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Structure studies of mitomycins. III. Structure of M-83
1Tokyo Research Laboratories, Kyowa Hakko Kogyo Co. Ltd, Japan.
Abstract:
7-N-(p-Hydroxyphenyl)mitomycin C* (I), C21H22N4O6.H2O, Mr = 444.45, orthorhombic, P2(1)2(1)2(1), a = 8.056 (2), b = 33.832 (9), c = 7.469 (1) A, V = 2036 (1) A3, Z = 4, Dx = 1.45 g cm-3, Cu K alpha, lambda = 1.54184 A, mu = 8.8 cm-1, F(000) = 936, T = 293 K, R = 0.041 for 1923 observed reflections with F greater than 3 sigma (F). Although the overall structure, except the p-hydroxyphenyl group, is similar to mitomycin C, the bond lengths in the quinone ring are significantly influenced by the substituent. The phenyl and quinone rings are nearly planar and the two rings form a dihedral angle of 46.36 (7) degrees. Two quinone O atoms deviate from the least-squares planes of the quinone ring on the same side of the plane.
Insights
The crystal structure of 7-N-(p-Hydroxyphenyl)mitomycin C was determined. The p-hydroxyphenyl substituent influences quinone ring bond lengths, affecting the overall molecular conformation.
Area of Science:
- Crystallography
- Medicinal Chemistry
- Molecular Biology
Background:
- Mitomycin C is a potent antitumor antibiotic.
- Structural modifications of mitomycin C are explored to understand structure-activity relationships.
Purpose of the Study:
- To determine the crystal structure of 7-N-(p-Hydroxyphenyl)mitomycin C.
- To analyze the structural impact of the p-hydroxyphenyl substituent on the mitomycin C core.
Main Methods:
- Single-crystal X-ray diffraction analysis.
- Structure solution and refinement using crystallographic software.
Main Results:
- The crystal structure of 7-N-(p-Hydroxyphenyl)mitomycin C hydrate was determined in the orthorhombic system (P2(1)2(1)2(1)).
- The p-hydroxyphenyl group significantly influences bond lengths within the quinone ring compared to mitomycin C.
- The phenyl and quinone rings exhibit near planarity with a dihedral angle of 46.36 (7) degrees.
Conclusions:
- The structural data provides insights into how substituents modulate the electronic and conformational properties of mitomycin C.
- Understanding these structural changes is crucial for designing novel mitomycin C analogs with improved therapeutic potential.