1003002-92-3

Upstream product

• 3282-30-2 pivaloyl chloride 
• 173216-45-0 (R)-3-azido-2-benzylpropanol 
• 136010-67-8 (2R,3S)-2-benzyl-3-hydroxysuccinic acid 
• 100-39-0 benzyl bromide 
• 1003002-88-7 (2S)-2-benzyl-3-oxopropyl pivalate 
• 1003002-86-5 (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylpropyl pivalate 
• 1003002-90-1 (2R)-2-benzyl-3-hydroxypropyl pivalate 
• 129600-11-9 (S)-1-acetoxy-2-benzyl-3-(methanesulfonyloxy)propane 
• 254990-76-6 (R)-1-acetoxy-3-azido-2-benzylpropane 
• 110270-49-0 (R)-3-acetoxy-2-benzyl-1-propanol 

Downstream Products

• 1610595-74-8 C₁₆H₂₁NO₂S 
• 1621151-96-9 C₂₄H₃₁N₃O₄S 
• 1621152-21-3 C₂₄H₃₃N₃O₂S 

Relevant academic research and scientific papers

α-Methylated simplified resiniferatoxin (sRTX) thiourea analogues as potent and stereospecific TRPV1 antagonists

A series of α-methylated analogues of the potent sRTX thiourea antagonists were investigated as rTRPV1 ligands in order to examine the effect of α-methylation on receptor activity. The SAR analysis indicated that activity was stereospecific with the (R)-configuration of the newly formed chiral center providing high binding affinity and potent antagonism while the configuration of the C-region was not significant.

Stereospecific high-affinity TRPV1 antagonists: Chiral N-(2-benzyl-3- pivaloyloxypropyl) 2-[4-(methylsulfonylamino)phenyl]propionamide analogues

Previously, we reported the thiourea antagonists 2a and 2b as potent and high affinity TRPV1 antagonists. For further optimization of the lead compounds, a series of their amide and α-substituted amide surrogates were investigated and novel chiral N-(2-be

N-(3-acyloxy-2-benzylpropyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea derivatives as potent vanilloid receptor agonists and analgesics

A series of N-(3-acyloxy-2-benzylpropyl)-N′-(4-hydroxy-3-methoxybenzyl)thiourea derivatives were investigated as vanilloid receptor ligands in an effort to discover a novel class of analgesics. The proposed pharmacophore model of resiniferatoxin, which includes the C20-homovanillic moiety, the C3-carbonyl and the orthoester phenyl ring as key pharmacophoric groups, was utilized as a guide for drug design. The compounds were synthesized after several steps from diethylmalonate and evaluated in vitro in a receptor binding assay and in a capsaicin-activated channel assay. Additional evaluation of analgesic activity, anti-inflammatory activity and pungency was conducted in animal models by the writhing test, the ear edema assay, and the eye-wiping test, respectively. Among the new compounds, 23 and 28 were found to be the most potent receptor agonists of the series with Ki values of 19 nM and 11 nM, respectively. Their strong in vitro potencies were also reflected by an excellent analgesic profile in animal tests with ED50 values of 0.5 μg/kg for 23 and 1.0 μg/kg for 28. Relative to capsaicin these compounds appear to be ca. 600 and 300 times more potent. Both 23 and 28 were found to be less pungent than capsaicin based on the eye-wiping test. However, the compounds did not show significant anti-inflammatory activity. A molecular modeling study comparing the energy-minimized structures of resiniferatoxin and 35 demonstrated a good correlation in the spatial disposition of the corresponding key pharmacophores. The thioureas described in this investigation, which were designed as simplified resiniferatoxin surrogates, represent a novel class of potent vanilloid receptor agonists endowed with potent analgesic activity and reduced pungency.