Home Cart Sign in  
Chemical Structure| 29886-64-4 Chemical Structure| 29886-64-4

Structure of 29886-64-4

Chemical Structure| 29886-64-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations      Show More

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

Kim, Ho Young ; Lee, Ji Youn ; Hsieh, Chia-Ju ; Taylor, Michelle ; Luedtke, Robert R ; Mach, Robert H

Abstract: Previous studies have confirmed that the binding of D3 receptor antagonists is competitively inhibited by endogenous dopamine despite excellent binding affinity for D3 receptors. This result urges the development of an alternative scaffold that is capable of competing with dopamine for binding to the D3 receptor. Herein, an SAR study was conducted on metoclopramide that incorporated a flexible scaffold for interaction with the secondary binding site of the D3 receptor. The alteration of benzamide substituents and secondary binding fragments with aryl carboxamides resulted in excellent D3 receptor affinities (Ki = 0.8–13.2 nM) with subtype selectivity to the D2 receptor ranging from 22- to 180-fold. The β-arrestin recruitment assay revealed that 21c with 4-(pyridine-4-yl)benzamide can compete well against dopamine with the highest potency (IC50 = 1.3 nM). Computational studies demonstrated that the high potency of 21c and its analogs was the result of interactions with the secondary binding site of the D3 receptor. These compounds also displayed minimal effects for other GPCRs except moderate affinity for 5-HT3 receptors and TSPO. The results of this study revealed that a new class of selective D3 receptor antagonists should be useful in behavioral pharmacology studies and as lead compounds for PET radiotracer development.

Keywords: D3 receptor antagonists ; metoclopramide ; bitopic ligand ; β-arrestin recruitment assay ; computational chemistry

Alternative Products

Product Details of [ 29886-64-4 ]

CAS No. :29886-64-4
Formula : C11H8O2S
M.W : 204.25
SMILES Code : O=C(O)C1=CC=C(C2=CSC=C2)C=C1
MDL No. :MFCD03783559
InChI Key :FISAUHGRILVMDP-UHFFFAOYSA-N
Pubchem ID :736862

Safety of [ 29886-64-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 29886-64-4 ]

Aryls

Chemical Structure| 20608-89-3

A250354 [20608-89-3]

3-(Thiophen-3-yl)benzoic acid

Similarity: 1.00

Chemical Structure| 1192547-90-2

A843089 [1192547-90-2]

3-Methyl-4-(thiophen-3-yl)benzoic acid

Similarity: 0.95

Chemical Structure| 1261975-85-2

A560303 [1261975-85-2]

2-Methyl-6-(thiophen-3-yl)benzoic acid

Similarity: 0.91

Chemical Structure| 20608-87-1

A724582 [20608-87-1]

2-(Thiophen-3-yl)benzoic acid

Similarity: 0.91

Chemical Structure| 1261925-72-7

A478315 [1261925-72-7]

5-Methyl-2-(thiophen-3-yl)benzoic acid

Similarity: 0.91

Carboxylic Acids

Chemical Structure| 20608-89-3

A250354 [20608-89-3]

3-(Thiophen-3-yl)benzoic acid

Similarity: 1.00

Chemical Structure| 1192547-90-2

A843089 [1192547-90-2]

3-Methyl-4-(thiophen-3-yl)benzoic acid

Similarity: 0.95

Chemical Structure| 1261975-85-2

A560303 [1261975-85-2]

2-Methyl-6-(thiophen-3-yl)benzoic acid

Similarity: 0.91

Chemical Structure| 20608-87-1

A724582 [20608-87-1]

2-(Thiophen-3-yl)benzoic acid

Similarity: 0.91

Chemical Structure| 1261925-72-7

A478315 [1261925-72-7]

5-Methyl-2-(thiophen-3-yl)benzoic acid

Similarity: 0.91