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[ CAS No. 7051-34-5 ] {[proInfo.proName]}

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Chemical Structure| 7051-34-5
Chemical Structure| 7051-34-5
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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 [ 7051-34-5 ]

CAS No. :7051-34-5 MDL No. :MFCD00001306
Formula : C4H7Br Boiling Point : -
Linear Structure Formula :(C3H5)CH2Br InChI Key :AEILLAXRDHDKDY-UHFFFAOYSA-N
M.W : 135.00 Pubchem ID :81503
Synonyms :
Chemical Name :(Bromomethyl)cyclopropane

Calculated chemistry of [ 7051-34-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 5
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 : 27.1
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 2.03
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 1.9

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.7
Solubility : 2.69 mg/ml ; 0.0199 mol/l
Class : Very soluble
Log S (Ali) : -1.35
Solubility : 6.08 mg/ml ; 0.045 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.7
Solubility : 2.67 mg/ml ; 0.0198 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 7051-34-5 ]

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

Application In Synthesis of [ 7051-34-5 ]

* 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 [ 7051-34-5 ]

[ 7051-34-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 109-99-9 ]
  • ethyl p-benzoxyacetate [ No CAS ]
  • [ 61439-59-6 ]
  • [ 7051-34-5 ]
  • [ 63659-15-4 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; di-isopropyl ether; Petroleum ether; 200 ml of tetrahydrofurane are introduced into a 2 liter reactor equipped with a mechanical stirrer, a dropping funnel, a reflux condenser and a thermometer and are cooled before adding 6.6 g of lithium aluminum hydride under a nitrogen atmosphere. This suspension is cooled to -5° and 80 g (0.296 mol) of ethyl p-benzoxyacetate are added dropwise thereto in such a way that the temperature does not exceed 0°. The whole is then kept at ambient temperature for 3 hours. The reaction mixture is then cooled and the excess AlLiH4 is destroyed with an excess of sodium potassium double tartrate, the mixture is filtered and the residue is evaporated. The 2-(p-benzoxyphenyl)-ethanol is caused to crystallise by trituration in isopropyl ether. 58.4 g (yield=86percent) of this product are obtained; M.p.: 86°-88°. 2.6 g (0.055 mol) of sodium hydride are suspended in 20 ml of dimethylformamide in a 250 ml flask equipped with a magnetic stirrer, a dropping funnel and a reflux condenser. 11.4 g (0.05 mol) of 2-(p-benzoxyphenyl)-ethanol dissolved in 30 ml of the same solvent are then added. The mixture is gently heated to 30° and a further 70 ml of dimethylformamide are then added. A precipitate is observed. 7.42 g (0.055 mol) of cyclopropylmethyl bromide dissolved in 20 ml of dimethylformamide are then added and the mixture is heated for 8 hours to a temperature of 60°. Progressive disappearance of the solid product is observed. The reaction mixture is poured into water and extracted with ether, and the ether solution is washed with water, dried over sodium sulphate and evaporated to dryness. The solid residue is stirred for 30 minutes in petroleum ether; the insoluble 2(p-benzoxyphenyl)-ethanol which has not reacted is then filtered off, the solvent is evaporated and the residue is rectified. 5.9 (yield=74percent) of 4-[2-(cyclopropylmethoxy)-ethyl]-1-benzoxy-benzene are thus obtained.
  • 2
  • [ 109-99-9 ]
  • ethyl p-benzoxy-acetate [ No CAS ]
  • [ 61439-59-6 ]
  • [ 7051-34-5 ]
  • [ 63659-15-4 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; di-isopropyl ether; Petroleum ether; 200 ml of tetrahydrofurane are introduced into a 2 liter reactor equipped with a mechanical stirrer, a dropping funnel, a reflux condenser and a thermometer and are cooled before adding 6.6 g of lithium aluminium hydride under a nitrogen atmosphere. This suspension is cooled to -5° and 80 g (0.296 mol) of ethyl p-benzoxy-acetate are added dropwise thereto in such a way that the temperature does not exceed 0°. The whole is then kept at ambient temperature for 3 hours. The reaction mixture is then cooled and the excess AlLiH4 is destroyed with an excess of sodium potassium double tartrate, the mixture is filtered and the residue is evaporated. The 2-(p-benzoxyphenyl)-ethanol is caused to crystallise by trituration in isopropyl ether. 58.4 g (yield=86percent) of this product are obtained; M.p.: 86°-88°. 2.6 g (0.055 mol) of sodium hydride are suspended in 20 ml of dimethylformamide in a 250 ml flask equipped with a magnetic stirrer, a dropping funnel and a reflux condenser. 11.4 g (0.05 mol) of 2-(p-benzoxyphenyl)-ethanol dissolved in 30 ml of the same solvent are then added. The mixture is gently heated to 30° and a further 70 ml of dimethylformamide are then added. A precipitate is observed. 7.42 g (0.055 mol) of cyclopropylmethyl bromide dissolved in 20 ml of dimethylformamide are then added and the mixture is heated for 8 hours to a temperature of 60°. Progressive disappearance of the solid product is observed. The reaction mixture is poured into water and extracted with ether, and the ether solution is washed with water, dried over sodium sulphate and evaporated to dryness. The solid residue is stirred for 30 minutes in petroleum ether; the insoluble 2-(p-benzoxyphenyl)-ethanol which has not reacted is then filtered off, the solvent is evaporated and the residue is rectified. 5.9 g (yield=74percent) of 4-[2-(cyclopropyl-methoxy)-ethyl]-1-benzoxy-benzene are thus obtained.
  • 3
  • [ 403-01-0 ]
  • [ 7051-34-5 ]
  • [ 1040724-63-7 ]
YieldReaction ConditionsOperation in experiment
69% b) 4-Cyclopropylmethoxy-3-fluoro-ben?oic acid methyl ester 3-Fluoro-4-hydroxy-benzoic acid methyl ester (1.02 g, 6.0 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.45 g, 3.0 mmol, 0.5 eq) and K2CO3 (1.66 g, 12.0 mmol, 2.0 eq) were added ad the mixture was stirred at room temperature for 20 min. (Bromomethyl)cyclopropane (0,53 mL, 5.4 mmol, 0.9 eq) was added, and the mixture was refluxed for 2 days. The solvent was concentrated under reduced pressure, NaOH 10% was added, and it was extracted with DCM and dried.0.91 g of title product (yield 69%) were recovered and used without further purification.C12H13FO31H-NMR (dmso-d6): 0.34-0.37 (2PI5 m); 0.57-0.62 (2H. m); 1.22-1.26 (IH, m); 3.82 (3H, s); 3.99 (2H, d, J=6.8 Hz); 7.26 (IH, t, J=8.4 Hz); 7.67-7.77 (2H, m).
  • 4
  • [ 7051-34-5 ]
  • [ 35344-95-7 ]
  • [ 1082065-99-3 ]
YieldReaction ConditionsOperation in experiment
56% Preparation 53: 1 -Cyclopropylmethyl- 1 H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> <n="62"/>--61-Add lH-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> (0.200 g, 2.08 mmol) to a suspension of sodium hydride (0.092 g, 2.29 mmol) in DMF (3 mL) at 0 0C. Stir for 20 min. at 0 0C. Add a solution of l-(bromomethyl)cyclopropane (0.295 g, 2.18 mmol) in DMF (4 mL) dropwise to the reaction mixture. Stir reaction to ambient temperature for 18 hr. Quench with aqueous saturated sodium bicarbonate solution and add ethyl acetate. Separate organic layer. Extract aqueous layer twice with ethyl acetate, dry combined organics (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0: 100 to 60:40 ethyl acetate:hexanes) to give the title preparation (175 mg, 56percent). GC-MS: m/z = 150 [M+].
  • 5
  • [ 7051-34-5 ]
  • [ 540516-28-7 ]
  • [ 1100215-83-5 ]
  • [ 1100215-82-4 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 19h; A 0.1 M solution of 5-Bromo-1H-benzo[d]imidazol-2-yl)methanol (630 mg, 2.8 mmol) in dimethylformamide was stirred with 2.4 equiv of cesium carbonate and (0.3 mL, 1.2 equiv) of cyclopropylmethyl bromide at 50 C. for 19 h. At the end dimethylformamide was evaporated in vacuo. The residue was partitioned between ethyl acetate (70 mL) and water (30 mL). Organic layer was dried (sodium sulfate) and evaporated in vacuo to give 800 mg of crude product which by LC-MS was 75% pure. LC/MS (HPLC method 1): tR=2.1 min, 281(MH)+. Silica gel TLC (ethyl acetate:hexane=4: 1) revealed two major products with Rf=0.29 and 0.20, which without separation were used in the next step.
  • 6
  • [ 61439-59-6 ]
  • [ 7051-34-5 ]
  • [ 63659-15-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In dimethyl sulfoxide; at 10 - 30℃; Example - 1: Preparation of 1 - [(Benzyloxy) - 4 - (2 - cyclopropyl methoxy) ethyl] benzene:In a 1.0 lit flask charged 4-benzyloxy-2-phenyl ethanol (100 gms, 0.44 moles) in dimethyl sulfoxide (300 ml). Stirred and charged powdered potassium hydroxide (61.4 gms, 1.1 moles). Stirred and cooled to 10 - 150C. Charged cyclopropyl methyl bromide (71.1 gms, 0.53 moles). Raised the temperature to 25 - 300C and maintained. After 3 hours, the reaction mass was quenched in chilled water (600 ml) maintaining temperature below 5°C. The pH of the reaction solution was adjusted with dilute (1 :4) hydrochloric acid, extracted the solution with 3 x 200 ml of toluene and distilled out toluene under vacuum below 550C. Charged petroleum ether (250 ml) to the residual mass and cooled to 00C and maintained under stirring for 2 hours. Filtered the separated solid and washed with petroleum ether. Charcoalised the filtrate for 30 minutes and filtered through hyflow bed and distilled out solvent to get the product. Wt of the product = 90 - 92 gms.
  • 7
  • [ 7051-34-5 ]
  • [ 256652-04-7 ]
  • [ 1006714-36-8 ]
  • [ 2489-89-6 ]
  • 8
  • [ 95656-88-5 ]
  • [ 7051-34-5 ]
  • [ 932702-42-6 ]
YieldReaction ConditionsOperation in experiment
81% Sodium hydride (280 mmol) was added in portions to a cold (0 C.) solution of <strong>[95656-88-5]benzyl 3-hydroxypyrrolidine-1-carboxylate</strong> (76.9 mmol) in N,N-dimethylformamide (100 mL). The mixture was maintained for 60 min and was then treated with a solution of (bromomethyl)cyclopropane (231 mmol) in N,N-dimethylformamide (100 mL) and potassium iodide (0.66 mmol). The reaction mixture was allowed to warm to rt where it was maintained for 30 min. The reaction mixture was subjected to microwave irradiation for 2 h at 90 C. The reaction mixture was concentrated and the residue was diluted with ethyl acetate (200 mL) and water (200 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (3*200 mL) and the combined organic layers were washed with brine (2*200 mL) and dried (magnesium sulfate). The residue was purified by chromatography (20/1 petroleum ether/ethyl acetate) to provide the product in 81% yield.
  • 9
  • [ 7768-28-7 ]
  • [ 7051-34-5 ]
  • [ 1384452-88-3 ]
  • 10
  • [ 39903-01-0 ]
  • [ 7051-34-5 ]
  • [ 1620574-90-4 ]
YieldReaction ConditionsOperation in experiment
47% With sodium hydroxide; In dichloromethane; water; at 20℃; for 16h; To a stirred solution of <strong>[39903-01-0]2-amino-5-bromopyridine-3-ol</strong> (25 g, 132.9 mmol) in dichloromethane (150 mL) was added (bromomethyl)cyclopropane (35.88 g, 265.8 mmol), aliquat (7.5 g) and 40percent aqueous sodium hydroxide (150 mL) at RT, followed by stirring for 16 h. The reaction mixture was diluted with water (500 mL) and extracted with dichloromethane (2 x 500 mL). The combined organic layers were concentrated to dryness in vacuo and the resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25percent ethyl acetate in hexane) affording 5-bromo-3-(cyclopropylmethoxy)pyridin-2-amine as and off white solid ( 15 g, 47percent):
47% With sodium hydroxide; In dichloromethane; water; at 20℃; for 16h; Preparative Example 1 Step 1: 5-bromo-3-(cyclopropylmethoxy)pyridin-2-amine To a stirred solution of <strong>[39903-01-0]2-amino-5-bromopyridine-3-ol</strong> (25 g, 132.9 mmol) in dichloromethane (150 mL) was added (bromomethyl)cyclopropane (35.88 g, 265.8 mmol), aliquat (7.5 g) and 40percent aqueous sodium hydroxide (150 mL) at RT, followed by stirring for 16 h. The reaction mixture was diluted with water (500 mL) and extracted with dichloromethane (2 x 500 mL). The combined organic layers were concentrated to dryness in vacuo and the resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25percent ethyl acetate in hexane) affording 5-bromo-3- (cyclopropylmethoxy)pyridin-2-amine as and off white solid ( 15 g, 47percent): H NMR (300 MHz, DMSO-d6) delta 7.61 (s, 1H), 7.19 (s, 1H), 5.81 (s, 2H), 4 - 3.8 (m, 2H), 1.35 - 1.1 (m, 1H), 0.65 - 0.55 (m, 2H), 0.2 - 0.4 (m, 2H).
  • 11
  • [ 42726-73-8 ]
  • [ 7051-34-5 ]
  • 1-tert-butyl 3-methyl 2-(cyclopropylmethyl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% To a solution of NaH (6.89 g, 172.22 mmol, 60percent in mineral oil) in DMF (150 mL) was added <strong>[42726-73-8]tert-butyl methyl malonate</strong> (30 g, 172.22 mmol, 29.13 mL) and the reaction mixture was stirred at 25 °C for 2 h. Bromomethylcyclopropane (27.9 g, 206.67 mmol, 19.79 mL) was added dropwise slowly and stirred for 16 h. The reaction mixture was quenched by the addition of aq. NH4CI (300 mL) at 0 °C, extracted with EtOAc (3 chi 300 mL), washed with brine (3 chi 300 mL), dried over anhydrous Na2SC>4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:MTBE = 100: 1 to 4: 1) to provide the title compound (29.5 g, 75percent) as a white oil.
  • 12
  • [ 7051-34-5 ]
  • [ 52867-42-2 ]
  • methyl 5-(cyclopropylmethoxy)-2-methylpyrazole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 16h; To a stirred suspension of methyl 5-hydroxy-2-methyl-pyrazole-3-carboxylate (3.00 g, 19.0 mmol) and K2CO3 (2.90 g, 21.0 mmol) in DMF (19 mL) at room temperature was added cyclopropylmethyl bromide (2.0 mL, 21.0 mmol) and the reaction mixture stirred at 50 C for 16 h. The reaction mixture was diluted with water (190 mL) and the aqueous layer extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with water (2 x 100 mL), passed through a phase separator, and concentrated in vacuo. The crude material was purified by flash chromatography using a gradient of 0-50% EtOAc in isohexanes to afford the title compound (3.14 g, 78% Yield) as a colourless oil. 6H (300 MHz, d-Chloroform) 6.18 (s, 1H), 4.02 (s, 3H), 3.94 (d, J = 7.1 Hz, 2H), 3.85 (s, 3H), 1.33-1.20 (m, 1H), 0.64-0.57 (m, 2H), 0.36-0.31 (m, 2H).
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