Demethylasterriquinone B1 - CAS 78860-34-1
Category: Inhibitor
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Molecular Formula:
C32H30N2O4
Molecular Weight:
506.59
COA:
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Targets:
IGF-1R
Description:
Demethylasterriquinone B1 is a nonpeptidyl fungal metabolite and has been found to be a selective IR activator.
Purity:
≥98% by HPLC
Appearance:
Black Solid
Synonyms:
2-[2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione
MSDS:
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InChIKey:
XMGNJVXBPZAETK-UHFFFAOYSA-N
InChI:
InChI=1S/C32H30N2O4/c1-6-32(4,5)31-23(20-11-7-8-13-22(20)34-31)25-29(37)27(35)24(28(36)30(25)38)21-16-33-26-18(15-14-17(2)3)10-9-12-19(21)26/h6-14,16,33-35,38H,1,15H2,2-5H3
Canonical SMILES:
CC(=CCC1=CC=CC2=C1NC=C2C3=C(C(=O)C(=C(C3=O)O)C4=C(NC5=CC=CC=C54)C(C)(C)C=C)O)C
1.Effect of demethylasterriquinone b1 in hypertension associated vascular endothelial dysfunction.
Shah DI;Singh M Int J Cardiol. 2007 Sep 3;120(3):317-24. Epub 2007 Jan 22.
BACKGROUND: ;Activation of Akt stimulates phosphorylation of eNOS, production of nitric oxide and reduces oxidative stress. The study has been designed to investigate the effect of DAQ B1, an activator of Akt, in hypertension associated vascular endothelial dysfunction.;METHODS: ;Rats were uninephroctomized and DOCA (40 mg kg(-1), s.c.) was administered to rats to produce hypertension (MABP>140 mm Hg). Vascular endothelial dysfunction was assessed using isolated aortic ring preparation, electron microscopy of thoracic aorta and serum concentration of nitrite/nitrate. The expression of messenger RNA for p22phox and eNOS was assessed by reverse transcription-polymerase chain reaction. Serum TBARS and aortic superoxide anion were estimated to assess oxidative stress.;RESULTS: ;DAQ B1 (5 mg kg(-1), p.o.) or atorvastatin (30 mg kg(-1), p.o.) markedly improved acetylcholine induced endothelium dependent relaxation, vascular endothelial lining, expression of mRNA for eNOS and p22phox, serum nitrite/nitrate concentration and serum TBARS in hypertensive rats. However, this ameliorative effect of DAQ B1 has been prevented by L-NAME (25 mg kg(-1), i.p.), an inhibitor of eNOS.;CONCLUSION: ;Therefore, it may be concluded that DAQ B1 induced activation of Akt may activate eNOS and consequently reduce oxidative stress to improve hypertension associated vascular endothelial dysfunction.
2.Insulin receptor activation inhibits insulin secretion from human islets of Langerhans.
Persaud SJ;Asare-Anane H;Jones PM FEBS Lett. 2002 Jan 16;510(3):225-8.
There is no consensus on the role of insulin secreted from pancreatic beta-cells in regulating its own secretion, either in rodent islets or in human islets. We have now investigated whether there is an autocrine signalling role for insulin in human islets by determining insulin receptor expression and assessing the effects of insulin receptor activation using a non-peptidyl insulin mimetic termed L-783,281. Human insulin receptor mRNA was detected by PCR amplification of human islet cDNA, and translation of the message in human islets was confirmed by Western blotting. Perifusion experiments revealed that both glucose-stimulated and basal insulin secretion were significantly inhibited following human islet insulin receptor activation with L-783,281, and that signalling through phosphatidylinositol 3-kinase (PI 3-kinase) was responsible, at least in part, for this inhibitory effect. These studies indicate that human islets express insulin receptors and that they are functionally coupled to a PI 3-kinase-dependent inhibition of insulin secretion.
3.Total syntheses of demethylasterriquinone B1, an orally active insulin mimetic, and demethylasterriquinone A1.
Pirrung MC;Li Z;Park K;Zhu J J Org Chem. 2002 Nov 15;67(23):7919-26.
Two total syntheses of the unsymmetrical bis-indolylquinone natural product demethylasterriquinone B1 (also known as L-783,281) have been accomplished. The first exploits a known base-promoted condensation of indoles with bromanil, which stops at monoaddition using the sterically hindered 2-isoprenylindole. This permits addition of the second indole, 7-prenylindole, which gives both meta- and para-substituted bis-indolylquinone products. This regiochemical control problem was solved by extension of a method we recently developed for acid-promoted addition of indoles to 2,5-dichlorobenzoquinone. Under our original mineral acid conditions, reaction of 2-isoprenylindole with dichlorobenzoquinone fails, but it succeeds with 3-bromo-2,5-dichlorobenzoquinone using acetic acid as the promoter. The regiochemistry established in such selectively bromine-substituted quinones can be exploited in Stille couplings. As a model system, the synthesis of demethylasterriquinone A1 was accomplished using as the key step a Stille coupling of a 2,5-dibromobenzoquinone with an (N-isoprenylindol-3-yl)tin, producing the para-substituted bis-indolylquinone exclusively. Use of a (7-prenylindole)tin in coupling with a bromo-2,5-dichloro-4-indolylbenzoquinone gives the demethylasterriquinone B1 precursor.
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CAS 78860-34-1 Demethylasterriquinone B1

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