109837-32-3Relevant articles and documents
L-Proline derived nitrogenous steroidal systems: An asymmetric approach to 14-azasteroids
Singh, Ritesh,Panda, Gautam
, p. 19533 - 19544 (2013)
An efficient chiral pool approach using l-proline to access 14-azasteroids under mild reaction conditions has been described. The key step involves the intramolecular SN2′ cyclization reaction for the construction of critical C-ring in the nitrogen impregnated steroidal architectures bearing unsaturation at Δ9(11) position. In the endeavour to synthesize some new congeners, the remote electronic impact of the electron donating groups in A ring and heteroatoms like oxygen in B ring, on the propensity of C-ring cyclization was also observed.
Development of glycine-α-methyl-proline-containing tripeptides with neuroprotective properties
Cacciatore, Ivana,Fornasari, Erika,Di Stefano, Antonio,Marinelli, Lisa,Cerasa, Laura Serafina,Turkez, Hasan,Aydin, Elanur,Moretto, Alessandro,Ferrone, Alessio,Pesce, Mirko,Di Giacomo, Viviana,Reale, Marcella,Costantini, Erica,Di Giovanni, Pamela,Speranza, Lorenza,Felaco, Mario,Patruno, Antonia
, p. 553 - 563 (2016)
Herein is described the synthesis of novel glycine-α-methyl-proline-containing tripeptides (GPMeX tripeptides namely GPMeR, GPMeK, and GPMeH) with the aim of obtaining derivatives highly stable in human plasma and able to counteract neuroinflammatory processes that are distinctive of neurodegenerative pathologies. The syntheses of GPMeR, GPMeK, and GPMeH were all achieved both by introducing the ProMe residue into the Gly-Pro-Arg (GPR) sequence in place of the native Pro in P2 position and replacing the basic amino acid Arg in P3 position by Lys or His. Results showed that all novel GPMeX tripeptides are stable in human plasma (t1/2 > 51 h) and that GPMeH - generating stable intramolecular H-bond in a C11-turn by interaction of His imidazole ring and Gly carbonyl group - restored physiological levels of nitric oxide deriving from neuronal NOS (nNOS) activity, thus preventing the inflammatory response by suppression of the NF-kB activity and, consequently, the expression of inflammatory genes such as inducibile NOS (iNOS). Therefore, GPMeH could be a lead compound for further development of peptidomimetics able to contrast neuroinflammatory processes.
Discovery of 2-alkyl-1-arylsulfonylprolinamides as 11β-hydroxysteroid dehydrogenase type 1 inhibitors
Yu, Jianxin,Liu, Haiyan,Xia, Guangxin,Liu, Lin,Xu, Zhenmin,Chen, Qian,Ma, Chen,Sun, Xing,Xu, Jiajun,Li, Hua,Li, Ping,Shi, Yufang,Liu, Xuejun,Shen, Jingkang,Xiong, Bing
supporting information, p. 793 - 798,6 (2020/09/15)
On the basis of scaffold hopping, a novel series of 2-alkyl-1- arylsulfonylprolinamides was discovered as 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1) inhibitors. A representative compound 4ek, obtained through SAR and structure optimization studies, demonstrates excellent in vitro potency against 11β-HSD-1 and dose-dependent in vivo inhibition of 11β-HSD-1 in a prednisone/prednisolone transformation biomarker study in mice.
Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles
Gribkov, Denis V.,Pastine, Stefan J.,Schnuerch, Michael,Sames, Dalibor
, p. 11750 - 11755 (2008/03/15)
This paper describes the development of a new catalytic transformation, the ruthenium-catalyzed decarbonylative arylation of cyclic 2-amino esters, which replaces the ester group with an aryl ring at the sp3 carbon center. For example, proline ester amidine 1 is converted to 2-arylpyrrolidine 3 in the presence of arylboronic acids or esters as arene donors and Ru 3(CO)12 as the catalyst. This process provides a rapid access to a variety of 2-arylpyrrolidines and piperidines from commercially available proline, hydroxyproline, and pipecolinate esters. The examination of the substrate scope also showed that many arene boronic acids and boronate esters serve as coupling partners. The high chemoselectivity of this process was demonstrated and ascribed to the significant rate difference between the decarbonylative arylation and the C-H arylation. The decarbonylative arylation complements the C-H arylation, since the latter process lacks control over the extent of functionalization, affording a mixture of mono- and bis-arylpyrrolidines. When applied in tandem, these two processes provide 2,5-diarylpyrrolidines in two steps from the corresponding proline esters. It was also demonstrated that the required amidine or iminocarbamate directing group fulfills two major functions: first, it is essential for the ester activation step, which occurs via the coordination-assisted metal insertion into the acyl C-O bond; second, it facilitates the decarbonylation, via the stabilization of a metallacycle intermediate, assuring the formation of the 2-arylated products instead of the corresponding ketones observed before by others.
ASSYMMETRIC SYNTHESIS OF CYCLIC IMINO ACIDS VIA CHIRAL SCHIFF BASES
Bajgrowicz, Jerzy,Achquar, Abdelrhani El,Roumestant, Marie-Louise,Pigiere, Christian,Viallefont, Philippe
, p. 2165 - 2167 (2007/10/02)
A new method of synthesis of cyclic imino acids is reported.Diastereoselective alkylation of Schiff bases (derived from α-amino esters and (+) or (-) 2-hydroxypinan-3-one) with dihalogeno compounds, followed by hydrolytic cleavage and cyclization affords the imino esters.Reactions are highly enantioselective, with one exception corresponding to steric crowding.
