101349-12-6Relevant articles and documents
An expeditious and environmentally benign methodology for the synthesis of substituted indoles from cyclic enol ethers and enol lactones
Singh, Pankajkumar R.,Surpur, Mandar P.,Patil, Sachin B.
, p. 3335 - 3340 (2008)
A simple and environmentally friendly method is developed for the synthesis of substituted indoles from commercially available aryl hydrazines and cyclic enol ethers with Montmorillonite-K10 as a heterogeneous catalyst. The catalyst is non-toxic, inexpensive and recyclable and the process is clean, high yielding and operationally simple.
Design, synthesis, and structure - Activity relationship studies of novel 3-alkylindole derivatives as selective and highly potent myeloperoxidase inhibitors
Soubhye, Jalal,Aldib, Iyas,Elfving, Betina,Gelbcke, Michel,Furtmüller, Paul G.,Podrecca, Manuel,Conotte, Rapha?l,Colet, Jean-Marie,Rousseau, Alexandre,Reye, Florence,Sarakbi, Ahmad,Vanhaeverbeek, Michel,Kauffmann, Jean-Michel,Obinger, Christian,Nève, Jean,Prévost, Martine,Zouaoui Boudjeltia, Karim,Dufrasne, Francois,Van Antwerpen, Pierre
, p. 3943 - 3958 (2013)
Due to its production of potent antimicrobial oxidants including hypochlorous acid, human myeloperoxidase (MPO) plays a critical role in innate immunity and inflammatory diseases. Thus MPO is an attractive target in drug design. (Aminoalkyl)fluoroindole derivatives were detected to be very potent MPO inhibitors; however, they also promote inhibition of the serotonin reuptake transporter (SERT) at the same concentration range. Via structure-based drug design, a new series of MPO inhibitors derived from 3-alkylindole were synthesized and their effects were assessed on MPO-mediated taurine chlorination and low-density lipoprotein oxidation as well as on inhibition of SERT. The fluoroindole compound with three carbons in the side chain and one amide group exhibited a selectivity index of 35 (Ki/IC50) with high inhibition of MPO activity (IC50 = 18 nM), whereas its effect on SERT was in the micromolar range. Structure-function relationships, mechanism of action, and safety of the molecule are discussed.
Enantioselective Construction of Spirooxindole-Fused Cyclopentanes
Do?ekal, Vojtěch,Vopálenská, Andrea,Měrka, Pavel,Kone?ná, Klára,Jand'Ourek, Ond?ej,Pour, Milan,Císa?ová, Ivana,Vesely, Jan
, p. 12623 - 12643 (2021)
The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.
Structure-based design, synthesis, and pharmacological evaluation of 3-(Aminoalkyl)-5-fluoroindoles as myeloperoxidase inhibitors
Soubhye, Jalal,Prévost, Martine,Van Antwerpen, Pierre,Zouaoui Boudjeltia, Karim,Rousseau, Alexandre,Furtmüller, Paul G.,Obinger, Christian,Vanhaeverbeek, Michel,Ducobu, Jean,Nève, Jean,Gelbcke, Michel,Dufrasne, Fran?ois
, p. 8747 - 8759 (2010)
Oxidized low-density lipoproteins (LDLs) accumulate in the vascular wall and promote local inflammation, which contributes to the progression of the atheromatous plaque. The key role of myeloperoxidase (MPO) in this process is related to its ability to modify APO B-100 in the intima and at the surface of endothelial cells. A series of 3-(aminoalkyl)-5-fluoroindole analogues was designed and synthesized by exploiting the structure-based docking of 5-fluorotryptamine, a known MPO inhibitor. In vitro assays were used to study the effects of these compounds on the inhibition of MPO-mediated taurine chlorination and oxidation of LDLs. The kinetics of the interaction between the MPO redox intermediates, Compounds I and II, and these inhibitors was also investigated. The most potent molecules possessed a 4- or 5-carbon aminoalkyl side chain and no substituent on the amino group. The mode of binding of these analogues and the mechanism of inhibition is discussed with respect to the structure of MPO and its halogenation and peroxidase cycles.
Synthesis and antidepressant effect of novel aralkyl piperazine and piperidine derivatives targeting SSRI/5-HT1A/5-HT7
Gu, Zheng-Song,Wang, Wen-Tao,Qian, Hao,Zhou, Ai-Nan,Sun, Hong-Bin,Zhang, Qing-Wei,Li, Jian-Qi
supporting information, (2019/10/22)
A series of novel aralkyl piperazine and piperidine derivatives were synthesized, and evaluated for their serotonin reuptake inhibitory and 5-HT1A/5-HT7 receptors affinities activity. Antidepressant activities in vivo of the selective compound were screened using the forced swimming test (FST) and tail suspension test (TST). The results indicated that compound 19a exhibited high affinities for the 5-HT1A/5-HT7 receptors (5-HT1A, Ki = 12 nM; 5-HT7, Ki = 3.2 nM) coupled with potent serotonin reuptake inhibition (IC50 = 14 nM) and showed a marked antidepressant-like effect in the FST and TST models.
