84575-27-9

Basic information

• Product Name: 7-methoxyindoline-2,3-dione
• Synonyms: 7-methoxyindoline-2,3-dione;7-Methoxy-1H-indole-2,3-dione;7-Methoxyindoline;1H-Indole-2,3-dione,7-Methoxy-
• CAS NO: 84575-27-9
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• Mol File: 84575-27-9.mol

Chemical Properties

• Melting Point: 240-242℃
• Appearance: /
• Density: 1.346
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.69±0.20(Predicted)
• CAS DataBase Reference: 7-methoxyindoline-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 7-methoxyindoline-2,3-dione(84575-27-9)
• EPA Substance Registry System: 7-methoxyindoline-2,3-dione(84575-27-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 84575-27-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
7-methoxyindoline-2,3-dione serves as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of diverse chemical entities through reactions such as substitution, addition, and rearrangement, making it a valuable building block in the creation of novel molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 7-methoxyindoline-2,3-dione is utilized as a precursor for the development of new drugs. Its structural features enable the design of bioactive molecules with potential therapeutic effects. Researchers are exploring its use in the treatment of various diseases, including neurological disorders, inflammatory conditions, and cancer, by modulating specific biological targets and pathways.
Used in Material Science:
7-methoxyindoline-2,3-dione also finds applications in material science, where its unique chemical and physical properties can be harnessed to develop new materials with specific functionalities. For instance, it can be incorporated into the design of organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells, due to its ability to modulate charge transport and light emission properties.

Upstream product

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Downstream Products

• 1379768-31-6 C₂₈H₃₄N₂O₈ 
• 1379768-22-5 C₂₆H₃₀N₂O₈ 
• 1379768-21-4 C₂₆H₃₀N₂O₈ 
• 1092288-64-6 8-Methoxyquinoline 4-carboxylic acid 
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• 99545-46-7 3-Methoxy-2-(ω-methoxycarbonyl-propionylamino)-benzoesaeure-methylester 
• 5121-34-6 methyl 2-amino-3-methoxybenzoate 
• 68701-23-5 2-amino-3-methoxybenzoic acid hydrochloride 
• 3177-80-8 2-amino-3-methoxybenzoic acid 

Relevant articles and documents

Design, synthesis, and biological evaluation of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetate derivatives as anti-proliferative agents through ROS-induced cell apoptosis

A novel class of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetate derivatives were designed and synthesized as potent anti-proliferative agents. Most of these compounds showed potent anti-proliferative activity against some tumor cell lines, including SK-BR-3, MDA-MB-231, HCT-116, SW480, Ovcar-3, HL-60, Saos-2 and HepG2. Compounds 8c and 11h were identified as the most potent ones, while HL-60, HCT116 and MDA-MB-231 were the most sensitive cell lines. Mechanistic study revealed that compound 8c enhanced reactive oxygen species level by inhibiting TrxR and then induced apoptosis by activating apoptosis proteins, bax and cleaved-caspase 3 in HCT116?cells. Preliminary SAR analysis indicated that modifications of the double bond and ester group made great effects on the anti-proliferative activity. Our findings suggested that it was worth further studies on the antitumor potency of (2E)-(2-oxo-1, 2-dihydro-3H-indol-3-ylidene)acetates.

A versatile synthesis of unsymmetrical 3,3′-bioxindoles: Stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins

(Chemical Equation Presented) A new synthesis of 3,3′-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3′-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles w

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists

Leukocyte recruitment of sites of inflammation and tissue injury involves leukocyte rolling along the endothelial wall, followed by firm adherence of the leukocyte, and finally transmigration of the leukocyte across cell junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis. High-throughput screening of the Wyeth chemical library identified the quinoline salicylic acid class of compounds (1) as antagonists of P-selectin, with potency in in vitro and cell-based assays far superior to that of sLex. Through iterative medicinal chemistry, we identified analogues with improved P-selectin activity, decreased inhibition of dihydrooratate dehydrogenase, and acceptable CYP profiles. Lead compound 36 was efficacious in the rat AIA model of rheumatoid arthritis.

A VERSATILE AND EFFICIENT PROCESS TO 3-SUBSTITUTED INDOLES FROM ANILINES

Borane-mediated reductive elimination of α-thiomethyl-, α-hydroxy-, or α-alkoxy-, α'-substituted oxindoles affords 3-substituted indoles in high yield.Isatins, available via several routes from oxindoles, also afford indoles.

SYNTHETIC ANALOGS OF Peganum ALKALOIDS. I. SYNTHESIS OF METHOXY- AND HYDROXY-SUBSTITUTED DEOXYVASICINONES AND DEOXYPEGANINES

6-Methoxy-, 7-methoxy-, and 8-methoxydeoxyvasicinones have been synthesized by the reaction of substituted (3-methoxy-, 4-methoxy-, and 5-methoxy-) anthranilic acids with α-pyrrolidone.The demethylation of these compounds has given the corresponding hydroxy-substituted analogs of deoxyvasicinone, and the reduction of the products obtained with zinc in hydrochloric acid has given the hydroxy- and methoxy- analogs of deoxypeganine. 8-Hydrooxydeoxypeganine dimethyl-, ethyl-, and butylcarbamates have been obtained by the carbamoylation of 8-hydroxydeoxypeganine.