52791-05-6

Usage

Uses

Used in Pharmaceutical Research:
4-Chloro-6,7-dimethylenedioxyquinazoline is used as a building block in pharmaceutical research for the synthesis of novel drugs and medicinal compounds. Its unique reactivity and the ability to introduce different functional groups onto the quinazoline scaffold make it a valuable intermediate for the development of biologically active compounds.
Used in Drug Development:
4-Chloro-6,7-dimethylenedioxyquinazoline has potential applications in the development of new drugs for the treatment of various diseases and conditions. Its chemical structure and reactivity contribute to the creation of innovative therapeutic agents with improved efficacy and selectivity.
Used in Chemical Transformations:
The chloro group on the quinazoline ring of 4-chloro-6,7-dimethylenedioxyquinazoline provides unique reactivity, making it suitable for various chemical transformations. This allows researchers to modify the compound and introduce different functional groups onto the quinazoline scaffold, expanding its potential applications in drug discovery and medicinal chemistry.
Used in Synthesis of Biologically Active Compounds:
Due to its unique reactivity and the ability to introduce different functional groups, 4-chloro-6,7-dimethylenedioxyquinazoline is used in the synthesis of biologically active compounds. This enables the development of new therapeutic agents with improved pharmacological properties and potential applications in the treatment of various diseases and conditions.

InChI:InChI=1/C10H7ClN2O2/c11-10-6-3-8-9(15-2-1-14-8)4-7(6)12-5-13-10/h3-5H,1-2H2

Upstream product

• 52791-04-5 3,4,7,8-tetrahydro[1,4]dioxino[2,3-g]quinazolin-4-one 
• 99358-09-5 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid 
• 1145671-34-6 4-chloroquinazoline-6,7-diyl bis(2,2-dimethylpropanoate) 
• 1174662-16-8 [7-(2,2-dimethylpropanoyloxy)-4-oxo-3H-quinazolin-6-yl] 2,2-dimethylpropanoate 
• 16064-15-6 6,7-dihydroxyquinazolin-4(3H)-one 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 1145671-36-8 4-chloro-6,7-dihydroxyquinazoline 
• 107-04-0 1-Bromo-2-chloroethane 
• 1207868-16-3 7,8-dihydro[1,4]dioxino[2,3-g]quinazoline 
• 22013-33-8 6-amino-3,4-benzodioxane 

Downstream Products

• 1456819-61-6 (7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-yl)-(3'-methansulfonamidopheyl)amine hydrochloride 
• 1401243-69-3 (7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-yl)-(biphenyl-3'-yl)amine hydrochloride 

Relevant academic research and scientific papers

ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE 1 INHIBITORS,COMPOSITIONS AND USES THEREOF

The present invention relates to compounds of Formula (I), methods of using the compounds as ENPP1 inhibitors, and pharmaceutical compositions comprising such compounds.The compounds are useful in treating cancers and infectious diseases.

Development of a Potent Brain-Penetrant EGFR Tyrosine Kinase Inhibitor against Malignant Brain Tumors

The epidermal growth factor receptor (EGFR) is genetically altered in nearly 60% of glioblastoma tumors; however, tyrosine kinase inhibitors (TKIs) against EGFR have failed to show efficacy for patients with these lethal brain tumors. This failure is attributed to the inability of clinically tested EGFR TKIs to cross the blood-brain barrier (BBB) and achieve adequate pharmacological levels to inhibit various oncogenic forms of EGFR that drive glioblastoma. Through SAR analysis, we developed compound 5 (JCN037) from an anilinoquinazoline scaffold by ring fusion of the 6,7-dialkoxy groups to reduce the number of rotatable bonds and polar surface area and by introduction of an ortho-fluorine and meta-bromine on the aniline ring for improved potency and BBB penetration. Relative to the conventional EGFR TKIs erlotinib and lapatinib, JCN037 displayed potent activity against EGFR amplified/mutant patient-derived cell cultures, significant BBB penetration (2:1 brain-to-plasma ratio), and superior efficacy in an EGFR-driven orthotopic glioblastoma xenograft model.

COMPOSITIONS AND METHODS FOR TREATING CANCER

The present disclosure relates to compounds that are capable penetrating to the blood brain barrier to modulate the activity of EGFR tyrosine kinase. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers that have been determined to have altered glucose metabolism in the presence of inhibitors. The present disclosure also provides methods of administering to a subject a glucose metabolism inhibitor and a cytoplasmic p53 stabilizer.

COMPOSITIONS AND METHODS FOR TREATING CANCER

The present disclosure relates to compounds that are capable penetrating to the blood brain barrier to modulate the activity of EGFR tyrosine kinase. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers. The disclosure further relates to methods of treating Glioblastoma and other EGFR mediated cancers that have been determined to have altered glucose metabolism in the presence of inhibitors. The present dislcsoure also provides methods oadministering to a subject a glucose metabolism inhibitor and a cytoplasmic p53 stabilizer.

Quinazoline-based multi-tyrosine kinase inhibitors: Synthesis, modeling, antitumor and antiangiogenic properties

In this work the synthesis and the biological evaluation of some novel anilinoquinazoline derivatives carrying modifications in the quinazoline scaffold and in the aniline moiety were reported. Preliminary cytotoxicity studies identified three derivatives

Exploring Epidermal Growth Factor Receptor (EGFR) inhibitor features: The role of fused dioxygenated rings on the quinazoline scaffold

A number of dioxolane, dioxane, and dioxepine quinazoline derivatives have been synthetized, and evaluated as EGFR inhibitors. Their cytotoxic activity has been tested against two cell, lines overexpressing and not expressing EGFR. Most derivatives were a

QUINAZOLINE DERIVATIVES AS RAF KINASE MODULATORS AND METHODS OF USE THEREOF

Compounds according to formula (I), compositions and methods are provided for modulating the activity of RAF kinases, including BRAF kinase and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder mediated by RAF kinases. Formula (I): or a pharmaceutically acceptable salt, solvate, clathrate of hydrate thereof, wherein X is O or S(O)t; Ra is O or S.

1,4-Dioxane-fused 4-anilinoquinazoline as inhibitors of epidermal growth factor receptor kinase

The 4-anilinoquinazoline PD 153035 (1) is a potential antitumor agent which acts by inhibiting tyrosine kinase activity of epidermal growth factor receptor (EFGR) via competitive binding at the ATP site of enzyme. A series of cyclic analogues of PD 153035 bearing the 1,4-dioxane ring was prepared by reaction of 6-chloro derivative 5 with several aniline nucleophiles. These were evaluated for their ability to inhibit the EGFR kinase and the growth of primary human tumor cell cultures. All of the new 4-anilinoquinazolines exhibited less potency than PD 153035 against EGFR kinase. However, compounds 2b, 2c, 2e, 2g, and 2h showed higher inhibitory activities than PD 153035 against the growth of A431 tumor cell line. The compound 2b containing 3-chloroaniline ring was as potent as PD 153035 against EGFR kinase and showed about 5.4-fold better potency than PD1 53035 in the inhibition of growth of A431 cell line with good selectivity.

Bi-4-[1-(quinazolinyl-4)piperidyls] and bis{4-[1-(quinazolinyl-4)piperidyl]alkanes}

Disclosed are bi-4-[1-(quinazolinyl-4)piperidyls] and bis{4-[1-(quinazolinyl-4)piperidyl]alkanes}, e.g. 1,3-bis{4-[1-(6,7-dimethylquinazolinyl-4)piperidyl]propane}, having pharmacological activity in animals and useful for example, as anti-obesity and anti-diabetic agents. Said compounds may be prepared by reacting a 4-haloquinazoline with bi-4-piperidyl or a bis(piperidyl-4)alkane.

N,N-Bis(4-Quinazolinyl)alkanediamines

Disclosed are N,N'-Bis(4-Quinazolinyl)alkanediamines, e.g., N,N'-Bis(7-chloro-4-quinazolinyl)-1,9-nonanediamine, having pharmacological activity in animals and useful for example, as anti-obesity agents. Said compounds may be prepared by reacting a 4-haloquinazoline with an alkanediamine.