24688-36-6

Usage

Uses

Used in Pharmaceutical Industry:
2-methyl-6-nitro-4(3H)-Quinazolinone is utilized as an intermediate in the synthesis of a range of pharmaceuticals. It plays a crucial role in the production of antihistamines and anti-inflammatory drugs, contributing to the development of medications that alleviate allergy symptoms and reduce inflammation.
Used in Dye and Pigment Synthesis:
In the chemical industry, 2-methyl-6-nitro-4(3H)-Quinazolinone serves as a precursor for the synthesis of dyes and pigments. Its unique chemical structure allows for the creation of a variety of colorants used in different applications, such as textiles, plastics, and printing inks.
Used in Medicinal Chemistry Research:
2-methyl-6-nitro-4(3H)-Quinazolinone has garnered interest due to its potential anti-cancer properties. It is an important target for medicinal chemistry research, with scientists investigating its ability to target and combat cancer cells. This research aims to develop new therapeutic agents that can be used in cancer treatment, potentially improving patient outcomes and contributing to advancements in oncology.

InChI:InChI=1/C9H7N3O3/c1-5-10-8-3-2-6(12(14)15)4-7(8)9(13)11-5/h2-4H,1H3,(H,10,11,13)

Upstream product

• 1769-24-0 2-methyl-4-quinazolone 
• 7664-93-9 sulfuric acid 
• 703-63-9 2,4-dimethylquinazoline 
• 7697-37-2 nitric acid 
• 78-39-7 Triethyl orthoacetate 
• 616-79-5 2-amino-5-nitro-benzoic acid 
• 118-92-3 anthranilic acid 
• 611-09-6 5-nitroisatin 
• 91-56-5 indole-2,3-dione 
• 108-24-7 acetic anhydride 
• 3816-62-4 5-nitroanthranilic acid methyl ester 
• 75-05-8 acetonitrile 
• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 124-42-5 acetamidine hydrochloride 

Downstream Products

• 73673-70-8 2-(4-methyl-styryl)-6-nitro-3H-quinazolin-4-one 
• 17329-24-7 6-amino-3,4-dihydro-2-methyl-4-oxoquinazoline 
• 74151-22-7 4-chloro-6-nitro-2-methylquinazoline 
• 128031-43-6 6-Amino-2-{(E)-2-[4-((E)-styryl)-phenyl]-vinyl}-3H-quinazolin-4-one 
• 128031-42-5 6-Nitro-2-{(E)-2-[4-((E)-styryl)-phenyl]-vinyl}-3H-quinazolin-4-one 
• 163732-38-5 6-Amino-2-((E)-2-{4-[(E)-2-(4-chloro-phenyl)-vinyl]-phenyl}-vinyl)-3H-quinazolin-4-one 
• 163732-37-4 2-((E)-2-{4-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-vinyl)-6-nitro-3H-quinazolin-4-one 
• 179910-70-4 6-Amino-2-((E)-2-{4-[(E)-2-(4-dimethylamino-phenyl)-vinyl]-phenyl}-vinyl)-3H-quinazolin-4-one 
• 179910-66-8 2-((E)-2-{4-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-phenyl}-vinyl)-6-nitro-3H-quinazolin-4-one 
• 1226498-80-1 2-((E)-2-(4-bromo-phenyl)-vinyl)-6-nitro-3H-quinazolin-4-one 

Relevant academic research and scientific papers

Isoxazole formamido-4 (3H)-quinazolinone derivative as well as synthesis method and application thereof

The invention relates to a 6-(isoxazolyl-3-formamido)-4 (3H)-quinazolinone derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituent groups. The invention discloses structures and synthesis methods of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activity of protein tyrosine phosphatase, and the compounds can be further developed into drugs for treating Alzheimer's disease.

2-METHYL-QUINAZOLINES

The present invention describes 2-methyl-quinazoline compounds of general formula (I), 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. The 2-methyl substituted quinazoline compounds of general formula(I) effectively and selectively inhibit the Ras-Sos interaction without significantly targeting the EGFR receptor. They are therefore useful for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, such as cancer as a sole agent or in combination with other active ingredients.

Small molecules inhibit STAT3 activation, autophagy, and cancer cell anchorage-independent growth

Triple-negative breast cancers (TNBCs) lack the signature targets of other breast tumors, such as HER2, estrogen receptor, and progesterone receptor. These aggressive basal-like tumors are driven by a complex array of signaling pathways that are activated by multiple driver mutations. Here we report the discovery of 6 (KIN-281), a small molecule that inhibits multiple kinases including maternal leucine zipper kinase (MELK) and the non-receptor tyrosine kinase bone marrow X-linked (BMX) with single-digit micromolar IC50s. Several derivatives of 6 were synthesized to gain insight into the binding mode of the compound to the ATP binding pocket. Compound 6 was tested for its effect on anchorage-dependent and independent growth of MDA-MB-231 and MDA-MB-468 breast cancer cells. The effect of 6 on BMX prompted us to evaluate its effect on STAT3 phosphorylation and DNA binding. The compound's inhibition of cell growth led to measurements of survivin, Bcl-XL, p21WAF1/CIP1, and cyclin A2 levels. Finally, LC3B-II levels were quantified following treatment of cells with 6 to determine whether the compound affected autophagy, a process that is known to be activated by STAT3. Compound 6 provides a starting point for the development of small molecules with polypharmacology that can suppress TNBC growth and metastasis.

Synthesis and antibacterial activity of 6-amino-2-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3,4-dihydroquinazolin-4-one and its intermediate compounds

6-Amino-2-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3,4-dihydroquinazolin-4-one was synthesized in four steps. The synthesized product from each step was purified by washing and recrystallization. Purity testing was performed by examining the melting range and by thin layer chromatography. The molecular mass of the synthesized compound was determined using LC-MS. Structure of synthesized compound was elucidated using UV-visible, FT-IR, 1H NMR, 13C NMR, COSY, HMQC and HMBC. Screening for antibacterial activity was performed against Staphylococcus aureus ATCC 25923, Salmonella typhimurium ATCC 14028 and Escherichia coli ATCC 25922. The results indicated that the titled compound had been successfully synthesized and purified. The structure of desired compound was confirmed based on structural elucidation analysis. The result of testing the titled compound for the antibacterial activity was negative.

6-amino-4(3H)-quinazolinone derivatives and their synthesis method and use

The invention discloses 6-amino-4(3H)-quinazolinone derivatives and their synthesis method and use and belongs to the technical field of drug synthesis. The invention also relates to a use of the 6-amino-4(3H)-quinazolinone derivatives with a general formula (I) and its synthesis method in medical science, wherein in the general formula (I), X represents (CH2)n-1, n=1 to 10 and R1, R2 and R3 represent different substituents. The invention discloses the compound structures and their synthesis method and external acetylcholinesterase inhibition activity. The 6-amino-4(3H)-quinazolinone derivatives can be further studied and developed to form novel drugs for treating Alzheimer disease.

A convenient aqueous copper-catalyzed synthesis of quinazolinones

A simple and highly efficient method for the aqueous copper-catalyzed coupling reactions with the aid of a commercially available surfactant (TPGS-750-M) is reported. In an aqueous micellar medium, 2-halobenzoic acids derivatives reacted with amidines and guanidines and generated the corresponding quinazolinone derivatives in good to excellent yields in the range of room temperature to, at most, 50°C. In addition, the reaction medium can be recycled, and this method led to a significant improvement of the E factors in comparison with the previously reported process.

Transition-metal free synthesis of quinazolinones via tandem cyclization of 2-halobenzoic acids with amidines

A simple protocol for the synthesis of quinazoline-4(3H)-ones by tandem cyclization of 2-halobenzoic acids with amidines has been developed by using KOH as a base in DMSO at 120 °C. This protocol does not involve the use of any transition-metals or ligands or any coupling reagents. The present methodology is operationally simple, scalable and varieties of quinazolinone derivatives were obtained in good to excellent yields.

A highly efficient heterogeneous copper-catalyzed cascade reaction of 2-halobenzoic acids and amidines leading to quinazolinones

The heterogeneous cascade reaction of 2-halobenzoic acids and amidines was achieved in DMF at 60 °C in the presence of 10 mol% of MCM-41-immobilized tridentate nitrogen copper(i) complex [MCM-41-3N-CuI] using Cs2CO3 as base, yielding a variety of quinazolinone derivatives in good to excellent yields. This heterogeneous copper catalyst can be easily prepared from commercially available and inexpensive reagents, and recovered by a simple filtration of the reaction solution and reused for at least 10 times without any decreases in activity. This journal is

Synthesis, characterization and antimicrobial studies of novel quinazoline derivatives of sydnone

3-[2-Substituted-4-oxo-3,4-dihydroquinazolin-6-yl]sydnones 10a-i have been synthesized from 2-(acetylamino)benzoic acid 1 by conventional route. The newly synthesized compounds 10a-i have been characterized by IR, NMR spectroscopy as well as by elemental analysis. Compounds 10a-i have also been screened for their antimicrobial activity against four important species of bacteria. Some compounds are found active against these species.

Synthesis and antiproliferative evaluation of hybrids of indolin-2-one and quinazoline-4(3H)-one linked via imine bond

A novel series of hybrids of indolin-2-one and quinazolin-4(3H)-one linked via an imine bond were synthesized and tested for their inhibitory activity against the proliferation of a panel of five human cancer cell lines. We found that compound 5c bearing