Skip to main content
Article
Synthesis, Crystal Structure, and Rotational Energy Profile of 3-Cyclopropyl-1,2,4-benzotriazine 1,4-Di-N-oxide
Journal of Chemical Crystallography
  • Ujjal Sarkar
  • Rainer Glaser, Missouri University of Science and Technology
  • 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.

Department(s)
Chemistry
Keywords and Phrases
  • Crystal structure,
  • Cyclopropyl group,
  • N-oxide,
  • Rotational energy profile,
  • Tirapazamine
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2010 Springer Verlag, All rights reserved.
Publication Date
7-1-2010
Publication Date
01 Jul 2010
Disciplines
Citation Information
Ujjal Sarkar, Rainer Glaser, Zack D. Parsons, Charles Leslie Barnes, 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 Iss. 7 (2010) p. 624 - 629 ISSN: 1074-1542; 1572-8854
Available at: http://works.bepress.com/rainer-glaser/127/