109346-66-9

Basic information

• Product Name: (-)-7-OCTYLINDOLACTAM V
• Synonyms: (-)-Octylindolactam V;(2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-9-octyl-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one;n-Octylindolactam V;(-)-7-OCTYLINDOLACTAM V
• CAS NO: 109346-66-9
• Molecular Formula: C25H39N3O2
• Molecular Weight: 413.6
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 109346-66-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 649.4°Cat760mmHg
• Flash Point: 346.6°C
• Appearance: /
• Density: 1.059g/cm³
• Vapor Pressure: 9.41E-18mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: −20°C
• CAS DataBase Reference: (-)-7-OCTYLINDOLACTAM V(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-7-OCTYLINDOLACTAM V(109346-66-9)
• EPA Substance Registry System: (-)-7-OCTYLINDOLACTAM V(109346-66-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 109346-66-9(Hazardous Substances Data)

Usage

General Description

(-)-7-Octylindolactam V is a chemical compound that belongs to the class of indolactam alkaloids. It is a potent and specific activator of protein kinase C (PKC), which is an important enzyme involved in various cellular functions such as cell growth, differentiation, and apoptosis. (-)-7-OCTYLINDOLACTAM V has been studied for its potential therapeutic applications in the treatment of cancer and other diseases associated with abnormal PKC activity. Additionally, (-)-7-Octylindolactam V has been investigated for its role in regulating intracellular calcium levels and neurotransmitter release in the central nervous system. Overall, this chemical compound exhibits promising pharmacological properties and has the potential for further development as a therapeutic agent.

InChI:InChI=1/C25H39N3O2/c1-5-6-7-8-9-10-11-18-12-13-21-22-19(15-26-23(18)22)14-20(16-29)27-25(30)24(17(2)3)28(21)4/h12-13,15,17,20,24,26,29H,5-11,14,16H2,1-4H3,(H,27,30)/t20-,24-/m0/s1

Upstream product

• 4769-97-5 4-nitro-1H-indoIe 
• 214267-84-2 (-)-7-(trans-1-octenyl)-14-O-TBDMS-indolactam-V 
• 214267-83-1 (-)-7-bromo-14-O-TBDMS-indolactam-V 
• 112775-88-9 (-)-14-O-TBDMS-indolactam-V 
• 84590-48-7 indolactam V 
• 214267-85-3 (-)-7-n-octyl-14-O-TBDMS-indolactam-V 
• 160169-46-0 (10S,13S)-10-Isopropyl-9-methyl-5-octyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraene-13-carboxylic acid ethyl ester 
• 91403-61-1 (-)-14-O-acetyl indolactam V 
• 160096-23-1 (S)-2-[(3-{2-Ethoxycarbonyl-2-[(Z)-hydroxyimino]-ethyl}-7-octyl-1H-indol-4-yl)-methyl-amino]-3-methyl-butyric acid benzyl ester 
• 160096-22-0 (S)-3-Methyl-2-[methyl-(7-octyl-1H-indol-4-yl)-amino]-butyric acid benzyl ester 
• 160096-20-8 N-(7-Octyl-1H-indol-4-yl)-formamide 
• 160096-16-2 4-nitro-7-octylindole 
• 160096-21-9 Methyl-(7-octyl-1H-indol-4-yl)-amine 
• 160096-19-5 4-amino-7-octylindole 

Relevant articles and documents

Synthesis and biological activities of (-)-6-n-octyl-indolactam-V, a new potent analogue of the tumor promoter (-)-indolactam-V.

(-)-Indolactam-V (1) without a hydrophobic chain at positions 6 and 7 of the indole ring is a weak tumor promoter compared with teleocidin Bs. To investigate the effects of the hydrophobic substituent at position 6 of teleocidin Bs, we synthesized (-)-6-n-octyl-indolactam-V (2) by a palladium-catalyzed coupling reaction from (-)-6-bromo-indolactam-V (7) which had been obtained by microbial conversion with Streptoverticillium blastmyceticum NA34-17 as the key step. (-)-7-n-Octyl-indolactam-V (3) with potent biological activities comparable to those of teleocidin Bs was similarly synthesized from (-)-7-bromo-indolactam-V as a positive control. Compound 2 showed similar biological activities to those of 3, indicating that the effect of the hydrophobic substituent at position 6 of 1 was identical to that at position 7.

Substitution Reaction on the Indole Ring of (-)-Indolactam V, the Fundamental Structure of Teleocidins

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