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

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

Uses

Used in Pharmaceutical Industry:
(-)-7-OCTYLINDOLACTAM V is used as a therapeutic agent for the treatment of cancer and other diseases associated with abnormal PKC activity. Its ability to activate protein kinase C makes it a promising candidate for targeting various cellular functions and potentially inhibiting tumor growth and progression.
Used in Neuroscience Research:
(-)-7-OCTYLINDOLACTAM V is used as a research tool for studying the role of protein kinase C in regulating intracellular calcium levels and neurotransmitter release in the central nervous system. This can help scientists better understand the underlying mechanisms of various neurological disorders and develop targeted therapies for their treatment.

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

• 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 
• 214267-85-3 (-)-7-n-octyl-14-O-TBDMS-indolactam-V 
• 84590-48-7 indolactam V 
• 112775-88-9 (-)-14-O-TBDMS-indolactam-V 
• 214267-83-1 (-)-7-bromo-14-O-TBDMS-indolactam-V 
• 214267-84-2 (-)-7-(trans-1-octenyl)-14-O-TBDMS-indolactam-V 
• 38841-98-4 n-octylmagnesium chloride 
• 91403-61-1 (-)-14-O-acetyl indolactam V 
• 4769-97-5 4-nitro-1H-indoIe 
• 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 

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.

Protein Kinase C Modulators. Indolactams. 2. Alkylation of 4-Nitroindole by Grignard Reagents. Synthesis of (-)-7-Octylindolactam V

A method for the C-alkylation of 4-nitroindole at the 5 and 7 positions by alkyl Grignard reagents has been developed.The 4-nitro-7-octylindole thus prepared has been used as a starting material for the synthesis of the lyngbyatoxin analog, (-)-7-octylindolactam V.