29113-34-6

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
4-OXO-3,4-DIHYDROQUINAZOLINE-2-CARBOXYLIC ACID is used as a chemical compound in pharmaceutical research and drug development for its potential medicinal properties, including its antitumor activity and enzyme inhibitory effects.
Used in Antitumor Applications:
In the field of oncology, 4-OXO-3,4-DIHYDROQUINAZOLINE-2-CARBOXYLIC ACID is used as an antitumor agent, being studied for its potential to combat various types of cancer due to its ability to inhibit tumor growth and progression.
Used in Enzyme Inhibition:
4-OXO-3,4-DIHYDROQUINAZOLINE-2-CARBOXYLIC ACID is utilized as an enzyme inhibitor, targeting specific enzymes that play a role in disease processes, thereby offering therapeutic benefits in conditions that involve enzyme dysregulation.
Used in Cardiovascular Disease Treatment:
4-OXO-3,4-DIHYDROQUINAZOLINE-2-CARBOXYLIC ACID is being investigated for its potential role in treating cardiovascular diseases, where its chemical structure and properties may contribute to the management or mitigation of such conditions.
Used in Neurological Disorder Treatment:
In the realm of neurology, 4-OXO-3,4-DIHYDROQUINAZOLINE-2-CARBOXYLIC ACID is considered for its potential application in treating neurological disorders, given its capacity to interact with biological targets implicated in these conditions.
The chemical structure and properties of 4-OXO-3,4-DIHYDROQUINAZOLINE-2-CARBOXYLIC ACID make it a promising candidate for further research and development in the field of medicinal chemistry, with potential applications spanning across various therapeutic areas.

InChI:InChI=1/C9H6N2O3/c12-8-5-3-1-2-4-6(5)10-7(11-8)9(13)14/h1-4H,(H,13,14)(H,10,11,12)

Upstream product

• 853029-98-8 4-oxo-3,4-dihydroquinazoline-2-carbonitrile 
• 61068-77-7 (2-cyano-phenyl)-oxalamic acid 
• 29113-33-5 ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate 
• 612-24-8 o-nitrobenzonitrile 
• 105-36-2 ethyl bromoacetate 
• 28144-70-9 anthranilic acid amide 
• 1885-29-6 anthranilic acid nitrile 
• 861071-21-8 (2-cyano-phenyl)-oxalamic acid methyl ester 

Downstream Products

• 491-36-1 4-Hydroxyquinazoline 
• 118372-87-5 4-oxo-N-phenyl-3,4-dihydroquinazoline-2-carboxamide 
• 948762-40-1 N-(3-methylphenyl)-4-oxo-3,4-dihydroquinazoline-2-carboxamide 

Relevant academic research and scientific papers

Discovery of luotonin A analogues as potent fungicides and insecticides: Design, synthesis and biological evaluation inspired by natural alkaloid

The prevention and control of plant diseases and insect pests is the most crucial issue facing crop protection. To discover novel pesticide candidates with diverse chemical structures from natural products, a series of luotonin A analogues were designed, synthesized and evaluated for their antifungal and insecticidal activities. Most of these compounds exhibited potent activity against Botrytis cinerea, Magnaporthe oryzae and Aphis craccivora. Among them, the antifungal activity of compound 10s against B. cinerea was comparable to azoxystrobin (EC50 = 0.09 mM) and against M. oryzae (EC50 = 0.19 mM) was slightly weaker than that of azoxystrobin (EC50 = 0.17 mM). Compounds 10k and 10o are the most active compounds against A. craccivora having identical mortality value of 42.05% at 50 μg/mL, respectively, which were slightly lower than pymetrozine (51.14%) at the same concentration. Revealed morphological changes of the fungal cell surface by scanning electron microscopy indicated that luotonin A analogues might exert their antifungal activity by destroying fungal cell membrane and cell wall. Furthermore, the results of the in vivo protective and curative activities of the compound 10s against S. sclerotiorum and B. cinerea showed that the curative effect was stronger than its protective effect and the curative effects reached 67.17% and 73.82% at 80 μg/mL respectively. The above results further demonstrated the potential of luotonin A analogues as novel fungicides and insecticides.

Application of luotonin A derivatives in preparation of drugs for preventing or resisting plant diseases

The invention relates to natural pharmaceutical chemistry field and technical field of biopesticides and discloses application of any compound of luotonin A derivatives (Ia)-(Ii) in the preparation ofdrugs for preventing or resisting grape gray mold rot and rice blast. The compounds provided by the invention are derived from natural structure derivatives of a Chinese herbal medicine, namely peganum nigellastrum, have the characteristics of no pollution, safety and high efficiency, have the advantages of natural source pesticides, can be developed into plant source pesticides for producing environment-friendly and pollution-free agricultural products and belong to novel biopesticides.

Synthesis and evaluation of antiproliferative activity of novel quinazolin-4(3H)-one derivatives

Two series of novel quinazolin-4(3H)-one derivatives (10a–g and 11a–g) have been synthesized and evaluated for their in vitro antiproliferative activity against human HeLa, MIAPACA, MDA-MB-231, and IMR-31 cancer cell lines. The synthesized compounds were characterized by spectral (Fourier transform infrared, 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, high-resolution mass spectra) methods. Among them, compounds 11e and 11g exhibited potent in vitro antiproliferative activity with GI50 values 0.02, less than 0.01 μM against MIAPACA human cancer cell line. Significantly, compounds 10a, 10b, 10c, 10g, 11b, 11c, 11d, 11e, 11f showed activity with GI50 values ranging from 0.1 to 0.87 μM against human cancer cell lines MIAPACA, MDA-MB-231, and IMR-31. We have explored the probable binding mode and key active site interactions in HDAC8 and EHMT2 proteins. The docking results are complementary to the experimental results.

Application of Luotonin A to prevention and treatment of aphid

The invention discloses application of a Luotonin A compound to prevention and treatment of green peach aphid, Chinese scholar tree aphid, hickory nut aphid and alfalfa aphid. The compound is high in aphid killing activity, can prevent and treat aphid harms and can serve as a new aphid-killing forerunner to be developed. Due to the fact that the compound is from a natural product of Chinese herbal medicine peganum nigellastrum bunge, the compound has the advantages of being free of pollution, safe and efficient, has the advantages of natural source pesticide and can serve as new potential forerunner molecules of plant source pesticide for producing green and pollution-free agricultural products.

METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY

Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.

Copper-catalyzed domino synthesis of quinazolin-4(3 H)-ones from (Hetero)arylmethyl halides, bromoacetate, and cinnamyl bromide

Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed. Georg Thieme Verlag Stuttgart New York.

Short and efficient total synthesis of luotonin A and 22-hydroxyacuminatine using a common cascade strategy

(Chemical Equation Presented) Total syntheses of 22-hydroxyacuminatine and luotonin A were achieved in direct fashion and high overall yields (16% in eight steps and 47% in five steps, respectively). A mild cascade methodology was successfully applied in both syntheses as a common strategy. The new approach presents the advantages of short routes, high overall yields, use of stable intermediates, and ease of operations.

3-Propynyl-2-substituted carboxylic acid derivatives of quinazolinone

Alkylation of quinazolinone-2-carboxylic acids with propargyl bromide in dimethylformamide in the presence of potassium carbonate afforded 3-prop-2-ynyl quinazolinone-2-substituted carboxylic acid derivatives. Further reaction of 4b-c produced 5b-c, which indicates that N-alkylation occurs before esterification with a propynyl moiety.

Synthesis of 2-Substituted Quinazolines and Quinazolones as Potential Anthelmintics

2-Substituted quinazolines (5, 6) and quinazolones (9-18) have been synthesized starting from 2-aminobenzylamine (3) and 2-carbethoxyquinazolone (7), respectively.The compounds have been tested for their antihookworm activity against Ancylostoma ceylanicum in hamsters but none shows any significant activity.