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Questions and Answers
What is the common name for the azetidinone ring found in penicillins and cephalosporins?
The β-lactam ring
How do β-lactam antibiotics kill bacteria?
By inhibiting cell wall synthesis
Name the antimalarial drug that belongs to the 4-aminoquinoline class and is considered one of the most successful antimalarial agents.
Chloroquine
What is the IUPAC name for the heterocyclic compound found in chloroquine?
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Name two proton pump inhibitors (PPIs) used as anti-ulcer drugs that contain a pyridine moiety.
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Give an example of a non-aromatic heterocycle discussed in the text.
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Give an example of an aromatic heterocycle discussed in the text.
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What class of antibiotics do penicillins and cephalosporins belong to?
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What property of nitrogen heterocycles makes them valuable as organic bases?
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Name a valuable laboratory solvent that is a nitrogen heterocycle.
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Study Notes
Heterocyclic Compounds
- Heterocycles are cyclic compounds in which one or more of the ring atoms is not carbon, with the noncarbon atoms referred to as heteroatoms.
- Heterocycles are grouped into two classes: non-aromatic and aromatic.
Non-Aromatic Heterocycles
- Numbering always begins at the heteroatom, with the heteroatom of higher atomic number taking priority.
- Examples of non-aromatic heterocycles include morpholine, tetrahydrofuran, and dioxane (1,4-dioxane).
- Some non-aromatic heterocycles are useful as laboratory solvents, while others are useful as organic bases, such as piperidine, pyrrolidine, and morpholine.
- The basicities of nitrogen derivatives are comparable to those of similar acyclic amines, but physical properties make them more versatile.
- Morpholine and piperazine are weaker bases than piperidine due to an electron-withdrawing inductive effect from the second heteroatom.
Aromatic Heterocycles
- Pyridine is structurally related to benzene, with one CH unit replaced by N, contributing two electrons to the π electron system.
- Pyrrole, thiophene, pyrazole, and imidazole are five-membered aromatic heterocycles.
- Pyridine and pyrrole have aromatic stabilization, with six π electrons forming an energetically favorable closed shell.
- The nitrogen lone pair in pyrrole contributes to the aromatic sextet, making the nitrogen atom relatively electron deficient and influencing chemical reactivity.
Pharmaceutical Importance
- Heterocyclic compounds have pharmaceutical importance, with nitrogen mustards being among the first anticancer drugs developed.
- Aziridinium ion formation in vivo occurs through intramolecular ring closure, producing an intermediate aziridinium ion that inhibits DNA replication in cancer cells.
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Description
Explore the classification of heterocyclic compounds in organic chemistry, including non-aromatic and aromatic heterocycles. Study the properties and characteristics of these compounds, with a focus on heteroatoms. This quiz is based on PHR 109 by Faruque Azam.
