Synthesis, Crystal Structure, and Rotational Energy Profile of 3-Cyclopropyl-1,2,4-benzotriazine 1,4-Di-N-oxide

Author

Ujjal Sarkar
Rainer Glaser, Missouri University of Science and TechnologyFollow
Zack D. Parsons
Charles Leslie Barnes
Kent S. Gates

Abstract

1,2,4-Benzotriazine 1,4-di-N-oxides are potent antitumor drug candidates that undergo in vivo bioreduction leading to selective DNA damage in the low oxygen (hypoxic) cells found in tumors. Tirapazamine (TPZ) is the lead compound in this family. Here we report on the synthesis, crystal structure, and conformational analysis of a new analog, 3-cyclopropyl-1,2,4-benzotriazine 1,4-di-N-oxide (3). Compound 3 (C₁₀H₁₀N₃O₂) crystallized in the monoclinic space group C2/c. Unit cell parameters for 3: a = 16.6306 (12), b = 7.799 (5), c = 16.0113 (11) Å , α = 90, β = 119.0440 (10), γ = 90, and z = 8.

Recommended Citation

U. Sarkar et al., "Synthesis, Crystal Structure, and Rotational Energy Profile of 3-Cyclopropyl-1,2,4-benzotriazine 1,4-Di-N-oxide," Journal of Chemical Crystallography, vol. 40, no. 7, pp. 624 - 629, Springer Verlag, Jul 2010.

The definitive version is available at https://doi.org/10.1007/s10870-010-9707-9

Department(s)

Chemistry

Keywords and Phrases

Crystal structure; Cyclopropyl group; N-oxide; Rotational energy profile; Tirapazamine

International Standard Serial Number (ISSN)

1074-1542; 1572-8854

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2010 Springer Verlag, All rights reserved.

Publication Date

01 Jul 2010