By Ashutosh Kar
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Additional resources for Advanced Practical Medicinal Chemistry
With the advent of latest concepts and tools evolved in ‘Computer Aided Drug Design (CADD)’ one may logically design a new drug molecule on as much a rational basis as possible. It is, however, pertinent to mention here that ‘medicinal chemists’ have traditionally adopted synthesis as the ultimate-concrete-evidence of molecular structure(s) of natural products meticulously isolated from plant and animal sources. Over the years it has been universally accepted as an authentic and genuine proof-of-identity between an isolated natural substance and the compound produced by total-synthesis eventually confirmed the molecular structure arrived at through various physico chemical methods of analysis.
When the difference in ‘free energy’ of the two isomers are not significantly wide apart one may end-up with a mixture of isomers. Example. Conversion of isodihydrocarvone—a terpenoid derivative, into the corresponding dihydrocarvone analogue—a characteristic flavour in cloves, is accomplished by heating either with an acid or a base as illustrated below : *syn-addition. It indicates stereochemical facts that the added groups become attached to the same faces (syn) of the double bond. **anti-addition.
O—] : are a common protecting group for alcohols, such as : chlorotrimethyl silane [(CH3)3 SiCl] is at present frequently employed for protection of alcohols as silyl ethers. (d) Benzyl Groups. [C6H5—CH2—] : are specifically employed for protecting alcohols and carboxylic acids. (e) Cleavage of Benzyl Ethers and Esters. LM C H —CH —O— C —(Benzyl Ether) ; MN 6 5 2 OP PQ : are caused by reductive hydrogenolysis. It is pertinent to mention here that this specific reaction does not affect other ethers and O C6H5—CH2— C —OR (Benzyl Ester) esters.
Advanced Practical Medicinal Chemistry by Ashutosh Kar