90365-57-4

Basic information

• Product Name: (-)-INDOLACTAM V
• Synonyms: (2s-(2r*,5r*))-ethyl)-1-methyl-2-(1-methylethyl);3h-pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one,1,2,4,5,6,8-hexahydro-5-(hydroxym;(-)-INDOLACTAM V;(2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one;(-)-Ilv;3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-, (2S-(2R*,5R*))-;3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-, (2S,5S)-;Brn 4711877
• CAS NO: 90365-57-4
• Molecular Formula: C₁₇H₂₃N₃O₂
• Molecular Weight: 301.38
• Mol File: 90365-57-4.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 584 °C at 760 mmHg
• Flash Point: 307 °C
• Appearance: White to off-white solid.
• Density: 1.166 g/cm³
• Vapor Pressure: 1.75E-14mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: −20°C
• Solubility: DMSO: >10mg/mL, clear
• PKA: 14.39±0.10(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: (-)-INDOLACTAM V(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-INDOLACTAM V(90365-57-4)
• EPA Substance Registry System: (-)-INDOLACTAM V(90365-57-4)

Safety Data

• WGK Germany: 3
• RTECS: UY8547000
• Hazardous Substances Data: 90365-57-4(Hazardous Substances Data)

Usage

Description

Indolactam V (-) (90365-57-4) is a PKC activator acting at the phorbol ester binding site.1,2?Directs differentiation of human and mouse ESCs to pancreatic cells.3?? May be used, along with other agents, to differentiate human iPS cells into glucose-responsive insulin-secreting progeny.4?Increases regulator of G protein signaling 2 (RGS2) protein levels, a protein that regulates GPCR signaling.5

Uses

(-)-Indolactam V is an indole alkaloid compound which activates protein kinase C (PKC). Weak tumor promoter. Also directs differentiation of human embryonic stem cells, potentially into pancreatic lineage allowing for an effective diabetes therapy.

Biological Activity

Protein kinase C activator. Exhibits tumor promoting activity. Directs differentiation of human embryonic stem cells (ESCs) into pancreatic progenitors.

Biochem/physiol Actions

(-)-Indolactam V is a PKC activator shown to effect differentiation in embryonic stem cells leading to development of pancreatic precursors. It is active in the mouse model.

References

1) Fujiki?et al.?(1984),?Structure-activity studies on synthetic analogues (indolactams) of the tumor promoter teleocidin; Gan., 75?866 2) Heikkila and Ackerman (1989),?(-)-Indolactam V activates protein kinase C and induces changes in muscarinic receptor functions in SH-SY5Y human neuroblastoma cells; Biochem. Biophys. Res. Commun,?162?1207 3) Chen?et al.?(2009),?A small molecule that directs differentiation of human ESCs into the pancreatic lineage; Nat. Chem. Biol.,?5?258 4) Thalava?et al. (2011),?Indolactam V/GLP-1-mediated differentiation of human iPS cells into glucose-responsive insulin-secretin progeny; Gene Ther.,?18?283 5) Raveh (2014),?Identification of protein kinase C activation as a novel mechanism for RGS2 protein upregulation through phenotypic screening of natural product extracts; Mol. Pharmacol.,?86?406

InChI:InChI=1/C17H23N3O2/c1-10(2)16-17(22)19-12(9-21)7-11-8-18-13-5-4-6-14(15(11)13)20(16)3/h4-6,8,10,12,16,18,21H,7,9H2,1-3H3,(H,19,22)/t12-,16-/m0/s1

Upstream product

• 72-18-4 L-valine 
• 73-22-3 L-Tryptophan 
• 90365-52-9 des-methyl-(-)-indolactam V 
• 74-88-4 methyl iodide 
• 590-86-3 isovaleraldehyde 
• 131423-65-9 (S)-2-[3-((S)-2-Amino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 
• 61535-47-5 benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate 
• 131442-94-9 (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 102141-01-5 N-methyl-L-valyl-L-tryptophanol 
• 84590-47-6 (S)-13-Hydroxymethyl-10-isopropyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one 
• 84590-47-6 (+)-N¹³-desmethylindolactam-V 
• 117951-79-8 7,8-didehydro-8-norindolactam V 
• 117951-78-7 1,3,4,5,6,7-hexahydro-7-hydroxy-4-hydroxymethyl-7-isopropyl-6-oxopyrrolo<4,3,2-fg><3>benzazocine 

Downstream Products

• 107783-16-4 blastmycetin A 
• 119375-01-8 (-)-pendolmycin 
• 128805-95-8 (-)-2-Prenylindolactam V 
• 128805-96-9 (-)-5-prenyl-indolactam V 
• 112797-15-6 7-(3',3'-dimethylallyl)-indolactam-V 
• 97306-43-9 (-)-14-O-hexyl indolactam V 
• 70497-14-2 Lyngbyatoxin A 

Relevant articles and documents

Exploiting a C–N Bond Forming Cytochrome P450 Monooxygenase for C–S Bond Formation

C–S bond formation reactions are widely distributed in the biosynthesis of biologically active molecules, and thus have received much attention over the past decades. Herein, we report intramolecular C–S bond formation by a P450 monooxygenase, TleB, which normally catalyzes a C?N bond formation in teleocidin biosynthesis. Based on the proposed reaction mechanism of TleB, a thiol-substituted substrate analogue was synthesized and tested in the enzyme reaction, which afforded the unprecedented sulfur-containing thio-indolactam V, in addition to an unusual indole-fused 6/5/8-tricyclic product whose structure was determined by the crystalline sponge method. Interestingly, conformational analysis revealed that the SOFA conformation is stable in thio-indolactam V, in sharp contrast to the major TWIST form in indolactam V, resulting in differences in their biological activities.

The Synthesis and Biological Evaluation of Indolactam Alkaloids

In this work, we execute a general synthetic strategy to access novel indolactam alkaloids, which are agonists of protein kinase C. This protocol allowed for the most efficient reported syntheses of indolactam V (ILV) stereoisomers, while also affording t

Modular Total Synthesis of Protein Kinase C Activator (-)-Indolactam v

A concise, eight-step total synthesis of (-)-indolactam V, a nanomolar agonist of protein kinase C, is reported. The synthesis relies upon an efficient copper-catalyzed amino acid arylation to establish the indole C4-nitrogen bond. This cross-coupling met