- Syntheses and antimicrobial activities of five-membered ring heterocycles coupled to indole moieties
-
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.
- Pereira, Elisabeth Rodrigues,Sancelme, Martine,Towa, Jean-Jacques,Prudhomme, Michelle,Martre, Anne-Marie,Mousset, Guy,Rapp, Maryse
-
-
Read Online
- Intramolecular [4+2] cycloaddition in n-allyl- and n-propargyl-α-furyl lactams
-
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.
- Poplevin, Dmitry S.,Nikitina, Eugeniya V.,Zaytsev, Vladimir P.,Varlamov, Alexey V.,Tilve, Santosh G.,Zubkov, Fedor I.
-
-
Read Online
- Cesium salts as superior catalysts for solvent-free modifications of biosourced pterolactam
-
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.
- Dascalu, Anca-Elena,Ghinet, Alina,Lipka, Emmanuelle,Collinet, Marion,Rigo, Benoit,Billamboz, Muriel
-
-
- Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates
-
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
- Pa?dzierniok-Holewa, Agnieszka,Wal?cka-Kurczyk, Alicja,Musio?, Szymon,Stecko, Sebastian
-
p. 732 - 742
(2019/01/10)
-
- 3,5-Disubstituted-indole-7-carboxamides as IKKβ Inhibitors: Optimization of Oral Activity via the C3 Substituent
-
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
- 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)
-
- Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues
-
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.
- 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)
-
- N-[1-(Benzotriazol-1-yl)alkyl]amides from N-acyl-α-amino acids or N-alkylamides
-
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-[
- Adamek, Jakub,Mazurkiewicz, Roman,Pa?dzierniok-Holewa, Agnieszka,Ku?nik, Anna,Grymel, Miros?awa,Zielińska, Katarzyna,Simka, Wojciech
-
p. 5725 - 5729
(2015/03/30)
-
- 1-(N -acylamino)alkyl sulfones from N -acyl-α-amino acids or N -alkylamides
-
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
- Adamek, Jakub,Mazurkiewicz, Roman,Pazdzierniok-Holewa, Agnieszka,Grymel, Miroslawa,Kuznik, Anna,Zielinska, Katarzyna
-
p. 2765 - 2770
(2014/04/17)
-
- Process for preparing 4-amino-5-hexenoic acid from succinimide
-
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.
- -
-
Page/Page column 7
(2013/02/28)
-
- Expedient pyrrolizidine synthesis by propargylsilane addition to N-acyliminium ions followed by gold-catalyzed α-allenyl amide cyclization
-
(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
- Breman, Arjen C.,Dijkink, Jan,Van Maarseveen, Jan H.,Kinderman, Sape S.,Hiemstra, Henk
-
supporting information; experimental part
p. 6327 - 6330
(2009/12/24)
-
- Development of an electrolytic system for non-kolbe electrolysis based on the acid-base reaction between carboxylic acids as a substrate and solid-supported bases
-
We have successfully developed a novel electrolytic system for non-Kolbe electrolysis based on the acid-base reaction between carboxylic acids as a substrate and solid-supported bases. It was found that the acid-base reaction between carboxylic acids and solid-supported basespreferentially takes place to reduce the cell voltage in MeOH. On the basis of the electrolytic system, non-Kolbe electrolysis of various carboxylic acids was carried out to provide the corresponding methoxylated products in excellent yields. Copyright
- Tajima, Toshiki,Kurihara, Hitoshi,Fuchigami, Toshio
-
p. 6680 - 6681
(2008/02/06)
-
- ENANTIOPURE HETEROCYCLIC COMPOUND USEFUL FOR THE PREPARATION OF PEPTIDES WHICH CAN BE POTENTIALLY USED AS MEDICAMENTS
-
Enantiopure heterocyclic compound Enantiopure heterocyclic compound of formula (I) in which J is chosen from C, N, O and S; Z is H or a group for protecting the amino functional group, R3 denotes H or an organic residue, m is 0, 1 or 2 and n is 0, 1 or 2, and in which the heterocycle is preferably substituted with at least one substituent other than CH2-COOR3.
- -
-
Page/Page column 16
(2008/06/13)
-
- Amnesia-reversal activity of a series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones
-
A series of 5-alkoxy-1-arylsulfonyl-2-pyrrolidinones were prepared by condensation of arylsulfonyl chlorides with 5-alkoxy-2-pyrrolidinones.Most compounds reversed electroconvulsive shock-induced amnesia in mice, showing the typical inverted U-shaped dose
- Toja, E,Gorini, C,Zirotti, C,Barzaghi, F,Galliani, G
-
p. 403 - 413
(2007/10/02)
-
- SYNTHESIS OF γ-LACTAM ANALOGUES OF 1-ACETOXY CARBAPENEM DERIVATIVES
-
The syntheses of γ-lactam analogues of the 1-acetoxy carbapenem esters, from dl-pyroglutamic acid are described.Attempted deprotection to provide the free carboxylic acids resulted in degradation.Whilst the free acid of the 1-hydroxy carbapenem analogue was chemically stable, it lacked antibacterial activity.
- Coulton, S.,Francois, I.,Southgate, R.
-
p. 6923 - 6926
(2015/02/06)
-
- 1-benzenesulphonyl-2-oxo-5-alkoxypyrrolidines and medical methods of use thereof
-
Memory enhancing 1-(benzenesulfonyl)-2-oxo-5-alkoxy-pyrrolidines are prepared by alkylation of the corresponding pyrrolidones or pyrrolidone precursors.
- -
-
-
- A New -Type Annelation Useful for the Formation of Piperidine Skeletons
-
A -type annelation between α,α'-dimethoxylated amides 4 and allyltrimethylsilane (5) gave piperidine derivatives 6.It was applied to the synthesis of piperidine, indolizidine, quinolizidine, 1-azabicycloundecane, 1-aza-8-oxabicyclononane, 8-azabicyclooctane, and 9-azabicyclononane derivatives.
- Shono, Tatsuya,Matsumura, Yoshihiro,Uchida, Kenshi,Kobayashi, Hidekazu
-
p. 3243 - 3245
(2007/10/02)
-
- PSEUDOESTERS AND DERIVATIVES. XXII. SYNTHESIS OF 5-HYDROXY-3-PYRROLIN-2-ONES AND 5-HYDROXYPYRROLIDIN-2-ONES BY AMMONOLYSIS OF 5-METHOXYFURAN-2(5H)-ONES AND DERIVATIVES
-
The ammonolysis of 4-substituted 5-methoxyfuran-2(5H)-ones 4a-e under mild conditions affords the respective 5-hydroxy-3-pyrrolin-2-ones 5a-e.However, 4-dialkylamino derivatives 4f,g do not react with ammonia under the same conditions.Similar ammonolysis of furanone derivatives 7a,b, 10 and 13 yields the pyrrolidinones 8a,b and hexahydroisoindolones 11, and 14, respectively.The corresponding methoxylactams 6a-e, 9a-b and 12 are readily obtained by refluxing the hydroxylactams 5a-e, 8a,b and 11, respectively with acid-catalyzed methanol.
- Farina, Francisco,Martin, M. Victoria,Paredes, M. Carmen,Ortega, M. Carmen,Tito, Amelia
-
p. 1733 - 1739
(2007/10/02)
-
- A GENERAL METHOD FOR THE SYNTHESIS OF INDOLES BEARING A VARIETY OF SUBSTITUENTS AT THE β-POSITION, AND ITS APPLICATION TO THE SYNTHESIS OF L-TRYPTOPHAN
-
A general synthetic method of β-substituted indoles such as indolacetic acid, tryptamine and L-tryptophan has been exploited utilizing α-methoxylated amides, lactams, a carbamate, and sulfonamides, easily obtainable by an electrochemical method, as key intemediates.
- Shono, Tatsuya,Matsumura, Yoshihiro,Kanazawa, Takenobu
-
p. 1259 - 1262
(2007/10/02)
-
- Photolytic Dehydrochlorination of N-Chloro-N-alkyl Amides: Formaton of N-(α-Methoxyalkyl) Amides
-
The photoinduced dehydrochlorination, in methanol, of N-chloro-N-alkyl amides with one substitient at the α position to nitrogen gave good yields of N-(α-methoxyalkyl) amides and the parent amides as secondary products.N-Chloro amides disubstituted at the α position gave mostly parent amides.In most cases no products resulting from 1,5 hydrogen transfer of amidyl radicals were observed.The quantum yields of decomposition of N-chloro-N-methylpentanamide (1a) were significantly greater than unity, indicative of a chain process for dehydrochlorination.The reaction was affected by the solvent, addition of base or radical inhibitors, concentration of N-chloro amide, light intensity, and irradiation wavelenght.
- Phan, Xuan T.,Shannon, Paul J.
-
p. 5164 - 5170
(2007/10/02)
-
- SYNTHESIS OF 5-AMINO-2-PYRROLIDINONE AND ITS DERIVATIVES
-
Two routes to a new type of 2-pyrrolidinones having various nitrogen functions at the 5-position were described.The modified Curtius reaction of pyroglutamic acid derivatives (1 and 4) with diphenylphosphoryl azide (DPPA) gave 5-alkoxycarbonylamino-2-pyrr
- Kosugi, Yoshiyuki,Hamaguchi, Humiko,Nagasaka, Tatsuo,Ozawa, Naganori,Ohki, Sadao
-
p. 1245 - 1249
(2007/10/02)
-