75784-65-5

Usage

InChI:InChI=1/C13H19NO2/c1-13(2,3)16-12(15)10-6-8-11(9-7-10)14(4)5/h6-9H,1-5H3

Upstream product

• 4755-50-4 4-(dimethylamino)benzoyl chloride 
• 75-65-0 tert-butyl alcohol 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 10287-53-3 ethyl p-dimethyaminolbenzoate 
• 865-47-4 potassium tert-butylate 

Downstream Products

• 75784-67-7 C₁₂H₁₉NO₂Si 
• 1241978-78-8 4-[¹⁸F]-1,1-dimethylethyl ester benzoic acid 
• 10011-97-9 4-[¹⁸F]fluorobenzoic acid 
• 141762-27-8 N-succinimidyl 4-[18F]fluorobenzoate 

Relevant academic research and scientific papers

Ruthenium-catalyzed ester reductions applied to pharmaceutical intermediates

Ruthenium pincer complexes were synthesized and used for catalytic ester reductions under mild conditions (～5 bar of hydrogen). An experimental design approach was used to optimize the conditions for yield, purity, and robustness. Evidence for the catalytically active ruthenium dihydride species is presented. Observed intermediates and side products, as well as time-course data, were used to build mechanistic insight. The optimized procedure was further demonstrated through scaled-up reductions of two pharmaceutically relevant esters, both in batch and continuous flow.

Peptidomimetic growth hormone secretagogue derivatives for positron emission tomography imaging of the ghrelin receptor

The ghrelin receptor is a seven-transmembrane (7-TM) receptor known to have an increased level of expression in human carcinoma and heart failure. Recent work has focused on the synthesis of positron emission tomography (PET) probes designed to target and image this receptor for disease diagnosis and staging. However, these probes have been restricted to small-molecule quinalizonones and peptide derivatives of the endogenous ligand ghrelin. We describe the design, synthesis and biological evaluation of a series of 4-fluorobenzoylated growth hormone secretagogues (GHSs) derived from peptidic (GHRP-1, GHPR-2 and GHRP-6) and peptidomimetic (G-7039, [1-Nal4]G-7039 and ipamorelin) families in order to test locations for the insertion of fluorine-18 for PET imaging. The peptidomimetic G-7039 was found to be the most suitable for 18F-radiolabelling as its non-radioactive 4-fluorobenzoylated analogue ([1-Nal4,Lys5(4-FB)]G-7039), had both a high binding affinity (IC50 = 69 nM) and promising in vitro efficacy (EC50 = 1.1 nM). Prosthetic group radiolabelling of the precursor compound [1-Nal4]G-7039 using N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB) delivered the PET probe [1-Nal4,Lys5(4-[18F]-FB)]G-7039 in an average decay-corrected radiochemical yield of 48%, a radio-purity ≥ 99% and an average molar activity of >34 GBq/μmol. This compound could be investigated as a PET probe for the detection of diseases that are characterised by overexpression of the ghrelin receptor.

PEPTIDOMIMETICS FOR IMAGING THE GHRELIN RECEPTOR

ABSTRACT The present invention concerns compositions comprising and methods of identification and use of imaging agents. The imaging agents comprise a growth hormone secretagogues having a conjugated fluoride. The imaging agents of the present invention may be used for detection, diagnosis and/or staging of prostate or other forms of cancer, and may also be used for cardiac disease.