57965-29-4Relevant articles and documents
The C-F bond as a tool in the conformational control of amides
Briggs, Caroline R.S.,O'Hagan, David,Howard, Judith A.K.,Yufit, Dmitrii S.
, p. 9 - 13 (2003)
The conformation of 2-fluoro-N-(2-fluoroethyl)-propionamide 4 in the solid state indicates the influence of both a β-fluorine-amide gauche effect and an α-fluoroamide effect. The structure reveals the influence of two recently observed stereoelectronic effects associated with the C-F bond, which has resulted in the successful prediction of the solid state conformation of amide 4. A gauche relationship (-69.9°) was observed for atoms N(1)-C(4)-C(5)-F and a syn planar (2.0°) relationship was observed for N(1)-C(3)-C(2)-F. The paper demonstrates the predictive power of using the C-F bond as a tool in influencing the conformation of amides and peptides.
Prototypic 18F-Labeled Argininamide-Type Neuropeptide Y Y1R Antagonists as Tracers for PET Imaging of Mammary Carcinoma
Keller, Max,Maschauer, Simone,Brennauer, Albert,Tripal, Philipp,Koglin, Norman,Dittrich, Ralf,Bernhardt, Günther,Kuwert, Torsten,Wester, Hans-Jürgen,Buschauer, Armin,Prante, Olaf
supporting information, p. 304 - 309 (2017/03/17)
The neuropeptide Y (NPY) Y1 receptor (Y1R) selective radioligand (R)-Nα-(2,2-diphenylacetyl)-Nω-[4-(2-[18F]fluoropropanoylamino)butyl]aminocarbonyl-N-(4-hydroxybenzyl)argininamide ([18F]23), derived from the high-affinity Y1R antagonist BIBP3226, was developed for imaging studies of Y1R-positive tumors. Starting from the argininamide core bearing amine-functionalized spacer moieties, a series of fluoropropanoylated and fluorobenzoylated derivatives was synthesized and studied for Y1R affinity. The fluoropropanoylated derivative 23 displayed high affinity (Ki = 1.3 nM) and selectivity toward Y1R. Radiosynthesis was accomplished via 18F-fluoropropanoylation, yielding [18F]23 with excellent stability in mice; however, the biodistribution study revealed pronounced hepatobiliary clearance with high accumulation in the gall bladder (>100 %ID/g). Despite the unfavorable biodistribution, [18F]23 was successfully used for imaging of Y1R positive MCF-7 tumors in nude mice. Therefore, we suggest [18F]23 as a lead for the design of PET ligands with optimized physicochemical properties resulting in more favorable biodistribution and higher Y1R-dependent enrichment in mammary carcinoma.
Synthesis and antiviral activity of substituted bisaryl amide compounds as novel influenza virus inhibitors
Hao, Lan-Hu,Li, Yan-Ping,He, Wei-Ying,Wang, Hui-Qiang,Shan, Guang-Zhi,Jiang, Jian-Dong,Li, Yu-Huan,Li, Zhuo-Rong
, p. 117 - 124 (2012/11/07)
The influenza virus is a persistent cause of mortality and morbidity on an annual basis and thus presents itself as an important target for pharmaceutical investigation. In this work, substituted bisaryl amide compounds were found to be a new class of potential anti-influenza agents, and a series of substituted bisaryl amide compounds were synthesised and evaluated for their anti-influenza virus activities. The analysis of the results produced a preliminary structure-activity relationship study (SAR). Compounds 1a, 1g, 1h, 1j, 1l and 1n exhibited clear antiviral activities against the influenza A (A/Guangdong Luohu/219/2006, H1N1) virus with 50% inhibitory concentrations (IC50) for virus growth ranging from 12.5 to 59.0 μM. Specifically, compound 1j also possessed antiviral activity against both oseltamivir-resistant influenza (A/Jinnan/15/2009) virus and influenza B (B/Jifang/13/97) virus with IC 50 values of 9.2 μM and 21.4 μM, respectively. Compound 1j is thus worth further investigation as an anti-influenza virus candidate.
