5059-37-0

Basic information

• Product Name: (3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol
• Synonyms: 1H-Indole, 1-b-D-glucopyranosyl-;(3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol
• CAS NO: 5059-37-0
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.28848
• Mol File: 5059-37-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol(5059-37-0)
• EPA Substance Registry System: (3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol(5059-37-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5059-37-0(Hazardous Substances Data)

Usage

Chemical structure

The compound consists of an indole molecule linked to a D-glucose molecule through a β-glycosidic bond.

Occurrence

It is commonly found in plants.

Biological activities

Known for its potential anti-inflammatory and antioxidant properties.

Potential applications

Studied for its potential role in cancer prevention and treatment.

Interest in medicinal chemistry

Garnered interest due to its diverse biological activities and potential therapeutic applications.

Glycoside interaction

As a glycoside, it has the ability to interact with various cellular targets.

Drug development and research

Considered a promising candidate for further drug development and research.

Upstream product

• 39264-64-7 1-(β-D-glucopyranosyl)indoline 
• 133-89-1 UDP-glucose 
• 120-72-9 indole 
• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 
• 496-15-1 1-indoline 
• 39264-63-6 1-(β-D-galactopyranosyl)indoline 
• 10257-28-0 D-Galactose 

Downstream Products

• 4196-37-6 1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole 
• 716379-93-0 3,3-dibromo-1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indolin-2-one 
• 716379-97-4 3-benzylidene-1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indolin-2-one 
• 5059-38-1 1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1H-indole 
• 716379-95-2 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indoline-2,3-dione 

Relevant articles and documents

Synthesis of 1,3- and 2,3-diglycosylated indoles as potential trisaccharide mimetics

Diglycosylated heteroaromatics may serve as metabolically stable mimetics of trisaccharides. Herein, the preparation of several 1,3- and 2,3-diglycosylindoles by direct C-glycosylation of monoglycosylated precursors is described. Georg Thieme Verlag Stuttgart ? New York.

Synthesis, cytotoxic activities and cell cycle arrest profiles of naphtho[2,1-α]pyrrolo[3,4-c]carbazole-5,7(6H,12H)-dione glycosides

Naphtho[2,1-α]pyrrolo[3,4-c]carbazole-5,7(6H,12H)-dione (NPCD) is known to be a very potent and selective cyclin D1-CDK4 inhibitors and could induce strong G1 phase arrest in breast tumor cell lines. In this work, the synthesis of five NPCD glycosides and

Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives

In the course of structure-activity relationship studies, diversely substituted 1-(β-D-glucopyranosyl)-isoindigo derivatives were prepared from commercially available indolines. Their antiproliferative activities were evaluated toward a panel of human solid cancer cell lines (PC 3, DLD-1, MCF-7, M4Beu, A549, PA 1), a murine cell line (L929) and a human fibroblast primary culture to get an insight into the substitution pattern required for the best biological potencies.