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[ CAS No. 2550-36-9 ] {[proInfo.proName]}

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Chemical Structure| 2550-36-9
Chemical Structure| 2550-36-9
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Product Citations

Product Citations      Expand+

Henderson, Ian M. ; Zeng, Fanxun ; Bhuiyan, Nazmul H. , et al. DOI: PubMed ID:

Abstract: Interest in development of potent, selective inhibitors of the phosphatase from the receptor type protein tyrosine phosphatase PTPRD as antiaddiction agents is supported by human genetics, mouse models and studies of our lead compound PTPRD phosphatase inhibitor, 7-butoxy illudalic acid analog 1 (7-BIA). We now report structure-activity relationships for almost 70 7-BIA-related compounds and results that nominate a 7- cyclopentyl methoxy analog as a candidate for further development. While efforts to design 7-BIA analogs with substitutions for other parts failed to yield potent inhibitors of PTPRDs phosphatase, ten 7-position substituted analogs displayed greater potency at PTPRD than 7-BIA. Several were more selective for PTPRD vs the receptor type protein tyrosine phosphatases S, F and J or the nonreceptor type protein tyrosine phosphatase N1 (PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B), phosphatases at which 7-BIA displays activity. In silico studies aided design of novel analogs. A 7-position cyclopentyl methoxy substituted 7-BIA analog termed NHB1109 displayed 600-700 nM potencies in inhibiting PTPRD and PTPRS, improved selectivity vs PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B phosphatases, no substantial potency at other protein tyrosine phosphatases screened, no significant potency at any of the targets of clin.-useful drugs identified in EUROFINS screens and significant oral bioavailability. Oral doses up to 200 mg/kg were well tolerated by mice, though higher doses resulted in reduced weight and apparent ileus without clear organ histopathol. NHB1109 provides a good candidate to advance to in vivo studies in addiction paradigms and toward human use to reduce reward from addictive substances.

Keywords: Receptor type protein tyrosine phosphatase ; Cell adhesion molecule ; Addiction ; Drug reward ; Opiates ; Stimulants

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Janssens, Liesl K ; Ametovski, Adam ; Sparkes, Eric , et al. DOI: PubMed ID:

Abstract: Over 200 synthetic cannabinoid receptor agonists (SCRAs) have been identified as newpsychoactive substances. EffectivemonitoringandcharacterizationofSCRAsarehindered by the rapid pace of structural evolution. Ahead of possible appearanceontheillicitdrugmarket,newSCRAsweresynthesized tocompletea systematic libraryof cumyl-indole-(e.g.,CUMYL CPrMICA,CUMYL-CPMICA)andcumyl-indazole-carboxamides (e.g.,CUMYL-CPrMINACA,CUMYL-CPMINACA), encompass ing butyl, pentyl, cyclopropylmethyl, cyclobutylmethyl, cyclo pentylmethyl, andcyclohexylmethyl tails.Comprehensivepharma cologicalcharacterizationwasperformedwiththreeassayformats, monitoring the recruitment of either wild-type or C-terminally truncated(βarr2d366)β-arrestin2totheactivatedcannabinoid1 receptor(CB1)ormonitoringGβγ-mediatedmembranehyperpolarization.Alteredcompoundcharacterizationwasobservedwhen comparingderivedpotency(EC50)andefficacy(Emax)values frombothassaysmonitoringthesameoradifferentsignalingevent, whereasrangesandrankingordersweresimilar.Structure?activityrelationships(SAR)wereassessedinthreefold, resultinginthe identificationof thependant tailasacriticalpharmacophore,withtheoptimalchainlengthforCB1activationapproximatingann pentyl (e.g., cyclopentylmethyl or cyclohexylmethyl tail). The activityof the SCRAs encompassing cyclic tails decreasedwith decreasingnumberofcarbonsformingthecyclicmoiety,withCUMYL-CPrMICAshowingtheleastCB1activityinallassayformats. The SARs were rationalized viamolecular docking, demonstrating the importance of the optimal steric contributionof the hydrophobictail.WhileSARconclusionsremainedlargelyunchanged, thedifferential compoundcharacterizationbybothsimilar anddifferentassaydesignsemphasizestheimportanceofdetailingspecificassaycharacteristicstoallowadequateinterpretationof potenciesandefficacies.

Keywords: structure?activity relationship ; functional assays ; membrane potential ; βarrestin2 recruitment ; new psychoactive substances ; molecular docking

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Product Details of [ 2550-36-9 ]

CAS No. :2550-36-9 MDL No. :MFCD00001509
Formula : C7H13Br Boiling Point : No data available
Linear Structure Formula :- InChI Key :UUWSLBWDFJMSFP-UHFFFAOYSA-N
M.W : 177.08 Pubchem ID :137636
Synonyms :

Calculated chemistry of [ 2550-36-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.52
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 3.36
Log Po/w (WLOGP) : 2.96
Log Po/w (MLOGP) : 3.06
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 2.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.182 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.162 mg/ml ; 0.000916 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.476 mg/ml ; 0.00269 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.2

Safety of [ 2550-36-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:1993
Hazard Statements:H225 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2550-36-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2550-36-9 ]

[ 2550-36-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 83465-22-9 ]
  • [ 2550-36-9 ]
  • [ 83471-08-3 ]
  • 2
  • [ 40187-51-7 ]
  • [ 2550-36-9 ]
  • [ 189393-76-8 ]
  • 3
  • [ 123-75-1 ]
  • [ 103-71-9 ]
  • [ 2550-36-9 ]
  • [ 774-07-2 ]
  • 1-cyclohexylmethyl-3-phenyl-7-pyrrolidin-1-yl-1<i>H</i>-pyrimido[4,5-<i>d</i>]pyrimidine-2,4-dione [ No CAS ]
  • 4
  • [ 2550-36-9 ]
  • [ 22916-47-8 ]
  • 1-cyclohexylmethyl-3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-3<i>H</i>-imidazol-1-ium; bromide [ No CAS ]
  • 5
  • [ 50820-65-0 ]
  • [ 2550-36-9 ]
  • [ 182345-37-5 ]
YieldReaction ConditionsOperation in experiment
74% To a solution of commercially available l//-<strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> (0.35 g, 2.0 mmol) and cyclohexylmethyl bromide (0.31 mL, 2.2 mmol) in DMF (2 mL) was added sodium hydride (92 mg, 2.3 mmol). After stirring at room temperature for 3 hr, the solution was diluted with water (25 mL) and ethyl acetate (75 mL), the organic layer was washed again with dilute NaHCO3 (25 mL) and then brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane, 1:24) to provide l-cyclohexylmethyl-l//-<strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> as a white solid (0.40 g, 74% yield). 1H NMR (400 MHz, DMSO) δ 8.10 (s, IH), 7.62 (m, 2H), 7.58 (d, IH, J = 3.1 Hz), 6.52 (d, IH, J= 3.1 Hz), 4.10 (d, 2H, J= IA Hz), 3.85 (s, 3H), 1.77 (m, IH), 1.65-1.57 (m 3H), 1.46 (m, 2H), 1.19 (m, 3H), 0.98 (m, 2H).
32% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 8h; 1H-<strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> (300mg, 1.71mmol) was dissolved in dimethyl formamide (7ml). Bromomethyl cyclohexane (0.5ml, 3.42mmol) and sodium hydride (150mg, 3.42mmol) were added dropwise thereto at 0, and then the mixture was stirred for 8 hours at room temperature. 1N hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (150mg, 32%). [611] NMR:1H-NMR(400HMz, CDCl3); δ 7.29-7.39 (m, 2H), 7.19 (d, 1H), 7.13 (m, 1H), 7.00-7.09 (m, 2H), 6.66 (m, 1H), 4.83 (s, 2H), 2.06 (s, 3H)
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