Indoles acetals

LY311727 is an indole acetic acid based selective inhibitor of human non-pancreatic secretory phospholipase A2 (hnpsPLA2) under development by Lilly as a potential treatment for sepsis. The synthesis of LY311727 involved a Nenitzescu indolization reaction as a key step. The Nenitzescu condensation of quinone 4 with the p-aminoacrylate 39 was carried out in CH3NO2 to provide the desired 5-hydroxylindole 40 in 83% yield. Protection of the 5-hydroxyl moiety in indole 40 was accomplished in H2O under phase transfer conditions in 80% yield. Lithium aluminum hydride mediated reduction of the ester functional group in 41 provided the alcohol 42 in 78% yield. 

NSAIDs are of diverse chemical structures salicylates (aspirin, sulphasalazine), indole acetic acids (indomethacin, etodolac), heteroaryl acetic acids (diclofenac), arylpropionic acids (ibuprofen, naproxen), anthranilic acids (mefenamic acid) and enolic acids (piroxicam, meloxicam). 

Application of Pd-Catalyzed Annulation to the Synthesis of the Indole Acetic Acid... 

Eventually, indole acetic acid 2 was prepared from iodoaniline 28 and propargyl alcohol derivative 61 via the newly developed coupling reaction followed by a cyanide displacement-hydrolysis sequence, as shown in Scheme 4.16. 

Scheme 4.15 Fisher indole and oxidation approach to indole acetic acid 2.

Chlorogenic acid forms a 1 1 complex with caffeine, which can be crystallized from aqueous alcohol and yields very little free caffeine on extraction with chloroform. Other compounds with which caffeine will complex in this way include isoeugenol, coumarin, indole-acetic acid, and anthocyanidin. The basis for this selection was the requirement for a substituted aromatic ring and a conjugated double bond in forming such a complex. This kind of complex does modify the physiological effects of caffeine.14 Complex formation will also increase the apparent aqueous solubility of caffeine in the presence of alkali benzoates, cinnamates, citrates, and salicylates.9... 

Auxins Derivative of tryptophan - e.g. indole acetic acid. Controls H+/K+ balance and growth... 

Defensive Compounds. The sweetish smell of Noterus species is due to the presence of phenyl acetic acid 14 as the main constituent of the pygidial gland secretion. Furthermore, some additional aromatics and 3-indole acetic acid 30 could be identified [82,104]. 

The addition of a surfactant counter-ion reduced the retention factor at low pH due to the surface modification of the stationary phase material. Covering the surface of the stationary phase with the surfactant reduces the hydro-phobicity of the stationary phase material. The addition of the tetrabutyl-ammonium counter-ion increased the retention factor at high pH. The pKa of the indole acetate was 5.15 without surfactant, 4.85 with octyl sulfate ion, and 5.60 with tetrabutylammonium ion. That is, the addition of a same-charged hydrophobic ion reduced the pKa value, and the addition of the counter-ion increased the pKa value. The difference in the pKa value on the addition of surfactant is not constant it is affected by the kind of ion and the concentration. It is difficult to estimate the pKa change. 

The role of serotonin (5-hydroxytryptamine, 5-HT) has also been extensively studied in depressed patients. Whereas the overall psycho-physiological effects of noradrenaline in the CNS appear to be linked to drive and motivation, 5-HT is primarily involved in the expression of mood. It is not surprising therefore to find that the serotonergic system is abnormal in depression. This is indicated by a reduction in the main 5-HT metabolite, 5-hydroxy indole acetic acid (5-HIAA), in the cerebrospinal fluid of severely depressed patients and a reduction in 5-HT and 5-HIAA in the limbic regions of the brain of suicide victims. The 5-HT receptor function also appears to be abnormal in depression. This is indicated by an increase in the density of cortical 5-HT2a receptors in the brains of suicide victims and also on the platelet membrane of depressed patients. Platelets may be considered as accessible models of the nerve terminal. 

The ability of HRP to degrade the plant hormone indole-3-acetic acid (lAA) in the absence of hydrogen peroxide was noted as early as 1955 (136). Plant peroxidases are now known to be of major importance in the metabolism of lAA (137) (note that they are often referred to as indole acetic acid oxidases in the older literature). The mechanism of lAA oxidation by HRP C is complex and has been studied experimentally in great detail by several groups (23, 137). Reaction products include indole-3-methanol, indole-3-aldehyde, and 3-methylene oxin-dole, which is probably a nonenzymatic conversion product of indole-3-methylhydroperoxide. The most important developments in this area have been reviewed (23). 

Q89 Indometacin is an indole acetic acid derivative that has a lov/er frequency of gastrointestinal side-effects compared v/ith naproxen. Indometacin may cause headache and dizziness as side-effects. 

Indometacin is an indole acetic acid derivative, while naproxen is a propionic acid derivative. Both are non-steroidal anti-inflammatory drugs (NSAIDs). Indometacin is associated with a higher incidence of side-effects, particularly gastrointestinal as well as headache and dizziness. 

Dialkyltryptaminesfrom 3-Indole-Acetic Acid. Col. Czech. Chem. Com. There are several other methods given with this formula but they are not as good as the one given below. If you do not have a big, complete library, then you may need a translator to understand this and some of the other foreign journals. 

Oxidase, p-indolyl-acetic acid Call Tiss Oxidase, indole-acetic acid Stem pith 584 Palmitic acid, methyl ester Lf, Rt, St, Bk,... 

Brand Name(s) Indocin, Indocin IV, Indocin SR, Indo-Lemmon Chemical Class Indole acetic acid derivative... 

It is indole acetic acid derivative possessing potent antiinflammatory property and having a good analgesic and antipyretic action also. Mechanism of action is same as other NSAIDs. 

P Inhibition of indole-acetic acid action Phthalamates 19... 

For hormonal treatments, whole apices of intact epicotyls were sprayed with 0.1% 2,4-dichlorophenoxyacetic acid (2,4-D), or they were decapitated, i.e., the plumule and hook were detached (6), followed by application of 2.5 mg lanolin paste containing a suspension of indole-acetic acid (IAA, 0.5%, w/w) on each cut apex. Control tissue received lanolin paste alone. Both regulators caused massive swelling of the... 

Arabidopsis thalina, 236-238 Archaebacteria, 272 Auxin, (indole acetic acid, IAA), 218— 223,238... 

Avsian-Kretchmer O, Cheng JC, Chen L, Moctezuma E, Sung ZR. 2002. Indole acetic acid distribution coincides with vascular differentiation pattern during Arabidopsis leaf ontogeny. Plant Physiol 130 199-209. 

The indomethacin hydrolysis product 2-methyl-5-methoxy indole acetic acid fluoresces at 385 nm after excitation at 300 nm in 0.1N NaOH,(41) and at 387 nm after excitation at 312 nm in pH 11.6 buffer(42). The latter procedure claimed a threefold increase in detectability. Neither method distinguishes indomethacin from salicylates. Clinical studies employing subjects administered aspirin must use a separation prior to fluorescence analysis. Without adequate separation the indole metabolites as well as salicylate, produce a positive assay bias. 

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