Trans-(4-Methylcyclohexylcarbamoyl)phosphonic acid: A representative matrix metalloproteinase (MMP) inhibitor

Shmuel Cohen; Yiffat Katz; Reuven Reich; Eli Breuer

doi:10.1107/S1600536805025936

Trans-(4-Methylcyclohexylcarbamoyl)phosphonic acid: A representative matrix metalloproteinase (MMP) inhibitor

Shmuel Cohen^*
, Yiffat Katz
, Reuven Reich
, Eli Breuer

^*Corresponding author for this work

School of Pharmacy

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

1 Scopus citations

Abstract

The title compound, C₈H₁₆NO₄P, is the first carbamoylphosphonic acid for which the crystal structure has been solved. The -PO₃H₂ group has three distinct P-O bond distances of 1.483(1), 1.506(1) and 1.545 (2) Å. Hydrogen bonds of types P-O-H⋯O=C and N-H⋯O=P [2.416 (2) and 2.954 (2) Å, respectively] connect the molecules to form a chain of condensed ten-membered hydrogen-bonded rings. The second P-O-H group of each phosphonic acid is hydrogen-bonded to an O=P group of the next chain, so serving to link adjacent chains together.

Original language	English
Pages (from-to)	o3008-o3010
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	61
Issue number	9
DOIs	https://doi.org/10.1107/S1600536805025936
State	Published - 1 Sep 2005

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title = "Trans-(4-Methylcyclohexylcarbamoyl)phosphonic acid: A representative matrix metalloproteinase (MMP) inhibitor",

abstract = "The title compound, C8H16NO4P, is the first carbamoylphosphonic acid for which the crystal structure has been solved. The -PO3H2 group has three distinct P-O bond distances of 1.483(1), 1.506(1) and 1.545 (2) {\AA}. Hydrogen bonds of types P-O-H⋯O=C and N-H⋯O=P [2.416 (2) and 2.954 (2) {\AA}, respectively] connect the molecules to form a chain of condensed ten-membered hydrogen-bonded rings. The second P-O-H group of each phosphonic acid is hydrogen-bonded to an O=P group of the next chain, so serving to link adjacent chains together.",

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T1 - Trans-(4-Methylcyclohexylcarbamoyl)phosphonic acid

T2 - A representative matrix metalloproteinase (MMP) inhibitor

AU - Cohen, Shmuel

AU - Katz, Yiffat

AU - Reich, Reuven

AU - Breuer, Eli

PY - 2005/9/1

Y1 - 2005/9/1

N2 - The title compound, C8H16NO4P, is the first carbamoylphosphonic acid for which the crystal structure has been solved. The -PO3H2 group has three distinct P-O bond distances of 1.483(1), 1.506(1) and 1.545 (2) Å. Hydrogen bonds of types P-O-H⋯O=C and N-H⋯O=P [2.416 (2) and 2.954 (2) Å, respectively] connect the molecules to form a chain of condensed ten-membered hydrogen-bonded rings. The second P-O-H group of each phosphonic acid is hydrogen-bonded to an O=P group of the next chain, so serving to link adjacent chains together.

AB - The title compound, C8H16NO4P, is the first carbamoylphosphonic acid for which the crystal structure has been solved. The -PO3H2 group has three distinct P-O bond distances of 1.483(1), 1.506(1) and 1.545 (2) Å. Hydrogen bonds of types P-O-H⋯O=C and N-H⋯O=P [2.416 (2) and 2.954 (2) Å, respectively] connect the molecules to form a chain of condensed ten-membered hydrogen-bonded rings. The second P-O-H group of each phosphonic acid is hydrogen-bonded to an O=P group of the next chain, so serving to link adjacent chains together.

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Trans-(4-Methylcyclohexylcarbamoyl)phosphonic acid: A representative matrix metalloproteinase (MMP) inhibitor

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