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Chemical Structure| 7051-34-5 Chemical Structure| 7051-34-5
Chemical Structure| 7051-34-5

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CAS No.: 7051-34-5

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Henderson, Ian M. ; Zeng, Fanxun ; Bhuiyan, Nazmul H. ; Luo, Dan ; Martinez, Maria ; Smoake, Jane , et al.

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

Janssens, Liesl K ; Ametovski, Adam ; Sparkes, Eric ; Boyd, Rochelle ; Lai, Felcia ; Maloney, Callan J , et al.

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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Alternative Products

Product Details of Cyclopropylmethyl bromide

CAS No. :7051-34-5
Formula : C4H7Br
M.W : 135.00
SMILES Code : BrCC1CC1
MDL No. :MFCD00001306
InChI Key :AEILLAXRDHDKDY-UHFFFAOYSA-N
Pubchem ID :81503

Safety of Cyclopropylmethyl bromide

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

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