91403-61-1

Basic information

• Product Name: [(2S,5S)-1-methyl-3-oxo-2-(propan-2-yl)-2,3,4,5,6,8-hexahydro-1H-[1,4]diazonino[7,6,5-cd]indol-5-yl]methyl acetate
• Synonyms: 14-O-Acetylindolactam V;3H-Pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one, 5-[(acetyloxy)methyl]-1,2,4,5,6,8-hexahydro-1-methyl-2-(1-methylethyl)-, (2S,5S)-
• CAS NO: 91403-61-1
• Molecular Formula: C₁₉H₂₅N₃O₃
• Molecular Weight: 343.4201
• Mol File: 91403-61-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 573.9°C at 760 mmHg
• Flash Point: 300.9°C
• Density: 1.154g/cm³
• Vapor Pressure: 3.53E-13mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: [(2S,5S)-1-methyl-3-oxo-2-(propan-2-yl)-2,3,4,5,6,8-hexahydro-1H-[1,4]diazonino[7,6,5-cd]indol-5-yl]methyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,5S)-1-methyl-3-oxo-2-(propan-2-yl)-2,3,4,5,6,8-hexahydro-1H-[1,4]diazonino[7,6,5-cd]indol-5-yl]methyl acetate(91403-61-1)
• EPA Substance Registry System: [(2S,5S)-1-methyl-3-oxo-2-(propan-2-yl)-2,3,4,5,6,8-hexahydro-1H-[1,4]diazonino[7,6,5-cd]indol-5-yl]methyl acetate(91403-61-1)

Safety Data

• Hazardous Substances Data: 91403-61-1(Hazardous Substances Data)

Upstream product

• 84590-48-7 indolactam V 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 84590-42-1 (R)-2-[3-((R)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 84590-40-9 (R)-2-[3-((R)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid methyl ester 
• 110595-78-3 (R)-2-[3-((R)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 
• 84590-33-0 N-Boc-4-nitrotryptophanol 
• 84590-47-6 desmethylindolactam-V 
• 84590-34-1 (+/-)-N-Boc-4-aminotryptophanol 
• 84590-32-9 N-Boc-4-nitrotryptophan ethyl ester 
• 84590-31-8 N-acetyl-4-nitrotryptophan ethyl ester 
• 84590-30-7 DL-4-nitrotryptophan ethyl ester 
• 3227-19-8 acetylamino-(4-nitro-indol-3-ylmethyl)-malonic acid diethyl ester 
• 3633-96-3 acetylamino-(4-nitro-indol-3-ylmethyl)-malonic acid 

Downstream Products

• 121706-11-4 (-)-n-Hexyl indolactam V 
• 99414-59-2 1-methylindolactam-V 
• 95676-82-7 (10R,13R)-10-Isopropyl-13-methoxymethyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one 
• 96304-70-0 1-geranylindolactam-V 
• 96304-69-7 1-prenylindolactam-V 
• 109346-66-9 (-)-7-octylindolactam V 

Relevant articles and documents

Design and physicochemical properties of new fluorescent ligands of protein kinase C isozymes focused on CH/π interaction

Phorbol ester-type tumor promoters such as indolactam-V (IL-V, 1) bind to the C1 domains of protein kinase C (PKC) isozymes. A more convenient method to investigate the interaction between each tumor promoter and PKC C1 domain is needed. Focusing on our recent finding that the indole ring of IL-V is involved in the CH/π interaction with Pro-11 of the PKCδ-C1B domain, we developed new fluorescent probes (2-4) from IL-V by forming a pyrroloindazole ring. Compound 2 without a substituent at the pyrroloindazole ring bound most strongly to PKC C1 domains with a potency similar to IL-V, but its fluorescent intensity was the weakest of any of the probes. Although the binding affinity of 3 with a methyl group was significantly weaker than that of IL-V, 4 with a trifluoromethyl group showed moderate affinity and the most potent fluorescence intensity. The fluorescence intensity and emission maxima of 4 changed significantly when bound to the PKCδ-C1B peptide in both the presence and absence of phosphatidylserine. These results suggest that 4 could be a useful probe for analyzing the interaction of tumor promoters with PKC C1 domains.

Synthesis, conformation and PKC isozyme surrogate binding of indolinelactam-Vs, new conformationally restricted analogues of (-)-indolactam-V

New conformationally restricted analogues of tumor promoter (-)-indolactam-V (1), indolinelactam-Vs (8, 11) and their hexyl derivatives at position 1 or 7 (9, 10, 12, 13), were synthesized from 1. (3R)-Indolinelactam-V (8) adopted a conformation similar to the twist form of 1 with a cis amide, while the conformation of (3S)-indolinelactam-V (11) was close to that of the sofa form of 1 with a trans amide. 7-Hexyl derivatives of 8 and 11 (10, 13) showed binding affinities for C1 domains of protein kinase C (PKC) isozymes compared to 1, but exhibited little selectivity among these PKC isozymes. However, introduction of the hexyl group at position 1 of 8 and 11 significantly enhanced their binding selectivity for novel PKC isozymes. The best selectivity for novel PKC isozymes was observed in (3S)-1-hexylindolinelactam-V (12) with a sofa-like conformation. These results suggest that a sofa-restricted analogue of 1 with a hydrophobic chain at an appropriate position would be a promising lead for designing agents with a high selectivity for novel PKC isozymes.

Synthesis and Stereochemistry of Indolactam-V, An Active Fragment of Teleocidins. Structural Requirements for Tumor-Promoting Activity.

(-)-Indolactam-V, which is an active fragment of the potent tumor promoters teleocidins and has also been isolated as a Streptoverticillium metabolite, has been synthesized starting from 4-nitrogramine.The absolute stereochemistry of (-)-indolactam-V has been determined to be (9S, 12S), which suggests that teleocidins and related compounds are biosinthesyzed from L-amino acids.Three unnatural diastereoisomers were also synthesized.The NMR spectra of (-)- and (+/-)-indolactam-V and its derivatives showed that they exist in two conformational states in solution.The structures of the two conformers were deduced from the chemical shifts, coupling constants and nuclear Overhauser effects to be SOFA and TWIST from which are characterized by trans and cis amide bonds, respectively.The calculated ratio of the two conformers was consistent with the observed ratio.