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Many of the drugs in human medicine are chiral because they bind to enzymes and receptors to elicit biological activity. Both enzymes and receptors are chiral and therefore in a chiral drug molecule one of the enantiomer is more active than the other. Most of the drugs are also heterocyclic in nature. In the present study we have conceived ideas of what heterocycles might show activity against a particular disease based on their bindings at enzyme or receptor level and investigated the role of chirality in these molecules. Novel synthetic methodologies were developed for the enantioselective synthesis of these heterocycles possessing chiral centers and we believe these synthetic methodologies will be useful for the synthesis of other drugs. Using the above general concepts we have synthesized novel enantiomerically pure chiral heterocylces such as 5-aryl oxindoles, which have shown potent activity as progesterone receptor antagonists, spiro-oxindoles, for possible use as cancer therapeutics, ortho-ortho disubstituted bipheyl lactams, for possible implications in CNS and cancer therapy, and conformationally restricted sulfonamides as HIV-1 protease inhibitors for treatment of AIDS.