3460-54-6Relevant academic research and scientific papers
Desulfurization strategy in the construction of azoles possessing additional nitrogen, oxygen or sulfur using a copper(I) catalyst
Guin, Srimanta,Rout, Saroj Kumar,Gogoi, Anupal,Nandi, Shyamapada,Ghara, Krishna Kanta,Patel, Bhisma K.
, p. 2757 - 2770 (2013/01/15)
A tandem and convergent approach to various N-, O-, or S-containing azoles has been developed by exploiting the thiophilic property of copper( I) iodide used in a catalytic quantity. The present protocol gives access to amino-substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter- or intramolecular attack of suitable nucleophiles. For aminotetrazoles and triazoles an excellent regioselectivity has been achieved through proper tuning of the pKa values of the parent amines attached to unsymmetrical thioureas. The method represents an autocatalytic process in which copper( I) iodide gets converted to copper(II) sulfide which in turn transforms to active copper(II) oxide that effectively carries forward the catalytic cycle. The fate of the copper catalyst has also been studied using scanning electron microscopic (SEM) and energy-dispersive X-ray spectroscopic (EDS) analyses which give an insight into the mechanism for this catalytic process.
Symmetrical and unsymmetrical analogues of isoxyl; active agents against Mycobacterium tuberculosis
Bhowruth, Veemal,Brown, Alistair K.,Reynolds, Robert C.,Coxon, Geoffrey D.,Mackay, Simon P.,Minnikin, David E.,Besra, Gurdyal S.
, p. 4743 - 4747 (2008/12/23)
Symmetrical and unsymmetrical analogues of the antimycobacterial agent isoxyl-have been synthesized and tested against Mycobacterium tuberculosis H37Rv and Mycobacterium bovis BCG, some showing an increased bactericidal effect. In particular, compounds 1-(p-n-butylphenyl)-3-(4-propoxy-phenyl) thiourea (10) and 1-(p-n-butylphenyl)-3-(4-n-butoxy-phenyl) thiourea (11) showed an approximate 10-fold increase in in vitro potency compared to isoxyl, paralleled by increased inhibition of mycolic acid biosynthesis in M. bovis BCG. Interestingly, these isoxyl analogues showed relatively poor inhibition of oleate production, suggesting that the modifications have changed the spectrum of biological activity.
