16064-15-6

Usage

Uses

Used in Pharmaceutical Industry:
6,7-dihydroxyquinazolin-4(3H)-one is used as a potential anticancer agent for its ability to target and inhibit the growth of cancer cells. Its structural attributes allow it to interact with specific biological targets, making it a candidate for the development of new cancer therapies.
Used in Antioxidant Applications:
As an antioxidant, 6,7-dihydroxyquinazolin-4(3H)-one is utilized to counteract oxidative stress and protect cells from damage caused by reactive oxygen species, which is crucial in the prevention and treatment of various diseases and conditions associated with oxidative stress.
Used in Neurological Disorder Treatment:
6,7-dihydroxyquinazolin-4(3H)-one and its derivatives are explored for their potential in treating neurological disorders due to their capacity to modulate neuronal functions and protect the nervous system from degeneration, offering hope for the development of novel therapeutics for conditions such as Alzheimer's and Parkinson's diseases.
The ongoing research and development of 6,7-dihydroxyquinazolin-4(3H)-one and its derivatives are expected to yield new insights and advancements in medicinal chemistry, potentially leading to the discovery of innovative pharmaceuticals with significant therapeutic benefits.

Upstream product

• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 
• 179688-53-0 6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one 
• 4101-33-1 6,7-dimethoxy-N,N-quinazoline 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 

Downstream Products

• 183321-74-6 erlotinib 
• 183319-69-9 erlotinib hydrochloride 
• 1312937-41-9 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline 
• 1312937-40-8 4-methoxyquinazoline-6,7-diol 
• 938185-04-7 (7-acetoxy-4-chloro-quinazolin-6-yl) acetate 
• 938185-10-5 N-(3-ethynylphenyl)-6,7-diacetoxy-4-quinazolinamine 
• 938185-06-9 N-(3-ethynylphenyl)-6,7-dihydroxy-4-quinazolinamine 

Relevant academic research and scientific papers

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.

A compound for the treatment of tumor (by machine translation)

Formula (I) indicated by the compound or its pharmaceutically acceptable salt, or solvate thereof: Wherein R1 Is selected from R2 , R3 Are independently selected from H, halogen, alkyl, Or R2 And R3 Connected with a carbon atom containing 1 - 2 heteroatoms 1 substituted or multi-substituted six-membered aromatic heterocycle; R4 , R5 , R6 Are respectively represents a benzene ring on the 0 - 3 substituted, R4 , R5 , R6 Are independently selected from H, halogen atom, C1 - 6 Alkyl, C1 - 6 Alkoxy, hydroxy, amino, carboxyl, nitro, CH3 O (CH2 )n CH2 O -, Wherein n is 1 - 6 of the integer. The present invention provides the compounds in the preparation of a medicament for the treatment of tumor in use. Compound of the present invention the potency is clear. (by machine translation)

Application of novel compound in preparing medicine for treating tumor

The invention discloses application of a compound as shown in the formula (I), a pharmaceutically acceptable salt or a solvent compound of the compound in preparing a medicine for treating tumor. In the formula, R1 is selected from formulae as shown in the description; R2 and R3 are respectively independently selected from H, halogen, alkyl and a formula as shown in the description; or R2 and R3 form a one-substituted or polysubstituted hexahydric aromatic heterocyclic ring with 1-2 heteroatoms together with carbon atoms connected with R2 and R3; R4, R5 and R6 respectively represent 0-3 substitution on a benzene ring; R4, R5 and R6 are respectively and independently selected from H, halogen atoms, C1-C6 alkyl, C1-C6 alkoxy, hydroxyl, amino, carboxyl, nitryl, CH3O(CH2)nCH2O- and a formula as shown in the description; and in the formula, n is an integer of 1-6. The compound disclosed by the invention is definite in medicinal effect when being used for treating tumor.

COUPLING COMPOUNDS OF NSAID ANTI-INFLAMMATORY AND ANALGESIC DRUGS AND EGFR KINASE INHIBITORS, SYNTHESIS METHODS AND APPLICATIONS THEREOF

The present invention discloses coupling compounds of a structure as shown in Formula I, II or III formed by connecting NSAID anti-inflammatory and analgesic drugs and EGFR inhibitors by ester bonds or pharmaceutically acceptable salts or stereoisomers thereof or prodrug molecules thereof: where R is a NSAID anti-inflammatory and analgesic drug. In the present invention, the coupling compounds obtained by coupling NSAID anti-inflammatory and analgesic drugs with EGFR inhibitors have excellent therapeutic effects of tumors and provide new drugs for clinic treatment options.

NOVEL FLUORINATED DERIVATIVES AS EGFR INHIBITORS USEFUL FOR TREATING CANCERS

A novel class of fluorinated derivatives of Formula I have been prepared and found to be useful in the treatment of cancers and other EGFR related disorders.

Synthesis and Evaluation of Novel Erlotinib-NSAID Conjugates as More Comprehensive Anticancer Agents

A series of novel anticancer agents were designed and synthesized based on coupling of different nonsteroidal anti-inflammatory drugs (NSAIDs) with the epidermal growth-factor receptor (EGFR) tyrosine kinase inhibitor, erlotinib. Both the antiproliferative and pharmacokinetic activity of the target compounds were evaluated using HCC827 and A431 tumor cell lines. Among the derivatives made, compounds 10a, 10c, and 21g showed superb potency, comparable to that of erlotinib. Furthermore, preliminary SAR analysis showed that when the NSAIDs were conjugated via linkage to C-6 OH versus linkage to C-7 OH of the quinazoline nucleus, superior anticancer activity was achieved. Finally, the in vitro pharmacokinetic profile of several conjugates demonstrated the desired dissociation kinetics as the coupled molecules were effectively hydrolyzed, releasing both erlotinib and the specific NSAID in a time-dependent manner. The conjugation strategy represents a unique and simplified approach toward combination therapy, particularly for the treatment of cancers where both EGFR overexpression and inflammation play a direct role in disease progression.

PHARMACEUTICAL COMPOUNDS TARGETED BY MIF AFFINITY-TETHERED MOIETIES

There is disclosed a compound, a pharmaceutical composition and a method of treatment using a pharmaceutical composition comprising a tethering moiety that is capable of binding to a macrophage migration inhibitory factor (MIF) polypeptide, optionally linked to a linker moiety and further covalently bound to a drug moiety or imaging agent. More specifically, there is disclosed a genus of affinity-tethering moieties covalently bound to a drug moiety or imaging agent either directly or optionally via a linker moiety to covalently link the tethering moiety to a drug moiety. Without being bound by theory, the disclosed pharmaceutical compounds are targeted to cancer cells or immune cells via an affinity-tethering moiety that hitch-hikes to or into its target cell while bound to endogenous MIF.

PREPARATION PROCESS OF ERLOTINIB

Preparation process of erlotinib or its salts comprising: reacting 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline with 3-ethynylaniline or a salt thereof in the presence of a base and a reaction-inert solvent, and optionally, treating the compound obtained with a pharmaceutically acceptable acid to form the corresponding pharmaceutically acceptable salt. The compound 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline can be prepared either from 4-methoxyquinazoline-6,7-diol or 6,7-bis(2-methoxyethoxy)quinazolinone. The compounds 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline and 4-methoxyquinazoline-6,7-diol are new intermediates useful for the preparation of erlotinib or its salts.

Preparation process of erlotinib

Preparation process of erlotinib or its salts comprising: reacting 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline with 3-ethynylaniline or a salt thereof in the presence of a base and a reaction-inert solvent, and optionally, treating the compound obtained with a pharmaceutically acceptable acid to form the corresponding pharmaceutically acceptable salt. The compound 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline can be prepared either from 4-methoxyquinazoline-6,7-diol or 6,7-bis(2-methoxyethoxy)quinazolinone. The compounds 6,7-bis(2-methoxyethoxy)-4-methoxyquinazoline and 4-methoxyquinazoline-6,7-diol are new intermediates useful for the preparation of erlotinib or its salts.

Three-point variation of a gefinitib quinazoline core

A versatile four-step process describing the controlled systematic variation of a key quinazoline core from one intermediate is highlighted.