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The secondary amine/nitric oxide complex ion R2N[N(O)NO](-) as nucleophile and leaving group in SNAr reactions

  1. Author:
    Saavedra, J. E.
    Srinivasan, A.
    Bonifant, C. L.
    Chu, J. X.
    Shanklin, A. P.
    Flippen-Anderson, J. L.
    Rice, W. G.
    Turpin, J. A.
    Davies, K. M.
    Keefer, L. K.

  2. Author Address

    NCI, SAIC Frederick, Intramural Res Support Program, Frederick, MD 21702 USA. NCI, SAIC Frederick, Intramural Res Support Program, Frederick, MD 21702 USA. NCI, Comparat Carcinogenesis Lab, Chem Sect, Frederick, MD 21702 USA. USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA. So Res Inst, Frederick, MD 21702 USA. George Mason Univ, Dept Chem, Fairfax, VA 22030 USA. Saavedra JE NCI, SAIC Frederick, Intramural Res Support Program, Frederick, MD 21702 USA.
    1. Year: 2001
  2. Journal: Journal of Organic Chemistry
    1. 66
    2. 9
    3. Pages: 3090-3098
  4. Type of Article: Article
  1. Abstract:

    Ions of structure R2N[N(O)NO](-) and their alkylation products have seen increasing use as nitric oxide (NO)-generating agents for biomedical research applications. Were we show that such diazeniumdiolate anions can readily displace halide from a variety of electrophilic aza- or nitroaromatic substrates to form O-2-arylated derivatives of structure R2N-N(O)=N=OAr. The site of arylation and the cis arrangement of the oxygens were confirmed by X-ray crystallography. Displacement by various nucleophiles showed R2N[N(O)NO](-) to be a reasonably good leaving group, with rate constants for displacement by hydroxide, methoxide, and isopropylamine that were between those of chloride and fluoride in the SNAr reactions we surveyed. The Meisenheimer intermediate could be spectrally observed. These O-2-aryl diazeniumdiolates proved capable of reacting with the nucleophilic sulfur of the HIV-1 p7 nucleocapsid protein's zinc finger assembly to eject the zinc, disrupting a structural motif critical to viral replication and suggesting possible utility in the drug discovery realm.

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