Crystal structures of two alanylpiperidine analogues

Kalina Mambourg; Nikolay Tumanov; Gilles Henon; STEVE LANNERS; Javier Garcia-Ladona; Johan Wouters

doi:10.1107/S2056989021010392

Crystal structures of two alanylpiperidine analogues

Kalina Mambourg, Nikolay Tumanov, Gilles Henon, STEVE LANNERS, Javier Garcia-Ladona, Johan Wouters

Research output: Contribution to journal › Article › peer-review

Abstract

The structure of ethyl 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylate, C₁₉H₂₈N2O₅S, I, a compound of interest as activator of Ubiquitin C-terminal Hydrolase-L1 (UCH-L1), was determined by single-crystal X-ray diffraction (SCXRD) analysis. In order to find new activators, a derivative of compound I, namely, 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylic acid, C17H24N2O5S, II, was studied. The synthesis and crystal structure are also reported. Despite being analogues, different crystal packings are observed. Compound II bears a carboxylic group, which favors a strong hydrogen bond. A polymorph risk assessment was carried out to study interactions in compound II.

Original language	English
Pages (from-to)	1095-1098
Number of pages	4
Journal	Acta Crystallographica. Section E: Crystallographic Communications
Volume	77
DOIs	https://doi.org/10.1107/S2056989021010392
Publication status	Published - 1 Nov 2021

Keywords

Alanylpiperidine derivatives
Crystal structure
Polymorph risk assessment
UCH-L1 activator

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10.1107/S2056989021010392

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title = "Crystal structures of two alanylpiperidine analogues",

abstract = "The structure of ethyl 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylate, C19H28N2O5S, I, a compound of interest as activator of Ubiquitin C-terminal Hydrolase-L1 (UCH-L1), was determined by single-crystal X-ray diffraction (SCXRD) analysis. In order to find new activators, a derivative of compound I, namely, 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylic acid, C17H24N2O5S, II, was studied. The synthesis and crystal structure are also reported. Despite being analogues, different crystal packings are observed. Compound II bears a carboxylic group, which favors a strong hydrogen bond. A polymorph risk assessment was carried out to study interactions in compound II.",

keywords = "Alanylpiperidine derivatives, Crystal structure, Polymorph risk assessment, UCH-L1 activator",

author = "Kalina Mambourg and Nikolay Tumanov and Gilles Henon and STEVE LANNERS and Javier Garcia-Ladona and Johan Wouters",

year = "2021",

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doi = "10.1107/S2056989021010392",

language = "English",

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T1 - Crystal structures of two alanylpiperidine analogues

AU - Mambourg, Kalina

AU - Tumanov, Nikolay

AU - Henon, Gilles

AU - LANNERS, STEVE

AU - Garcia-Ladona, Javier

AU - Wouters, Johan

PY - 2021/11/1

Y1 - 2021/11/1

N2 - The structure of ethyl 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylate, C19H28N2O5S, I, a compound of interest as activator of Ubiquitin C-terminal Hydrolase-L1 (UCH-L1), was determined by single-crystal X-ray diffraction (SCXRD) analysis. In order to find new activators, a derivative of compound I, namely, 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylic acid, C17H24N2O5S, II, was studied. The synthesis and crystal structure are also reported. Despite being analogues, different crystal packings are observed. Compound II bears a carboxylic group, which favors a strong hydrogen bond. A polymorph risk assessment was carried out to study interactions in compound II.

AB - The structure of ethyl 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylate, C19H28N2O5S, I, a compound of interest as activator of Ubiquitin C-terminal Hydrolase-L1 (UCH-L1), was determined by single-crystal X-ray diffraction (SCXRD) analysis. In order to find new activators, a derivative of compound I, namely, 1-[N-(4-methylphenyl)-N-(methylsulfonyl)alanyl]piperidine-4-carboxylic acid, C17H24N2O5S, II, was studied. The synthesis and crystal structure are also reported. Despite being analogues, different crystal packings are observed. Compound II bears a carboxylic group, which favors a strong hydrogen bond. A polymorph risk assessment was carried out to study interactions in compound II.

KW - Alanylpiperidine derivatives

KW - Crystal structure

KW - Polymorph risk assessment

KW - UCH-L1 activator

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U2 - 10.1107/S2056989021010392

DO - 10.1107/S2056989021010392

M3 - Article

AN - SCOPUS:85119432581

VL - 77

SP - 1095

EP - 1098

JO - Acta Crystallographica. Section E: Crystallographic Communications

JF - Acta Crystallographica. Section E: Crystallographic Communications

ER -

Crystal structures of two alanylpiperidine analogues

Abstract

Keywords

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