- Synthesis of 6-formylindolo[3,2-b]carbazole, an extremely potent ligand for the aryl hydrogen (Ah) receptor
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Dichloroacetylation of 2,3-diindolylmethane followed by a tandem cyclization-hydrolysis reaction under acidic conditions gave the title compound.
- Tholander, Joakim,Bergman, Jan
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- Synthesis of 2,3′-diindolylmethanes and substituted indolo[3,2-b]carbazoles
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Three different synthetic routes to substituted 2,3′- diindolylmethanes, and the syntheses of substituted indolo[3,2-b]carbazoles are described. The first rigid proof of an acylation in the 2-position of a 1,3-unsubstituted indole is also presented in the
- Wahlstro?m, Niklas,Stensland, Birgitta,Bergman, Jan
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- Enhancement of chemically-induced HL-60 cell differentiation by 3,3′-diindolylmethane derivatives
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3,3′-Diindolylmethane (DIM, 1) and its derivatives have been prepared, and their enhancing effects on chemically-induced HL-60 cell differentiation were analyzed. Among the prepared compounds, IndDIM (12) showed the most potent enhancing effect on HL-60 cell differentiation induced by chemicals, including retinoids, 1,25-dihydroxyvitamin D3, 12-O-tetradecanoyl phorbol-13-acetate and dimethyl sulfoxide.
- Noguchi-Yachide, Tomomi,Tetsuhashi, Masashi,Aoyama, Hiroshi,Hashimoto, Yuichi
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- Protocols for the Syntheses of 2,2′-Bis(indolyl)arylmethanes, 2-Benzylated Indoles, and 5,7-Dihydroindolo[2,3- b]carbazoles
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The electrophilic substitution reaction of 4,7-dihydroindole with aryl-aldehydes as an electrophilic partner followed by an oxidation step to deliver 2,2′-bis(indolyl)arylmethanes was studied for the first time. The reaction afforded regioselectivity at the 2,2′-positions of indole in an operationally simple and inexpensive procedure with a variety of substrates. To the best of our knowledge, this is the first set of examples of 2,2′-bis(indolyl)arylmethanes obtained in a substituent-free manner. A facile method from dipyrromethanes to the corresponding 2-benzylindoles was also reported. In addition, 2,2′-bis(indolyl)arylmethanes were converted to 5,7-dihydroindolo[2,3-b]carbazoles.
- Lafzi, Ferruh,Kilic, Haydar,Saracoglu, Nurullah
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p. 12120 - 12130
(2019/10/11)
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- PHOTOPROTECTIVE COMPOSITIONS CONTAINING MALASSEZIA-DERIVED COMPOUNDS AND/OR CHEMICAL ANALOGS THEREOF
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The present invention relates to compounds, compositions, and methods for modulating skin pigmentation and treating or preventing UV-induced skin damage, erythema, aging of the skin, sunburn, and hyperpigmentation in a subject. The compounds, compositions, and methods of the present invention generally involve Malassezia-derived compounds, including malassezin and indirubin, and/or chemical analogs thereof. Other applications of the compounds and compositions disclosed herein include, but are not limited to, improving hyperpigmentation caused by a hyperpigmentation disorder, inducing melanocyte apoptosis, and modulating arylhydrocarbon receptor (AhR) activity, melanogenesis, melanin production, melanosome biogenesis, melanosome transfer, melanocyte activity, and melanin concentration.
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- MALASSEZIN AND ANALOGS THEREOF AS SKIN BRIGHTENING AGENTS
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The present invention relates to compounds, compositions, and methods for brightening skin. The compounds, compositions, and methods of the present invention generally involve compounds produced by a Malassezia yeast, and chemical analogs thereof. In addi
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- Indolo[3,2-b]carbazole structure unit-containing piezochromic material and application thereof
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The invention discloses an indolo[3,2-b]carbazole structure unit-containing piezochromic material. The piezochromic material has a structural formula shown in the description; and in the description, R represents a hydrogen atom, a methyl group, an ethyl group or an isopropyl group, n represents 1, 2 or 3, and Ar represents one of groups also shown in the description. The invention also discloses an application of the indolo[3,2-b]carbazole structure unit-containing piezochromic material in electroluminescent devices. The piezochromic material has the advantages of no toxicity, simple preparation technology, low cost and excellent piezochromic performance.
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Paragraph 0059; 0072
(2017/08/30)
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- SYNTHESIS OF DIINDOLYLMETHANES AND INDOLO[3,2-B]CARBAZOLES, COMPOUNDS FORMED THEREBY, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or
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Paragraph 0124-0125
(2016/03/05)
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- Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b ]carbazoles
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Various diindolylmethanes were prepared from propargylic ethers and substituted indoles via a platinum-catalyzed tandem indole annulation/arylation cascade. The resulting diindolylmethanes could be converted to natural product malassezin by formylation or indolo[3,2-b]carbazoles by cyclization.
- Shu, Dongxu,Winston-Mcpherson, Gabrielle N.,Song, Wangze,Tang, Weiping
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supporting information
p. 4162 - 4165
(2013/09/12)
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- ANALOGS OF INDOLE-3-CARBINOL AND THEIR USE AS AGENTS AGAINST INFECTION
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Compounds useful as antibacterial agents are provided. The compounds are analogs of indole-3-carbinol and have a backbone selected from dihydroindolo[2,3-b]carbazole, 2,2'-diindolylmethane, 2',3-diindolylmethane, and 3,3'-diindolylmethane. The compounds are useful therapeutic and prophylactic treatment of bacterial infections in mammals. Methods of synthesis of the compounds are provided, as are pharmaceutical compositions containing the compounds.
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Page/Page column 65
(2010/04/23)
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- Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
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Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of indole-3-carbinol metabolites wherein the structures and substituents of the compounds are selected to enhance the compounds' overall efficacy, particularly with respect to therapeutic activity, oral bioavailability, long-term safety, patient tolerability, and therapeutic window. The compounds are useful not only in treatment of cancer but also in prevention of cancer. One preferred class of the novel compounds have the structure of formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, and R12 are defined herein. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.
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Page/Page column 20-21
(2008/06/13)
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- Malassezin - A novel agonist of the Arylhydrocarbon receptor from the yeast Malassezia furfur
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The yeast Malassezia furfur converts tryptophan into several indole compounds. One of these, malassezin, was identified as (2- 1H-indol-3-ylmethyl)-1H-indole-3-carbaldehyde (1). It was synthesized from N-Boc-indole-3-carbaldehyde in five steps with 12% ov
- Wille, Gregor,Mayser, Peter,Thoma, Wiebke,Monsees, Thomas,Baumgart, Annette,Schmitz, Hans-Joachim,Schrenk, Dieter,Polborn, Kurt,Steglich, Wolfgang
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p. 955 - 960
(2007/10/03)
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- Syntheses of 6-substituted indolo[3,2-b]carbazoles, including 6- formylindolo[3,2-b]carbazole, an extremely efficient ligand for the TCDD (Ah) receptor
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A number of 6-substituted indolo[3,2-b]carbazoles have been synthesized using 2,3-diindolylmethane 5 as a crucial precursor. Most notably, 6- formylindolo[3,2-b]carbazole 3 has been synthesized, and thereby a previously assigned structure has been confirmed. 6-Formylindolo[3,2-b]carbazole 3 is an extremely efficient ligand for the TCDD (Ah) receptor. A much improved synthesis of 2,3-diindolylmethane 5 has also been developed.
- Tholander, Joakim,Bergman, Jan
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p. 6243 - 6260
(2007/10/03)
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- Electrophilic Substitution in Indoles. Part 15. The Reaction between Methylenedi-indoles and p-Nitrobenzenediazonium Fluoroborate.
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p-Nitrobenzenediazonium fluoroborate (2 mol equiv.) reacts under aqueous conditions with 3,3'-methylenedi-indole (9a) and N,N-dimethyl-3,3'-methylenedi-indole (9c) to give, in each instance, high yields of the corresponding 3-p-nitrophenylazoindoles (13a) and (13c).When 1 mol equiv. of diazonium salt is used, the methylenedi-indole (9a) gives 1 mol equiv. of the 3-(p-nitrophenylazo)indole (13a) and some methylenedi-indole is recovered.In dry acetonitrile, 3,3'-methylenedi-indol gives, with 1 mol equiv. of diazonium salt, a mixture of 3-(p-nitrophenylazo)indole (13a) (0.45 mol equiv.) and the unstable 3-(p-nitrophenylazo)-2,3'-methylenedi-indole (16a) (0.42 mol equiv.).The latter was also synthesized from indole-2,3-dione and chloroacetylindole via indol-2-yl, indol-3-yl, and 2,3'-methylenedi-indole.Essentially similar results were obtained with N,N-dimethyl-3,3'-methylenedi-indole (9c) and the diazonium salt.The unsymmetrical compounds 3-indol-3-ylmethyl-1,2-dimethylindole (9d) and 3-indol-3-ylmethyl-2-methylindole (9e), with 2 mol equiv. of diazonium salt in aqueous solution, each give high yields of the two possible 3-p-nitrophenylazoindoles.With 1 mol equiv. of the diazonium salt only the 2-methyl-3-p-nitrophenylazo derivatives are obtained, together with 3,3'-methylenedi-indole.In dry acetonitrile, with either 1 or 2 mol equiv. of diazonium salt, the unsymmetrical methylenedi-indoles each give only the 2-methyl-3-p-nitrophenylazoindoles.The displacement of an indolylmethyl residue from methylenedi-indoles by the diazonium salt, and the formation of the azo coupled rearrangement product (16a) provides firm evidence that azo coupling of 3-alkylindoles to give the 2,3-disubstituted indoles proceeds by initial attack at the 3-position followed by rearrangement, rather than by direct substitution at the 2-position.
- Jackson, Anthony H.,Prasitpan, Noojaree,Shannon, Patrick V. R.,Tinker, Alan C.
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p. 2543 - 2552
(2007/10/02)
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