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(3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine

(3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine

Catalog No. BCN1481
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20mg $298 In stock
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Quality Control of (3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine

Chemical structure

(3S,7S)-5,6-Dehydro-4

(3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine Dilution Calculator

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(3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine Molarity Calculator

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Chemical Properties of (3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine

Cas No. 227289-51-2 SDF Download SDF
SMILES c1cc(ccc1CC[C@H]2CC=C[C@H](O2)c3ccc(cc3)O)O
Standard InChIKey WNMSDVNIAXMQRI-MOPGFXCFSA-N
Standard InChI InChI=1S/C19H20O3/c20-16-9-4-14(5-10-16)6-13-18-2-1-3-19(22-18)15-7-11-17(21)12-8-15/h1,3-5,7-12,18-21H,2,6,13H2/t18-,19+/m1/s1
Type of Compound Phenols Appearance Powder
Formula C19H20O3 M.Wt 296.4
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of (3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3738 mL 16.8691 mL 33.7382 mL 67.4764 mL 84.3455 mL
5 mM 0.6748 mL 3.3738 mL 6.7476 mL 13.4953 mL 16.8691 mL
10 mM 0.3374 mL 1.6869 mL 3.3738 mL 6.7476 mL 8.4345 mL
50 mM 0.0675 mL 0.3374 mL 0.6748 mL 1.3495 mL 1.6869 mL
100 mM 0.0337 mL 0.1687 mL 0.3374 mL 0.6748 mL 0.8435 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Preparation of (3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine

This product is isolated and purified from the herbs of Alpinia blepharocalyx

References on (3S,7S)-5,6-Dehydro-4''-de-O-methylcentrolobine

Discovery of 2-((R)-4-(2-Fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1R,2s,3S,5S,7S)-5-hydroxyadamantan-2-yl)pyrimidine-4-carboxamide (SKI2852): A Highly Potent, Selective, and Orally Bioavailable Inhibitor of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1).[Pubmed: 27798827]


A series of picolinamide- and pyrimidine-4-carboxamide-based inhibitors of 11β-hydroxysteroid dehydrogenase type 1 was synthesized and evaluated to optimize the lead compound 9. The combination of the replacement of a pyridine ring of 9 with a pyrimidine ring and the introduction of an additional fluorine substituent at the 2-position of the phenyl ring resulted in the discovery of a potent, selective, and orally bioavailable inhibitor, 18a (SKI2852), which demonstrated no CYP and PXR liabilities, excellent PK profiles across species, and highly potent and sustainable PD activity. Repeated oral administration of 18a significantly reduced blood glucose and HbA1c levels and improved the lipid profiles in ob/ob mice. Moreover, the HbA1c-lowering effect of metformin was synergistically enhanced in combination with 18a.

Cy7-(3S,7S)-26-Amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid.[Pubmed: 23586109]


Optical fluorescence imaging is increasingly used to monitor biological functions of specific targets in small animals (1-4). However, the intrinsic fluorescence of biomolecules poses a problem when fluorophores that absorb visible light (350–650 nm) are used. Near-infrared (NIR) fluorescence (650–1,000 nm) detection avoids the natural background fluorescence interference of biomolecules, providing a high contrast between target and background tissues in small animals. NIR fluorophores have a wider dynamic range and minimal background fluorescence as a result of reduced scattering compared with visible fluorescence detection. NIR fluorophores also have high sensitivity, attributable to low background fluorescence, and high extinction coefficients, which provide high quantum yields. The NIR region is also compatible with solid-state optical components, such as diode lasers and silicon detectors. NIR fluorescence imaging is a noninvasive alternative to radionuclide imaging in small animals (4, 5). Prostate-specific membrane antigen (PSMA) is a cell-surface glycoprotein with a molecular weight of ~100 kDa. It is a unique, type II, transmembrane-bound glycoprotein that is overexpressed on prostate tumor cells and in the neovasculature of most solid prostate tumors, but not in the vasculature of normal tissues (6, 7). PSMA has also been detected in other tissues such as the kidneys, the proximal small intestine, and the salivary glands (7). PSMA was found to have N-acetyl α-linked acidic dipeptidase (NAALADase) or glutamate carboxypeptidase II activity (8). PSMA may play an important role in the progression of prostate cancer and glutamatergic neurotransmission, as well as in the absorption of folate (9). In the central nervous system, PSMA metabolizes N-acetyl-aspartyl-glutamate, and in the proximal small intestine it removes γ-linked glutamates from poly-γ-glutamate folate and folate hydrolase (7). PSMA can be used as a marker for the detection of metastatic cancers with imaging agents. Although a commercially available monoclonal antibody (111In-labeled Capromomab pendetide (111In-CYT-356)) is in clinical use for the detection of prostate cancer, the results obtained with this antibody are not entirely reliable (10). In addition, this IgG antibody has limited access to tumors and also may produce low signal/noise ratios because the target is the intracellular domain of PSMA (11, 12). IRDye800CW-(3S,7S)-26-Amino-5,13,20-trioxo-4,6,12,21-tetraazahexacosane-1,3,7,22-tetracarboxylic acid (YC-27, also known as 800CW-3) is a small molecule inhibitor of NAALADase (13). YC-27 was able to visualize PSMA-positive tumors in nude mice, but accumulation of signal was high in the kidney. Chen et al. (14) evaluated a series of dye-3 conjugates with Cy5.5, IGC, IRDye800RS, and Cy7 in nude mice bearing human PSMA-positive xenografts. Injected Cy7-3 exhibited good tumor accumulation with lower liver and kidney accumulation than YC-27.

rac-(2R*,3S*,5S*,6R*,7S*,8S*)-7,8-Dichloro-bicyclo-[2.2.2]octane-2,3,5,6-tetrayl tetra-acetate.[Pubmed: 21582188]


The title compound, C(16)H(20)Cl(2)O(8), contains a central bicyclo-[2.2.2]octane skeleton with slightly twisted conformation. In this structure, the C-C bond lengths are in the range 1.525 (2)-1.552 (2) Å. Two sides of this skeleton have cis,cis acet-oxy substituents and the Cl atoms have a trans arrangement. An extensive network of weak C-H⋯O interactions stabilizes the crystal structure.

(3S,3aS,5aS,7S,8S,10aS,10bR)-7,8-Dihydr-oxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-deca-hydro-cyclo-hepta-[e]indene-3a(1H)-carboxylic acid.[Pubmed: 21202969]


The mol-ecule of the title compound, C(20)H(32)O(4), is built up from three fused five-membered, six-membered and seven-membered rings. The five-membered ring has an envelope conformation, whereas the six- and seven-membered rings have chair conformations. The crystal structure is stabilized by strong inter-molecular O-H⋯O hydrogen bonds, forming a three-dimensional network. The absolute configuration was assigned on the basis of earlier chemical studies.

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