ChemInform Abstract: REACTIONS OF AMINES. XVIII. OXIDATIVE REARRANGEMENT OF AMIDES WITH LEAD TETRAACETATE

Baumgarten, Henry E.; Smith, Howard L.; Staklis, Andris

doi:10.1002/chin.197609096

Cited by 2 publications

(2 citation statements)

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“…46 Much effort has been devoted to the development of modified reagents to optimize the Hofmann rearrangement since the classical method for this transformation, involving the use of an alkaline solution of bromine, is unsatisfactory and unreliable. 35 A variety of oxidants and bases have been proposed as modified agents, e.g., iodine(III) reagents such as PhI(OAc) 2 , 47 MeOBr, 48 NBS-CH 3 ONa, 49 NBS-KOH, 46 lead tetraacetate, 50 and benzyltrimethylammonium tribromide. 51 These modified methods, however, require more than 1 equiv or an excess amount of the oxidizing reagent, which is not very convenient.…”

Section: Methods For the Synthesis Of Carbamatesmentioning

confidence: 99%

Organic Carbamates in Drug Design and Medicinal Chemistry

2015

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The carbamate group is a key structural motif in many approved drugs and prodrugs. There is an increasing use of carbamates in medicinal chemistry and many carbamate derivatives are specifically designed to make drug-target interactions through their carbamate moiety. In this review, we present properties and stabilities of carbamates, reagents and chemical methodologies for the synthesis of carbamates, and recent application of carbamates in drug design and medicinal chemistry.

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Section: Methods For the Synthesis Of Carbamatesmentioning

confidence: 99%

Organic Carbamates in Drug Design and Medicinal Chemistry

2015

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“…37 The compound was prepared by means of a two-step procedure reported in the literature: 36 Synthesis of Cyclobutylcarbamic Acid Benzyl Ester (13). 38 To a stirred solution of NaHCO 3 Synthesis of (R,S)-2-Oxocyclobutylcarbamic Acid Benzyl Ester (15). 36 The compound was prepared following a literature procedure: 36 Synthesis of (S)-1-Methyl-3-(2-oxo-3-oxetanyl)urea (19a).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

N-(2-Oxo-3-oxetanyl)carbamic Acid Esters as N-Acylethanolamine Acid Amidase Inhibitors: Synthesis and Structure–Activity and Structure–Property Relationships

et al. 2012

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The β-lactone ring of N-(2-oxo-3-oxetanyl)amides, a class of N-acylethanolamine acid amidase (NAAA) inhibitors endowed with anti-inflammatory properties, is responsible for both NAAA inhibition and low compound stability. Here, we investigate the structure−activity and structure−property relationships for a set of known and new β-lactone derivatives, focusing on the new class of N-(2-oxo-3-oxetanyl)carbamates. Replacement of the amide group with a carbamate one led to different stereoselectivity for NAAA inhibition and higher intrinsic stability, because of the reduced level of intramolecular attack at the lactone ring. The introduction of a syn methyl at the β-position of the lactone further improved chemical stability. A tert-butyl substituent in the side chain reduced the reactivity with bovine serum albumin. (2S,3R)-2-Methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester (27, URB913/ARN077) inhibited NAAA with good in vitro potency (IC 50 = 127 nM) and showed improved stability. It is rapidly cleaved in plasma, which supports its use for topical applications.

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ChemInform Abstract: REACTIONS OF AMINES. XVIII. OXIDATIVE REARRANGEMENT OF AMIDES WITH LEAD TETRAACETATE

Abstract: Aus den Amiden (I) entstehen bei der Oxidation mit Bleitetraacetat die Isocyanate (II),die in die entsprechenden Urethane, Harnstoffe und Amine umgewandelt werden können.

Cited by 2 publications

References 1 publication

Organic Carbamates in Drug Design and Medicinal Chemistry

Organic Carbamates in Drug Design and Medicinal Chemistry

N-(2-Oxo-3-oxetanyl)carbamic Acid Esters as N-Acylethanolamine Acid Amidase Inhibitors: Synthesis and Structure–Activity and Structure–Property Relationships

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