Synthese von 2‐Amino‐3‐cyano‐pyrrolen

Roth, H. J.; Eger, Kurt

doi:10.1002/ardp.19753080304

Cited by 41 publications

(16 citation statements)

References 6 publications

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“…Syntheses of the 2amino-3-cyanopyrroles were accomplished by treating α-hydroxyketones 2a-c with suitable primary amines 3a-f in hot toluene in the presence of a catalytic amount of trichloroacetic acid. After initial formation of the unisolated α-aminoketones 4, addition to the reaction mixture of malononitrile led to ring-closure and heterocycle formation [33,34]. Using this approach, pyrroles 5a-g were prepared in good yields (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1 H -pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor

McGeary

Tan

Selleck

et al. 2017

European Journal of Medicinal Chemistry

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A SAR study on derivatives of 2-amino-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile 5a revealed that the 3-carbonitrile group, vicinal 4,5-diphenyl and N-benzyl side chains of the pyrrole are important for the inhibitory potencies of these compounds against members representing the three main subclasses of metallo-β-lactamases (MBLs), i.e. IMP-1 (representing the B1 subgroup), CphA (B2) and AIM-1 (B3). Coupling of 5a with a series of acyl chlorides and anhydrides led to the discovery of two N-acylamide derivatives, 10 and 11, as the two most potent IMP-1 inhibitors in this series. However, these compounds are less effective towards CphA and AIM-1. The N-benzoyl derivative of 5a retained potent in vitro activity against each of MBLs tested (with inhibition constants in the low μM range). Importantly, this compound also significantly enhanced the sensitivity of IMP-1, CphA- or AIM-1-producing cell cultures towards meropenem. This compound presents a promising starting point for the development of a universal MBL inhibitor, targeting members of each of the major subgroups of this family of enzymes.

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Section: Chemistrymentioning

confidence: 99%

Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1 H -pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor

McGeary

Tan

Selleck

et al. 2017

European Journal of Medicinal Chemistry

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“…Consequently, we designed another synthetic route (route 2) using a Knorr reaction and diazotization as the key steps (Scheme ). Compound 7 was synthesized from L ‐alanine using a Dakin–West reaction, and was converted to compound 6 by a Lewis acid‐catalyzed Knorr reaction in a sealed tube under anhydrous conditions . Compound 6 was transformed to compound 3 following diazotization and hydrolysis reactions .…”

Section: Resultsmentioning

confidence: 99%

ChemInform Abstract: Preparation of Novel Pyrrolo[2,3‐b]pyridine Derivatives via a New Concise Synthetic Approach.

et al. 2015

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The pyrrolo[2,3‐b]pyridine core structure, a bioisostere of quinolones, is found in several molecules that possess important biological activity. We describe here a new, concise, three‐step synthesis of pyrrolo[2,3‐b]pyridines starting from L‐alanine. A series of 4,7‐dihydro‐4‐oxo‐1H‐pyrrolo[2,3‐b]pyridine‐5‐carboxylic acid derivatives, which have not been previously reported, were synthesized using this approach.

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“…'H-NMR (D6-DMSO): 6 (ppm) 1,95 (s, CH,); 2,05 (s, CH,); 2,95 (s, 6H); 7,O (2d, 4H-Ar); 8,23 (s, H); 11,2 (s, NH). 2,7 g (0,Ol mol) 2b werden in 10 ml DMSO gelost und mit 250 mg Natriumhydrid versetzt. Man laBt abreagieren, wobei sich die Losung dunkelviolett farbt.…”

Section: -(4-dimethylaminobenzyliden7amino-3-cyano-45-dimethylpyrrounclassified

Zur Synthese potentieller 5‐Lipoxygenasehemmstoffe, 1. Mitt.

Folkers¹,

Roth²

1986

Archiv der Pharmazie

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Folkers und Roth Arch. Pharm. gewaschen. Feine gelbliche Kristalle, Doppel-Schmp. 147-148"; 177-178" (= 3). Ausb.: 56 % d. Th. CI6Hl4N2O, (346.3) Ber. C 55.5 H 4.07 N 8.1 Gef. C 55.5 H 4.04 N 8.0 Mo1.-Masse 328 (Mt-H20) (ms). 2-Methyl-4-(2-nitrophenyl)-5-0~0-5, 7-dihydrofuro[3,4-b]pyridin-3-carbonaure (5)3 mmol3 werden rnit 20 ml50proz. H2S04 20 h bei 100" geriihrt. Die klare, braune Losung wird mit H20 verdiinnt, mit KOH auf pH -3 gebracht und rnit Et20 extrahiert. Der Riickstand der organischen Phase wird rnit wenig MeOH angerieben. Feine gelbliche Nadeln, Schmp. 236240"

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Synthese von 2‐Amino‐3‐cyano‐pyrrolen

Cited by 41 publications

References 6 publications

Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1 H -pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor

Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1 H -pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor

ChemInform Abstract: Preparation of Novel Pyrrolo[2,3‐b]pyridine Derivatives via a New Concise Synthetic Approach.

Zur Synthese potentieller 5‐Lipoxygenasehemmstoffe, 1. Mitt.

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