Indoles Indole-3-carbinol

Indoles Indole-3-carbinol, indole-3-acetonitrile, l-tryptophan Cruciferous vegetables (including brussel sprouts, kale, cabbage, broccoli, cauliflower, spinach, watercress, turnip, radish) Pungent flavor... 

A similar reaction affords a simple route to cyclopent[b]indoles. Indole-3-carbinol (68) reacts with j8-methylstyrene in the presence of titanium tetrachloride to give compound (70) <93TL8527>. The presumed four-membered spiroindolenine (69) in this sequence receives support from the observation that the conversion of the D-tryptophan derived compound (71) to its mesylate leads to the formation of racemic cyclopent[b]indole (73) via the achiral intermediate (72) (Scheme 17) <93TL439>. 

Se-enriched broccoli was not more effective (Table 1) than enriched garlic (3) in reducing the number of tumors this Ending proves that the combination of sulforaphane, indole carbinol, and chlorophyll with Se did not provide additional protection against mammary tumors. (Adapted from Finley... 

R = -C7His) first with TFA/TEA mixture in chloroform and then via addition of NaOH in EtOH provided the isomeric 2-vinylindoles 743 and 744 (NMR ratio of 2 1) in which the indole was desulfonylated. In the case of the corresponding transformation of the indole carbinols 742 when R = Ar or HetAr other conditions were necessary. Direct elimination of water, and hydrolysis of carbinols 742 with ethanolic aqueous NaOH resulted in the formation of the aromatic 2-vinylindoles 745. 

Jellinck PH, Forkert PG, Riddick DS, Okey AB, Michnovicz JJ, Bradlow HL. 1993. Ah receptor binding properties of indole carbinols and induction of hepatic estradiol hydroxylation. Biochem. Pharmacol. 45 1129-36... 

Scheme 7 Oxidation of indole carbinols using the Fe(N03)3-9H20/TEMP0 catalytic system. ...

Indole derivatives with carbonyl units (Scheme 7) have been found in natural products, possess versatile bioactivity and are important intermediates in many organic syntheses. The introduction of the carbonyl moieties to indoles significantly enhances their reactivity and can be achieved by oxidation of indole carbinols with Fe(N03)3-9H20/TEMP0/NaCl at room temperature and atmospheric pressure of dioxygen, using toluene as a solvent. NaCl is an important accelerator for the oxidation, reducing the reaction time from 15 to 2 h however, the role of Cl is not quite clear. 

Chemistry and biological properties of polyfunctional indole-3-carbinol derivatives [l-(indol-3-yl)glycerols and related compounds, (3-hydroxytryptamines, and ascorbigens] 95F369. 

D. F. Birt, B. Walker, M. G. Tibbels, and E. Bresnick, Anti-mutagenesis and antipromotion by apigenin, robinctin and indole-3-carbinol. Car.sinogenesis 7 959 (1986). 

Dash wood RH, Arbogst DN, Fong AT, Pereira C, Hendricks JD and Baily GS. 1989. Quantitative interrelationships between aflatoxin B1 carcinogen dose, indole-3-carbinol anto-carcinogen dose, target organ DNA adduction and final tumor response. Carcinogenesis 10 175-181. 

Tanaka T, Mori Y, Morishita Y, Hara A, Ohno T, Kojinna T and Mori H. 1990. Inhibitory effect of sinigrin and indole-3-carbinol on diethylenitrosamine-induced hepatocarcinogenesis in male AC/N rats. Carcinogenesis 11 1403—1406. 

Gao X, Petroff BK, Oluola O, Georg G, Terranova PF, Rozman KK (2002) Endocrine disruption by indole-3-carbinol and tamoxifen blockage of ovulation. Toxicol Appl Pharmacol 183 179-188... 

Triflates also undergo Heck reactions and Gribble and Conway reported several such couplings of l-(phenylsulfonyl)indol-3-yl triflate (34) to afford 3-vinylindoles 224 [183]. Cyclohexene, allyl bromide, and methyl propiolate failed to react under these conditions, but triphenylphosphine afforded 225 in excellent yield (93%), and divinyl carbinol yielded the rearranged enal 226 (82% yield). 

Indenopyrene, see Indeno[l,2,3-crf pyrene l//-Indole, see Indole Indolene, see Indoline Inexit, see Lindane Inhibisol, see 1,1,1-Trichloroethane Insecticide 497, see Dieldrin Insecticide 4049, see Malathion Insectophene, see a-Endosulfan, p-Endosulfan Intox 8, see Chlordane Inverton 245, see 2,4,5-T lodomethane, see Methyl iodide IP, see Indeno[l,2,3-crf pyrene IP3, see Isoamyl alcohol Ipaner, see 2,4-D IPE, see Isopropyl ether IPH, see Phenol Ipersan, see Trifluralin Iphanon, see Camphor Isceon 11, see Trichlorofluoromethane Isceon 122, see Dichlorodifluoromethane Iscobrome, see Methyl bromide Iscobrome D, see Ethylene dibromide Isoacetophorone, see Isophorone a-Isoamylene, see 3-Methyl-l-butene Isoamyl ethanoate, see Isoamyl acetate Isoamylhydride, see 2-Methylbutane Isoamylol, see Isoamyl alcohol Isobac, see 2,4-Dichlorophenol Isobenzofuran-l,3-dione, see Phthalic anhydride 1,3-Isobenzofurandione, see Phthalic anhydride IsoBuAc, see Isobutyl acetate IsoBuBz, see Isobutylbenzene Isobutane, see 2-Methylpropane Isobutanol, see Isobutyl alcohol Isobutene, see 2-Methylpropene Isobutenyl methyl ketone, see Mesityl oxide Isobutyl carbinol, see Isoamyl alcohol Isobutylene, see 2-Methylpropene Isobutylethylene, see 4-Methyl-l-pentene Isobutyl ketone, see Diisobutyl ketone Isobutyl methyl ketone, see 4-Methyl-2-pentanone Isobutyltrimethylmethane, see 2,2,4-Trimethylpentane Isocumene, see Propylbenzene Isocyanatomethane, see Methyl isocyanate Isocyanic acid, methyl ester, see Methyl isocyanate Isocyanic acid, methylphenylene ester, see 2,4-Toluene-diisocyanate... 

NT218 Arif, J. M., C. G. Gairola, G. J. Kelloff, R. A. Lubet, and R. C. Gupta. Inhibition of cigarette smoke-related DNA adducts in rat tissues by indole-3-carbinol. Mutat Res 2000 452(1) 11-18. 

Serum sex hormones effect. DION (300 mg androstenedione, 150 mg dehydro-epiandrosterone, 540 mg saw palmetto, 300 mg indole-3-carbinol, 625 mg chrysin, 750 mg Tribulus terrestris), administered daily to healthy 30- to 59-year-old men for 28 days, produced no change in serum concentrations of total T and PSA. DION increased the concentrations of serum androstenedione (342%), free T (38%), DHT (71%), and estradiol (103%). Serum high-density lipoprotein (HDL) cholesterol concentrations were reduced by 5 mg/dL in DION (p < 0.05). Increases in serum free T (r = 0.01), androstenedione (r = 0.01), DHT (r = 0.03), or estradiol (r = 0.07) concentrations in DION were not related to age. The ingestion of androstenedione combined with herbal products increased serum-free T concentrations in older men, but herbal products did not prevent the conversion of... 

The side chain on the fused five-membered ring can, interestingly, form part of a piperidine or piperazine ring. The scheme for preparing the first of these takes advantage of the reactivity of the indole 3 position. The relatively weak base, sodium hydroxide, thus catalyzes the addition of bromoindole (16-1) to the carbonyl group in 4-iV-methylpiperidone (16-2) to afford carbinol (16-3). This product dehydrates in the presence of acid catalytic reduction of the thus-produced olefin then affords the... 

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