114118-70-6Relevant articles and documents
(Z)-1,4-diamino-2-butene as a vector of boron, fluorine, or iodine for cancer therapy and imaging: synthesis and biological evaluation.
Martin, Benedicte,Posseme, Francoise,Le Barbier, Caroline,Carreaux, Francois,Carboni, Bertrand,Seiler, Nikolaus,Moulinoux, Jacques-Philippe,Delcros, Jean-Guy
, p. 2863 - 2871 (2002)
Polyamine vectors are attractive for tumor targeting. We envisaged (Z)-1,4-diamino-2-butene (Z-DAB), an unsaturated analogue of putrescine as vector of (10)B, (18)F and (131)I for boron neutron capture therapy (BNCT), and tumor imaging by positron emission tomography or scintigraphy respectively. In the present work, the synthesis and characterization of new derivatives of Z-DAB were reported. Z-DAB was actively transported in cells via the polyamine transport system and converted into the spermidine analogue.(E)-2-iodo-1,4-diamino-2-butene (E-I-DAB) was not taken up by the polyamine transport system and may not be suitable for tumor imaging. In contrast, (Z)-2-[4-(5,5-dimethyl-dioxaborinan-2-yl)phenyl]methyl-1,4-diamino-2-butene (Z-4-Bbz-DAB) was a substrate of the transport system and allowed significant boron accumulation in 3LL cells. Its potential in BNCT will be evaluated.
But-2-ene-1,4-diamine and But-2-ene-1,4-diol as Donors for Thermodynamically Favored Transaminase- and Alcohol Dehydrogenase-Catalyzed Processes
Martínez-Montero, Lía,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
supporting information, p. 1618 - 1624 (2016/10/13)
Both cis- and trans-but-2-ene-1,4-diamines have been prepared and efficiently applied as sacrificial cosubstrates in enzymatic transamination reactions. The best results were obtained with the cis-diamine. The thermodynamic equilibrium of the stereoselective transamination process is shifted to the amine formation due to tautomerization of 5H-pyrrole into 1H-pyrrole, achieving high conversions (78–99%) and enantiomeric excess (up to >99%) by using a small excess of the amine donor. Furthermore, when the reaction proceeded, a strong coloration was observed due to polymerization of 1H-pyrrole. A structurally related compound, cis-but-2-ene-1,4-diol, has been utilized as cosubstrate in different alcohol dehydrogenase (ADH)-mediated bioreductions. In this case, high conversions (91–99%) were observed due to a lactonization process. Both strategies are convenient from both synthetic and atom economy points of view in the production of valuable optically active products. (Figure presented.).
Fungicidal Activity of the Synthetic Putrescine Analogue, (E)-1,4-Diaminobut-2-ene, and Derivatives
Havis, Neil D.,Walters, Dale R.,Foster, Sally A.,Martin, William P.,Cook, Fiona M.,Robins, David J.
, p. 61 - 70 (2007/10/03)
The putrescine analogue, (E)-1,4-diaminobut-2-ene (E-BED), synthesized as the dihydrochloride salt, controlled five economically important crop pathogens, Erysiphe graminis DC f.sp. hordei Marchal, Uromyces viciae-fabae (Pers.) Schroet, Botrytis fabae Sardina, Podosphaera leucotricha (Ell. & Ev.) Salm. and Phytophthora infestans (Mont) De Bary. The Z-isomer, Z-BED, was also fungicidal, although less so than E-BED. Post-inoculation treatment with E-BED gave greater control of powdery mildew infection on barley and rust and chocolate spot on broad bean than did pre-inoculation application. It was also effective in vitro against Botrytis cinerea Pers. ex Fr., Pyricularia oxyzae Br. & Cav. and Pyrenophora avenae Ito & Karibay. When P. avenae was grown in the presence of E-BED dihydrochloride at 81.5 mg litre-1, growth was reduced by 58 percent and there were significant reductions in soluble ornithine decarboxylase (ODC) and S-adenosylmethionine decarboxylase (AdoMetDC) activity. These changes were accompanied by a sevenfold increase in putrescine concentration, a 60 percent increase in spermine concentration and a 32 percent reduction in spermidine concentration within the fungal tissue.
A Simple Conversion of Alkohols into Amines
Fabiano, Emmanuel,Golding, Bernard T.,Sadeghi, Majid M.
, p. 190 - 192 (2007/10/02)
In a convenient one-pot sequence, treatment of alcohols and α-hydroxyesters with hydrazoic acid, di-isopropyl azodicarboxylate and an excess of triphenylphosphine in tetrahydrofuran, followed by addition of water or aqueous acid, yields amines or amino-acid esters in moderate to good overall yields.
