4119-10-2

Basic information

• Product Name: 2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]-
• CAS NO: 4119-10-2
• Molecular Formula: C18H15N3O2
• Molecular Weight: 305.336
• Mol File: 4119-10-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]-(4119-10-2)
• EPA Substance Registry System: 2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]-(4119-10-2)

Safety Data

• Hazardous Substances Data: 4119-10-2(Hazardous Substances Data)

Usage

General Description

The chemical "2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]-" is a quinazolinedione derivative with a substituted indole group. It is a heterocyclic compound with potential biological and pharmacological activities. The presence of the indole group suggests potential interactions with serotonin receptors, which are involved in various physiological functions including mood regulation and gastrointestinal motility. 2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]- may be of interest in medicinal chemistry for the development of new drugs targeting serotonin receptors or other related biological pathways. Further research is needed to fully understand its pharmacological potential and possible therapeutic applications.

Upstream product

• 98260-32-3 2-chloro-3-<2-(indol-3-yl)ethyl>-4(3H)-quinazolinone 
• 61-54-1 tryptamine 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 41470-85-3 2-trichloromethyl-benzo[d][1,3]oxazin-4-one 

Downstream Products

• 84-26-4 rutaecarpine 

Relevant articles and documents

A SHORT SYNTHESIS OF RUTECARPINE AND/OR VASICOLINONE FROM 2-CHLORO-3-(INDOL-3-YL)ETHYLQUINAZOLIN-4(3H)-ONE: EVIDENCE FOR THE PARTICIPATION OF THE SPIRO INTERMEDIATE

A new route to rutecarpine and/or vasicolinone from 2-chloro-4-quinazolone through an acid catalyzed cyclization of 2-chloro-3-indolylethylquinazolin-4-one has been developed and the mechanism of the cyclization reaction clarified.

Studies of Rutaecarpine and Related Quinazolinocarboline Alkaloids

Quinazolinocarboline alkaloids, e.g., rutaecarpine (1), can readily be synthesized by treating tryptamine with 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (quickly generated in situ from trifluoroacetic anhydride (TFAA) and 2H-3,1-benzoxazine-2,4(1H)-dione.The product formed, 3--2-(trifluoromethyl)-4-(3H)-quinazolinone (5), is then cyclized (HCl/HOAc) to 13b-(trifluoromethyl)-13b,14-dihydrorutaecarpine (6), whereupon CF3H is eliminated by treatment with base.The sequence can conveniently be performed as a three-reaction one-pot procedure giving rutaecarpine (1) in 99percent yield within 3h.The approach can readily be extended to the synthesis of evodiamine (2), 13,13b-dehydroevodiamine (38a), and 13b,14-dihydrorutaecarpine (21).Thus treatment of 3--4(3H)-quinazolinone (19) with TFAA affected cyclization to 13b-(trifluoroacetyl)-13b,14-dihydrorutaecarpine (20), which can be readily hydrolyzed to 13b,14-dihydrorutaecarpine (21).