Dutta, A. K.; Ryan, W.; Thomas, B. F.; Singer, M.; Compton, D. R.; Martin, B. R.; Razdan, R. K. published the artcile< Synthesis, pharmacology, and molecular modeling of novel 4-alkyloxy indole derivatives related to cannabimimetic aminoalkyl indoles (AAIs)>, COA of Formula: C19H34O2, the main research area is alkyloxy indole derivative preparation cannabimimetic structure.
Several novel 4-alkyloxy-aminoalkyl indole derivatives I (R = H, alkyl or alkylnaphthyl) were synthesized from 4-benzyloxyindole. Alkylation of 4-benzyloxyindole with 4-(2-chloroethyl)morpholine (NaH/HMPA) formed 4-benzyloxy-1-[2-(4-morpholinyl)ethyl]-1H-indole. Deprotection using palladium hydroxide on carbon/hydrogen followed by alkylation with the appropriate alkyl bromide gave the target compounds In the synthesis of two of the derivatives, the appropriate alkyl bromides were prepared from the com. available 1-naphthylethyl bromide using the chain lengthening sequences. In receptor binding assay and in vivo testing, the long chain alkoxy compounds (Ki = 127 nM) showed affinity for the CB1 receptor which was approx. 16-35-fold less than that of WIN 55,225. However, the pharmacol. profile of one of the derivatives mimics that of WIN 55,212. An examination of the SAR of these analogs shows that translocating the naphthyl group in AAIs from the C-3 position to C-4 via an oxygen (ether linkage) decreases activity which is in contrast to previous findings that a naphthylcarbonyl at C-4 retains activity. The present work points to the importance of the role of a keto group in the interaction with the receptor. Mol. modeling work suggests that, although reasonable superposition of key structural features between Δ9-THC and AAIs can be made, the overlay is not straightforward. The present study also illustrates the difficulty in accommodating AAIs into the cannabinoid pharmacophore and it seems likely that a unique pharmacophore will need to be developed. Only then will the similarities to and differences from the classical cannabinoid pharmacophore be clearly delineated.
Bioorganic & Medicinal Chemistry published new progress about Cannabinoid receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, COA of Formula: C19H34O2.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics