105763-77-7

Basic information

• Product Name: 2,4-Dichloro-6-methoxyquinazoline
• Synonyms: 2,4-Dichloro-6-methoxyquinazoline;6-Methoxy-2,4-dichloroquinazoline;2,4-Dichloro-6-methoxyqui...;Quinazoline,2,4-dichloro-6-methoxy-
• CAS NO: 105763-77-7
• Molecular Formula: C₉H₆Cl₂N₂O
• Molecular Weight: 229.06
• Product Categories: API intermediates
• Mol File: 105763-77-7.mol

Chemical Properties

• Melting Point: 171 °C
• Boiling Point: 315.923 °C at 760 mmHg
• Flash Point: 144.865 °C
• Appearance: white or almost white power
• Density: 1.450
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.67±0.30(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-6-methoxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-6-methoxyquinazoline(105763-77-7)
• EPA Substance Registry System: 2,4-Dichloro-6-methoxyquinazoline(105763-77-7)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN2811
• HazardClass: IRRITANT
• Hazardous Substances Data: 105763-77-7(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
2,4-Dichloro-6-methoxyquinazoline is used as a herbicide for controlling the growth of unwanted plants. Its chemical properties allow it to target specific plant species, making it a valuable tool in crop protection and management.
Used in Pharmaceutical Industry:
2,4-Dichloro-6-methoxyquinazoline is used as a potential pharmaceutical agent due to its unique structure and biological activities. Its antifungal and antibacterial properties make it a candidate for the development of new drugs to combat resistant infections.
Used in Chemical Research:
2,4-Dichloro-6-methoxyquinazoline is used as a subject of scientific research to explore its synthesis, properties, and potential applications. Its quinazoline structure offers opportunities for the development of new compounds with specific biological activities, contributing to the advancement of chemical science.

Upstream product

• 32618-84-1 6-Methoxyquinazolin-2,4-dione 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 23842-82-2 2-amino-5-methoxybenzonitrile 
• 109103-45-9 3-(hydroxyimino)-5-methoxyindolin-2-one 
• 57-13-6 urea 
• 6705-03-9 2-Amino-5-methoxybenzoic acid 
• 1882-69-5 5-methoxy-2-nitro-benzoic acid 
• 61948-86-5 5-methoxy-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 

Downstream Products

• 124309-84-8 2-chloro-6-methoxy-N-methyl-N-phenylquinazolin-4-amine 
• 364386-47-0 (1R,2S)-N-tert-butoxycarbonyl-2-(2-chloro-6-methoxyquinazolin-4-yl)aminocyclohexylamine 
• 1216814-90-2 (2-chloro-6-methoxy-quinazoline-4-yl)-(4-methoxy-phenyl)methylamine 
• 1313892-51-1 C₂₀H₁₅BrN₄O 
• 1313891-20-1 4-(4-chlorophenyl)-N-(6-methoxy-2-(pyridin-3-yl)quinazolin-4-yl)thiazol-2-amine 
• 769158-53-4 2-((2-chloro-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl)benzonitrile 
• 20197-97-1 2-chloro-6-methoxy-3H-quinazolin-4-one 
• 952434-87-6 2-chloro-6-methoxy-4-methyl-quinazoline 
• 952434-89-8 2-chloro-4,6-dimethoxyquinazoline 

Relevant articles and documents

Discovery of 2-aryloxy-4-amino-quinazoline derivatives as novel protease-activated receptor 2 (PAR2) antagonists

Protease-activated receptor 2 (PAR2) is a member of G protein-coupled receptor and its activation initiates diverse inflammatory responses. Recent studies suggest that antagonists of PAR2 may provide a novel therapeutic strategy for inflammatory diseases. In this study, we have developed a series of 2-aryloxy-4-amino-quinazoline derivatives as PAR2 antagonists and examined their effects against LPS-induced inflammatory responses in RAW 264.7 macrophages. Among these derivatives, compound 2f displayed the greatest antagonistic activity with the IC50 value of 2.8 μM. Binding modes of the newly identified PAR2 antagonists were analyzed by molecular docking using IFD/MM-GBSA methods in the putative binding site of PAR2 homology model. Moreover, 2f demonstrated significant inhibitory effects on the LPS-activated pro-inflammatory mediators including nitric oxide (NO), prostaglandin E2 (PGE2), interleukin-1β (IL-1β), interleukin-6 (IL-6) and tumor necrosis factor-α (TNF-α) through the regulation of various intracellular signaling pathways involving nuclear factor-κB (NF-κB), activator protein 1 (AP-1) and the mitogen-activated protein kinases (MAPK). Furthermore, administration of 2f significantly reduced the mortality of LPS-induced sepsis in mice. These results provide useful insights into the development of novel PAR2 antagonists with anti-inflammatory activity in vitro and in vivo.

One-pot cascade ring enlargement of isatin-3-oximes to 2,4-dichloroquinazolines mediated by bis(trichloromethyl)carbonate and triarylphosphine oxide

An efficient and convenient one-pot cascade synthesis of 2,4-dichloroquinazolines directly from isatin-3-oximes with the addition of bis(trichloromethyl)carbonate and triarylphosphine oxide was developed, leading to substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a range of functional groups. Thus, the method represents a convenient and practical strategy for the synthesis of substituted 2,4-dichloroquinazolines.

INHIBITORS OF CYCLIN-DEPENDENT KINASES

Provided herein are inhibitors of cyclin-dependent kinases (CDKs), pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of diseases.

Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles

Molecular hybridization is a powerful strategy in drug discovery. A series of novel diarylbenzopyrimidine (DABP) analogues were developed by the hybridization of FDA-approved drugs etravirine (ETR) and efavirenz (EFV) as potential HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs). Substituent modifications resulted in the identification of new DABPs with the combination of the strengths of the two drugs, especially compound 12d, which showed promising activity toward the EFV-resistant K103N mutant. 12d also had a favorable pharmacokinetic (PK) profile with liver microsome clearances of 14.4 μL/min/mg (human) and 33.2 μL/min/mg (rat) and an oral bioavailability of 15.5% in rat. However, its activity against the E138K mutant was still unsatisfactory; E138K is the most prevalent NNRTI resistance-associated mutant in ETR treatment. Further optimizations resulted in a highly potent compound (12z) with no substituents on the phenyl ring and a 2-methyl-6-nitro substitution pattern on the 4-cyanovinyl-2,6-disubstitued phenyl motif. The antiviral activity of this compound was much higher than those of ETR and EFV against the WT, E138K, and K103N variants (EC50 = 3.4, 4.3, and 3.6 nM, respectively), and the cytotoxicity was decreased while the selectivity index (SI) was increased. In particular, this compound exhibited acceptable intrinsic liver microsome stability (human, 34.5 μL/min/mg; rat, 33.2 μL/min/mg) and maintained the good PK profile of its parent compound EFV and showed an oral bioavailability of 16.5% in rat. Molecular docking and structure-activity relationship (SAR) analysis provided further insights into the binding of the DABPs with HIV-1 reverse transcriptase and provided a deeper understanding of the key structural features responsible for their interactions.

HEPARANASE INHIBITORS AND USE THEREOF

The invention relates to functionalized quinazoline compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds as heparanase inhibitors for the treatment of diseases or conditions related to heparanse activity.

Pyrimidine derivatives, preparation method therefor and application of pyrimidine derivatives

The invention belongs to the field of drug synthesis and relates to novel pyrimidine derivatives, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, preparation methods of thenovel pyrimidine derivatives and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof and use of the novel pyrimidine derivatives and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of therapeutic agents, particularly PAK inhibitors. The derivatives disclosed by the invention are represented by a general formula (I) or (II), wherein each substituent is as defined in claims.

Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles

The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.

The therapeutic compound, use and related method (by machine translation)

PROBLEM TO BE SOLVED: To provide a pharmaceutical composition containing a compound or its salt which prevents or treats a central nervous system disease in which integration dysfunction syndrome and agnosia are enumerated as exemplary disorders.SOLUTION: The pharmaceutical composition includes the compound or its salt represented by chemical formula (A) which modulates striatal-enriched protein tyrosine phosphatase (STEP).

SUBSTITUTED QUINAZOLINE COMPOUNDS AND PREPARATION AND USES THEREOF

The present invention relates quinazolinone compounds of Formula (I), as well as their preparation and uses, and further relates pharmaceutical compositions comprising these compounds and their uses； wherein the compounds or pharmaceutical compositions disclosed herein can be used for antagonizing the orexin receptor. The present invention also relates to uses of the compounds or pharmaceutical compositions in treating or preventing neurological and psychiatric disorders and diseases of the central nervous system in mammals, especially in humans.

OCTAHYDROPYRROLO [3, 4-c] PYRROLE DERIVATIVES AND USES THEREOF

The invention relates to octahydropyrrolo [3, 4-c] pyrrole derivatives and uses thereof. Compounds and pharmaceutical compositions comprising the compounds provided herein are used for antagonizing orexin receptors. The invention also relates to processes for preparing the compounds and pharmaceutical compositions, and uses thereof in treating or preventing a disease related to orexin receptors.