38072-88-7Relevant academic research and scientific papers
Syntheses and antimicrobial activities of five-membered ring heterocycles coupled to indole moieties
Pereira, Elisabeth Rodrigues,Sancelme, Martine,Towa, Jean-Jacques,Prudhomme, Michelle,Martre, Anne-Marie,Mousset, Guy,Rapp, Maryse
, p. 380 - 385 (1996)
Indole-substituted oxazolidinones, oxazolones, pyrrolidinone, imidazolidinone and imidazolones were synthesized. Their inhibitory potencies towards protein kinase C and protein kinase A were determined and their in vitro activities against Streptomyces chartreusis, Streptomyces griseus, Bacillus cereus, Candida albicans and Escherichia coli were examined. The inhibition of Streptomyces sporulation observed for some of them could not be linked to in vitro protein kinase C inhibition. All proved inactive against C. albicans but three of them exhibited a marked activity towards E. coli. This effect extends to other Gram-negative bacteria.
Intramolecular [4+2] cycloaddition in n-allyl- and n-propargyl-α-furyl lactams
Poplevin, Dmitry S.,Nikitina, Eugeniya V.,Zaytsev, Vladimir P.,Varlamov, Alexey V.,Tilve, Santosh G.,Zubkov, Fedor I.
, p. 451 - 457 (2018)
The size of nitrogen heterocycle in N-allyl- and N-propargyl-α-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-γ-(α-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230°С. Substituted δ-valero- and ε-caprolactams underwent partial Diels–Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-α-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.
Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates
Pa?dzierniok-Holewa, Agnieszka,Wal?cka-Kurczyk, Alicja,Musio?, Szymon,Stecko, Sebastian
, p. 732 - 742 (2019/01/10)
A catalyst-free reaction of 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates with silyl enolates was developed to prepare β-amino carbonyl compounds. The reported method is a useful approach for the preparation of N-protected β-amino esters as
Cesium salts as superior catalysts for solvent-free modifications of biosourced pterolactam
Dascalu, Anca-Elena,Ghinet, Alina,Lipka, Emmanuelle,Collinet, Marion,Rigo, Benoit,Billamboz, Muriel
, p. 32 - 39 (2019/03/27)
γ-Lactam derivatives are widespread biologically active compounds, covering a large range of activities. Following our interest in both medicinal and green chemistries, we developed an original, cesium salts-mediated, scalable and solvent-free methodology to transform biosourced pyroglutamic acid and its derivatives to their N,N′-aminals, N,O,N,S-acetals and C5-substituted γ-lactams in good to excellent yields. This protocol is applicable to a large range of substrates, conducting to C5-substituted γ-lactam derivatives as potential new biologically active compounds.
3,5-Disubstituted-indole-7-carboxamides as IKKβ Inhibitors: Optimization of Oral Activity via the C3 Substituent
Kerns, Jeffrey K.,Busch-Petersen, Jakob,Fu, Wei,Boehm, Jeffrey C.,Nie, Hong,Muratore, Michael,Bullion, Ann,Lin, Guoliang,Li, Huijie,Davis, Roderick,Lin, Xichen,Lakdawala, Ami S.,Cousins, Rick,Field, Rita,Payne, Jeremy,Miller, David D.,Bamborough, Paul,Christopher, John A.,Baldwin, Ian,Osborn, Ruth R.,Yonchuk, John,Webb, Edward,Rumsey, William L.
supporting information, p. 1164 - 1169 (2018/11/23)
IκB kinase β (IKKβ or IKK2) is a key regulator of nuclear factor kappa B (NF-κB) and has received attention as a therapeutic target. Herein we report on the optimization of a series of 3,5-disubstituted-indole-7-carboxamides for oral activity. In doing so
Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues
Baudelet, Davy,Da?ch, Adam,Rigo, Beno?t,Lipka, Emmanuelle,Gautret, Philippe,Homerin, Germain,Claverie, Christelle,Rousseau, Jolanta,Abuhaie, Cristina-Maria,Ghinet, Alina
supporting information, p. 2226 - 2244 (2016/07/15)
The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp2-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.
1-(N -acylamino)alkyl sulfones from N -acyl-α-amino acids or N -alkylamides
Adamek, Jakub,Mazurkiewicz, Roman,Pazdzierniok-Holewa, Agnieszka,Grymel, Miroslawa,Kuznik, Anna,Zielinska, Katarzyna
, p. 2765 - 2770 (2014/04/17)
A variety of N-(1-methoxyalkyl)amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)alkyl sulfones in good yiel
N-[1-(Benzotriazol-1-yl)alkyl]amides from N-acyl-α-amino acids or N-alkylamides
Adamek, Jakub,Mazurkiewicz, Roman,Pa?dzierniok-Holewa, Agnieszka,Ku?nik, Anna,Grymel, Miros?awa,Zielińska, Katarzyna,Simka, Wojciech
, p. 5725 - 5729 (2015/03/30)
A variety of N-(1-methoxyalkyl)amides react with benzotriazole in the presence of PPh3·HBF4 and organic bases (Hünig's base, DBU or DABCO) or solid-state-supported bases (SiO2-Pip or IRA-67) in CHCl3 to give N-[
Process for preparing 4-amino-5-hexenoic acid from succinimide
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Page/Page column 7, (2013/02/28)
The present invention relates to a competitive process for the preparation of 4-amino-5-hexenoic acid and intermediates thereof. This compound is a well-known anti-epileptic drug for which several syntheses have been developed, all of them presenting drawbacks. The preparation process according to the present invention is very competitive from an economical point of view and is adapted to industrial scale preparation of 4-amino-5-hexenoic acid.
Expedient pyrrolizidine synthesis by propargylsilane addition to N-acyliminium ions followed by gold-catalyzed α-allenyl amide cyclization
Breman, Arjen C.,Dijkink, Jan,Van Maarseveen, Jan H.,Kinderman, Sape S.,Hiemstra, Henk
supporting information; experimental part, p. 6327 - 6330 (2009/12/24)
(Chemical Equation Presented) A reaction sequence, involving the addition of (substituted) propargylsilanes to lactam-derived N-acyliminium ions followed by gold-catalyzed cyclization of the resulting α-allenyl amide, is applied in expedient syntheses of
