34954-65-9

Basic information

• Product Name: 3-METHOXY-ISATOIC ANHYDRIDE
• Synonyms: 3-METHOXY-ISATOIC ANHYDRIDE;8-METHOXY-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;REF DUPL: 3-Methoxy-isatoic anhydride;2H-3,1-Benzoxazine-2,4(1H)-dione, 8-methoxy-;8-methoxy-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
• CAS NO: 34954-65-9
• Molecular Formula: C₉H₇NO₄
• Molecular Weight: 193.16
• Mol File: 34954-65-9.mol

Chemical Properties

• Melting Point: 255-260 °C
• Appearance: /
• Density: 1.376 g/cm³
• Refractive Index: 1.565
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Very Slightly, Heated)
• PKA: 10.42±0.20(Predicted)
• CAS DataBase Reference: 3-METHOXY-ISATOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXY-ISATOIC ANHYDRIDE(34954-65-9)
• EPA Substance Registry System: 3-METHOXY-ISATOIC ANHYDRIDE(34954-65-9)

Safety Data

• Hazardous Substances Data: 34954-65-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxyisatoic anhydride is used as a reagent for the synthesis of Tryptanthrin (T947000) and its analogs, which are known for their antitubercular properties. These compounds are valuable in the development of new treatments for tuberculosis, a disease that poses significant global health challenges.
Additionally, 3-Methoxyisatoic anhydride is utilized in the preparation of quinazolin-2-ylamino-quinazolin-4-ols. These compounds act as non-nucleoside inhibitors of bacterial DNA polymerase III, which are essential in the development of novel antibiotics to combat bacterial infections, particularly those caused by drug-resistant strains.

InChI:InChI=1/C9H7NO4/c1-13-6-4-2-3-5-7(6)10-9(12)14-8(5)11/h2-4H,1H3,(H,10,12)

Upstream product

• 3177-80-8 2-amino-3-methoxybenzoic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1026003-01-9 2-tert-Butoxycarbonylamino-3-methoxy-benzoic acid 
• 76-02-8 trifluoroacetyl chloride 
• 14963-96-3 3-methoxyphthalic anhydride 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 

Downstream Products

• 3177-80-8 2-amino-3-methoxybenzoic acid 
• 467432-89-9 2-amino-N-(4-bromo-phenyl)-3-methoxy-benzamide 
• 1235480-79-1 2-amino-N-(4-sec-butyl-phenyl)-3-methoxy-benzamide 
• 1332526-74-5 C₂₀H₂₃N₃OS 
• 1332527-07-7 C₁₅H₁₄N₂OS 
• 1332527-02-2 C₁₄H₁₂N₂O₂ 
• 63478-14-8 2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-6-methoxyaniline 
• 13135-94-9 (2-Amino-3-methoxy-benzoylamino)-acetic acid 
• 76745-47-6 3-methoxyanthranilic hydrazide 
• 88187-56-8 2-(3-Methoxy-2-methylamino-benzoyl)-5-methyl-hex-4-enoic acid ethyl ester 
• 106782-78-9 3-methoxy-2-aminobenzamide 

Relevant articles and documents

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.

Synthesis of Ring-Fused, N-Substituted 4-Quinolinones Using p Ka-Guided, Base-Promoted Annulations with Isatoic Anhydrides: Total Synthesis of Penicinotam

An anionic annulation strategy employing isatoic anhydrides and a wide assortment of enolizable partners was developed to afford over 80 novel ring-fused, N-substituted 4-quinolinones, an underrepresented privileged template. Multiple factors governing the efficiency of the transformation were determined, resulting in a reliable and tunable synthetic platform applicable for a broad range of substrates with variable deprotonation susceptibility, such as tetramic and tetronic acids, cyclic 1,3-diketones, and cycloalkanones. Application to the synthesis of bioactive, pyrrolizine-fused 4-quinolinone, penicinotam 3, resulted in the most brief and highest yielding total synthesis of the alkaloid in three steps and a 36% overall yield.

Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita

To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification.

Isatoic anhydride and its process for synthesis of derivatives of

The invention discloses a synthesis method of isatoic anhydride and a derivative thereof, relating to the technical field of chemical synthesis. In the presence of catalysis of an organic selenium catalyst, isatin or a derivative thereof is oxidized by using hydrogen peroxide to prepare the isatoic anhydride and the derivative thereof. The synthesis method disclosed by the invention is simple and easily available in raw materials, low in cost, clean in oxidizing agent, free from a metal catalyst, and environmentally friendly, can be carried out in a neutral environment, and is small in corrosion to equipment.

Quinazoline dione derivatives and preparation method and application thereof

The invention provides novel quinazoline dione derivatives and a preparation method and application thereof. The compounds include compounds with the structure shown in the general formula V in the description and pharmaceutically acceptable salts or hydrates thereof. The compounds are active ligands of novel cannabinoid II receptors (CB2) and can be used for preparing medicine for treating, preventing and relieving CB2 receptor-mediated diseases, wherein the medicine is an agonist or partial agonist or inverse agonist or antagonist of CB2 receptors.

2-Pyridylquinolone antimalarials with improved antimalarial activity and physicochemical properties

A series of 2-pyridylquinolones has been prepared in 5-7 steps and through lead optimisation, antimalarial activity as low as 12 nM against Plasmodium falciparum (Pf) has been achieved. Compared with previous analogues in this series, selected molecules h

Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita

A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L-1, which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the molecule. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L-1 for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress.

A simple heterocyclic fusion reaction and its application for expeditious syntheses of rutaecarpine and its analogs

In the search for new inhibitors of cholinesterases, a simple heterocyclic fusion reaction of isatoic anhydride 8 and 3,4-dihydroisoquinoline 22 was discovered which involves a spontaneous dehydrogenation upon heating. Applying the reaction, the bioactive natural alkaloid rutaecarpine and several substituted derivatives out of tryptamines and anthranilic acids or isatoic anhydrides, respectively, can be synthesized without tedious chromatographic purification. This provides simple and fast access to larger amounts of compounds with this privileged structure in medicinal chemistry.

A phosgene and peroxide-free one-pot tandem synthesis of isatoic anhydrides involving anthranilic acid, boc anhydride and 2-chloro-N-methyl pyridinium iodide

A phosgene and peroxide-free approach for the synthesis of isatoic anhydrides has been described. The synthesis involves the carbamate formation with boc anhydride followed by in situ cyclization to afford the isatoic anhydride. The importance of this synthetic strategy is in the ease of operation, scalability and preparation from readily available raw materials.

BENZODIAZEPINONE COMPOUNDS AND METHODS OF TREATMENT USING SAME

The invention provides 1,4-benzodiazepinone compounds, pharmaceutical compositions, and methods of treating autoimmune disorders, chronic inflammatory disorders, and hyperproliferative disorders. For example, the 1,4-benzodiazepinone compounds and pharmaceutical compositions are contemplated to be useful for treating rheumatoid arthritis, graft-versus-host disease, inflammatory bowel disease, and the like.