(-)-Indolactam V - CAS 90365-57-4
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
(-)-Indolactam V
Catalog Number:
90365-57-4
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;(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;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*))-;Indolactam V
CAS Number:
90365-57-4
Description:
(-)-Indolactam V is an indole alkaloid compound which activates protein kinase C (PKC), which strongly directs human ES cell-derived definitive endoderm into pancreatic endoderm. It is weak tumor promoter. It binds to PKC regulatory domains of mouse skin PKCη and rat brain PKCγ with Ki values of 3.4 nM and 1 μM, respectively. It induces differentiation of human embryonic stem cells into pancreatic progenitors through activation of PKC signaling at 1 μM. It may be used as an effective diabetes therapy. It may share an RA-dependent signaling pathway, allowing ultimately to streamline the process of efficient pancreatic endoderm derivation. It was predicted to be a biosynthetic intermediate and was confirmed via in vitro prenylation by LtxC due to the structural relatedness of the lyngbyatoxins and teleocidin. It induces differentiation of a substantial number of Pdx1-expressing cells from human ESCs.
Molecular Weight:
301.38
Molecular Formula:
C17H23N3O2
Quantity:
Milligrams-Grams
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC(C)C1C(=O)NC(CC2=CNC3=C2C(=CC=C3)N1C)CO
InChI:
InChI=1S/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
InChIKey:
LUZOFMGZMUZSSK-LRDDRELGSA-N
Targets:
PKC
Chemical Structure
CAS 90365-57-4 (-)-Indolactam V

Related PKC Products


CAS 165800-06-6 Zoledronic acid monohydrate

Zoledronic acid monohydrate
(CAS: 165800-06-6)

Zoledronic acid (zoledronate) is a bisphosphonate bone resorption inhibitor, an inhibitor of farnesyl diphosphate (FPP) synthase which results in downstream inh...

CAS 60857-08-1 Prostratin

Prostratin
(CAS: 60857-08-1)

Prostratin is an activator of protein kinase C (PKC) and also an activator of nuclear factor KB (NF-KB) mediated through activation of the IKKs (IKB kinases). I...

CAS 75567-37-2 Ingenol Mebutate

Ingenol Mebutate
(CAS: 75567-37-2)

Ingenol Mebutate is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death. It is effective for field treatment of actinic kera...

PKC-IN-1
(CAS: 1046787-18-1)

PKC-IN-1 has been found to be a PKCβII inhibitor that probably has biological activity in antineoplastic studies. Ki: 14.9 nM.

CAS 169939-94-0 Ruboxistaurin

Ruboxistaurin
(CAS: 169939-94-0)

Ruboxistaurin, also called as LY 333531, initially developed for the treatment of diabetic retinopathy, inhibits isolated enzymes PKCβI and PKCβII with a half-m...

CAS 30220-46-3 Ingenol

Ingenol
(CAS: 30220-46-3)

Ingenol, the analogue of Ingenol 3-Angelate found in the seeds of Euphorbia lathyris L, is an extremely weak PKC (protein kinase C) activator ( Ki=30 μM, ED50=2...

CAS 125314-64-9 RO31-8220

RO31-8220
(CAS: 125314-64-9)

Ro 31-8220 is a PKC-inhibitor, which inhibits stimulated fluid pinocytosis of human PMNs induced by the PKC-activators phorbol myristate acetate or diacylglycer...

CAS 17673-25-5 Phorbol

Phorbol
(CAS: 17673-25-5)

Phorbol, derived from the roots of Euphorbia pekinensis Rupr., as a tumor promoter it is able to activate protein kinase C.

CAS 87745-28-6 Bryostatin 2

Bryostatin 2
(CAS: 87745-28-6)

Bryostatin 2, an analog of Bryostatin 1, is an activator of PKC (protein kinase C) with anti-tumor properties. Bryostatin 2 inhibits DNA synthesis at 100 nM in ...

CAS 170364-57-5 Enzastaurin

Enzastaurin
(CAS: 170364-57-5)

Enzastaurin HCL is the hydrochloride salt of enzastaurin, a synthetic macrocyclic bisindolemaleimide with potential antineoplastic activity. Binding to the ATP-...

CAS 163751-35-7 rac-3-Hexadecanamido-2-methoxypropan-1-ol Phosphocholine Monohydrate

rac-3-Hexadecanamido-2-methoxypropan-1-o
(CAS: 163751-35-7)

The Pharmacological activity of this molecular is Growth Inhibition of Malignant Cells in vivo and in vitro and cytotoxic properties may result inhibition of pr...

CAS 169939-93-9 Ruboxistaurin Hydrochloride

Ruboxistaurin Hydrochloride
(CAS: 169939-93-9)

Ruboxistaurin, also called as LY 333531, initially developed for the treatment of diabetic retinopathy, inhibits isolated enzymes PKCβI and PKCβII with a half-m...

CAS 138489-18-6 Ro 31-8220 Mesylate

Ro 31-8220 Mesylate
(CAS: 138489-18-6)

Ro 31-8220 inhibits rat brain PKC activity with IC50 of 23 nM, and does not show any high degree of selectivity between PKC-α, PKC-β, PKC-γ, and PKC-ε.

CAS 133053-19-7 Go6983

Go6983
(CAS: 133053-19-7)

GO6983 is a potent protein kinase C (PKC) inhibitor. GO6893 displays cardioprotective properties; reduces polymorphonuclear leukocyte adherence and infiltration...

CAS 62996-74-1 Staurosporine

Staurosporine
(CAS: 62996-74-1)

Staurosporine is broad spectrum protein kinase inhibitor. Enzymes inhibited include protein kinase C (IC50 = 3 nM), protein kinase A (IC50 = 7 nM), p60v-src tyr...

CAS 90365-57-4 (-)-Indolactam V

(-)-Indolactam V
(CAS: 90365-57-4)

(-)-Indolactam V is an indole alkaloid compound which activates protein kinase C (PKC), which strongly directs human ES cell-derived definitive endoderm into pa...

CAS 37558-16-0 Phorbol 12,13-dibutyrate

Phorbol 12,13-dibutyrate
(CAS: 37558-16-0)

Phorbol 12,13-dibutyrate, a protein kinase C activator, stimulates the phosphorylation of Na+,K+- ATPase, thereby inhibiting its activity.

CAS 193620-69-8 TAS-301

TAS-301
(CAS: 193620-69-8)

TAS-301 is a potent and selective constrictive remodeling regulator on renarrowing after balloon overstretch injury of porcine coronary artery. TAS-103 inhibits...

CAS 164658-13-3 CGP60474

CGP60474
(CAS: 164658-13-3)

CGP60474 is a promising inhibitor of PKC with a high degree of selectivity versus other serine/threonine and tyrosine kinases and show competitive kinetics rela...

CAS 425637-18-9 Sotrastaurin

Sotrastaurin
(CAS: 425637-18-9)

Sotrastaurin, also known as AEB-701, is an orally available pan-protein kinase C (PKC) inhibitor with potential immunosuppressive and antineoplastic activities....

Reference Reading


1.Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2.
Nathel NF1, Shah TK1, Bronner SM1, Garg NK1. Chem Sci. 2014 Jun 1;5(6):2184-2190.
We report the total syntheses of (-)-indolactam V and the C7-substituted indolactam alkaloids (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2. The strategy for preparing indolactam V relies on a distortion-controlled indolyne functionalization reaction to establish the C4-N linkage, in addition to an intramolecular conjugate addition to build the conformationally-flexible nine-membered ring. The total synthesis of indolactam V then sets the stage for the divergent synthesis of the other targeted alkaloids. Specifically, late-stage sp2-sp3 cross-couplings on an indolactam V derivative are used to introduce the key C7 substituents and the necessary quaternary carbons. These challenging couplings, in addition to other delicate manipulations, all proceed in the presence of a basic tertiary amine, an unprotected secondary amide, and an unprotected indole. Thus, our approach not only enables the enantiospecific total syntheses of four indolactam alkaloids, but also serves as a platform for probing complexity-generating and chemoselective transformations in the context of alkaloid total synthesis.
2.Synthesis of (-)-epi-indolactam V by an intramolecular Buchwald-Hartwig C-N coupling cyclization reaction.
Mari M1, Bartoccini F, Piersanti G. J Org Chem. 2013 Aug 2;78(15):7727-34. doi: 10.1021/jo4013767. Epub 2013 Jul 25.
The synthetic efforts toward the concise synthesis of (-)-indolactam V from simple and commercially available starting materials using palladium- and copper-catalyzed intramolecular N-arylation strategy for the elaboration of the requisite nine-membered lactam ring as the key step are described. The incorporation of a turn-inducing structural element along the linear precursor was fundamental to achieve the heterocyclization step as well as obtain the correct regio- and chemoselectivity. The stereoselective nature in the C-N coupling cyclization reaction is interpreted in terms of minimization of allylic strain at the transition state for the palladium-amido complex formation. Meanwhile, the synthesis of the (-)-epi-indolactam V and its enantiomer have been accomplished.