The application of the adopted protocol to isolated aldoxime intermediates provided the corresponding nitriles with yields comparable to those using the one-pot procedure.
Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin
Rommelmann, Philipp,Betke, Tobias,Gr?ger, Harald
supporting information, p. 1521 - 1527 (2017/10/25)
An alternative route toward enantiomerically highly enriched N-acyl amino nitriles based on the Cu(OAc)2-catalyzed dehydration of aldoximes, which are readily available from N-acyl l- or d-α-amino aldehydes through condensation with hydroxylamine, has been developed. The desired products were obtained with high conversion and in enantiomeric excesses of 97-99% ee. Furthermore, this method has been applied in the synthesis of an N-chloroacetylated 2-cyanopyrrolidine, which represents a building block for the synthesis of Vildagliptin.
Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source
An, Xiao-De,Yu, Shouyun
supporting information, p. 5064 - 5067 (2015/11/03)
The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and α,β-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.
