3790-46-3Relevant academic research and scientific papers
Discovery of 3,3′-pyrrolidinyl-spirooxindoles as cardioprotectant prohibitin ligands
Elderwish, Sabria,Audebrand, Ana?s,Nebigil, Canan G.,Désaubry, Laurent
, (2019/11/26)
The scaffold proteins prohibitins-1 and 2 (PHB1/2) play many important roles in coordinating many cell signaling pathways and represent emerging targets in cardiology and oncology. We previously reported that a family of natural products derivatives, flavaglines, binds to PHB1/2 to exert cardioprotectant and anti-cancer effects. However, flavaglines also target the initiation factor of translation eIF4A, which doesn't contribute to cardioprotection and may even induce some adverse effects. Herein, we report the development of a convenient and robust synthesis of the new PHB2 ligand 2′-phenylpyrrolidinyl-spirooxindole, and its analogues. We discovered that these compounds displays cardioprotective effect against doxorubicin mediated cardiotoxicity and uncovered the structural requirement for this activity. We identified in particular some analogues that are more cardioprotectant than flavaglines. Pull-down experiments demonstrated that these compounds bind not only to PHB2 but also PHB1. These novel PHB ligands may provide the basis for the development of new drugs candidates to protect the heart against the adverse effects of anticancer treatments.
A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and β-carbolines
Wu, Tom Y. H.,Schulte, Peter G.
, p. 4033 - 4035 (2007/10/03)
(matrix presented) Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. β-Carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R1. Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R2. If X = Br, Suzuki coupling can be used to introduce R3. After derivatization, the indole derivatives are activated with methyl iodide and released under mild basic condition.
The Meisenheimer Rearrangement in Heterocyclic Synthesis. III. Derivatives of the 1H-Oxazepinoindole, Thienooxazepine and Benzothienooxazepine Ring Systems
Bremner, John B.,Browne, Elaine J.,Davies, Peter E.
, p. 1335 - 1343 (2007/10/02)
The new heterocyclic derivatives 3-methyl-1-phenyl-3,4,5,10-tetrahydro-1H-oxazepino-indole (5c), 6-methyl-4-phenyl-4,6,7,8,-tetrahydrothienooxazepine (6f), and 3-methyl-1-phenyl-1,3,4,5-tetrahydrolbenzothienooxazepin
