Podcast
Questions and Answers
What is the main purpose of bioisosterism in medicinal chemistry?
What is the main purpose of bioisosterism in medicinal chemistry?
- To increase toxicity of a compound
- To completely change the chemical structure of a compound
- To enhance desired biological or physical properties without significant changes in chemical structure (correct)
- To reduce bioavailability of a compound
How do classical bioisosters affect the overall topology of a molecule?
How do classical bioisosters affect the overall topology of a molecule?
- Slightly modify it (correct)
- Significantly change it
- Have no impact on it
- Keep it identical
Which type of bioisosters have similar physical or chemical properties to the original functional group?
Which type of bioisosters have similar physical or chemical properties to the original functional group?
- Neutral bioisosters
- Enhanced bioisosters
- Classical bioisosters (correct)
- Non-classical bioisosters
How do bioisosters contribute to modifying the activity of a lead compound?
How do bioisosters contribute to modifying the activity of a lead compound?
What is the primary benefit of exchanging one bioisoster for another in medicinal chemistry?
What is the primary benefit of exchanging one bioisoster for another in medicinal chemistry?
What is a characteristic feature of classical bioisosteres?
What is a characteristic feature of classical bioisosteres?
Which of the following is an example of a monovalent classical bioisostere?
Which of the following is an example of a monovalent classical bioisostere?
What distinguishes non-classical bioisosteres from classical bioisosteres?
What distinguishes non-classical bioisosteres from classical bioisosteres?
In what scenarios might substituting a chloride (-Cl) group with a cyano (-C≡N) group be beneficial?
In what scenarios might substituting a chloride (-Cl) group with a cyano (-C≡N) group be beneficial?
How might replacing a phenyl ring with a thiophene ring impact a molecule's pharmacokinetic properties?
How might replacing a phenyl ring with a thiophene ring impact a molecule's pharmacokinetic properties?
Bioisosterism is a concept in __________ chemistry that refers to the relationship between two or more molecules that have similar biological activity due to their similar structures.
Bioisosterism is a concept in __________ chemistry that refers to the relationship between two or more molecules that have similar biological activity due to their similar structures.
The purpose of exchanging one bioisoster for another is to enhance the desired biological or physical properties of a compound without making significant changes in __________ structure.
The purpose of exchanging one bioisoster for another is to enhance the desired biological or physical properties of a compound without making significant changes in __________ structure.
Bioisosterism is used to reduce toxicity, change bioavailability, or modify the activity of the ______ compound.
Bioisosterism is used to reduce toxicity, change bioavailability, or modify the activity of the ______ compound.
Classical bioisosters are chemical substituents or groups that have similar physical or chemical properties to the original ______ group.
Classical bioisosters are chemical substituents or groups that have similar physical or chemical properties to the original ______ group.
By modifying certain substituents, the pharmacological activity of the chalcone and its ______ is also modified.
By modifying certain substituents, the pharmacological activity of the chalcone and its ______ is also modified.
Monovalent atoms and groups for H include F, H OH, NH F, OH, NH, or ______ for H
Monovalent atoms and groups for H include F, H OH, NH F, OH, NH, or ______ for H
Divalent atoms and groups include –C=S, –C=O, –C=NH, –C=C–, whereas trivalent atoms and groups include [–CH =, –N =], [–P =, –As =], and ______
Divalent atoms and groups include –C=S, –C=O, –C=NH, –C=C–, whereas trivalent atoms and groups include [–CH =, –N =], [–P =, –As =], and ______
Tetravalent atoms and groups include =N+=, =C=, =P+=, =As+=, while ring equivalents are ______
Tetravalent atoms and groups include =N+=, =C=, =P+=, =As+=, while ring equivalents are ______
Non-classical bioisosters differ from classical bioisosters in that they do not obey the steric and electronic definition of classical isosteres and may not have the same number of atoms as a replacement, yet they aim to provide similar sterics and electronic profiles. They focus on maintaining similar sterics and electronic profiles to the original functional group. For example, a chloride (-Cl) group may often be replaced by a trifluoromethyl (-CF3) group or by a cyano (-C≡N) group. Non-classical bioisosters prioritize providing similar sterics and electronic profiles, regardless of the ______ of atoms in the replacement.
Non-classical bioisosters differ from classical bioisosters in that they do not obey the steric and electronic definition of classical isosteres and may not have the same number of atoms as a replacement, yet they aim to provide similar sterics and electronic profiles. They focus on maintaining similar sterics and electronic profiles to the original functional group. For example, a chloride (-Cl) group may often be replaced by a trifluoromethyl (-CF3) group or by a cyano (-C≡N) group. Non-classical bioisosters prioritize providing similar sterics and electronic profiles, regardless of the ______ of atoms in the replacement.
Aromatic rings can be replaced with different aromatic rings such as thiophene or naphthalene, which may improve efficacy, change specificity of binding, or reduce metabolically labile sites on the molecule, resulting in better pharmacokinetic properties. For example, a phenyl (-C6H5) ring can often be replaced by a different aromatic ring such as thiophene or naphthalene. This substitution may impact the molecule's pharmacokinetic properties by enhancing efficacy, altering binding specificity, or reducing metabolically labile sites, leading to better ______ properties.
Aromatic rings can be replaced with different aromatic rings such as thiophene or naphthalene, which may improve efficacy, change specificity of binding, or reduce metabolically labile sites on the molecule, resulting in better pharmacokinetic properties. For example, a phenyl (-C6H5) ring can often be replaced by a different aromatic ring such as thiophene or naphthalene. This substitution may impact the molecule's pharmacokinetic properties by enhancing efficacy, altering binding specificity, or reducing metabolically labile sites, leading to better ______ properties.
Study Notes
Bioisosterism in Medicinal Chemistry
- Bioisosterism is a concept in medicinal chemistry that refers to the relationship between two or more molecules with similar biological activity due to their similar structures.
Purpose of Bioisosterism
- The main purpose of bioisosterism is to enhance the desired biological or physical properties of a compound without making significant changes in molecular structure.
Types of Bioisosteres
- Classical bioisosteres are chemical substituents or groups that have similar physical or chemical properties to the original functional group.
- Non-classical bioisosters differ from classical bioisosters in that they do not obey the steric and electronic definition of classical isosteres and may not have the same number of atoms as a replacement, yet they aim to provide similar sterics and electronic profiles.
Characteristics of Bioisosteres
- Classical bioisosteres affect the overall topology of a molecule by replacing functional groups with similar physical or chemical properties.
- Monovalent classical bioisosters include F, H, OH, NH, and I for H.
- Divalent classical bioisosters include –C=S, –C=O, –C=NH, –C=C–, and –N=N–.
- Trivalent classical bioisosters include –CH=, –N=, –P=, and –As=.
- Tetravalent classical bioisosters include =N+=, =C=, =P+=, and =As+=.
- Ring equivalents of classical bioisosters include aromatic rings like thiophene or naphthalene.
Impact of Bioisosteres on Pharmacokinetic Properties
- Replacing a phenyl ring with a thiophene ring may impact a molecule's pharmacokinetic properties by enhancing efficacy, altering binding specificity, or reducing metabolically labile sites, leading to better pharmacokinetic properties.
- Substituting a chloride (-Cl) group with a cyano (-C≡N) group or a trifluoromethyl (-CF3) group may be beneficial in certain scenarios.
Modifying Activity of Lead Compounds
- Bioisosters contribute to modifying the activity of a lead compound by replacing functional groups with similar physical or chemical properties, thereby enhancing or altering its biological activity.
Studying That Suits You
Use AI to generate personalized quizzes and flashcards to suit your learning preferences.
Description
Explore the concept of bioisosterism in medicinal chemistry, focusing on the relationship between molecules with similar biological activity due to their analogous structures. Learn about chemical substituents that produce comparable biological properties in the same compound.
