1205-08-9Relevant articles and documents
Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids
Müller, Erno,Péczely, Gábor,Skoda-F?ldes, Rita,Takács, Eszter,Kokotos, George,Bellis, Evagelos,Kollár, László
, p. 797 - 802 (2005)
Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF6] or [bmim][BF4] (where bmim=1-butyl-3-methyl- imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity.
Synthesis and docking studies of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamide analogues as potential alkaline phosphatase inhibitors
Iqbal, Zafar,Iqbal, Ambreen,Ashraf, Zaman,Latif, Muhammad,Hassan, Mubashir,Nadeem, Humaira
, p. 646 - 654 (2019)
A series of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i were synthesized as alkaline phosphatase inhibitors. The intermediate 5-substituted 1,3,4-oxadiazole-2-thione 4 was synthesized starting with hippuric acid. Hippuric acid in the first step was converted into corresponding methyl ester 2 which upon reaction with hydrazine hydrate furnished the formation of hydrazide 3. The hippuric acid hydrazide was then cyclized into 5-substituted 1,3,4-oxadiazole-2-thione 4. The intermediate 4 was then reacted with alkyl or aryl halides 5a–5i to afford the title compounds N-(5-(methylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i. The bioassay results showed that compounds 6a–i exhibited good to excellent alkaline phosphatase inhibitory activity. The most potent activity was exhibited by the compound 6i having IC50 value 0.420 μM, whereas IC50 value of standard (KH2PO4) was 2.80 μM. Molecular docking studies was performed against alkaline phosphatase enzyme (PDBID 1EW2) to check binding affinity of the synthesized compounds 6a–i against target protein. The docking results showed that three compounds 6c, 6e, and 6i have maximum binding interactions with binding energy values of ?8 kcal/mol. The compound 6i displayed the interactions of oxadiazole ring nitrogen with amino acid His265 having a binding distance 2.13 ?. It was concluded from our results that synthesized compounds, especially compound 6i may serve as lead structure to design more potent inhibitors of human alkaline phosphatase.
The influence of some aliphatic alcohols on the enzymic hydrolysis of methyl hippurate.
Dickinson,Rees,Collett
, p. 631 - 636 (1972)
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Stabilization of the Max Homodimer with a Small Molecule Attenuates Myc-Driven Transcription
Struntz, Nicholas B.,Chen, Andrew,Deutzmann, Anja,Wilson, Robert M.,Stefan, Eric,Evans, Helen L.,Ramirez, Maricela A.,Liang, Tong,Caballero, Francisco,Wildschut, Mattheus H.E.,Neel, Dylan V.,Freeman, David B.,Pop, Marius S.,McConkey, Marie,Muller, Sandrine,Curtin, Brice H.,Tseng, Hanna,Frombach, Kristen R.,Butty, Vincent L.,Levine, Stuart S.,Feau, Clementine,Elmiligy, Sarah,Hong, Jiyoung A.,Lewis, Timothy A.,Vetere, Amedeo,Clemons, Paul A.,Malstrom, Scott E.,Ebert, Benjamin L.,Lin, Charles Y.,Felsher, Dean W.,Koehler, Angela N.
, p. 711 - 14,723 (2019)
The transcription factor Max is a basic-helix-loop-helix leucine zipper (bHLHLZ) protein that forms homodimers or interacts with other bHLHLZ proteins, including Myc and Mxd proteins. Among this dynamic network of interactions, the Myc/Max heterodimer has
Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)
Brittain, William D. G.,Cobb, Steven L.
supporting information, p. 5793 - 5798 (2021/08/01)
This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite
Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao
supporting information, p. 2713 - 2718 (2021/06/25)
In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.
