Structure–activity relationships of the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ol series of monoamine reuptake inhibitors

Mahaney, Paige E.; Kim, Callain Y.; Coghlan, Richard D.; Cohn, Stephen T.; Heffernan, Gavin D.; Huselton, Christine; Terefenko, Eugene A.; Vu, A. T.; Zhang, Puwen; Burroughs, Kevin D.; Cosmi, Scott; Bray, Jeffrey D.; Johnston, Grace H.; Deecher, Darlene C.; Trybulski, Eugene J.

doi:10.1016/j.bmcl.2009.07.050

Bioorganic & Medicinal Chemistry Letters

2009

DOI: 10.1016/j.bmcl.2009.07.050

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Structure–activity relationships of the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ol series of monoamine reuptake inhibitors

Paige E. Mahaney¹,

Callain Y. Kim²,

Richard D. Coghlan³

et al.

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Cited by 12 publications

(1 citation statement)

References 14 publications

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“…For implementation of this approach, Eastern fragments 10 and 11 were required. They were obtained in as hort approach from known epoxyalcohols 5 [6] and 6, [7] by coupling with diacid 7 [5] using the Shiina protocol [8] and regio-and stereoselective epoxide openingo fd erived esters 8 and 9 under Brønsted acidic conditions with NH 4 Cl and NaN 3 as an itrogen source (Scheme 1). [9] Smalla mountso fl ikewise obtained C2-esters could be removed by chromatography.S ubsequent azide reductionb yh ydrogenation in the presence of Pd/C gave amino alcohols 12 and 13 which may be used without further purification.…”

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confidence: 99%

SAR Studies of the Leupyrrins: Design and Total Synthesis of Highly Potent Simplified Leupylogs

Wosniok

Knopf

Dreisigacker

et al. 2020

Chemistry A European J

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Leupyrrins are highly potent antifungal agents. As tructure-activity-relationship study of natural and synthetic derivatives is reported which reveals importanti nsights into the biological relevance of several structural subunits leading to the discovery of highly potent but drastically simplified leupylogs that incorporate as table and readily availablea romatic side chain. For their synthesis ac oncise strategy is described that enablesashort and versatile access.

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mentioning

confidence: 99%

SAR Studies of the Leupyrrins: Design and Total Synthesis of Highly Potent Simplified Leupylogs

Wosniok

Knopf

Dreisigacker

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Enantioselective Palladium‐Catalyzed Carbene Insertion into the N−H Bonds of Aromatic Heterocycles

et al. 2017

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C3‐substituted indoles and carbazoles react with α‐aryl‐α‐diazoesters under palladium catalysis to form α‐(N‐indolyl)‐α‐arylesters and α‐(N‐carbazolyl)‐α‐arylesters. The products result from insertion of a palladium‐carbene ligand into the N−H bond of the aromatic N‐heterocycles. Enantioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselectivity (up to 99 % ee). The method was applied to synthesize the core of a bioactive carbazole derivative in a concise manner.

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Asymmetric N‐Alkylation of 1H‐Indoles via Carbene Insertion Reaction

Peng,

Huang,

et al. 2023

Angewandte Chemie

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An intermolecular enantioselective N‐alkylation reaction of 1H‐indoles has been developed by cooperative rhodium and chiral phosphoric acid catalyzed N‐H bond insertion reaction. N‐Alkyl indoles with newly formed stereocenter adjacent to the indole nitrogen atom are produced in good yields (up to 95%) with excellent enantioselectivities (up to >99% ee). Importantly, both α‐aryl and α‐alkyl diazoacetates are tolerated, which is extremely rare in asymmetric X‐H (X = N, O, S et al.) and C‐H insertion reactions. With this method, only 0.1 mol% of rhodium catalyst and 2.5 mol% of chiral phosphoric acid are required to complete the conversion as well as achieve the high enantioselectivity. Computational studies reveal the cooperative relay of rhodium and chiral phosphoric acid, and the origin of the chemo and stereoselectivity.

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Structure–activity relationships of the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ol series of monoamine reuptake inhibitors

Cited by 12 publications

References 14 publications

SAR Studies of the Leupyrrins: Design and Total Synthesis of Highly Potent Simplified Leupylogs

SAR Studies of the Leupyrrins: Design and Total Synthesis of Highly Potent Simplified Leupylogs

Enantioselective Palladium‐Catalyzed Carbene Insertion into the N−H Bonds of Aromatic Heterocycles

Asymmetric N‐Alkylation of 1H‐Indoles via Carbene Insertion Reaction

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