Glossary of Med Chem: Isosterism

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What is a bioisostere?
A compound resulting from the exchange of an atom with another similar atom or group of atoms.

The objective is to create a new compound with similar biological properties to the parent compound.
What are isosteres?
A compound resulting from the exchange of an atom with another similar atom or group of atoms.

-similar physical and chemical properties

molecules or ions of similar size containing the same number of atoms and valence electrons (ex: O2-, F-, Ne)
What are stereoisomers?
isomers whose molecules have the same atoms bonded to each other but differ in the way these atoms are arranged in space.
What are the three types of stereoisomers?
1. Geometric (cis/trans) isomers
2. Optical Isomers
3. Constitutional Isomers
What are enatiomers?
-optical isomers
-mirror images of each other
-not identical
-have 1 or more chiral carbons
-rotate the plane of polarized light equally, but in opposite directions
-same physical properties
-same chemical properties

(A type of optical isomer)
What are geometric (cis-trans) isomers?
-same molecular formula
-different geometric configuration (atoms are attached in different spatial arrangements on either side of a double bond)
"MJ pose"
Trans isomer
What are the two types of optical isomers?
What are the two types of geometrical isomers?
Define Isomers
molecules of identical atomic compositions (molecular formulas), but with different bonding arrangements of atoms or orientation of their atoms in space.

(optical, geometric and conformational isomerism)
Define Optical Isomers
molecules with the same atomic composition but different bonding arrangements between atoms.

-same molecular formula
-different bonding arrangements
-distinct chemical entities
-different chemical and physical properties
Define Steroisomers
-Identical molecular formula
-Identical bonding arrangement
-different orientations of atoms in space
-different orientations cannot interconvert freely by bond rotation.

-differ only in relative spatial orientations of atoms

-Three Types: optical, geometric, conformational
Define Conformational Isomers
-different relative spatial arrangements of atoms
-rotation about sigma bonds
-aka Rotamers
What is another name for conformational isomers?
What are diastereomers?
-optical isomers
-NOT mirror images
-at least two chiral carbons
-sterochemistry of one chiral carbon will be the same
-DIFFERENT physical and chemical properties
-split light in different directions

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