68935-42-2Relevant academic research and scientific papers
A one-pot three-component reaction for the preparation of highly functionalized tryptamines
Yeo, Se Jeong,Liu, Yongxiang,Wang, Xiang
, p. 813 - 818 (2012/02/01)
We have developed a general one-pot method to provide highly functionalized tryptamine derivatives, via a Fischer indole type pathway. In this article, we demonstrate optimal conditions for a one-pot indole synthesis, allowing for the synthesis of a broad scope of 2-methyl tryptamine derivatives and a precursor for the synthesis of the core structure of some akuammiline alkaloids. Additionally, further modification of the indole products is described.
Synthesis of tryptamine derivatives via a direct, one-pot reductive alkylation of indoles
Righi, Marika,Topi, Francesca,Bartolucci, Silvia,Bedini, Annalida,Piersanti, Giovanni,Spadoni, Gilberto
experimental part, p. 6351 - 6357 (2012/10/08)
An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile approach employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates several functional groups. The new procedure was efficiently applied to a gram-scale synthesis of both luzindole, a reference MT2-selective melatonin receptor antagonist, and melatonin.
Indolyl esters and amides related to indomethacin are selective COX-2 inhibitors
Kalgutkar, Amit S.,Crews, Brenda C.,Saleh, Sam,Prudhomme, Daniel,Marnett, Lawrence J.
, p. 6810 - 6822 (2007/10/03)
Previous studies from our laboratory have revealed that esterification/amidation of the carboxylic acid moiety in the nonsteroidal anti-inflammatory drug, indomethacin, generates potent and selective COX-2 inhibitors. In the present study, a series of reverse ester/amide derivatives were synthesized and evaluated as selective COX-2 inhibitors. Most of the reverse esters/amides displayed time-dependent COX-2 inhibition with IC 50 values in the low nanomolar range. Replacement of the 4-chlorobenzoyl group on the indole nitrogen with a 4-bromobenzyl moiety resulted in compounds that retained selective COX-2 inhibitory potency. In addition to inhibiting COX-2 activity in vitro, the reverse esters/amides also inhibited COX-2 activity in the mouse macrophage-like cell line, RAW264.7. Overall, this strategy broadens the scope of our previous methodology of neutralizing the carboxylic acid group in NSAIDs as a means of generating COX-2-selective inhibitors and is potentially applicable to other NSAIDs.
Compounds effective in the treatment of circadian rhythms and related disorders, the novel pharmaceutical preparations and novel method of application
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, (2008/06/13)
The novel compounds of formula: STR1 in which R is isopropyl, cyclohexyl, phenyl, CH 3, Br or I; or H R 1 is CH 3 or cyclopropyl and R 2 is H or Br, and when R 1 is cyclopropyl and R 2 is H, R is other than H, and when R 1 is CH 3 and R 2 is H, R is other than H, and when R 1 is CH 3 and R 2 is H, R is other than I, and when R is CH 3 and R 2 is H, R 1 is other than CH 3, and when R is phenyl and R 2 is H, R 1 is other than CH 3, exhibit superior activity in the treatment of pathologies which interfere with the circadian rhythm. A novel method of preparation is described according to which the pharmaceutical compositions containing the novel compounds, as well as compounds already known, are administered transdermally. The novel method of administration results in sustained peripheral blood level. Novel pharmaceutical compositions are described suitable for transdermal administration.
2-Substituted 5-methoxy-N-acyltryptamines: Synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity
Spadoni,Stankov,Duranti,Biella,Lucini,Salvatori,Fraschini
, p. 4069 - 4074 (2007/10/02)
A series of 2-substituted 5-methoxy-N-acyltryptamines was synthesized and their affinity for the melatonin receptor, isolated from whole quail brains, was tested in a succession of in vitro ligand-receptor binding experiments, using 2-[125I]iod
Synthesis and evaluation of the antiovulatory activity of a variety of melatonin analogues
Flaugh,Crowell,Clemens,Sawyer
, p. 63 - 69 (2007/10/04)
A series of melatonin analogues was synthesized and examined for ovulation-blocking activity. Deviation from the 5-methoxy group or substitution of the 1 position prevented activity. Activity was not particularly sensitive to minor variations in the N-acyl group nor was it significantly altered by methylation of position 2 or the α-methylene; however, a pronounced enhancement resulted from halogenation of the 6 position.
