1. Answer ALL of the following parts.
(a) Using an appropriate example define the term lead compound.
(b) In the context of biologically active compounds explain the difference between
adirect analogue, a functional analogue and a structural analogue.
(c) The following compound is biologically active and a library of analogues is needed for screening. Available in the lab you have a range of five substituted benzoyl chlorides (Ar1COCl to Ar5COCl) and three aliphatic alcohols (R1OH to
R3OH) and all the other general reagents and solvents needed to make amides and esters.
(i) Draw the structure of the ‘scaffold’ molecule upon which you would base your library.
(ii) Using a solution-phase approach describe how you might make a library
of derivatives using the compounds available.
(iii) How many derivatives could you make using your scaffold and the other compounds available?
(iv) If one of the acid chlorides available was 2-methylbenzoyl chloride and one alcohol was cyclohexanol draw the analogue which you could make.
(d) Comment briefly on the advantages and disadvantages of solid-phase approach to combinatorial chemistry.
(e) Describe briefly what is meant by ‘rational drug design’ and comment on the scientific advances that have enabled this type of research to be undertaken.
2. Answer all parts:
(a) Using the materials and reagents below describe how you could construct a small library of analogues of the lead compound given using a parallel synthesis approach. In your answer explain the strategy involved, state the total number of different structures that your library would contain and draw the structure of a representative member of the library.
(b) Describe briefly the key aspects that must be considered during the selection
of a new drug discovery programme.
(c) Discuss briefly the basis of Lipinski’s ‘Rule of Five’.
(d) Describe what is meant by ‘rational drug design’ and comment on the scientific advances that have enabled us to undertake this type of research.
(e) Describe briefly the advantages and disadvantages of the solution phase approach to combinatorial chemistry.
(f) Giving an example, describe what is meant by ‘bioisosteric replacement’.
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