80909-58-6Relevant academic research and scientific papers
Synthesis of N-trifluoromethyl amides from carboxylic acids
Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
supporting information, p. 2245 - 2255 (2021/08/12)
Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
Design, synthesis and biological evaluation of cyclic angiotensin II analogues with 3,5 side-chain bridges: Role of C-terminal aromatic residue and ring cluster for activity and implications in the drug design of AT1 non-peptide antagonists
Roumelioti, Panagiota,Polevaya, Ludmila,Zoumpoulakis, Panagiotis,Giatas, Nektarios,Mutule, Ilze,Keivish, Tatjana,Zoga, Anastasia,Vlahakos, Demetrios,Iliodromitis,Kremastinos, Demetrios,Grdadolnik, Simona Golic,Mavromoustakos, Thomas,Matsoukas, John
, p. 2627 - 2633 (2007/10/03)
The novel amide linked Angiotensin II (ANG II) cyclic analogues: γ,ε-cyclo(3, 5)-[Sar1-Glu3-Lys5-Ile8] ANG II (I) and γ, ε-cyclo(3, 5)-[Sar1-Glu3-Lys5-Phe8] ANG II (II) have been designed, synthesized and bioassayed in anesthetized rabbits in order to unravel structural ring cluster characteristics important for receptor activation. Analogue I with Ile at position 8 was an inhibitor of Angiotensin II while analogue II with Phe at position 8 was found to be an agonist. Similar results were reported for cyclic compounds that have reversed the linking between positions 3 and 5. The overall results show that positions 3 and 5 do not govern the biological activity of the synthetic analogues. It also appears that the aromatic ring cluster (Tyr-His-Phe) in agonist peptides is an essential stereo-electronic feature for Angiotensin II to exert its biological activity. A non-peptide mimetic of ANG II, 1-[2′-[(N-benzyl)tetrazol-5-yl]biphenyl-4-yl]methyl]-2- hydroxymethylbenzimidazole (BZI8) has been designed and synthesized. This molecule is more rigid and much less active than AT1 non-peptide mimetic losartan probably because it lacks to mimic the orientation of tetrazole and the pharmacophore segments of butyl chain and imidazole ring.
Monofunctional electrophilic and nucleophilic derivatives of meso-tetraphenylporphyrin for attachment to peptides
Matthews,Pouton,Threadgill
, p. 1809 - 1811 (2007/10/02)
4-Nitrophenyl N-[4-(10,15,20-triphenylporphyrin-5-yl)phenyl]carbamate and 5-[4-(N-glycylamino)phenyl]-10,15,20-triphenylporphyrin have been synthesised from a readily prepared monofunctionalised porphyrin; they couple efficiently with the side-chains of e
