141071-79-6Relevant articles and documents
Sodium Iodide/Hydrogen Peroxide-Mediated Oxidation/Lactonization for the Construction of Spirocyclic Oxindole-Lactones
Li, Guofeng,Huang, Liwu,Xu, Jiecheng,Sun, Wangsheng,Xie, Junqiu,Hong, Liang,Wang, Rui
supporting information, p. 2873 - 2877 (2016/09/16)
The sodium iodide/hydrogen peroxide-mediated oxidation/lactonization of indolepropionic acids was achieved, affording the corresponding spirocyclic oxindole-lactones in moderate to high yields. This metal-free procedure features mild reaction conditions, non-toxicity and easy handling, with hydrogen peroxide (H2O2) as a clean oxidant. (Figure presented.).
Synthesis and evaluation of analogues of N-phthaloyl-l-tryptophan (RG108) as inhibitors of DNA methyltransferase 1
Asgatay, Saa?dia,Champion, Christine,Marloie, Ga?l,Drujon, Thierry,Senamaud-Beaufort, Catherine,Ceccaldi, Alexandre,Erdmann, Alexandre,Rajavelu, Arumugam,Schambel, Philippe,Jeltsch, Albert,Lequin, Olivier,Karoyan, Philippe,Arimondo, Paola B.,Guianvarc'H, Dominique
, p. 421 - 434 (2014/02/14)
DNA methyltransferases (DNMT) are promising drug targets in cancer provided that new, more specific, and chemically stable inhibitors are discovered. Among the non-nucleoside DNMT inhibitors, N-phthaloyl-l-tryptophan 1 (RG108) was first identified as inhibitor of DNMT1. Here, 1 analogues were synthesized to understand its interaction with DNMT. The indole, carboxylate, and phthalimide moieties were modified. Homologated and conformationally constrained analogues were prepared. The latter were synthesized from prolinohomotryptophan derivatives through a methodology based amino-zinc-ene-enolate cyclization. All compounds were tested for their ability to inhibit DNMT1 in vitro. Among them, constrained compounds 16-18 and NPys derivatives 10-11 were found to be at least 10-fold more potent than the reference compound. The cytotoxicity on the tumor DU145 cell line of the most potent inhibitors was correlated to their inhibitory potency. Finally, docking studies were conducted in order to understand their binding mode. This study provides insights for the design of the next-generation of DNMT inhibitors.
New small molecule inhibitors of hepatitis C virus
Wei, Wanguo,Cai, Cuifang,Kota, Smitha,Takahashi, Virginia,Ni, Feng,Strosberg, A. Donny,Snyder, John K.
scheme or table, p. 6926 - 6930 (2010/06/16)
New small molecule inhibitors of HCV were discovered by screening a small library of indoline alkaloid-type compounds. An automated assay format was employed which allowed identification of dimerization inhibitors of core, the capsid protein of the virus. These compounds were subsequently shown to block production of infectious virus in hepatoma cells.
Aminomethylation of chiral silyl enol ethers: access to β2-homotryptophane and β2-homolysine derivatives
Moumné, Roba,Larregola, Maud,Boutadla, Youcef,Lavielle, Solange,Karoyan, Philippe
, p. 4704 - 4707 (2008/09/21)
We describe here the aminomethylation of chiral silyl enol ether derivatives using iminium ion. The choice of judicious precursors with adequate protecting groups for the silylation/aminomethylation step was required to achieve the synthesis of β2-homotryptophane in few steps. The same methodology was used to prepare a β2-homolysine derivative.
Synthetic N-pyridinyl(methyl)-indol-3-ylpropanamides as new potential immunosuppressive agents
Carbonnelle, Delphine,Lardic, Morgane,Dassonville, Alexandra,Verron, Elise,Petit, Jean-Yves,Duflos, Muriel,Lang, Francois
, p. 686 - 693 (2008/02/11)
Several N-pyridinyl(methyl)-indol-3-ylpropanamides were synthesized and pharmacological evaluations of their immunosuppressive potential were performed. Among thirteen compounds tested in vitro on murine T proliferation, three showed interesting inhibitin
New scalable asymmetric aminomethylation reaction for the synthesis of β2-amino acids
Moumne, Roba,Denise, Bernard,Guitot, Karine,Rudler, Henri,Lavielle, Solange,Karoyan, Philippe
, p. 1912 - 1920 (2008/02/06)
β-Amino acids are useful tools in the design of peptidomimetics, and the development of new methods for their syntheses, particularly the synthesis of β2-amino acids, remains an important challenge. Here we report a new scalable route based on the aminomethylation of silyl ketene N,O-acetals by Mannich-type iminium electrophiles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
New N-pyridinyl(methyl)-indolalkanamides acting as topical inflammation inhibitors
Dassonville, Alexandra,Bretéché, Anne,Evano, Johan,Duflos, Muriel,Le Baut, Guillaume,Grimaud, Nicole,Petit, Jean-Yves
, p. 5441 - 5444 (2007/10/03)
The authors have described the synthetic way to new N-pyridinyl(methyl) indolylpropanamides acting as non acidic NSAIDs. Pharmacomodulation was carried out at N-1 and C-5 of the indole ring and at the level of the propanamide chain. N-(pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propanamide 32 represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone.
Heterocyclic compounds, their preparation and their therapeutic use
-
, (2008/06/13)
A compound of formula (I): STR1 wherein Y1, Y2, Y3 and Y4 are each hydrogen, halogen, nitro, cyano, hydroxyl, thiol, amino, alkyl, haloalkyl, alkylthio, a protected or unprotected carboxyl, a protected or unprotected sulfonamide, or tetrazol; one of R1 and R2 is hydrogen, alkyl, aryl, aralkyl, oxazolyl, or a protected or unprotected carboxyl and the other of R1 and R2 is hydrogen, alkyl, aryl or aralkyl; and R3 is hydrogen or an amino protecting group, and pharmaceutically acceptable salts or esters thereof. The compounds are effective for treating dementia, Alzheimer's disease and delirium and are effective as sedatives.
(1-Benzylindole-3-yl)alkanoic acids; novel nonsteroidal inhibitors of steroid 5α-reductase (I)
Sawada, Kozo,Hirai, Hideo,Golden, Patrick,Okada, Satoshi,Sawada, Yuki,Hashimoto, Masashi,Tanaka, Hirokazu
, p. 1683 - 1687 (2007/10/03)
A novel series of indole-3-alkanoic acids with varied N-benzyl substituents were synthesized as nonsteroidal inhibitors of steroid 5α- reductase. The structure-activity relationships in this series were studied and the optimum carboxylic acid side chain w
1-indolyalkyl-4-(alkoxypyrimidinyl)piperazines
-
, (2008/06/13)
Certain 1-indolylalkyl-4-(alkoxypyrimidinyl)piperazines of Formula I are useful antidepressant agents. The STR1 substituents R1, R2 and R5 are hydrogen or lower alkyl; R3 and R4 are hydrogen, alkyl, alkoxy, alkythio, carboxamido, halo, or trifluoromethyl; R6 is alkoxy; and n is the integer 2 or 3.
