53003-18-2

Usage

Uses

Used in Organic Synthesis:
4-Chloro-5-methylisatin is used as a building block in organic synthesis for the production of various pharmaceuticals, dyes, and natural products. Its chemical structure allows for the creation of a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-CHLORO-5-METHYLISATIN is used as a key intermediate in the synthesis of various drugs. Its unique chemical properties enable the development of new medications with potential therapeutic benefits.
Used in Dye Industry:
4-CHLORO-5-METHYLISATIN is used as a precursor in the production of dyes, contributing to the development of new colorants for various applications, including textiles, plastics, and printing inks.
Used in Natural Products:
4-CHLORO-5-METHYLISATIN is utilized in the synthesis of natural products, such as alkaloids and other bioactive compounds, which have potential applications in medicine, agriculture, and other fields.
Used as a Reagent for Organic Compound Identification:
4-CHLORO-5-METHYLISATIN is used as a reagent for the identification and detection of various organic compounds. Its unique chemical properties make it a valuable tool in analytical chemistry for the characterization of organic substances.
Used in Biological and Pharmacological Research:
4-Chloro-5-methylisatin has been studied for its potential biological and pharmacological activities, including antibacterial and antiviral properties. This research aims to explore its potential as a therapeutic agent in the treatment of various diseases and conditions.

Upstream product

• 155184-79-5 N-(3-chloro-4-methyl-phenyl)-2-hydroxyimino-acetamide 
• 7745-89-3 3-chloro-4-methylaniline hydrochloride 
• 95-74-9 3-chloro-p-toluidine 

Downstream Products

• 155184-82-0 2-amino-5-methyl-6-chlorobenzoic acid 
• 15068-35-6 2-chloro-3-methylbenzoic acid 
• 450407-83-7 2-(N-tert-butyloxycarbonyl)amino-5-methyl-6-chlorobenzoic acid 
• 450407-84-8 methyl 2-(N-tert-butyloxycarbonyl)amino-5-methyl-6-chlorobenzoate 
• 342411-56-7 methyl 2-amino-5-methyl-6-chlorobenzoate 
• 53003-14-8 4-chloro-5-methyl-1-morpholin-4-ylmethyl-indole-2,3-dione 

Relevant academic research and scientific papers

Synthesis of substituted tryptanthrin via aryl halides and amines as antitumor and anti-MRSA agents

The natural alkaloid, tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione), and its analogues are found to exhibit potent antitumor and anti-MRSA activities. An efficient and convenient method has been developed for the synthesis of tryptanthrin D-ring derivatives through the reaction of substituted tryptanthrins and secondary amines in moderate to good yields. Some of the new compounds exhibited antitumor activities against the human tumor cell lines A549, HCT116 and MDA-MB-231, with mean IC50 values at low micromolar levels. In addition, some of the compounds showed excellent anti-MRSA activities and were more effective than vancomycin, with MIC values of 0.31–1.25 μg/mL for Mu50,RN4220, and Newman strains.

Synthesis and in vitro antitumor activity of thiophene analogues of 5-chloro-5,8-dideazafolic acid and 2-methyl-2-desamino-5-chloro-5,8-dideazafolic acid

N-[5-[N-(2-Amino-5-chloro-3,4-dihydro-4-oxoquinazolin-6-yl)methylamino]-2- thenoyl]-L-glutamic acid (6) and N-[5-[N-(5-chloro-3,4-dihydro-2-methyl-4-oxoquinazolin-6-yl)methylamino]-2- thenoyl]-L-glutamic acid (7), the first reported thiophene analogues of 5-chloro-5,8-dideazafolic acid, were synthesized and tested as inhibitors of tumor cell growth in culture. 4-Chloro-5-methylisatin (10) was converted stepwise to methyl 2-amino-5-methyl-6-chlorobenzoate (22) and 2-amino-5-chloro-3,4-dihydro-6-methyl-4-oxoquinazoline (19). Pivaloylation of the 2-amino group, followed by NBS bromination, condensation with di-tert-butyl N-(5-amino-2-thenoyl)-L-glutamate (28), and stepwise cleavage of the protecting groups with ammonia and TFA yielded 6. Treatment of 9 with acetic anhydride afforded 2,6-dimethyl-5-chlorobenz[1,3-d]oxazin-4-one (31), which on reaction with ammonia, NaOH was converted to 2,6-dimethyl-5-chloro-3,4-dihydroquinazolin-4-one (33). Bromination of 33, followed by condensation with 28 and ester cleavage with TFA, yielded 7. The IC50 of 6 and 7 against CCRF-CEM human leukemic lymphoblasts was 1.8±0.1 and 2.1±0.8 μM, respectively.