Synthesis, Crystal Structure, and Rotational Energy Profile of 3-Cyclopropyl-1,2,4-benzotriazine 1,4-Di-N-oxide
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.
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
Keywords and Phrases
Crystal structure; Cyclopropyl group; N-oxide; Rotational energy profile; Tirapazamine
International Standard Serial Number (ISSN)
Article - Journal
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01 Jul 2010