[ CAS No. 637-59-2 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 637-59-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 637-59-2 ]

SDS Specification

Alternatived Products of [ 637-59-2 ]

Product Citations

Structure-activity studies of PTPRD phosphatase inhibitors identify a 7-cyclopentymethoxy illudalic acid analog candidate for development

Henderson, Ian M. ; Zeng, Fanxun ; Bhuiyan, Nazmul H. , et al. Biochem. Pharmacol.,2022,195,114868. DOI: 10.1016/j.bcp.2021.114868 PubMed ID: 34863978

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

Purchased from AmBeed: 37595-74-7 ; 637-59-2 ; 103-63-9 ; 64473-35-4 ; 20443-99-6 ; 939-26-4 ; 3814-32-2 ; 3814-30-0 ; 36881-42-2 ; 17247-58-4 ; 589-15-1 ; 2550-36-9 ; 7051-34-5 ; 161043-38-5 ; 161395-96-6 ; 59311-24-9 ; 78358-86-8 ; 83642-03-9 ...More

Product Details of [ 637-59-2 ]

CAS No. :	637-59-2	MDL No. :	MFCD00000257
Formula :	C₉H₁₁Br	Boiling Point :	-
Linear Structure Formula :	(C₆H₅)CH₂CH₂CH₂Br	InChI Key :	XMZQWZJMTBCUFT-UHFFFAOYSA-N
M.W :	199.09	Pubchem ID :	12503
Synonyms :

Calculated chemistry of [ 637-59-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.89
TPSA :	0.0 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.45
Log Po/w (XLOGP3) :	3.72
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	3.71
Log Po/w (SILICOS-IT) :	3.51
Consensus Log Po/w :	3.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.66
Solubility :	0.0432 mg/ml ; 0.000217 mol/l
Class :	Soluble
Log S (Ali) :	-3.41
Solubility :	0.0772 mg/ml ; 0.000388 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.47
Solubility :	0.00678 mg/ml ; 0.000034 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.45

Safety of [ 637-59-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 637-59-2 ]

* 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.

Upstream synthesis route of [ 637-59-2 ]
Downstream synthetic route of [ 637-59-2 ]

[ 637-59-2 ] Synthesis Path-Upstream 1~1

1
[ 637-59-2 ]
[ 113100-86-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 4, p. 523 - 528
[2] Patent: CN102757444, 2016, B,

[ 637-59-2 ] Synthesis Path-Downstream 1~4

1
[ 2307-69-9 ]
[ 637-59-2 ]
[ 124-18-5 ]
[ 112-95-8 ]
[ 4215-86-5 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 2125 - 2133

2
[ 4138-26-5 ]
[ 637-59-2 ]
[ 259268-48-9 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 205 - 213

3
[ 639068-43-2 ]
[ 637-59-2 ]
cis-1-tert-butoxycarbonyl-3,5-dimethyl-4-(3-phenylpropan-1-yl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; N,N-dimethyl-formamide;	1) Synthesis of cis-1-tert-butoxycarbonyl-3,5-dimethyl-4-(3-phenylpropan-1-yl)piperazine To a suspension of 10 g (46.66 mmol.) of <strong>[639068-43-2]cis-1-tert-butoxycarbonyl-3,5-dimethyl piperazine</strong> and 12.90 g (93.3 mmol.) of potassium carbonate in N,N-dimethylformamide (50 ml) was added, at room temperature, 11.15 g (56 mmol.) of 1-bromo-3-phenylpropane. The mixture was stirred for 40 hours at 120° C., which was then cooled to room temperature. To the reaction system was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a column chromatography (ethyl acetate/hexane 20-30percent) to give the object compound as a yellow oily product. The yield was 12.21 g (79percent). 1H-NMR (CDCl3, 200 MHz) delta: 1.00 (6H, d, J=5.8 Hz), 1.45 (9H, s), 1.57-1.69 (2H, m), 2.43-2.62 (6H, m), 2.67-2.85 (2H, s), 3.68-3.96 (2H, m), 7.13-7.35 (5H, m). IR (neat): 2974, 2931, 2856, 1695, 1454, 1427, 1273, 1248, 1174, 1142, 748, 700 cm-1.

Reference： [1]Patent: US6235731,2001,B1

4
[ 637-59-2 ]
[ 114676-59-4 ]
(2R,4R)-methyl 4-hydroxy-1-(3-phenylpropyl)pyrrolidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	General procedure: To a solution of 19 (1.0 equiv.) and K2CO3 (2.0 equiv.) inanhydrous DMF (2 mL) was added an appropriate alkyl halide (1.0 equiv), and themixture was stirred at room temperature or 80 °C (rt for X = CH2, 80°C for X = CH2CH2; CH2CH2CH2)under N2 atmosphere for appropriate hours. After completion of thereaction (monitored by TLC), the resulting mixture was concentrated in vacuo. The residue was dissolvedin ethyl acetate and washed twice with brine. The organic layer was dried, concentrated in vacuoand the residue was purified by column chromatography on silica gel eluted with DCM/EA (2:1)to give compound 20 as a colorlessoil.(2S,4R)-methyl-1-benzyl-4-hydroxypyrrolidine-2-carboxylate(20a). Yield 88percent.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2434 - 2437

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Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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