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[ CAS No. 20443-99-6 ] {[proInfo.proName]}

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Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
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3d Animation Molecule Structure of 20443-99-6
Chemical Structure| 20443-99-6
Chemical Structure| 20443-99-6
Structure of 20443-99-6 * Storage: {[proInfo.prStorage]}
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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 [ 20443-99-6 ]

CAS No. :20443-99-6 MDL No. :MFCD03208523
Formula : C7H5BrCl2 Boiling Point : -
Linear Structure Formula :- InChI Key :RGLQSFFFIREZFV-UHFFFAOYSA-N
M.W : 239.92 Pubchem ID :10988373
Synonyms :

Calculated chemistry of [ 20443-99-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.3
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.49
Log Po/w (XLOGP3) : 3.99
Log Po/w (WLOGP) : 3.74
Log Po/w (MLOGP) : 4.25
Log Po/w (SILICOS-IT) : 4.11
Consensus Log Po/w : 3.72

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.22
Solubility : 0.0145 mg/ml ; 0.0000604 mol/l
Class : Moderately soluble
Log S (Ali) : -3.69
Solubility : 0.0488 mg/ml ; 0.000203 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.89
Solubility : 0.00307 mg/ml ; 0.0000128 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.73

Safety of [ 20443-99-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 UN#:3261
Hazard Statements:H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20443-99-6 ]

* 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 [ 20443-99-6 ]
  • Downstream synthetic route of [ 20443-99-6 ]

[ 20443-99-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 1777-82-8 ]
  • [ 20443-99-6 ]
YieldReaction ConditionsOperation in experiment
99% With ethyl 2,2-dibromoacetoacetate; triphenylphosphine In dichloromethane at 20℃; for 0.25 h; General procedure: Ethyl α,α-dibromoacetoacetate 2a (0.41 mmol, 1.2 equiv), alcohols 1a-1s (0.34 mmol, 1.0 equiv) and Ph3P (0.68 mmol, 2.0 equiv) were added under ambient temperature to 3 mL of DCE in air. After stirred at room temperature for appropriate time (monitored by TLC), the reaction was quenched by addition of H2O (3 mL) and then extracted with ethyl acetate (3×3 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel with petroleum ether or mixture of petroleum ether and ethyl acetate as eluent to afford the corresponding products 3a-3s.
98% With phosphorus tribromide In dichloromethane; N,N-dimethyl-formamide at 80℃; To a 100 mL round bottom flask was added 2,4-dichlorobenzyl alcohol (17.7 g, 0.1 mol)And dichloromethane (30 mL) and DMF (1 mL), followed by the addition of phosphorus tribromide (9.2 g, 0.034 mol), slowly warming to 80 ° C, stirring for 2 to 3 hours, Indicating that the raw material point disappeared, distillation was 2,4 - dichloro Bian bromine 23.52g, yield 98percent.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 90 - 93
[2] Patent: CN106117028, 2016, A, . Location in patent: Paragraph 0057; 0058
[3] Organic Process Research and Development, 2002, vol. 6, # 2, p. 190 - 191
[4] Monatshefte fur Chemie, 2004, vol. 135, # 10, p. 1251 - 1255
[5] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
[6] Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3569 - 3584
[7] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350
  • 2
  • [ 95-73-8 ]
  • [ 20443-99-6 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 1693,1695
[2] Journal of the American Chemical Society, 1968, vol. 90, # 13, p. 3473 - 3478
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 43 - 67
[4] European Journal of Organic Chemistry, 1999, # 7, p. 1709 - 1718
[5] Patent: US2005/245554, 2005, A1, . Location in patent: Page/Page column 32-33
  • 3
  • [ 874-42-0 ]
  • [ 20443-99-6 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 38, p. 6681 - 6683
  • 4
  • [ 95-73-8 ]
  • [ 6425-26-9 ]
  • [ 20443-99-6 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 41, p. 7047 - 7050
  • 5
  • [ 1058649-24-3 ]
  • [ 20443-99-6 ]
Reference: [1] Comptes Rendus Chimie, 2010, vol. 13, # 12, p. 1468 - 1473
[2] Tetrahedron Letters, 2010, vol. 51, # 25, p. 3274 - 3276
  • 6
  • [ 877468-98-9 ]
  • [ 20443-99-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 25, p. 3274 - 3276
  • 7
  • [ 6574-98-7 ]
  • [ 20443-99-6 ]
Reference: [1] Patent: CN106117028, 2016, A,
  • 8
  • [ 50-84-0 ]
  • [ 20443-99-6 ]
Reference: [1] Patent: CN106117028, 2016, A,
  • 9
  • [ 20443-99-6 ]
  • [ 95-00-1 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 2556,2557
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 4328,4330,4333
  • 10
  • [ 20443-99-6 ]
  • [ 19719-28-9 ]
Reference: [1] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350
[2] Patent: CN106117028, 2016, A,
  • 11
  • [ 773837-37-9 ]
  • [ 20443-99-6 ]
  • [ 6306-60-1 ]
Reference: [1] Patent: CN106117028, 2016, A, . Location in patent: Paragraph 0059; 0060
[2] Applied Organometallic Chemistry, 2018, vol. 32, # 4,
  • 12
  • [ 151-50-8 ]
  • [ 20443-99-6 ]
  • [ 6306-60-1 ]
Reference: [1] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350
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