Phenanthridine: Difference between revisions

Latest revision as of 05:49, 16 February 2025

Phenanthridine[edit]

Phenanthridine is a heterocyclic aromatic organic compound with the molecular formula C__H_N. It is a tricyclic structure consisting of three fused benzene rings, two of which are connected by a nitrogen atom. Phenanthridine is an important scaffold in medicinal chemistry and is found in various natural products and synthetic compounds with biological activity.

Structure and Properties[edit]

Phenanthridine is a planar molecule with a conjugated system of π-electrons, which contributes to its aromaticity. The presence of the nitrogen atom in the ring system imparts basicity to the compound, allowing it to form salts with acids. The compound is typically a pale yellow solid at room temperature and is soluble in organic solvents such as ethanol and chloroform.

Synthesis[edit]

The synthesis of phenanthridine can be achieved through several methods, one of the most notable being the Pictet-Hubert reaction. This reaction involves the cyclization of an N-arylamide precursor under acidic conditions to form the phenanthridine ring system. The Pictet-Hubert reaction is a valuable tool in organic synthesis for constructing the phenanthridine core efficiently.

Applications[edit]

Phenanthridine and its derivatives have a wide range of applications in the field of medicinal chemistry. They are known for their biological activities, including antitumor, antimicrobial, and antiviral properties. Phenanthridine derivatives are also used as fluorescent probes in biochemistry and molecular biology due to their ability to intercalate into DNA.

Related Compounds[edit]

Phenanthridine is structurally related to other nitrogen-containing heterocycles such as quinoline and isoquinoline. These compounds share similar aromatic properties and are also of significant interest in pharmaceutical research.

Related Pages[edit]

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-'''Phenanthridine''' is a [[polycyclic aromatic hydrocarbon]] that consists of three [[benzene]] rings connected by two [[carbon]] atoms. It is a basic structure of many natural and synthetic compounds. The name "phenanthridine" is derived from the three rings it contains: phenyl, anthracene, and pyridine.
+== Phenanthridine ==
-== Structure and Synthesis ==
+[[File:Pictet-Hubert_reaction_V1.svg|thumb|right|300px|Schematic of the Pictet-Hubert reaction, a key method for synthesizing phenanthridine.]]
-Phenanthridine is a tricyclic compound, meaning it contains three rings. The rings are fused together, sharing two carbon atoms. The structure of phenanthridine is similar to that of [[anthracene]], but with a nitrogen atom replacing one of the carbon atoms in the central ring.
-Phenanthridine can be synthesized through several methods. One common method is the [[Bischler-Napieralski reaction]], which involves the cyclization of a [[N-phenylethylamine]] derivative. Another method is the [[Pictet-Spengler reaction]], which involves the condensation of a [[beta-phenylethylamine]] derivative with an [[aldehyde]] or [[ketone]].
+'''Phenanthridine''' is a heterocyclic aromatic organic compound with the molecular formula C__H_N. It is a tricyclic structure consisting of three fused benzene rings, two of which are connected by a nitrogen atom. Phenanthridine is an important scaffold in medicinal chemistry and is found in various natural products and synthetic compounds with biological activity.
-== Properties and Uses ==
+== Structure and Properties ==
-Phenanthridine is a colorless, crystalline solid. It is soluble in most organic solvents, but insoluble in water. It has a melting point of 101-102 degrees Celsius and a boiling point of 360 degrees Celsius.
-Phenanthridine is used as a starting material in the synthesis of many natural and synthetic compounds. It is also used as a [[ligand]] in [[coordination chemistry]].
+Phenanthridine is a planar molecule with a conjugated system of π-electrons, which contributes to its aromaticity. The presence of the nitrogen atom in the ring system imparts basicity to the compound, allowing it to form salts with acids. The compound is typically a pale yellow solid at room temperature and is soluble in organic solvents such as ethanol and chloroform.
-== Health Effects ==
+== Synthesis ==
-Exposure to phenanthridine can cause irritation to the eyes, skin, and respiratory tract. Ingestion can cause nausea, vomiting, and abdominal pain. Long-term exposure can lead to liver and kidney damage.
-== See Also ==
+The synthesis of phenanthridine can be achieved through several methods, one of the most notable being the [[Pictet-Hubert reaction]]. This reaction involves the cyclization of an N-arylamide precursor under acidic conditions to form the phenanthridine ring system. The Pictet-Hubert reaction is a valuable tool in organic synthesis for constructing the phenanthridine core efficiently.
-* [[Polycyclic aromatic hydrocarbon]]
-* [[Benzene]]
-* [[Anthracene]]
-* [[Pyridine]]
-* [[Bischler-Napieralski reaction]]
-* [[Pictet-Spengler reaction]]
-[[Category:Polycyclic aromatic hydrocarbons]]
+== Applications ==
-[[Category:Tricyclic compounds]]
-[[Category:Organic compounds]]
-[[Category:Chemical synthesis]]
-{{stub}}
+Phenanthridine and its derivatives have a wide range of applications in the field of [[medicinal chemistry]]. They are known for their biological activities, including antitumor, antimicrobial, and antiviral properties. Phenanthridine derivatives are also used as fluorescent probes in [[biochemistry]] and [[molecular biology]] due to their ability to intercalate into [[DNA]].
+== Related Compounds ==
+Phenanthridine is structurally related to other nitrogen-containing heterocycles such as [[quinoline]] and [[isoquinoline]]. These compounds share similar aromatic properties and are also of significant interest in pharmaceutical research.
+== Related Pages ==
+* [[Heterocyclic compound]]
+* [[Aromaticity]]
+* [[Organic synthesis]]
+* [[Medicinal chemistry]]
+[[Category:Heterocyclic compounds]]
+[[Category:Organic chemistry]]
+[[Category:Medicinal chemistry]]