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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

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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Product Details of [ 2550-36-9 ]

CAS No. :2550-36-9 MDL No. :MFCD00001509
Formula : C7H13Br Boiling Point : -
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 Ų

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:
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.

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

[ 2550-36-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 2550-36-9 ]
  • [ 2344-80-1 ]
  • [ 5664-21-1 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 4, p. 429 - 434
  • 2
  • [ 100-49-2 ]
  • [ 2550-36-9 ]
YieldReaction ConditionsOperation in experiment
33.3% With pyridine; phosphorus tribromide In toluene at 0 - 20℃; for 11 h; Large scale 1.4 kg of the colorless liquid, 8.4 L of toluene and 969.8 g of pyridine were added to a 20 L four-neck flask, the system was cooled to 0 to 10° C., then a mixture of 1.66 kg of phosphorus tribromide and 7 L of toluene was dropwise added, the temperature was controlled below 5° C. The dropwise addition was finished in about 1 h, the temperature was increased to room temperature and reacted for 10 h. Then the temperature was cooled to below 20° C., about 2.5 L of a sodium hydroxide solution having a concentration of 5percent was dropwise added, then 1.85 kg of solid sodium hydroxide was added to form a mixture. Liquid separation was performed for the mixture, an obtained water phase was extracted twice with 4 L of toluene, organic phases obtained after the extraction were combined and washed with saturated salt water, the washed organic phases was dried with anhydrous sodium sulfate and then concentrated to obtain 1.73 kg of a crude product, reduced pressure distillation was performed to obtain 722.8 g of a product having a purity of 97.5percent and a yield of 33.3percent. 1H MR(400 MHz, CDCl3): δ3.82 (m, 1H), 1.79 to 1.53(m,6H), 1.13 to 0.90 (m, 6H).
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2901 - 2910
[2] Patent: US2016/319312, 2016, A1, . Location in patent: Paragraph 0083
[3] Journal of the American Chemical Society, 1926, vol. 48, p. 2392
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 142, p. 344[5] Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 548
[6] Journal of Medicinal Chemistry, 1971, vol. 14, # 8, p. 733 - 737
[7] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982, p. 1017 - 1024
[8] Journal of the American Chemical Society, 1968, vol. 90, # 19, p. 5208 - 5210
[9] Journal of the American Chemical Society, 1980, vol. 102, # 22, p. 6736 - 6744
  • 3
  • [ 3725-11-9 ]
  • [ 2550-36-9 ]
YieldReaction ConditionsOperation in experiment
90.3% at 20 - 80℃; 200 g of cyclohexylmethanol and 222.6 g of sodium carbonate were added to 1 L of toluene, stirred and cooled to 10-20 C.At this temperature, 515 g of p-toluenesulfonyl chloride (dissolved in 2L of toluene) was added dropwise over 2.5 hours. After the dropwise addition, the amount was increased to 30.Esterification at ~35°C until the cyclohexane methanol GC content is 3percent and filtration to obtain the organic phase intermediate filtrate, intermediate the organic phaseThe body filtrate was transferred to a 5L four-necked flask equipped with a magnetic stirrer, and 344 g of sodium bromide was added thereto while stirring at 20-35°C.15-crown-5catalyst 10g, after the completion of the addition, the temperature was raised to 70-80°C, and the reaction was incubated until the organic phase intermediate GC content was 3.6percent.At 40°C, the organic phase filtrate is filtered and recovered. Distillation of toluene is performed and distillation is performed to obtain a pale yellow transparent product. The pale yellow transparent product is dried.After the product (bromomethyl)cyclohexane140.2 g, GC content 98percent, yield 90.3percent.
Reference: [1] Patent: CN107652162, 2018, A, . Location in patent: Paragraph 0010-0013
  • 4
  • [ 931-50-0 ]
  • [ 2550-36-9 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 142, p. 344[2] Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 548
[3] Journal of the American Chemical Society, 1926, vol. 48, p. 2392
[4] Patent: US2016/319312, 2016, A1,
  • 5
  • [ 286-08-8 ]
  • [ 52428-01-0 ]
  • [ 6294-39-9 ]
  • [ 31061-99-1 ]
  • [ 2550-36-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 879 - 886
  • 6
  • [ 286-08-8 ]
  • [ 52428-01-0 ]
  • [ 31061-99-1 ]
  • [ 2550-36-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 879 - 886
  • 7
  • [ 108-85-0 ]
  • [ 2550-36-9 ]
Reference: [1] Patent: US2016/319312, 2016, A1,
  • 8
  • [ 2043-61-0 ]
  • [ 2550-36-9 ]
Reference: [1] Patent: US2016/319312, 2016, A1,
  • 9
  • [ 931-51-1 ]
  • [ 2550-36-9 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 142, p. 344[2] Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 548
  • 10
  • [ 286-08-8 ]
  • [ 2404-35-5 ]
  • [ 52428-01-0 ]
  • [ 6294-39-9 ]
  • [ 31061-99-1 ]
  • [ 34825-93-9 ]
  • [ 2550-36-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983, p. 879 - 886
  • 11
  • [ 52470-92-5 ]
  • [ 1121-49-9 ]
  • [ 82166-21-0 ]
  • [ 2550-36-9 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2084 - 2090
  • 12
  • [ 65826-86-0 ]
  • [ 591-49-1 ]
  • [ 1121-49-9 ]
  • [ 2550-36-9 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2084 - 2090
  • 13
  • [ 2550-36-9 ]
  • [ 5469-33-0 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 37, p. 5254 - 5256
  • 14
  • [ 2550-36-9 ]
  • [ 58717-02-5 ]
Reference: [1] Patent: US2016/319312, 2016, A1,
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