Indole compounds

CombiSMoG potential function, which was derived from 1000 protein-ligand complex 3D structures. After inspection of 100,000 candidates, the hve best hits were ranked by a force field calculation. The (i )-isomer of the indole compound 59 (K = 30 pM Fig. 16.8) is the highest-scoring compound and has the highest affinity of all synthesized molecules, whereas the (S) -isomer has only K = 230 pM [131,132]. 

BakF, F Widdel (1986) Anaerobic degradatiion of indolic compounds by sulfate-reducing enrichment cultures, and description of Desulfobacterium indolicum gen. nov., sp. nov. Arch Microbiol 146 170-176. 

The fused indolopyrrolizidine 137 can be transformed into the tetrahydropyrrolizinoquinolone 138 upon reaction with Bu OK while oxygen is bubbled into the solution. (This is an apparently general strategy for the oxidation of indoles.) Compound 138 may then be oxidized with w-chloroperbenzoic acid (MCPBA) to give the dihydropyrido-pyrrolizine 139 <1997TL2997> (Scheme 37). 

Indole chemiluminescence (J> p. 112, I80,i8ia)j can a]so be regarded as a special type of Schiff s base chemiluminescence, for the indole compounds very probably react via a hydroperoxide derived from the respective indolenine form. 

The indole compound was described by Flynn et al. [73] and is prepared in a similar manner as the thiophene 103 and furan 108. One method involved a similar synthesis as described in Scheme 25, using the relevant starting material. However, an alternative synthesis involved a one-pot, room-temperature synthesis, Scheme 27. The o-iodotrifluoroacetanilide 110 was coupled to the alkyne 111 under Sonogashira conditions in MeCN. K2CO3 and the aryliodo compound 107 was added and the reaction stirred to produce the protected product 112 with a 77% yield. Deprotection to the corresponding phenol 113 was performed using AICI3. 

Many pyridine-indole compounds are biologically active. A growing number of methods for the preparation of indolylstannanes have been developed. 2-Trialkylstannylindoles, for example, have been synthesized via directed metalation followed by reaction with tin chloride [91-93]. The latest indolylstannane syntheses include Fukuyama s free radical approach to 2-trialkylstannylindoles from novel isonitrile-alkenes [94], and its extension to an isonitrile-alkyne cascade [95]. Assisted by the chelating effect of the SEM group oxygen atom, direct metalation of 1-SEM-indole and transmetalation with BujSnCl afforded 2-(tributylstannyl)-l//-indole 108, which was then coupled with 2,6-dibromopyridine to give adduct 109. 

Table V gives quantitative values of volatile fatty acids and phenolic/indolic compounds found in the aerosol phase and in settled dust of piggeries, respectively. The results from the aerosol phase coincide, particularly as far as acetic acid is concerned. For the investigations of the settled dust the coefficients of variation (CV) and the relative values (%) characterizing the percentage of the single compounds as part of the total amount are quoted. The values are corrected with the dry matter content of the dust. Main components are acetic acid andp-cresol, respectively.

Table VI compares results from air, dust and slurry investigations on VFA and phenolic/indolic compounds in piggeries. Relative values are used. When comparing the results derived from investigations on dust, air or slurry it is necessary to use relative values because of the different dimensions, for experience shows that in spite of large quantitative differences between two samples within the group of carboxylic acids and within the group of phenolic/indolic compounds the proportions of the components remain rather stable (36). In the group of VFA acetic acid is the main component in air, dust, and slurry followed by propionic and butyric acid. The other three acids amount to less than 25%. In the group of phenols/ indoles p-cresol is the main component in the four cited investigations. However, it seems that straw bedding can reduce the p-cresol content in this case phenol is the main component, instead (37).

Table VII Amounts of volatile fatty acids and phenolic/indolic compounds emitted from piggeries by dust and air, respectively. The recognition odour thresholds for butyric acid and p-cresol are included. 1)=HARTUNG (34), 2) =LOGTENBERG and STORK (38), 3)=CORMACK et al. (42), 4) =LEONARDOS et al. (43).

Organonitrogen compounds are quite stable throughout most refining processes. Basic heteroatomic species such as pyridine and quinoline can be found as well as nonbasic pyrrole and indole compounds. 

Stevens, R. W., Nakao, K., Kawamura, K., Uchida, C., Fujiwara, S. Indole compounds as COX-2 inhibitors (Pfizer Inc.), W09905104. 

Small amounts of 2-phenylisatogen (79a) are formed, together with a number of dimeric indole compounds, as a result of the oxidation of 1-hydroxy-2-phenylindole (78a) with a variety of oxidizing agents (Scheme 6). 

The chemical synthesis of the Amanita toxins has presented several problems, in particular those related to the formation of the sulfur bridge. The latter has been explored with model compounds.[2 31 It has been found that the synthesis of the (sulfanyl)indole moiety can be achieved by reacting an indole compound with an alkanesulfenyl chloride. A model tryptathionine compound has been prepared by reacting A-acyl-L-cysteine and /V-acyl-L-tryptophan in the presence of A-chlorosuccinimide in glacial acetic acid at room temperature.[4] The sulfanylation reaction has been subsequently exploited for the selective chemical modification of tryptophan residues in proteins using 2-nitrophenylsulfenyl chlorideJ5 ... 

EXTENSIONS AND COMMENTARY TMA was the very first totally synthetic psychedelic phenethylamine that was found to be active in man, for which there had been any attempt to describe such drug effects in any detail. This was the report of research done in Canada, and it appeared in 1955, six years before my own report on the material. There was an earlier report on TMPEA which is mentioned in the appropriate recipe, but there were few details given. Also there had been interest in reports that adrenalin that had become old and discolored seemed to elicit central effects in man. The oxidation products were identified as the deeply colored indolic compound adrenochrome and the colorless analogue adrenolutin. The controversy that these reports created just sort of died away, and the adrenochrome family has never been accepted as being psychedelic. Noone in the scientific community today is looking in and about the area, and at present this is considered as an interesting historical footnote. But, in any case, they are not phenethylamines and so not part of this book. 

Cyclization of a variety of alkylideneketenes generated by the Meldrum s acid method has provided a number of useful syntheses of nitrogen heterocycles. Thus, for example, FVP of 382 leads to the azepinone 383177, and the indole compounds 384 may give... 

Now let s talk about Mike. While Mike did not make nearly as many compounds as Charles (8 versus 30) some of his contributions appear to be inventive. For example, Mike came up with an alternative route that allowed entry into the indole compounds that will be part of the claimed invention. Assuming the process of making those indole compounds is claimed in the final patent (remember that claims can change throughout the patent application prosecution), then there is no doubt that Mike would be an inventor of that claimed subject matter. However, even if the process itself is not claimed, Mike still is likely a co-inventor because it appears that he designed... 

A. K. Sheinkman, G. V. Samoilenko, S. N. Baranov, P. A. Gurevich, and A. N. Prilepskaya, IVAll-Union Colloquium "Chemistry and Pharmacology of Indole Compounds [in Russian], Shtiintsa, Kishinev (1975), P- 71. 

Auerbach SB, Rutter JJ, Juliano PJ. Substituted piperazine and indole compounds increase extracellular serotonin in rat diencephalon as determined by in vivo microdialysis. Neuropharmacology 1991 30 307-311. 

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