85879-93-2Relevant articles and documents
A modular lead-oriented synthesis of diverse piperazine, 1,4-diazepane and 1,5-diazocane scaffolds
James, Thomas,Maclellan, Paul,Burslem, George M.,Simpson, Iain,Grant, J. Andrew,Warriner, Stuart,Sridharan, Visuvanathar,Nelson, Adam
supporting information, p. 2584 - 2591 (2014/04/17)
Piperazines are found widely in commercially-available compounds and bioactive molecules (including many drugs). However, in the vast majority of these molecules, the piperazine ring is isolated (i.e. not fused to another ring) and is not substituted on any of its carbon atoms. A modular synthetic approach is described in which combinations of cyclic sulfamidate and hydroxy sulfonamide building blocks may be converted into piperazines and related 1,4-diazepine and 1,5-diazocane scaffolds. By variation of the combinations of building blocks used, it was possible to vary the ring size, substitution and configuration of the resulting heterocyclic scaffolds. The approach was exemplified in the synthesis of a range of heterocyclic scaffolds that, on decoration, would target lead-like chemical space. It was demonstrated that lead-like small molecules based on these scaffolds would likely complement those found in large compound collections. This journal is the Partner Organisations 2014.
Use of Liquid Crystal Induced Circular Dichroism for Absolute Configurational Assignments of β-Amino Alcohols
Rinaldi, Peter L.,Wilk, Melody
, p. 2141 - 2146 (2007/10/02)
Dissolution of small quantities of chiral β-amino alcohols in liquid crystalline N-(p-methoxybenzylidene)-p-n-butylaniline (MBBA) results in induced rotations due to the formation of a cholesteric (chiral) liquid crystal phase.The induced rotations are several orders of magnitude larger than those observed for β-amino alcohols in isotropic solutions, and the signs of these rotations can be correlated with the absolute configurations of the chiral amino alcohols when standard conformational analysis arguments and the preference of elongated molecules to align with MBBA are considered.