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Chemical Structure| 69966-55-8 Chemical Structure| 69966-55-8

Structure of 69966-55-8

Chemical Structure| 69966-55-8

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Product Citations

Product Citations

Tian, Gui-Long ; Hsieh, Chia-Ju ; Taylor, Michelle ; Lee, Ji Youn ; Riad, Aladdin A. ; Luedtke, Robert R. , et al.

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

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Product Details of [ 69966-55-8 ]

CAS No. :69966-55-8
Formula : C6H6BrN
M.W : 172.02
SMILES Code : BrCC1=CC=CN=C1
MDL No. :MFCD08669746
InChI Key :KHCXGFNZZRXOND-UHFFFAOYSA-N
Pubchem ID :245934

Safety of [ 69966-55-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 69966-55-8 ]

* 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 [ 69966-55-8 ]

[ 69966-55-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 69966-55-8 ]
  • [ 22300-52-3 ]
  • [ 1248676-31-4 ]
  • [ 1248676-67-6 ]
  • 2
  • [ 69966-55-8 ]
  • [ 137215-27-1 ]
  • [ 1362585-92-9 ]
YieldReaction ConditionsOperation in experiment
57% With potassium carbonate; In acetone; at 20℃; General procedure: A mixture of 44 (300 mg, 1.56 mmol), K2CO3 (372 mg, 2.34 mmol), and halogenated compound (1 equiv) in acetone (10 mL) was stirred for 0.5-3.5 h at rt. After filtering the mixture and removing the solvent in vacuo, the residue was purified by column chromatography (eluent: hexane/EtOAc 85:15) to obtain the target compounds (11-23) as white solids.
 

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