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[ CAS No. 15268-31-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 15268-31-2
Chemical Structure| 15268-31-2
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Quality Control of [ 15268-31-2 ]

COA NMR CNMR HPLC LC-MS

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Product Citations

Product Citations

Tian, Gui-Long ; Hsieh, Chia-Ju ; Taylor, Michelle , et al. DOI: PubMed ID:

Abstract: The difference in the secondary binding site (SBS) between the dopamine 2 receptor (D2R) and dopamine 3 receptor (D3R) has been used in the design of compounds displaying selectivity for the D3R versus D2R. In the current study, a series of bitopic ligands based on Fallypride were prepared with various secondary binding fragments (SBFs) as a means of improving the selectivity of this benzamide analog for D3R versus D2R. We observed that compounds having a small alkyl group with a heteroatom led to an improvement in D3R versus D2R selectivity. Increasing the steric bulk in the SBF increase the distance between the pyrrolidine N and Asp110, thereby reducing D3R affinity. The best-in-series compound was (2S,4R)-trans-27 which had a modest selectivity for D3R versus D2R and a high potency in the β-arrestin competition assay which provides a measure of the ability of the compound to compete with endogenous dopamine for binding to the D3R. The results of this study identified factors one should consider when designing bitopic ligands based on Fallypride displaying an improved affinity for D3R versus D2R.

Keywords: Dopamine 2 receptor ; Dopamine 3 receptor ; Fallypride ; Bitopic ligands ; PET imaging

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 98-98-6 ; ;

Product Details of [ 15268-31-2 ]

CAS No. :15268-31-2 MDL No. :MFCD01075747
Formula : C6H4N2O Boiling Point : No data available
Linear Structure Formula :- InChI Key :-
M.W : 120.11 Pubchem ID :-
Synonyms :

Safety of [ 15268-31-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P272-P280-P285-P302+P352-P304+P340-P305+P351+P338-P311-P321-P330-P333+P313-P337+P313-P363-P403+P233-P405-P501 UN#:2811
Hazard Statements:H302-H317-H319-H331-H334 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 15268-31-2 ]

* 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.

  • Downstream synthetic route of [ 15268-31-2 ]

[ 15268-31-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 52537-00-5 ]
  • [ 15268-31-2 ]
  • 6-Chloro-1-(pyridin-3-ylcarbamoyl)indoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Example 19 6-Chloro-1-(3-pyridylcarbamoyl)indoline (E19) The title compound was prepared as in the method of (Example 2) from 3-pyridylisocyanate and <strong>[52537-00-5]6-chloroindoline</strong> (D36) to give (E19) (1.54 g, 73%) m.p. 204-5 C. NMR (DMSO-d6) delta: 3.19 (2H, t, J=8), 4.19 (2H, t, J=8), 6.93-6.99 (1H, m), 7.23 (1H, d, J=8), 7.31-7.38 (1H, m), 7.88 (1H, s), 7.94-8.02 (1H, m), 8.24 (1H, d, J=6), 8.72 (1H, s), 8.82 (1H, s). Found: C, 61.34; H, 4.60; N, 15.38 C14 H12 N3 OCl requires: C, 61.43; H, 4.42; N, 15.35
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1598 - 1612
[2]Patent: US5834494,1998,A
[3]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2767 - 2773
  • 2
  • [ 65826-95-1 ]
  • [ 15268-31-2 ]
  • 5-methyl-1-(3-pyridylcarbamoyl)indoline [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1598 - 1612
[2]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2767 - 2773
  • 3
  • [ 35216-39-8 ]
  • [ 15268-31-2 ]
  • 1-(3-methanesulfonyl-phenyl)-3-pyridin-3-yl-urea [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2767 - 2773
  • 4
  • [ 15268-31-2 ]
  • [ 303994-99-2 ]
  • 1-(4-<i>tert</i>-butyl-5-cyano-thiazol-2-yl)-3-pyridin-3-yl-urea [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 235 - 238
  • 5
  • [ 1197159-91-3 ]
  • [ 15268-31-2 ]
  • [ 1197159-92-4 ]
YieldReaction ConditionsOperation in experiment
56% With dmap; In dichloromethane; at 20℃; for 48h; To a stirred mixture of <strong>[1197159-91-3]4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline</strong> (140 mg, 0.40 mmoles) and a catalytic amount of dimethylaminopyridine (DMAP) in methylene chloride 100 (mL), was added a small excess of aryl isocyanate (0.61 mmoles). The mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to half of its original volume and the separated precipitate was collected by filtration and washed with methanol (15 ml) and then with diethyl ether. In some cases the crude product obtained was purified by Silica gel column chromatography by eluting it with appropriate solvents, depending upon the polarity of the products.The following compounds were prepared according to Procedure A:Example 2Preparation of 1-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]-3-pyridin-3-ylureaStarting from <strong>[1197159-91-3]4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline</strong> (0.08 g 0.23 mmoles) and 3-pyridyl isocyanate (30 mg, 0.25 mmoles) the title compound was isolated as a white solid. The product was purified by Silica gel column chromatography by eluting it with 10% MeOH: ethyl acetate. Yield; 60 mg (56%); (M+H)=463.5.
56% With dmap; In dichloromethane; at 20℃; for 48h; General procedure: To a stirred mixture of <strong>[1197159-91-3]4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline</strong> (140 mg, 0.40 mmoles) and a catalytic amount of dimethylaminopyridine (DMAP) in methylene chloride 100 (mL), was added a small excess of aryl isocyanate (0.61 mmoles). The mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to half of its original volume and the separated precipitate was collected by filtration and washed with methanol (15 ml) and then with diethyl ether. In some cases the crude product obtained was purified by Silica gel column chromatography by eluting it with appropriate solvents, depending upon the polarity of the products.
Reference： [1]Patent: US2009/291079,2009,A1 .Location in patent: Page/Page column 37
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 2636 - 2645
[3]Patent: US2017/119778,2017,A1 .Location in patent: Paragraph 0931; 0933-0934

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