49667-81-4

Usage

Molecular weight

177.20 g/mol

Structure

Benzene ring with an amino group attached to the nitrogen and a 2-hydroxyethyl group attached to the carbon

Uses

Reagent in organic synthesis, pharmaceutical research, production of drugs such as antineoplastic and antiviral agents
Versatile building block for creating complex organic molecules with potential therapeutic applications

InChI:InChI=1/C9H12N2O2/c10-8-4-2-1-3-7(8)9(13)11-5-6-12/h1-4,12H,5-6,10H2,(H,11,13)

Upstream product

• 118-48-9 isatoic anhydride 
• 141-43-5 ethanolamine 
• 271-58-9 anthranil 

Downstream Products

• 85094-71-9 3-(2-hydroxyethyl)-2-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 67090-21-5 3-(2-hydroxyethyl)-2-phenyl-quinazoline-(3H)-4-one 
• 1448791-15-8 2-(4-chloro-6-(3,4,5-trimethoxyphenylamino)-1,3,5-triazin-2-ylamino)-N-(2-hydroxyethyl)benzamide 
• 1448791-34-1 N-(2-hydroxyethyl)-2-(4-(3,4,5-trimethoxyphenylamino)-1,3,5-triazin-2-ylamino)benzamide 
• 1042434-98-9 2-[(2-chloro-5-fluoro-4-pyrimidinyl)amino]-N-(2-hydroxyethyl)benzamide 
• 1042434-77-4 2-[(2,5-dichloro-4-pyrimidinyl)amino]-N-(2-hydroxyethyl)benzamide 
• 3416-96-4 N-[2-(4,5-dihydro-thiazol-2-yl)-phenyl]-toluene-4-sulfonamide 
• 3770-67-0 N-[2-(4,5-dihydrooxazol-2-yl)phenyl]-4-methylbenzenesulfonamide 
• 2940-68-3 3-(2-Chloroethyl)-4(3H)-quinazolinone 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 

Relevant academic research and scientific papers

Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives

Twenty 2,3-disubstituted quinazolin-4(3H)-one derivatives 1–20 were successfully synthesized in moderate to good yields (25–82%). Their syntheses were based on a one pot tandem ring opening procedure followed by iodine-catalyzed oxidative cyclization of isatoic anhydride with aldehydes, using water as the only solvent under both classical and microwave irradiation conditions. Cytotoxicity assays of the prepared compounds against three human cancer cell lines (HeLa, MCF-7, and A549) indicated that 2, 3, and 20 possessed moderate activities against MCF-7 cells (IC50 = 47.2 μM, 43.9 μM, and 44.9 μM, respectively). Good cytotoxic activities against A549 cells were observed for 3 and 8 with IC50 values of 30.7 μM and 29.8 μM, respectively, which were comparable to the positive control, 5-fluorouracil (5-FU, IC50 = 27.9 μM). Furthermore, compound 4 exhibited slightly stronger activity (IC50 = 23.6 μM) than the positive control 5-FU against the A549 cell line.

Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines

Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.

Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions

Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.

Synthesis and pharmacological characterization of 2-aminobenzaldehyde oxime analogs as dual inhibitors of neutrophil elastase and proteinase 3

Proteinase 3 (Pr3), and human neutrophil elastase (HNE) are two major neutrophilic serine proteases (NsPs) expressed in neutrophil azurophil granules. Emerging data suggest that excessive release of proteases mediates tissue damage, and therefore prolonged neutrophil accumulation has an important role in the pathogenesis of many diseases. Thus, HNE and Pr3 inhibitors may prove to be targets for the generation of agents in the treatment of neutrophilic inflammatory disease. Sivelestat is the only commercially available selective HNE inhibitor. Therefore, sivelestat was chosen as the model structure in an attempt to obtain more potent anti-NsPs agents. In the present study, a series 2-aminobenzaldehyde oxime and 2-aminobenzoate analogs were synthesized and their inhibitory effects on NsPs (CatG, Pr3, and HNE) were determined, respectively. The results of structure-activity relationships studies concluded that a hydroxyl oxime moiety plays an important role in ligand-enzyme affinity through hydrogen bonding. As compound 6 had more potency and showed dual inhibitory effects on NE and Pr3, both in vitro and in vivo experiments were carried out to evaluate its selectivity, effects in cell-based assays, and efficacy in models of inflammation and damage. Compound 6 had the potential to reduce paw edema induced by LPS and HNE, as well as acute lung injury, and may be approved as a candidate for the development of new agents in the treatment of neutrophilic inflammatory diseases.

An efficient one pot synthesis of 2-amino quinazolin-4(3H)-one derivative via MCR strategy

A novel multi-component reaction strategy was developed for the construction of important building blocks, 2-amino 3-substituted quinazolinone derivatives from isatoic anhydride and amine with electrophilic cyanating compound, N-cyano-4-methyl-N-phenylbenzenesulfonamide (NCTS). The quinazolinone synthesis proceeds via a sequential series of reactions such as nucleophilic attack of the amine group on the carbonyl group of isatoic anhydride followed ring opening and subsequent decarboxylation, nucleophilic attack of amine to nitrile, followed by heterocyclization.

ANTHRANILAMIDE INHIBITORS OF AURORA KINASE

The present invention relates to a compound represented by the following formula: or a pharmaceutically acceptable salt thereof; where R1, R2, R3, R4, r and s are as previously defined. Compounds of the present invention are useful in the treatment of diseases associated with Aurora kinase activity such as cancer.

FIBRATE COMPOUNDS HAVING PPAR AGONIST ACTIVITY

There are provided derivatives having PPAR agonist activity. The derivatives include compounds and/or their pharmaceutically acceptable salts; the compounds having the formula (I) wherein A has the structure (II) or (III); X is chosen from -CH2-, -O-, -NH-, and -S-; Y is chosen from -O-, -NH-, and -S-; Z, which may be located in any position of substitution, is hydrogen or halogen; R1 and R2, which may be the same or different, are independently chosen from hydrogen and C1-C8 alkyl, or R1 and R2 together form a carbocyclic ring having from 4 to 6 carbon atoms; R3 is chosen from hydrogen and C1-C8 alkyl; R4, R5, and R6, which may be the same or different, are independently chosen from hydrogen and C1-C8 alkyl; and n is 1 to 6. Various embodiments and variants are provided. In accordance with other aspects, the invention also provides methods of producing a PPARα agonist activity in a mammal, the methods including administering to the mammal an effective amount of certain derivative(s) of the first aspect of the invention, a method of producing a PPARα agonist activity and a PPARα agonist activity in a mammal, the method including administering to the mammal an effective amount of certain derivative(s); and a pharmaceutical composition that includes the derivative(s) of the first aspect of the invention and one or more pharmaceutically-acceptable excipients. Various embodiments and variants are provided.

Reaction of isatoic anhydride with bifunctional reagents: Synthesis of some new quinazolone fused heterocycles, 2-substituted anilinoheterocyclic derivatives and other related compounds

A new synthesis of quinazolone fused heterocycles (2, 5, 8), anilinoheterocycles (4, 7, 10, 12, 14) and substituted 2-aminoquinoline (15, 16) based on the reaction of isatoic anhydride (1) with different active bifunctional compounds in presence of glacial acetic acid and freshly fused sodium acetate is described. Structures of the newly prepared compounds are established by chemical and spectral data.

Studies on quinazolines. VII. Reactions of anthranilamide with β- diketones; new approaches toward the synthesis of tetrahydropyrido[2,1- b]quinazolin-11-one derivatives

Condensation of anthranilamide and its derivatives with various 1,3- cyclohexanediones 5a,b or 2,4-pentanediones under acidic conditions produced a variety of heterocycles, leading to the synthesis of tetrahydropyridol[2,1- b]-quinazolin-11-one derivatives. Condensation of anthranilamide with 5a or 5b in the presence of p-toluenesulfonic acid at the reflux temperature of tetrahydrofuran (THF) afforded compound 6a (40%) and compound 7a (22%) or compound 6b (47%) and compound 7b (39%), respectively. However, reflux of anthranilamide with 5a or 5b in 6% ethanolic hydrogen chloride provided compounds 6a and 6b in 77% and 73% yields, respectively. Heating 7a with 5a in 6% ethanolic hydrogen chloride furnished 6a in 82.4% yield. Reaction of anthranilamide with 5c under the same conditions resulted in the formation of 11 (57%). Treatment of compounds 6a and 6b with NaBH4 furnished 8a,b (89, 87% yields), which were subsequently subjected to the Mitsunobu reaction to produce 6,7,8,9-tetrahydro-9-methyl-11H-pyrido[2,1-b]quinazolin-11-one (9a) and 6,7,8,9-tetrahydro-7,7,9-trimethyl-11H-pyrido[2,1-b]quinazolin-11-one (9b) in 56 and 72% yields, respectively. However, heating 14 with 15a in CH3CN in the presence of p-toluenesulfonic acid furnished 19 in 31% yield. Under similar conditions, treatment of 21 with 15a provided 23a (42.4% yield), a key intermediate for the synthesis of rutaecarpine. Analogous reaction of 21 with 15b, 15c and 5a provided 22b-d in 63-99.3% yield, respectively.