56633-72-8Relevant academic research and scientific papers
Asymmetric "clip-Cycle" Synthesis of Pyrrolidines and Spiropyrrolidines
Maddocks, Christopher J.,Ermanis, Kristaps,Clarke, Paul A.
, p. 8116 - 8121 (2020/11/02)
The development of an asymmetric "clip-cycle"synthesis of 2,2- and 3,3-disubstituted pyrrolidines and spiropyrrolidines, which are increasingly important scaffolds in drug discovery programs, is reported. Cbz-protected bis-homoallylic amines were activate
Synthesis of 2-Fluoroalkyl 4-Substituted Azepanes
Masson, Guillaume,Rioton, Sarah,Gomez Pardo, Domingo,Cossy, Janine
, p. 5497 - 5507 (2019/09/06)
Synthesis of di- and tri-substituted fluoroalkylated azepanes was achieved by ring expansion of pyrrolidines via a regioselective attack of nucleophiles on a bicyclic azetidinium intermediate. A broad scope of azepanes, substituted at C4 and bearing a α-t
Access to Enantio-enriched Substituted α-Trifluoromethyl Azepanes from l -Proline
Masson, Guillaume,Rioton, Sarah,Gomez Pardo, Domingo,Cossy, Janine
, p. 5019 - 5022 (2018/08/24)
4-Substituted α-trifluoromethyl azepanes C were synthesized via the ring expansion of trifluoromethyl pyrrolidines A, which were synthesized from l-proline via a regioselective ring-opening of a bicyclic azetidinium intermediate B by various nucleophiles.
TRICYCLIC FUSED PYRIMIDINE COMPOUNDS AS INHIBITORS OF p97 COMPLEX
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, (2017/09/29)
Tricyclic fused pyrimidine compounds having an arylalkyl amine substituent at the P4 position and a substituted 1H-indol-1-yl, 1H-indol-3-yl, indanyl, indazol-1-yl, indazol-3-yl, benzotriazol-1-yl or 1H-benz[d]imidazol-1-yl group at the P2 position well as optional aliphatic, functional and/or aromatic components substituted at other positions of the tricyclic compounds of the invention. These compounds are inhibitors of the AAA proteasome complex containing p97 and are effective medicinal agents for treatment of diseases associated with p97 bioactivity such as cancer.
Structure-antiproliferative activity studies on l-proline- and homoproline-4-: N -pyrrolidine-3-thiosemicarbazone hybrids and their nickel(II), palladium(II) and copper(II) complexes
Dobrova, Aliona,Platzer, Sonja,Bacher, Felix,Milunovic, Miljan N. M.,Dobrov, Anatolie,Spengler, Gabriella,Enyedy, éva A.,Novitchi, Ghenadie,Arion, Vladimir B.
, p. 13427 - 13439 (2016/09/04)
Two water-soluble thiosemicarbazone-proline (H2L1) and thiosemicarbazone-homoproline hybrids (H2L2) were synthesised. By reaction of H2L1 with NiCl2·6H2O, PdCl2 and CuCl2·2H2O in ethanol, the series of square-planar complexes [Ni(H2L1)Cl]Cl·1.3H2O (1·1.3H2O), [Pd(H2L1)Cl]Cl·H2O (2·H2O) and [Cu(H2L1)Cl]Cl·0.7H2O (3·0.7H2O) was prepared, and starting from H2L2 and CuCl2·2H2O in methanol, the complex [Cu(H2L2)Cl2]·H2O (4·H2O) was obtained. The compounds have been characterised by elemental analysis, spectroscopic methods (IR, UV-vis and NMR spectroscopy), ESI mass spectrometry and single crystal X-ray crystallography (H2L1, 1, 2 and 4). As a solid, 1 is diamagnetic, while it is paramagnetic in methanolic solution. The effective magnetic moment of 3.26 B.M. at room temperature indicates the change in coordination geometry from square-planar to octahedral upon dissolution. The in vitro anticancer potency of ligand precursors H2L1 and H2L2 and metal complexes 1-4 was studied in three human cancer cell lines (A549, CH1 and SW480) and in noncancerous murine embryonal fibroblasts (NIH/3T3), and the mechanism of cell death was also assayed by flow cytometry. Clear-cut structure-activity relationships have been established. The metal ions exert marked effects in a divergent manner: copper(ii) increases, whereas nickel(ii) and palladium(ii) decrease the cytotoxicity of the hybrids. The antiproliferative activity of H2L1 and metal complexes 1-3 decreases in all three tumour cell lines in the following rank order: 3 > H2L1 > 1 > 2. The role of square-planar geometry in the underlying mechanism of cytotoxicity of the metal complexes studied seems to be negligible, while structural modifications at the terminal amino group of thiosemicarbazide and proline moieties are significant for enhancing the antiproliferative activity of both hybrids and copper(ii) complexes.
Synthesis of (-)-(S, S)-clemastine by invertive N → C aryl migration in a lithiated carbamate
Fournier, Anne M.,Brown, Robert A.,Farnaby, William,Miyatake-Ondozabal, Hideki,Clayden, Jonathan
supporting information; experimental part, p. 2222 - 2225 (2010/08/04)
The first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer, has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of α-methyl-p-chlorobenzyl alcohol by invertive aryl migration on lithiation. The (S,S)-stereochemistry of the product confirms the invertive nature of the rearrangement.
The synthesis of bicyclic piperazine-2-carboxylic acids from L-proline
Hanessian, Stephen,Sharma, Raman
, p. 1231 - 1239 (2007/10/03)
The stereocontrolled synthesis of two diastereomeric bicyclic piperazine-2-carboxylic acids from L-proline is described.
The synthesis of a novel benzodiazocine via an intramolecular Staudinger/aza-Wittig cyclization
O'Neil, Ian A.,Murray, Clare L.,Potter, Andrew J.,Kalindjian, S. Barret
, p. 3609 - 3610 (2007/10/03)
The novel pyrrolobenzodiazocine (1) has been prepared by an intramolecular Staudinger/aza Wittig protocol from the precursor azido aldehyde (2) in a remarkable 93% yield. Aldehyde (2) was prepared by coupling protected homoprolinol with 2-azidobenzoic aci
