Quinazoline

Base Information

• Chemical Name: Quinazoline
• CAS No.: 253-82-7
• Molecular Formula: C8H6N2
• Molecular Weight: 130.149
• Hs Code.: 29339900
• European Community (EC) Number: 205-965-3
• NSC Number: 72372
• UNII: UB9QUR18NL
• DSSTox Substance ID: DTXSID7075214
• Nikkaji Number: J5.442I
• Wikipedia: Quinazoline
• Wikidata: Q426278
• Pharos Ligand ID: T2L8KQJGCG73
• Metabolomics Workbench ID: 55437
• ChEMBL ID: CHEMBL301359
• Mol file: 253-82-7.mol

Synonyms:Quinazoline;Quinazolines

Chemical Property of Quinazoline

Chemical Property:

• Appearance/Colour: Beige to brownish crystalline powder
• Vapor Pressure: 0.0545mmHg at 25°C
• Melting Point: 46-48 °C(lit.)
• Refractive Index: 1.653
• Boiling Point: 241.845 °C at 760 mmHg
• PKA: 3.43(at 20℃)
• Flash Point: 106.667 °C
• PSA: 25.78000
• Density: 1.183 g/cm³
• LogP: 1.62980
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: H2O: freely soluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 130.053098200
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99%, ^*data from raw suppliers

Quinazoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=NC=N2
• General Description: Quinazoline is a nitrogen-containing heterocyclic compound with a fused benzene and pyrimidine ring structure, known for its diverse pharmacological applications, including potential roles as an anticancer and antimicrobial agent. Its derivatives, such as quinazolinones, are also significant in medicinal chemistry due to their therapeutic properties. Quinazoline can be synthesized through efficient catalytic methods, such as ruthenium-catalyzed dehydrogenative coupling, which offers a sustainable approach to accessing these bioactive scaffolds.

Technology Process of Quinazoline

There total 71 articles about Quinazoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

4-(α-benzyl-α-hydroxybenzyl)quinazoline (187336-04-5) → phenyl benzyl ketone (451-40-1) + quinazoline (253-82-7)

Guidance literature:

With tetra-n-butylammonium cyanide; In tetrahydrofuran; for 1h; Heating;

DOI:10.1248/cpb.46.199

Reference yield: 88.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-amino-1-benzylamine (4403-69-4) → quinazoline (253-82-7)

Guidance literature:

With 3-nitropyridine; In acetonitrile; at 110 ℃; for 16h; Reagent/catalyst; Sealed tube;

DOI:10.1002/ejoc.201800746

Reference yield: 86.0%

2-anisyl-4-quinazolinyl ketone (55326-11-9) → quinazoline (253-82-7) + 2-Methoxybenzoic acid (579-75-9) + 4-(2-Methoxy-phenyl)-3,4-dihydro-quinazoline-4-carboxylic acid (99933-60-5)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; for 1h;

upstream raw materials:

3,4-dihydroquinazoline

ammonium acetate

o-aminobenzaldehyde

N,N'-(2-nitro-benzylidene)-bis-formamide

Downstream raw materials:

2,4-diaminoquinazoline

quinazoline-N-oxide

4-Hydroxyquinazoline

1,2,3,4-tetrahydroquinazoline

Refernces

Identification of potent pyrazolo[4,3-h]quinazoline-3-carboxamides as multi-cyclin-dependent kinase inhibitor

10.1021/jm901710h

The study focuses on the identification and development of potent pyrazolo[4,3-h]quinazoline-3-carboxamides as inhibitors of multiple cyclin-dependent kinases (CDKs), which are enzymes that play a crucial role in regulating the cell cycle and have been implicated in cancer development. The researchers aimed to create compounds that could inhibit CDKs both in vitro and in vivo, with improved inhibitory activity, physical properties, and pharmacokinetic behavior compared to the initial hit compound. The study led to the identification of compound 59, which showed significant in vivo efficacy in an ovarian carcinoma xenograft model and could be a potential antineoplastic agent. The chemicals used in the study were primarily a series of pyrazolo[4,3-h]quinazoline derivatives, including the initial hit compound 1 and the optimized compound 59, along with various reagents and conditions for their synthesis and testing. These chemicals served the purpose of inhibiting the activity of CDKs, which are targets for antitumor therapy, and were evaluated for their ability to modulate CDK activity, affect cell cycle progression, and inhibit tumor growth.

Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand-Promoted Ruthenium-Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines

10.1021/acs.orglett.9b01082

This study explores a ruthenium-catalyzed ligand-promoted coupling reaction for the synthesis of quinazoline and quinazolinone derivatives. The in situ formed ruthenium catalytic system ([Ru]/L) selectively catalyzes the dehydrogenative coupling of 2-aminophenyl ketones with amines to quinazoline products and the deaminogenic coupling of 2-aminobenzamides with amines to quinazolinone products. This approach is highly efficient and avoids reactive reagents and toxic byproducts. Quinazolines and quinazolinones are nitrogen heterocyclic scaffolds with various pharmacological activities used as therapeutics for diseases such as benign prostatic hyperplasia, cancer, and antimicrobial infections. This study optimizes the reaction conditions using a cationic ruthenium hydride complex and a catechol ligand, demonstrating broad substrate scope and scalability. Mechanistic insights indicate the formation of an imine intermediate that undergoes isomerization, cyclization, and dehydrogenation steps to generate the final product.

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