Synthesis of racemic α-amino acids of the series of 4- and 7-azaindoles

Azimov, V. A.; Uritskaya, M. Ya.; Yakhontov, L. N.

doi:10.1007/bf00760279

Cited by 2 publications

(4 citation statements)

References 4 publications

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“…However, in the case of 4 a , 4‐azagramine ( 4 b ) was found to be robustly resistant to this alkylation strategy, as the methylation of 4 b produced an insoluble brick red tar which promptly decomposed under subsequent reaction conditions. Therefore, 4 f was synthesized using an alternative route (Scheme 1A) [36] . In this method, 4 b was refluxed in xylenes in the presence of acetamidomalonate and catalytic NaOH to generate intermediate 4 c , which was then saponified and decarboxylated/deacylated via extended reflux in 20 % aqueous HCl.…”

Section: Resultsmentioning

confidence: 99%

“… Synthetic methods used to produce azaindole‐containing substrate analogs. (A) Known synthetic method for ethyl ester 7 e [35] applied to 5 a , 6 a , and 7 a , alongside an alternative route adapted for 4 a [36] . (B) Method for synthesizing ethyl ester 2e modified from literature [37] .…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, 4 f was synthesized using an alternative route (Scheme 1A). [36] In this method, 4 b was refluxed in xylenes in the presence of acetamidomalonate and catalytic NaOH to generate intermediate 4 c, which was then saponified and decarboxylated/deacylated via extended reflux in 20 % aqueous HCl. The pure 4 f racemate was recovered via recrystallization without the need for column purification.…”

Section: Synthesis Of Aza-trp and Aza-cywp Analogsmentioning

confidence: 99%

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Unlocking New Prenylation Modes: Azaindoles as a New Substrate Class for Indole Prenyltransferases

Gardner,

Johnson,

Dimas

et al. 2023

ChemCatChem

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Aza‐substitution, the replacement of aromatic CH groups with nitrogen atoms, is an established medicinal chemistry strategy for increasing solubility, but current methods of accessing functionalized azaindoles are limited. In this work, indole‐alkylating aromatic prenyltransferases (PTs) were explored as a strategy to directly functionalize azaindole‐substituted analogs of natural products. For this, a series of aza‐L‐tryptophans (Aza‐Trp) featuring N‐substitution of every aromatic CH position of the indole ring and their corresponding cyclic Aza‐L‐Trp‐L‐proline dipeptides (Aza‐CyWP), were synthesized as substrate mimetics for the indole‐alkylating PTs FgaPT2, CdpNPT, and FtmPT1. We then demonstrated most of these substrate analogs were accepted by a PT, and the regioselectivity of each prenylation was heavily influenced by the position of the N‐substitution. Remarkably, FgaPT2 was found to produce cationic N‐prenylpyridinium products, representing not only a new substrate class for indole PTs but also a previously unobserved prenylation mode. The discovery that nitrogenous indole bioisosteres can be accepted by PTs thus provides access to previously unavailable chemical space in the search for bioactive indolediketopiperazine analogs.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Aza-trp and Aza-cywp Analogsmentioning

confidence: 99%

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Unlocking New Prenylation Modes: Azaindoles as a New Substrate Class for Indole Prenyltransferases

Gardner,

Johnson,

Dimas

et al. 2023

ChemCatChem

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“…Synthesis of the first amino acid representative of the 4‐azaindole series, 4‐azatryptophan (4‐AW), was described by the Yakhontov group in 1968 [84] . A synthetic strategy based on the Erlenmeyer‐Plöchl amino acid synthesis [85] has been chosen.…”

Section: Synthesis Of Aw Derivatives Via Dehydro Aw Intermediatementioning

confidence: 99%

Tailor‐Made Amino Acids in Pharmaceutical Industry: Synthetic Approaches to Aza‐Tryptophan Derivatives

Han

Lyutenko

Sorochinsky

et al. 2021

Chemistry A European J

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Over the recent years there has been a noticeable upsurge of interest in aza‐analogs of tryptophan which are isosteric to the latter and found numerous applications in medicinal, bioorganic chemistry, and peptide research. In the present review article, five aza‐tryptophan derivatives are profiled, including aza‐substitution in the positions 2, on the five‐membered ring, as well as in positions 4, 5, 6, and 7 on the six‐membered ring. A detailed and comprehensive literature overview of the synthetic methods for the preparation of these aza‐tryptophans is presented and general facets of the biological properties and most promising applications are discussed.

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Synthesis of racemic α-amino acids of the series of 4- and 7-azaindoles

Cited by 2 publications

References 4 publications

Unlocking New Prenylation Modes: Azaindoles as a New Substrate Class for Indole Prenyltransferases

Unlocking New Prenylation Modes: Azaindoles as a New Substrate Class for Indole Prenyltransferases

Tailor‐Made Amino Acids in Pharmaceutical Industry: Synthetic Approaches to Aza‐Tryptophan Derivatives

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