55496-52-1

Basic information

• Product Name: 4-Chloro-7-methoxyquinazoline
• Synonyms: 4-CHLORO-7-METHOXYQUINAZOLINE;4-CHLORO-6-METHOXY-QUINAZOLINE;Quinazoline, 4-chloro-7-methoxy-
• CAS NO: 55496-52-1
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.62
• Mol File: 55496-52-1.mol

Chemical Properties

• Boiling Point: 323 °C at 760 mmHg
• Flash Point: 149.1 °C
• Appearance: /
• Density: 1.333 g/cm³
• Vapor Pressure: 0.000509mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.00±0.30(Predicted)
• CAS DataBase Reference: 4-Chloro-7-methoxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-7-methoxyquinazoline(55496-52-1)
• EPA Substance Registry System: 4-Chloro-7-methoxyquinazoline(55496-52-1)

Safety Data

• Hazardous Substances Data: 55496-52-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-7-methoxyquinazoline is used as a potential active pharmaceutical ingredient for its possible anticancer properties, given the known applications of quinazoline derivatives in this field. It may contribute to the development of new drugs targeting various types of cancer.
Used in Antiviral Applications:
In the field of antiviral research, 4-Chloro-7-methoxyquinazoline is considered for its potential to inhibit viral replication and activity, thereby serving as a component in the development of antiviral medications.
Used in Antibacterial Applications:
4-Chloro-7-methoxyquinazoline is also used as a candidate for antibacterial agents, where it may help in the creation of new antibiotics to combat bacterial infections, especially those resistant to existing treatments.
Further research is essential to determine the specific applications and effectiveness of 4-Chloro-7-methoxyquinazoline in these areas, as its properties and uses may vary based on the context of its implementation.

InChI:InChI=1/C9H7ClN2O/c1-13-6-2-3-7-8(4-6)11-5-12-9(7)10/h2-5H,1H3

Upstream product

• 16064-24-7 7-methoxyquinazoline-4(3H)-one 
• 128495-46-5 4-fluoro-3-methoxybenzaldehyde 
• 630423-39-1 4,6-dimethoxyisoquinolin-1(2H)-one 
• 630422-98-9 7-fluoro-6-methoxyisoquinolin-1(2H)-one 
• 1409964-67-5 (E)-3-(4-fluoro-3-methoxyphenyl) acryloyl azide 
• 16064-24-7 7-methoxyquinazolin-4-ol 
• 4294-95-5 4-methoxyanthranilic acid 
• 50413-30-4 methyl 2-amino-4-methoxybenzoate 
• 38469-83-9 4-methoxy-2-nitro-benzonitrile 
• 38487-91-1 2-amino-p-anisamide 
• 33844-22-3 4-methoxy-2-nitro-benzoic acid amide 

Downstream Products

• 1613479-53-0 C₁₅H₁₀F₂N₂O₂ 
• 942507-42-8 3-(cyano-dimethyl-methyl)-N-[3-(7-methoxy-quinazolin-4-ylamino)-4-methyl-phenyl]-benzamide 

Relevant articles and documents

Discovery of BPR1R024, an Orally Active and Selective CSF1R Inhibitor that Exhibits Antitumor and Immunomodulatory Activity in a Murine Colon Tumor Model

Colony-stimulating factor-1 receptor (CSF1R) is implicated in tumor-associated macrophage (TAM) repolarization and has emerged as a promising target for cancer immunotherapy. Herein, we describe the discovery of orally active and selective CSF1R inhibitors by property-driven optimization of BPR1K871 (9), our clinical multitargeting kinase inhibitor. Molecular docking revealed an additional nonclassical hydrogen-bonding (NCHB) interaction between the unique 7-aminoquinazoline scaffold and the CSF1R hinge region, contributing to CSF1R potency enhancement. Structural studies of CSF1R and Aurora kinase B (AURB) demonstrated the differences in their back pockets, which inspired the use of a chain extension strategy to diminish the AURA/B activities. A lead compound BPR1R024 (12) exhibited potent CSF1R activity (IC50 = 0.53 nM) and specifically inhibited protumor M2-like macrophage survival with a minimal effect on antitumor M1-like macrophage growth. In vivo, oral administration of 12 mesylate delayed the MC38 murine colon tumor growth and reversed the immunosuppressive tumor microenvironment with the increased M1/M2 ratio.

Design, Synthesis and Bioevaluation of Two Series of 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines

Two series of 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines were designed initially as potential acetylcholine esterase inhibitors. Biological evaluation demonstrated that N-(1-benzylpiperidin-4-yl)quinazolin-4-amines significantly inhibited AChE activity. Especially, two compounds of them were found to be the most potent with relative AChE inhibition percentages of 87 percent in comparison to donepezil. The docking studies with AChE showed similar interactions between donepezil and four derivatives. N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines also exhibited significant DPPH scavenging effects. The two series of compound also exerted moderate to good cytotoxicity against three human cancer cell lines, including SW620 (human colon cancer), PC-3 (prostate cancer), and NCI?H23 (lung cancer), with 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one being the most cytotoxic agent. 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one significantly induced early apoptosis and arrested the SW620 cells at G2/M phase. From this study, two compounds of N-(1-benzylpiperidin-4-yl)quinazolin-4-amines could serve as new leads for further design and AChE inhibitors, while 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one could serve as a new lead for the design and development of more potent anticancer agents.

Drug-like property optimization: Discovery of orally bioavailable quinazoline-based multi-targeted kinase inhibitors

In an effort to develop new cancer therapeutics, we have reported clinical candidate BPR1K871 (1) as a potent anticancer compound in MOLM-13 and MV4-11 leukemia models, as well as in colorectal and pancreatic animal models. As BPR1K871 lacks oral bioavailability, we continued searching for orally bioavailable analogs through drug-like property optimization. We optimized both the physicochemical properties (PCP) as well as in vitro rat liver microsomal stability of 1, with concomitant monitoring of aurora kinase enzyme inhibition as well as cellular anti-proliferative activity in HCT-116 cell line. Structural modification at the 6- and 7-position of quinazoline core of 1 led to the identification of 34 as an orally bioavailable (F% = 54) multi-kinase inhibitor, which exhibits potent anti-proliferative activity against various cancer cell lines. Quinazoline 34 is selected as a promising oral lead candidate for further preclinical evaluation.

IDENTIFICATION AND USE OF ERK5 INHIBITORS

The present invention covers heterocyclic compounds of general formula (I) in which T, U, Y, Z, R1 and R3 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of cancer disorders, as a sole agent or in combination with other active ingredients.

Hepatitis C virus inhibitors

Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Molecular targeting anticancer photosensitizer AKT - phthalocyanine conjugates

The invention discloses a molecularly targeted anticancer photosensitizer erlotinib-phthalocyanine conjugate and application thereof. An erlotinib structural unit with a long alkoxy chain is introduced into the periphery of a metal phthalocyanine big ring, so that the amphipathicity, biocompatibility and targeting property of the photosensitizer can be improved. The conjugate is difficult to aggregate, and the cellular uptake ratio is improved; and meanwhile, the compounds are simple in structure, an isomer does not exist, and the product is easy to purify. According to the compound, the targeting property of the photosensitizer in photodynamics therapy is expected to be improved, and the activity of the photosensitizer in photodynamics therapy is enhanced. The synthetic method is simple, fewer side reactions are carried out, the yield is high, the raw materials are readily available, the cost is low, and the industrial production is realized.

Small-molecule phosphodiesterase probes: Discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1

PDE1 is a family of calcium-activated, dual substrate phosphodiesterases expressed in both the CNS and periphery that play a role in the integration of intracellular calcium and cyclic nucleotide signaling cascades. Exploration of the potential in targeting this family of enzymes to treat neuropsychiatric disorders has been hampered by a lack of potent, selective, and brain penetrable PDE1 inhibitors. To identify such compounds we used high-throughput screening, structure-based design, and targeted synthetic chemistry to discover the 4-aminoquinazoline 7a (PF-04471141) and the 4-indanylquinazoline 27 (PF-04822163) each of which are PDE1 inhibitors that readily cross the blood brain barrier. These quinazoline-based PDE1-selective inhibitors represent valuable new tools to study the biological processes regulated by PDE1 and to begin to determine the potential therapeutic utility of such compounds to treat neuropsychiatric disorders.

Discovery of a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine and a 1-aryloxyisoquinoline series of TRPA1 antagonists

A series of TRPA1 antagonists is described having a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine or a 1-aryloxyisoquinoline scaffold. These compounds have high ligand efficiency and favorable physical properties and may thus serve as scaffolds for further optimization.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula (I) are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Design, synthesis and analgesic properties of novel conformationally-restricted N-acylhydrazones (NAH)

A set of six azaheterocycles were designed as conformationnaly-constrained N-acylhydrazones and tested as analgesics.