• 1. One-pot synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion
  Fei Ji,Mei-Fang Lv,Wen-Bin Yi,Chun Cai Org. Biomol. Chem. 2014 12 5766
• 2. Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: application to the synthesis of the alkaloid tryptanthrin
  Shenghai Guo,Yan Li,Li Tao,Wenwen Zhang,Xuesen Fan RSC Adv. 2014 4 59289
• 3. Palladium-catalyzed allylation of tautomerizable heterocycles with alkynes
  Chuan-Jun Lu,Dong-Kai Chen,Hong Chen,Hong Wang,Hongwei Jin,Xifu Huang,Jianrong Gao Org. Biomol. Chem. 2017 15 5756
• 4. 902. Polyazanaphthalenes. Part VII. Some derivatives of quinazoline and 1,3,5-triazanaphthalene
  V. Oakes,H. N. Rydon,K. Undheim J. Chem. Soc. 1962 4678
• 5. 492. Cyclic amidines. Part XV. Derivatives of tricycloquinazoline
  M. W. Partridge,H. J. Vipond,J. A. Waite J. Chem. Soc. 1962 2549

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Quinazolines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Benzodiazines Quinazolines

Introduction to 6-Methylquinazolin-4-ol (CAS No. 19181-53-4)

6-Methylquinazolin-4-ol, identified by the Chemical Abstracts Service registry number 19181-53-4, is a heterocyclic organic compound belonging to the quinazoline family. This compound has garnered significant attention in the field of pharmaceutical chemistry due to its structural versatility and potential biological activities. Quinazoline derivatives are well-documented for their roles in drug discovery, particularly as scaffolds for developing therapeutic agents targeting various diseases, including cancer and infectious disorders.

The molecular structure of 6-Methylquinazolin-4-ol consists of a fused benzene ring and a pyrimidine ring, with a methyl substituent at the 6-position and a hydroxyl group at the 4-position. This particular arrangement imparts unique electronic and steric properties, making it a valuable intermediate in synthetic chemistry. The presence of the hydroxyl group enhances its reactivity, allowing for further functionalization through esterification, etherification, or oxidation reactions, which can tailor its biological profile for specific applications.

In recent years, 6-Methylquinazolin-4-ol has been extensively studied for its pharmacological properties. Preliminary in vitro studies have suggested that this compound exhibits inhibitory effects on certain kinases and enzymes implicated in tumor progression. Specifically, research indicates that derivatives of 6-Methylquinazolin-4-ol may interfere with the activity of cyclin-dependent kinases (CDKs) and tyrosine kinases, which are critical regulators of cell cycle progression and signal transduction pathways. Such findings position this compound as a promising candidate for further development into anticancer therapies.

Moreover, the quinazoline core is known to possess antimicrobial and anti-inflammatory properties. Investigations have demonstrated that modifications of the 6-Methylquinazolin-4-ol scaffold can lead to compounds with enhanced efficacy against bacterial and fungal pathogens. The hydroxyl group at the 4-position serves as a key site for derivatization, enabling the creation of analogs with improved pharmacokinetic profiles and reduced toxicity. These attributes make 6-Methylquinazolin-4-ol an attractive building block for novel antimicrobial agents.

The synthesis of 6-Methylquinazolin-4-ol typically involves multi-step organic reactions starting from readily available precursors such as anthranilic acid or 2-amino benzothiazole. Advances in synthetic methodologies have enabled more efficient and scalable production processes, facilitating its use in both academic research and industrial applications. For instance, catalytic hydrogenation and palladium-catalyzed cross-coupling reactions have been employed to introduce functional groups at specific positions on the quinazoline ring, enhancing its utility in drug development.

Recent studies have also explored the role of 6-Methylquinazolin-4-ol in modulating immune responses. Research suggests that certain derivatives may activate toll-like receptors (TLRs) or other pattern recognition receptors (PRRs), thereby influencing inflammatory pathways. This immunomodulatory potential opens up possibilities for developing therapeutic strategies against autoimmune diseases and chronic inflammation conditions. The ability to fine-tune the chemical structure of 6-Methylquinazolin-4-ol allows researchers to balance efficacy with selectivity, minimizing off-target effects.

In conclusion, 6-Methylquinazolin-4-ol (CAS No. 19181-53-4) represents a versatile pharmacophore with significant therapeutic implications. Its unique structural features and reactivity make it a valuable tool for medicinal chemists seeking to develop novel treatments for cancer, infections, and inflammatory diseases. As research continues to uncover new biological functions associated with quinazoline derivatives, compounds derived from 6-Methylquinazolin-4-ol are likely to play an increasingly important role in modern medicine.

• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)