51226-47-2

Usage

Appearance

Yellow to orange crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Usage

Intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds

Medical applications

Building block for anti-cancer drugs, fluorescent probe for detecting and imaging specific biological molecules

Hazardous nature

Potentially hazardous, should be handled with caution

Health risks

Harmful if ingested or inhaled, can cause irritation to the skin and eyes

Upstream product

• 7570-47-0 5-nitro-2-methylindole 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 95-20-5 2-methyl-1H-indole 
• 220465-91-8 1-(2-aminophenyl)prop-1-yne 
• 615-43-0 2-iodophenylamine 
• 875-79-6 1,2-dimethylindole 

Downstream Products

• 1204478-54-5 (3R,3aR,8bS)-methyl 3a,4-dimethyl-7-nitro-3-phenyl-3,3a,4,8b-tetrahydrocyclopenta[b]indole-1-carboxylate 
• 120627-52-3 (1,2-Dimethyl-5-nitro-1H-indol-4-yl)-acetonitrile 

Relevant academic research and scientific papers

ISOINDOLINE COMPOUNDS FOR THE TREATMENT OF SPINAL MUSCULAR ATROPHY AND OTHER USES

Disclosed is a compound of Formula (I) in which W and R1-R6 are defined herein. Also disclosed is a method of treating spinal muscular atrophy, as well as methods of using such compounds to increase SMN expression, increase EAAT2 expression, or increase the expression of a nucleic acid that encodes a translational stop codon introduced directly or indirectly by mutation or frameshift.

High-affinity inhibitors of dihydrofolate reductase: Antimicrobial and anticancer activities of 7,8-dialkyl-1,3-diaminopyrrolo[3,2-f]quinazolines with small molecular size

A series of 7,8-dialkylpyrrolo[3,2-f]quinazolines were prepared as inhibitors of dihydrofolate reductase (DHFR). On the basis of an apparent inverse relationship between compound size and antifungal activity, the compounds were designed to be relatively small and compact. Inhibitor design was aided by a GRID analysis of the three-dimensional structure of Candida albicans DHFR, which suggested that relatively small, branched alkyl groups at the 7- and 8-positions of the pyrroloquinazoline ring system would provide optimal interactions with a hydrophobic region of the protein. The compounds were potent inhibitors of fungal and human DHFR, with K(i) values as low as 7.1 and 0.1 pM, respectively, and were highly active against C. albicans and an array of tumor cell lines. In contrast to known lipophilic inhibitors of DHFR such as trimetrexate and piritrexim, members of this series of pyrroloquinazolines were not susceptible to P-glycoprotein-mediated multidrug resistance and also showed significant distribution into lung and brain tissue. The compounds were active in lung and brain tumor models and displayed in vivo activity against Pneumocystis carinii and C. albicans.

Synthesis and Photochromic Behavior of 5-Substituted Indolylfulgides

1,2-Dimethylindolylfulgides with 5-methylthio, 5-methoxy, or 5-dimethylamino group on the indole ring were synthesized and their photochromic properties were examined.Electron donating substituents lengthened the absorption maximum of the colored form and decreased the quantum yields of the photoreactions.The colored form of the dimethylaminoindolyl-substituted fulgide has λmax at 673 nm, the longest absorption maximum wavelength ever known as that of a fulgide.

ACETALS OF LACTAMS AND ACID AMIDES. 60. NOVEL APPROACH TO THE SYNTHESIS OF γ-CARBOLINES

N-Alkylation of 2-methyl-5-nitroindole followed by the Vilsmeyer reaction has given some 2-methyl-3-formyl-5-nitro-N-alkylindoles, which on reaction with DMF diethyl acetal afford 2-(β-dimethylamino)vinylindoles.Heating the latter with ammonia provided a novel synthesis of γ-carbolines.Condensation of 1,2-dimethyl-3-formyl-5-nitroindole with dimethylacetamide diethyl acetal gave 2-dimethylamino-6-nitro-9-methylcarbazole.