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8-Methoxy-4(1H)-quinazolinone
[CAS# 16064-27-0]

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Identification
Classification Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
Name 8-Methoxy-4(1H)-quinazolinone
Synonyms 8-Methoxyquinazolin-4-ol
Molecular Structure CAS # 16064-27-0, 8-Methoxy-4(1H)-quinazolinone, 8-Methoxyquinazolin-4-ol
Molecular Formula C9H8N2O2
Molecular Weight 176.17
CAS Registry Number 16064-27-0
EC Number 877-862-7
SMILES COC1=CC=CC2=C1N=CNC2=O
Properties
Solubility Very slightly soluble (0.12 g/L) (25 ºC), Calc.*
Density 1.32±0.1 g/cm3 (20 ºC 760 Torr), Calc.*
Melting point 298-300 ºC (methanol )**
Index of Refraction 1.628, Calc.*
Boiling Point 417.4±28.0 ºC (760 mmHg), Calc.*
Flash Point 206.2±24.0 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)
** LeMahieu, Ronald A.; Journal of Medicinal Chemistry 1983, V26(3), P420-5.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H302-H315-H319-H335    Details
Precautionary Statements P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Eye irritationEye Irrit.2AH319
Specific target organ toxicity - single exposureSTOT SE3H335
Skin irritationSkin Irrit.2H315
Acute toxicityAcute Tox.4H302
SDS Available
up Discovory and Applicatios
8-Methoxy-4(1H)-quinazolinone is a chemical compound that belongs to the quinazolinone class of heterocyclic compounds, which are characterized by a benzene ring fused to a pyrimidine ring. The discovery of quinazolinone derivatives dates back to the early 20th century, and since then, these compounds have been of interest due to their diverse biological activities. 8-Methoxy-4(1H)-quinazolinone, in particular, has gained attention in various fields, primarily in medicinal chemistry and drug development, owing to its unique structure and potential therapeutic properties.

The compound was first synthesized as part of a broader effort to explore the pharmacological potential of quinazolinone derivatives. Quinazolinone derivatives have been known to exhibit a range of biological activities, including anti-inflammatory, anticancer, and antimicrobial effects. The methoxy group at position 8 in 8-Methoxy-4(1H)-quinazolinone enhances its chemical stability and can influence its ability to interact with biological targets, making it a subject of interest for researchers seeking to develop new therapeutic agents.

One of the primary applications of 8-Methoxy-4(1H)-quinazolinone lies in its potential as a pharmaceutical intermediate. Quinazolinone derivatives have been extensively studied for their ability to inhibit certain enzymes and receptors, leading to their exploration as potential treatments for a variety of diseases, including cancer, Alzheimer's disease, and diabetes. The compound has shown promise in preclinical studies, with some research indicating that it may have activity against specific cancer cell lines. It is thought to exert its effects by interacting with enzymes that regulate cell growth, apoptosis, and signal transduction pathways.

In addition to its potential anticancer properties, 8-Methoxy-4(1H)-quinazolinone is also being explored for its antimicrobial and anti-inflammatory effects. The compound has demonstrated some ability to inhibit the growth of various microorganisms, including bacteria and fungi, which makes it a candidate for further development in the field of infectious disease treatment. Additionally, its anti-inflammatory properties could be of interest for managing conditions such as arthritis, as quinazolinone derivatives are known to interfere with inflammatory pathways in the body.

Another area where 8-Methoxy-4(1H)-quinazolinone may have applications is in the development of small-molecule inhibitors. The compound could be used as a lead structure for designing novel molecules that can target specific enzymes or receptors involved in disease processes. This is especially relevant in the search for new drugs targeting kinase enzymes, which play a central role in many signaling pathways related to cancer and other diseases.

In the broader context of chemical synthesis, 8-Methoxy-4(1H)-quinazolinone serves as an important building block for creating more complex quinazolinone derivatives. These derivatives can be tailored for specific applications in medicinal chemistry, such as the development of receptor ligands, enzyme inhibitors, or compounds with neuroprotective properties.

Overall, 8-Methoxy-4(1H)-quinazolinone is a compound with significant potential in drug development, particularly for its anticancer, antimicrobial, and anti-inflammatory properties. While much of its therapeutic potential is still being explored, the compound's unique chemical structure and the diverse biological activities of quinazolinone derivatives make it a promising candidate for future pharmaceutical research.
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