Search results for "Amide"

Synthesis of substituted 3-amino-N-phenyl-1H-indazole-1-carboxamides endowed with antiproliferative activity

2010

Abstract Several new N-phenyl-1H-indazole-1-carboxamides 1c–h and 4l,m were prepared by reacting phenyl isocyanate derivatives 3a,b with 3-amino-1H-indazole derivatives 2c,e,g or 1H-indazole 2l respectively. Chemical transformations of compounds 1a,b and 1g,h gave 3-acetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 5a,b, and 3,5-diamino-N-phenyl-1H-indazole-1-carboxamide derivatives 4i, j respectively. Finally, 3,5-diacetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 6a,b were prepared by acetylation of 4i, j. Some of synthesized compounds were evaluated for their in vitro antiproliferative activity against the full NCI tumor cell lines panel derived from nine clinically isolat…

Hydroxy-Directed Enantioselective Hydroxyalkylation in the Carbocyclic Ring of Indoles

2017

[EN] A Cinchona-derived squaramide catalyzes the reaction between hydroxyindoles and isatins leading to enantioenriched indoles substituted in the carbocyclic ring. The reaction proceeds efficiently with differently substituted isatins, yielding the desired products with excellent regioselectivity, good yields, and high enantiocontroi. Moreover, every position of the carbocyclic ring of the indole can be functionalized by using the appropriate starting hydroxyindole. The OH group was removed smoothly upon hydrogenolysis of the corresponding triflate.

The Halide Binding Behavior of 2-Carbamoyl-7-ureido-1H-indoles: Conformational Aspects

2009

Indole-based anion receptors with an carboxamide unit in 2- and an urea in 7-position were prepared and found to bind halides (as well as acetate and nitrate) in chloroform solutions at room temperature. Investigations of the binding behaviour show that the receptor is selective for chloride. Surprisingly, the truncated receptor 3 without the 2-carbamoyl substituent shows the highest affinity for Cl–. Thorough 1H, 13C and 15N NMR investigations indicate different binding modes for acetate, nitrate and halides to the receptor 2. The observation of a major conformational change of this receptor during the binding of the halide ions leads to an understanding of the relative binding affinities …

Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals

2015

Five compounds bearing electron-deficient pentafluorophenyl as well as electron-rich (salicylate or indole) aromatic moieties connected by amide or ester linkages were investigated by X-ray diffraction. In the crystals, various interactions (π–π, lone pair–π) between the different aromatic units are important structure controlling factors in addition to the stronger inter- or intramolecular hydrogen bonds induced by the amide and ester moieties. The hydrogen bonding leads to polymeric and macrocyclic assembly of the molecular building blocks.

Studies on the Biosynthesis of Paraherquamide: Synthesis and Incorporation of a Hexacyclic Indole Derivative as an Advanced Metabolite

2001

Studies on the synthesis of pentacyclic strychnos indole alkaloids. photocyclization of n-chloroacetyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b…

1985

Abstract Photocyclization of 2-chloroacetyl-1,2,3,4,5,6-hexahydro-1, 5-methanoazocino[4,3-b]indole ( 5 ) takes place at the indole 4-position to give a 1 ,2 ,3 ,4 , 5 ,6-hexahydro-2 ,11-ethano-1 ,5-methanoazocino [4 , 3-6] indole system. Consequently, the method appears to be unsuitable for constructing the pyrrolidine ring of pentacyclic Strychnos indole alkaloids.

Partialsynthese neuer Ergolinderivate aus Clavinalkaloiden, 4. Mitt. N-1-, C-2- und N-6-monosubstituierte Agroclavine

1985

Agroclavin (1) wird in flussigem Ammoniak/Kaliumamid mit Alkyliodid am Indolstickstoff alkyliert. 1 last sich mit N-Iodsuccinimid zu 2-Iod-1 (3) umsetzen. Mit der Bromcyan-Methode wird 6-Nor-1 (4b) gewonnen und danach an N-6 alkyliert. Partial Synthesis of New Ergoline Derivatives from Clavine Alkaloids, IV: Agroclavines Monosubstituted at N-1, C-2, and N-6 Agroclavine (1) is alkylated at the indole nitrogen with alkyl iodide in ammonia/potassium amide. It is convertible to 2-iodo-1 (3) with N-iodosuccinimide. Compound 6-nor-1 can be prepared by means of the cyanogen bromide method; alkylation at N-6 is described exemplarily for the ethyl derivative.

Validation of Dissolution Testing with Biorelevant Media: An OrBiTo Study.

2017

Dissolution testing with biorelevant media has become widespread in the pharmaceutical industry as a means of better understanding how drugs and formulations behave in the gastrointestinal tract. Until now, however, there have been few attempts to gauge the reproducibility of results obtained with these methods. The aim of this study was to determine the interlaboratory reproducibility of biorelevant dissolution testing, using the paddle apparatus (USP 2). Thirteen industrial and three academic laboratories participated in this study. All laboratories were provided with standard protocols for running the tests: dissolution in FaSSGF to simulate release in the stomach, dissolution in a singl…

Organocatalytic Enantioselective Friedel–Crafts Aminoalkylation of Indoles in the Carbocyclic Ring

2016

The first general catalytic method for the, so far elusive, enantioselective Friedel−Crafts functionalization of indoles in the carbocyclic ring is presented. This transformation contrasts with the usual tendency of these heterocycles to react at the azole ring. For this purpose, the four regioisomeric hydroxy carbocyclic-substituted indoles were reacted with several isatinderived ketimines, using a Cinchona alkaloid-based squaramide, in a low 0.5−5 mol % catalyst loading, as a bifunctional catalyst. This methodology allows the functionalization of indoles in every position of the carbocyclic ring in a regio- and enantioselective fashion, by switching only the position of the hydroxy group …

Nicethamid‐Analoge, VII. Darstellung eines nicethamid‐analogen Pyrrolo [3,4‐ b ]‐ und Pyrrolo [3,4‐ c ]pyridinons

1975

Die Synthese der potentiell analeptisch wirksamen cyclischen Nicethamid-Analoga 6-Athyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-on (9a) und 2-Athyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-3-on (9b) sowie der entsprechenden ringoffenen Verbindungen N-Athyl-2-methylnicotinamid (12a) and N-Athyl-4-methylnicotinamid (12b) wird beschrieben. Nicethamide-Analogues, VII. Synthesis of a Pyrrolo[3,4-b]- and Pyrrolo [3,4-c]pyridinone as Nicethamide Analogues The synthesis of the potentially analeptically active cyclic nicethamide analogues, 6-ethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one(9a) and 2-ethyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-3-one (9b) as well as the corresponding open-ring compounds N-e…