chroman 1

ROCK II inhibitor, highly potent and selective CAS# 1273579-40-0

chroman 1

Catalog No. BCC1480----Order now to get a substantial discount!

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Chemical structure

chroman 1

3D structure

Chemical Properties of chroman 1

Cas No. 1273579-40-0 SDF Download SDF
PubChem ID 66577033 Appearance Powder
Formula C24H28N4O4 M.Wt 436.5
Type of Compound N/A Storage Desiccate at -20°C
Synonyms ROCK-II inhibitor
Solubility DMSO : ≥ 50 mg/mL (114.55 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name (3S)-N-[2-[2-(dimethylamino)ethoxy]-4-(1H-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2H-chromene-3-carboxamide
SMILES CN(C)CCOC1=C(C=CC(=C1)C2=CNN=C2)NC(=O)C3CC4=C(C=CC(=C4)OC)OC3
Standard InChIKey ROFMCPHQNWGXGE-SFHVURJKSA-N
Standard InChI InChI=1S/C24H28N4O4/c1-28(2)8-9-31-23-12-16(19-13-25-26-14-19)4-6-21(23)27-24(29)18-10-17-11-20(30-3)5-7-22(17)32-15-18/h4-7,11-14,18H,8-10,15H2,1-3H3,(H,25,26)(H,27,29)/t18-/m0/s1
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.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of chroman 1

DescriptionChroman 1 is a highly potent ROCK2 inhibitor, with an IC50 of < 1 nM.In Vitro:Chroman 1 is a highly potent ROCK2 inhibitor, with an IC50 of < 1 nM. Chroman 1 also shows inhibitory activities against MRCK, with an IC50 of 150 nM, but has no effect on PKA (IC50, > 20000 nM) or AKT1 (IC50, > 20000 nM)[1].

References:
[1]. Yen Ting Chen, et al. Asymmetric synthesis of potent chroman-based Rho kinase (ROCK-II) inhibitors. Med.Chem.Commun., 2011, 2, 73-75.

Protocol

Kinase Assay [1]
Assays are performed using the HTRF KinEASE STK S2 kit. A 5 μL mixture of 1 μM STK2 substrate and 20 μM ATP in STK-buffer is added to the wells. Inhibitor (including Chroman 1, 20 nL) at various concentrations is then dispensed. Reaction is started by addition of 0.5 nM ROCK-II in STK-buffer (5 μL). After 4 h at room temperture (rt), the reaction is stopped by addition of 10 μL mixture of 1× STK antibody-Cryptate in detection buffer and 62.5 nM Sa-XL in detection buffer. After 1 h at rt, the plates are read on the Viewlux in HTRF mode[1].

References:
[1]. Yen Ting Chen, et al. Asymmetric synthesis of potent chroman-based Rho kinase (ROCK-II) inhibitors. Med.Chem.Commun., 2011, 2, 73-75.

chroman 1 Dilution Calculator

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Preparing Stock Solutions of chroman 1

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.291 mL 11.4548 mL 22.9095 mL 45.819 mL 57.2738 mL
5 mM 0.4582 mL 2.291 mL 4.5819 mL 9.1638 mL 11.4548 mL
10 mM 0.2291 mL 1.1455 mL 2.291 mL 4.5819 mL 5.7274 mL
50 mM 0.0458 mL 0.2291 mL 0.4582 mL 0.9164 mL 1.1455 mL
100 mM 0.0229 mL 0.1145 mL 0.2291 mL 0.4582 mL 0.5727 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.

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Background on chroman 1

IC50: <1 nM for ROCK-II

Chroman 1 is a highly potent ROCK-II inhibitor. ROCK is a member of the AGC kinase family of serine/threonine kinases that is comprised of two highly homologous isoforms, which are ROCK-I and ROCK-II.. As one of the downstream effectors of RhoA, ROCK regulates stress fiber formation and actin cytoskeletal organization via phosphorylation of myosin light chain. Currently, there is plenty of interest in the inhibition of Rho kinase (ROCK) to treat various diseases.

In vitro: Chroman 1 was found to be a sub-nanomolar ROCK-II inhibitor with excellent to moderate selectivity over related kinases studied as a preliminary assessment, such as AKT1, protein kinase A (PKA), and the highly homologous Cdc42-binding kinase. In addition, Chroman 1 also showed good in-vitro activity in the functional cell-based myosin light chain bis-phosphorylation assay [1].

In vivo: Pharmacokinetic evaluation in rats showed that Chroman 1 had moderately improved oral bioavailability (27–35%) relative to its lead compounds, which were benzodioxane and chroman. In addition, Chroman 1 also displayed an unique intriguing pharmacokinetic profile, which was with high systemic exposure through oral delivery [1].

Clinical trial: So far, there is no clinical study reported.

References:
[1] Chen YT,Bannister TD,Weiser A,Griffin E,Lin L,Ruiz C,Cameron MD,Schürer S,Duckett D,Schrter T,LoGrasso P,Feng Y.  Chroman-3-amides as potent Rho kinase inhibitors. Bioorg Med Chem Lett.2008 Dec 15;18(24):6406-9.

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References on chroman 1

Chroman-4-One Derivatives Targeting Pteridine Reductase 1 and Showing Anti-Parasitic Activity.[Pubmed:28282886]

Molecules. 2017 Mar 8;22(3). pii: molecules22030426.

Flavonoids have previously been identified as antiparasitic agents and pteridine reductase 1 (PTR1) inhibitors. Herein, we focus our attention on the chroman-4-one scaffold. Three chroman-4-one analogues (1-3) of previously published chromen-4-one derivatives were synthesized and biologically evaluated against parasitic enzymes (Trypanosoma brucei PTR1-TbPTR1 and Leishmania major-LmPTR1) and parasites (Trypanosoma brucei and Leishmania infantum). A crystal structure of TbPTR1 in complex with compound 1 and the first crystal structures of LmPTR1-flavanone complexes (compounds 1 and 3) were solved. The inhibitory activity of the chroman-4-one and chromen-4-one derivatives was explained by comparison of observed and predicted binding modes of the compounds. Compound 1 showed activity both against the targeted enzymes and the parasites with a selectivity index greater than 7 and a low toxicity. Our results provide a basis for further scaffold optimization and structure-based drug design aimed at the identification of potent anti-trypanosomatidic compounds targeting multiple PTR1 variants.

Crystal structure of 1'-ethyl-spiro[chroman-4,4'-imidazolidine]-2',5'-dione: a hydantoine derivative.[Pubmed:26594433]

Acta Crystallogr E Crystallogr Commun. 2015 Sep 12;71(Pt 10):o705-6.

The title compound, C13H13N2O3, a hydantoin derivative, crystallized with two mol-ecules (A and B) in an asymmetric unit. In mol-ecule A, the imidazolidine ring is twisted about the C-N bond involving the spiro C atom, while in mol-ecule B this ring is flat (r.m.s. deviation = 0.010 A). The pyran rings in both mol-ecules have distorted half-chair conformations. The mean plane of the imidazolidine ring is inclined to the aromatic ring of the chroman unit by 79.71 (11) degrees in mol-ecule A and 82.83 (12) degrees in mol-ecule B. In the crystal, pairs of N-Hcdots, three dots, centeredO hydrogen bonds link the individual mol-ecules to form A-A and B-B inversion dimers. The dimers are linked via N-Hcdots, three dots, centeredO and C-Hcdots, three dots, centeredO hydrogen bonds, forming sheets lying parallel to the bc plane, viz. (011). Within the sheets, the A and B mol-ecules are linked by C-Hcdots, three dots, centeredpi inter-actions.

Crystal structure determination as part of an undergraduate laboratory experiment: 1',3',3'-tri-methyl-spiro-[chromene-2,2'-indoline] and 1',3',3'-trimethyl-4-[(E)-(1,3,3-tri-methyl-indolin-2-yl-idene)meth-yl]spiro-[chr oman-2,2'-indoline].[Pubmed:27840731]

Acta Crystallogr E Crystallogr Commun. 2016 Oct 28;72(Pt 11):1659-1662.

The crystal structures of the title compounds, C19H19NO and C31H34N2O, were determined as part of an experiment in an undergraduate teaching laboratory that demonstrates the relationship between mol-ecular structure and function. 1',3',3'-Tri-methyl-spiro-[chromene-2,2'-indoline] is both a photoswitch and thermochromic mol-ecule. Students synthesized it and a bis-indoline adduct and compared the crystallographically determined structures to computed gas-phase models.

Discovery of (R)-1-(7-chloro-2,2-bis(fluoromethyl)chroman-4-yl)-3-(3-methylisoquinolin-5-yl)ur ea (A-1165442): a temperature-neutral transient receptor potential vanilloid-1 (TRPV1) antagonist with analgesic efficacy.[Pubmed:25100568]

J Med Chem. 2014 Sep 11;57(17):7412-24.

The synthesis and characterization of a series of selective, orally bioavailable 1-(chroman-4-yl)urea TRPV1 antagonists is described. Whereas first-generation antagonists that inhibit all modes of TRPV1 activation can elicit hyperthermia, the compounds disclosed herein do not elevate core body temperature in preclinical models and only partially block acid activation of TRPV1. Advancing the SAR of this series led to the eventual identification of (R)-1-(7-chloro-2,2-bis(fluoromethyl)chroman-4-yl)-3-(3-methylisoquinolin-5-yl)ur ea (A-1165442, 52), an analogue that possesses excellent pharmacological selectivity, has a favorable pharmacokinetic profile, and demonstrates good efficacy against osteoarthritis pain in rodents.

Description

Chroman 1 is a highly potent ROCK2 inhibitor, with an IC50 of 1 nM.

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