Diphenylbutylpiperidine-based cell autophagy inducers: Design, synthesis and SAR studies

Chen, Gang; Xia, Hongguang; Cai, Yu; Ma, Dawei; Yuan, Junying; Yuan, Chengye

doi:10.1039/c0md00236d

Cited by 8 publications

(6 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…55 This step occurred at the same rate and at a similar yield (83-90%) independent of the aryl group's ability to planarise with the alkene, suggesting that the aryl group is not offering significant stabilisation of the carbocation that may be formed during the reaction. 55 This step occurred at the same rate and at a similar yield (83-90%) independent of the aryl group's ability to planarise with the alkene, suggesting that the aryl group is not offering significant stabilisation of the carbocation that may be formed during the reaction.…”

Section: Synthesismentioning

confidence: 84%

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

et al. 2016

View full text Add to dashboard Cite

A versatile palladium-free route for the synthesis of 4-aryl-substituted phenylpyridines (ppy), starting from tert-butyl 4-oxopiperidine-1-carboxylate, is reported. Reaction with an aryllithium, followed by trifluoroacetic acid dehydration/deprotection and oxidation with 2-iodoylbenzoic acid and finally phenylation, gave 4 ligands (L(1-4)H): 2,4-diphenylpyridine, 4-(4-methoxyphenyl)-2-phenylpyridine, 2-phenyl-4-(o-tolyl)pyridine and 4-mesityl-2-phenylpyridine. These ligands were coordinated to iridium to give the corresponding Ir(L)2(A) complexes (Ir1-7), where A = ancillary ligand acetylacetate or 2-picolinate. This was used to demonstrate that, through a combination of ancillary ligand choice and torsional twisting between the 4-aryl substituents of the ppy ligands, it is possible to tune the phosphorescent emission of the complexes in the range 502-560 nm.

show abstract

Section: Synthesismentioning

confidence: 84%

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

et al. 2016

View full text Add to dashboard Cite

show abstract

“…These structures were determined through a combination of chemical shift and literature precedents [26] (see Supporting Information for details). Similarly, a wide range of mono-, di-, and polysubstituted phenols also gave the corresponding aryl alkyl ether (18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31) in high yields and ee's. For the monocyclic five-membered heterocycles (32-49), N-alkylation in general readily takes place to give products in high yield, except for pyrroles (43-45), which are prone to decompose under oxidative conditions.…”

Section: Methodsmentioning

confidence: 94%

“…In contrast, a pair of regioisomers were observed in unsymmetric pyrazole (40), as well as bicyclic N-nucleophiles such as indazole (50), and benzotriazole (53); similar regioselectivity issue were also seen in chemical Mitsunobu reactions. [27] Among the non-cyclic N-nucleophiles, only secondary sulfonamide gave reasonable to high yields (54 and 55); primary sulfonamides (such o-NsNH 2 [28] ) that are competent in classic conditions failed to give any detectable products. Our e-Mitsunobu conditions could also be readily applied to modify a series of complex bioactive compounds.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Azo‐free Mitsunobu‐type Reaction

Guo,

Jiang,

Zhu

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

The classic chemical Mitsunobu reaction suffers from the need of excess alcohol activation reagents and the generation of significant by‐products. Efforts to overcome these limitations have resulted in numerous creative solutions, but the substrate scope of these catalytic processes remains limited. Here we report an electrochemical Mitsunobu‐type reaction, which features azo‐free alcohol activation and broad substrate scope. This user‐friendly technology allows a vast collection of heterocycles as the nucleophile, which can couple with a series of chiral cyclic and acyclic alcohols in moderate to high yields and excellent ee’s. This practical reaction is scalable, chemoselective, uses simple Electrasyn setup with inexpensive electrodes and requires no precaution to exclude air and moisture. The synthetic utility is further demonstrated on the structural modification of diverse bioactive natural products and pharmaceutical derivatives and its straightforward application in a multiple‐step synthesis of a drug candidate.

show abstract

“…10-NCP protects against mutant huntingtin (Htt) toxicity in a primary culture model of HD, decreases the levels of diffuse and aggregated forms of mutant Htt and does not show toxicity [191]. A library of "open" and "close" compounds shows that substitution on the aromatic rings may increase the potency of compounds as autophagy inducers (e.g., compare penfluridol, 4.41a, with Ph-substituted compounds 4.41b-e) [192,193].…”

Section: Small Molecule Enhancers Of Rapamycin (Smers)mentioning

confidence: 98%

Targeting Unselective Autophagy of Cellular Aggregates

Seneci

2015

Chemical Modulators of Protein Misfolding and Neurodegenerative Disease

View full text Add to dashboard Cite

Diphenylbutylpiperidine-based cell autophagy inducers: Design, synthesis and SAR studies

Cited by 8 publications

References 18 publications

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

Electrochemical Azo‐free Mitsunobu‐type Reaction

Targeting Unselective Autophagy of Cellular Aggregates

Contact Info

Product

Resources

About