93879-42-6

Basic information

• Product Name: 1H-Indole-3-acetamide, 5-methoxy-1-(phenylmethyl)-
• CAS NO: 93879-42-6
• Molecular Formula: C18H18N2O2
• Molecular Weight: 294.353
• Mol File: 93879-42-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Indole-3-acetamide, 5-methoxy-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-acetamide, 5-methoxy-1-(phenylmethyl)-(93879-42-6)
• EPA Substance Registry System: 1H-Indole-3-acetamide, 5-methoxy-1-(phenylmethyl)-(93879-42-6)

Safety Data

• Hazardous Substances Data: 93879-42-6(Hazardous Substances Data)

Upstream product

• 1006-94-6 5-methoxylindole 
• 94685-18-4 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid ethyl ester 
• 57000-49-4 (5-methoxy-1H-indol-3-yl)acetic acid ethyl ester 
• 419569-93-0 methyl 1-benzyl-5-methoxy-1H-indole-3-acetate 
• 93871-13-7 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide 
• 94005-21-7 NSC₅₄₇₇₁ 
• 57-13-6 urea 

Downstream Products

• 40619-73-6 2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethylamine 
• 164083-03-8 4-[[3-(2-amino-2-oxoethyl)-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid ethyl ester 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 50-67-9 3-(2-aminoethyl)-1H-indol-5-ol 
• 164084-04-2 5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide 
• 164084-32-6 5-methoxy-2-(methylthio)-1-(phenylmethyl)-1H-indole-3-acetamide 

Relevant articles and documents

Aromatization of 1,6,7,7a-tetrahydro-2H-indol-2-ones by a novel process. Preparation of key-intermediate methyl 1-benzyl-5-methoxy-1H-indole-3-acetate and the syntheses of serotonin, melatonin, and bufotenin

Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

Indole inhibitors of human nonpancreatic secretory phospholipase A2. 1. Indole-3-acetamides

Phospholipases (PLAs) produce rate-limiting precursors in the biosynthesis of various types of biologically active lipids involved in inflammatory processes. Increased levels of human nonpancreatic secretory phospholipase A2 (hnps-PLA2) have been detected in several pathological conditions. An inhibitor of this enzyme could have therapeutic utility. A broad screening program was carried out to identify chemical structures which could inhibit hnps-PLA2. One of the lead compounds generated by the screening program was 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid (13a). We describe the syntheses, structure-activity relationships, and pharmacological activities of a series of indole-3-acetamides and related compounds derived from this lead. This SAR was undertaken with the aid of X- ray crystal structures of complexes between the inhibitors and hnps-PLA2 which were of great value in directing the SAR.