The structure of 2-methoxy-5-(2′,3′,4′-trimethoxyphenyl)tropone, an effective analog of colchicine

Miriam Rossi, John Link, James Lee

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

2-Methoxy-5-(2′,3′,4′-trimethoxyphenyl)tropone is an active analog of colchicine, a mitotic spindle inhibitor, which is missing the middle "B" ring. This compound crystallizes in the triclinic system, space group P1 ̄, with Z = 2; a = 10.135(2), b = 10.166(4), and c = 7.863(2) Å; α = 82.15(3), β = 103.49(3), and γ = 107.16(2){ring operator}; and V = 750.7(4) Å3. The structure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.063, using 2503 observed reflections and 271 parameters. Despite the absence of the middle ring, the conformation of the molecule is similar to that of colchicine, isocolchicine, and their derivatives. The troponoid ring is dissimilar to the phenyl ring in that it is not aromatic and does have alternating short and long bond lengths. The dihedral angle between the least-squares planes of the two rings is -57.4{ring operator}. Van der Waals surface representations of the analog and colchicine are presented to demonstrate the similarity and differences of these two molecules. The structural information of the analog is consistent with the interpretation of thermodynamic parameters which govern the interactions between brain tubulin and the analog.

Original languageEnglish (US)
Pages (from-to)470-476
Number of pages7
JournalArchives of Biochemistry and Biophysics
Volume231
Issue number2
DOIs
StatePublished - 1984
Externally publishedYes

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Colchicine
Least-Squares Analysis
Spindle Apparatus
Molecules
Bond length
Dihedral angle
Tubulin
Thermodynamics
Conformations
Brain
Derivatives
tropone

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

The structure of 2-methoxy-5-(2′,3′,4′-trimethoxyphenyl)tropone, an effective analog of colchicine. / Rossi, Miriam; Link, John; Lee, James.

In: Archives of Biochemistry and Biophysics, Vol. 231, No. 2, 1984, p. 470-476.

Research output: Contribution to journalArticle

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AB - 2-Methoxy-5-(2′,3′,4′-trimethoxyphenyl)tropone is an active analog of colchicine, a mitotic spindle inhibitor, which is missing the middle "B" ring. This compound crystallizes in the triclinic system, space group P1 ̄, with Z = 2; a = 10.135(2), b = 10.166(4), and c = 7.863(2) Å; α = 82.15(3), β = 103.49(3), and γ = 107.16(2){ring operator}; and V = 750.7(4) Å3. The structure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.063, using 2503 observed reflections and 271 parameters. Despite the absence of the middle ring, the conformation of the molecule is similar to that of colchicine, isocolchicine, and their derivatives. The troponoid ring is dissimilar to the phenyl ring in that it is not aromatic and does have alternating short and long bond lengths. The dihedral angle between the least-squares planes of the two rings is -57.4{ring operator}. Van der Waals surface representations of the analog and colchicine are presented to demonstrate the similarity and differences of these two molecules. The structural information of the analog is consistent with the interpretation of thermodynamic parameters which govern the interactions between brain tubulin and the analog.

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