L- indole

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

Triisopropylsilyl group of 2-[l-triisopropylsilyl-l//-indol-6-yl)perhydro-pyrido[l,2-u]pyrazine was removed by treatment with BU4NF in THF (01MIP5). 

Acetyl-3-(perhydropyrido[l, 2-u]pyrazin-2-yl)-1 //-indole was deacety-lated in boiling MeOH in the presence of NaOH, and the product, 3-(perhydropyrido[l,2-u]pyrazin-2-yl)-l//-indole was N-acylated with different arylsulfonyl chloride in THF at 0°C in the presence of (Me3Si)2NNa (99MIP12, 01USP6251893)). 

L//-Indole, 3<2-phenyl-l, 3-dithian-2-yl), 10 Indoles, 34 Indoles, 3-acyl-, 8 Indoles, 3 -alkyl, 8 Isocyanate, chlorosulfonyl [Sulfuryl chlonde isocyanate], 41 Isocyanate,2-propyl- [Propane, 2-iso-cyanato-], 96... 

CN ( )-l-[(l,l-dimethylethyl)amino]-3-[(2-methyl-l//-indol-4-yl)oxy]-2-propanolbenzoate (ester)... 

CN l-[3-[( 1 -Methylethyl)amino]-2-pyridinyl]-4-[[5-[(methylsulfonyl)amino]- l//-indol-2-yl]-carbonyljpiperazine monomethanesulfonate... 

CN 2-([(]-(4-chJorobenzoy])-5-methoxy-2-methyl-l//-indol-3-yl]acet>i]amino]-2-deoxy-D-glucose... 

RN 26807-65-8 MF C.fiHifiClNjOjS MW 365.84 EINECS 248-012-7 CN 3-(aminosulfonyl)-4-chloro-Al-(2,3-dihydro-2-methyl-l//-indol-1 -yl)benzamide... 

CN 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-l-piperazinyl)ethyl]-l//-indole... 

CN (R)-(l-methyl-l//-indol-3-yl)(4,5,6,7-tetrahydro-177-benzimidazol-5-yl)methanone monohydrochloride ramosetron... 

CN l-[2-[4-[5-chloro-l-(4-fluorophenyl)-l//-indol-3-yl]-l-piperidinyl]ethyl]-2-imidazolidinone... 

CiftHijNOjS 42399-49-5) see Diltiazem (4S)-3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2- ] 1 2-thiazme-6-sulfonainide 1,1-dioxide ( 10 16 2 65 154127-42-1) see Brinzolamide ( )-3 ,4"-dihydro-r-hydroxy-7 -methoxyspiro[cyclOpen-tane-l,2 (l -naphthalene]-r-acetonitrile (CirHjiNO 57 797-09-9) see Butorphanol 23-dihydro-3 hydroxy-l methyl-l indole-5,6-dione (C9H9NO3 54-06-8) see Caibazochrome... 

C jH2,NOSi) see Indanorex (lS-cii)-2,3-dihydro-l//-indene-l,2-diol (G7H10O2 6752S-22-7) see Indinavir sulfate (laS)-la,6a-dihydro-6//-indenori,2-6]oxirene (CgHjO 67528-26-1) see Indinavir sulfate (2,3-dihydro-l//-inden-4-yl)carbamimidothioic acid methyl ester monohydriodide (C, H 1N2S 40507-77-5) see Indanazoline 23-dibydro-l//-indole-2-carboxylic acid ethyl ester (C iH, N02 50501-07-0) see Perindopril... 

C2 H23N303S 66338-99-6) see Ceftazidime 2-etbyl-5-hydroxy-iV-(2-(l//-indol-3-yl)ethyl]pentanamide (C H24N202 52250-53-0) see Vincamine ethyl 2-hydroxyisobutyrate... 

C20H23NO4S 80138-94-9) see Levocabastine tranx-3-methyl-l-[(4-methylphenyl)sulfonyll-4-phenyl-4-piperidinecarboxylic acid phenylmethyl ester (C27H29NO4S 104907-69-9) see Levocabastine ( )-JV-methyl-2-[3-(l-methyl-4-piperidinyl)-l//-indol-S-yllethenesulfonamide... 

CjiHiyN iO . 9/022-35-0) see Mosapramine (25, 3a/f,7a5)>octahydro-l//-indole-2-carboxylic acid (C9H15NO2 145438-94-4) see Trandolapril (25,3a5 7a5)-octahydroindole-2-carboxylic acid (CyHi,N02 80875-98-5) see Perindopril [2S-(2a,3aa,7aP)]-octahydro-l/f-indole-2-carboxylic acid phenylmethyl ester... 

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. 

Adapting Gribble s method for synthesizing indol-3-yl triflate [37], Mdrour et al converted 2-formyl- l-(phenylsulfonyl)- l//-indole (31) to indol-2-yl triflate 32 in two steps. 32 was subsequently coupled with benzofuryl-2-boronic acid to furnish 2-benzofurylindole 33 [38, 39]. In another case, 2-bromoacetaniline was coupled with 2-formyl-3-furylboronic acid 35 [40]. The resulting Suzuki coupling adduct underwent a spontaneous cyclization, forming tricyclic furo[2,3-c]quinoline 36. 

Recently, Li successfully conducted the Suzuki and Stille reactions on the pyrazine ring of 3-bromoquinoxalin-2-ylamines [51]. Indolylquinoxaline 92 was obtained from the union of 3-bromoquinoxalin-2-ylamine 90 and l-phenylsulfonyl-2-tri-n-butylstannyl-l//-indole (91). A wide variety of heterocyclic stannanes bearing various functional groups underwent Stille coupling with 90 under the same conditions to give the corresponding adducts in 72-98% yields. 

Diethyl 2-hydro xy-2-(l-mcthyl-l//-indol-3-ylmetliyl)propanedioate (10 f) ... 

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... 

This enzyme [EC 4.1.1.48] catalyzes the conversion of l-(2-carboxyphenylamino)-l-deoxy-D-ribulose 5-phos-phate to generate l-(indol-3-yl)glycerol 3-phosphate, carbon dioxide, and water. In some organisms, this enzyme is part of a multifunctional protein together with one or more components of the system for the biosynthesis of tryptophan (/.e., anthranilate synthase, anthranilate phosphoribosyltransferase, tryptophan synthase, and phosphoribosylanthranilate isomerase). 

This pyridoxal-phosphate-dependent enzyme [EC 4.2.1.20] catalyzes the reaction of L-serine with l-(indol-3-yl)glycerol 3-phosphate to produce L-tryptophan and glyceraldehyde 3-phosphate. The enzyme will also catalyze (a) the conversion of serine and indole into tryptophan and water and (b) conversion of indoleglycerol phosphate into indole and glyceraldehyde phosphate. 

Mahboobi et al. described a novel synthesis of staurosporinone (293) (791). The intermolecular Michael addition of l-(indol-3-yl)-2-nitroethene (1472) to methyl indol-3-ylacetate (1313) provided with high diastereoselectivity methyl 2,3-bis(indol-3-yl)-4-nitrobutanoate (1473). Catalytic hydrogenation and lactamization afforded 2,3-bis(indol-3-yl)-y-butyrolactam (1474) in 87% yield. Oxidative cyclization of the ds-lactam 1474 with DDQ in the presence of catalytic amounts of p-TsOH led to staurosporinone (293) (791) (Scheme 5.249). 

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