Cinnoline: Difference between revisions

Latest revision as of 11:53, 15 February 2025

Overview of the chemical compound Cinnoline

Cinnoline is a heterocyclic aromatic organic compound with the chemical formula C₈H₆N₂. It is a bicyclic structure consisting of a benzene ring fused to a pyridazine ring. Cinnoline and its derivatives are of interest in medicinal chemistry due to their potential biological activities.

Structure and Properties[edit]

Cinnoline is a planar molecule with a fused ring system. The presence of nitrogen atoms in the pyridazine ring contributes to its aromaticity and chemical reactivity. The compound is typically a yellow crystalline solid at room temperature.

Synthesis[edit]

Cinnoline can be synthesized through various methods, one of which is the Widman-Stoermer reaction. This reaction involves the cyclization of o-aminobenzaldehydes with hydrazines to form the cinnoline ring system.

File:Widman-stoermer-reaction.png

Widman-Stoermer reaction mechanism for the synthesis of cinnoline.

Applications[edit]

Cinnoline derivatives have been studied for their potential use in pharmaceuticals. They exhibit a range of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The modification of the cinnoline core can lead to compounds with enhanced activity and selectivity.

Related Compounds[edit]

Cinnoline is structurally related to other heterocyclic compounds such as quinoline, isoquinoline, and phthalazine. These compounds share similar bicyclic structures but differ in the position and number of nitrogen atoms in the ring system.

Related pages[edit]

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-'''Cinnoline''' is a heterocyclic aromatic organic compound with the chemical formula C_8H_6N_2. It is characterized by a fused ring structure that consists of a benzene ring and a pyridine ring, sharing two adjacent carbon atoms. Cinnoline belongs to the class of compounds known as diazanaphthalenes, a subgroup of nitrogen-containing heterocycles. These compounds are of interest in medicinal chemistry due to their diverse biological activities and potential therapeutic applications.
+{{Short description|Overview of the chemical compound Cinnoline}}
+{{Chemical compound}}
+'''Cinnoline''' is a heterocyclic aromatic organic compound with the chemical formula C<sub>8</sub>H<sub>6</sub>N<sub>2</sub>. It is a bicyclic structure consisting of a benzene ring fused to a pyridazine ring. Cinnoline and its derivatives are of interest in medicinal chemistry due to their potential biological activities.
 ==Structure and Properties==
-Cinnoline has a bicyclic structure with nitrogen atoms at the 1 and 2 positions of the pyridine ring. This arrangement contributes to its unique chemical and physical properties. The presence of nitrogen atoms imparts basicity to the molecule, allowing it to participate in various chemical reactions. Cinnoline is a colorless solid at room temperature and has a distinct aromatic odor.
+Cinnoline is a planar molecule with a fused ring system. The presence of nitrogen atoms in the pyridazine ring contributes to its aromaticity and chemical reactivity. The compound is typically a yellow crystalline solid at room temperature.
 ==Synthesis==
-Several synthetic routes have been developed for the preparation of cinnoline and its derivatives. One common method involves the condensation of 1,2-diaminobenzene (o-phenylenediamine) with glyoxal, followed by oxidative cyclization. Another approach is the dehydrogenation of quinoline, which involves the removal of hydrogen atoms to form the cinnoline structure.
+Cinnoline can be synthesized through various methods, one of which is the [[Widman-Stoermer reaction]]. This reaction involves the cyclization of o-aminobenzaldehydes with hydrazines to form the cinnoline ring system.
+[[File:Widman-stoermer-reaction.png|thumb|right|300px|Widman-Stoermer reaction mechanism for the synthesis of cinnoline.]]
 ==Applications==
-Cinnoline and its derivatives exhibit a wide range of biological activities, making them valuable in the field of medicinal chemistry. They have been studied for their potential applications as antitumor, antibacterial, anti-inflammatory, and antiviral agents. Additionally, cinnoline derivatives are explored for their use in the development of phosphodiesterase inhibitors, which have implications in treating various diseases such as asthma, COPD, and erectile dysfunction.
+Cinnoline derivatives have been studied for their potential use in pharmaceuticals. They exhibit a range of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The modification of the cinnoline core can lead to compounds with enhanced activity and selectivity.
-==Safety and Toxicology==
+==Related Compounds==
-The safety and toxicological profile of cinnoline and its derivatives vary depending on the specific compound and its concentration. Like many aromatic heterocyclic compounds, cinnoline derivatives may exhibit toxicity, necessitating careful handling and evaluation in pharmaceutical development.
+Cinnoline is structurally related to other heterocyclic compounds such as [[quinoline]], [[isoquinoline]], and [[phthalazine]]. These compounds share similar bicyclic structures but differ in the position and number of nitrogen atoms in the ring system.
-==See Also==
+==Related pages==
+* [[Quinoline]]
+* [[Isoquinoline]]
+* [[Phthalazine]]
 * [[Heterocyclic compound]]
-* [[Pyridine]]
-* [[Benzene]]
-* [[Medicinal chemistry]]
-* [[Phosphodiesterase inhibitor]]
-[[Category:Organic compounds]]
 [[Category:Heterocyclic compounds]]
 [[Category:Nitrogen heterocycles]]
-{{Chemistry-stub}}