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Journal articles on the topic 'Hydroxyindoles'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Lee, Jintae, Tarun Bansal, Arul Jayaraman, William E. Bentley, and Thomas K. Wood. "Enterohemorrhagic Escherichia coli Biofilms Are Inhibited by 7-Hydroxyindole and Stimulated by Isatin." Applied and Environmental Microbiology 73, no. 13 (2007): 4100–4109. http://dx.doi.org/10.1128/aem.00360-07.

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ABSTRACT Since indole is present at up to 500 μM in the stationary phase and is an interspecies biofilm signal (J. Lee, A. Jayaraman, and T. K. Wood, BMC Microbiol. 7:42, 2007), we investigated hydroxyindoles as biofilm signals and found them also to be nontoxic interspecies biofilm signals for enterohemorrhagic Escherichia coli O157:H7 (EHEC), E. coli K-12, and Pseudomonas aeruginosa. The genetic basis of EHEC biofilm formation was also explored, and notably, virulence genes in biofilm cells were repressed compared to those in planktonic cells. In Luria-Bertani medium (LB) on polystyrene with

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2

Morton, D. J. "Methoxyindole production by the pineal gland appears to be dependent on the concentration of hydroxy precursors and their affinity for hydroxyindole-O-methyltransferase." Journal of Endocrinology 111, no. 1 (1986): 133–36. http://dx.doi.org/10.1677/joe.0.1110133.

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ABSTRACT Various pineal gland indole metabolites were separated by thin-layer chromatography after organ culture with tritiated serotonin. The amounts of methoxyindoles produced were remarkably constant and female rats in oestrus appeared to produce greater amounts than male rats. The results show a correlation between methylation and the concentration and affinity of the various hydroxyindoles for hydroxyindole-O-methyltransferase. J. Endocr. (1986) 111, 133–136

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3

Chirkova, Zhanna V. "SYNTHESIS OF N-HYDROXYINDOLES." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 60, no. 4 (2017): 4. http://dx.doi.org/10.6060/tcct.2017604.5560.

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The basic synthetic methods for obtaining N-hydroxyindoles were studied. The first method is intramolecular reductive cyclization of ortho-substituted nitroaromatic compounds by various reducing agents. Nitrophenyl acetaldehydes (synthesis by Acheson), N,N-disubstituted amino-2-nitrostyrenes (synthesis by Somei), ortho-nitroketoetheres of different structure or 1-(o-nitroarene)-1-cyanoalkylnitroketones, ortho-nitrophenylacetonitriles were used as substrates for the synthesis of N-hydroxyindoles. Titanium chloride (III), zinc in THF solution of ammonium chloride or in acetic acid, stannous chlo

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4

RAGHAVENDRA, G. JOSHI, S. GADAGINAMATH GURU, and G. PUJAR BASAYYA. "Synthesis and Antimicrobial Activity of some New 4-Isogramines, 4-Arylthiomethyl and 4-Arylazo Derivatives of 5-Hydroxyindoles." Journal of Indian Chemical Society Vol. 71, April 1994 (1994): 175–78. https://doi.org/10.5281/zenodo.5894221.

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Department of Chemistry, Karnatak. University, Dharwad-580 003 <em>Manuscript received 22 March 1993. accepted 3 June 1993</em> Mannich reaction of 5-hydroxyindoles (1-10) .with formaldehyde and secondary amines produced the 4-isogramines (11-48). The nucleophilic displacement of dimethylamine from 4-dimethylaminomethyl-5-hydroxyindoles (11-15) was effected by heating them with thiophenols to get 4-arylthiomethyl-5-hydroxyindoles (49-58). The treatment of 5-hydroxyindoles (1-4 and 6-9) with aryldiazonium salt solution afforded exclusively 4-arylazo-5-hydroxyindoles (59-74). All the compounds w

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5

Yamazaki, Yoshimitsu, and Yasuhiro Kawano. "Inhibitory Effect of Hydroxyindoles and their Analogues on Human Melanoma Tyrosinase." Zeitschrift für Naturforschung C 65, no. 1-2 (2010): 49–54. http://dx.doi.org/10.1515/znc-2010-1-209.

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A recent study showed that N-acylserotonin derivatives have strong inhibitory activity against tyrosinase. To clarify the role of the 5-hydroxy group in the indole ring, 2-, 4-, 5-, 6-, and 7-hydroxyindole and 11 related compounds such as 5-hydroxyindan and 6-hydroxyquinoline were tested for their inhibition of catecholase activity of tyrosinase from human HMVII melanoma cells. 6-Hydroxyindole (5) and 7-hydroxyindole (6) were potent inhibitors, while 5-hydroxyindole (4) was a weaker inhibitor than the above-mentioned compounds (IC50 = 20, 79, 366, and 342 μM for 5, 6, 4, and kojic acid, respec

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6

Somei, Masanori. "1-Hydroxyindoles." HETEROCYCLES 50, no. 2 (1999): 1157. http://dx.doi.org/10.3987/rev-98-sr(h)8.

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7

Kikugawa, Yasuo, Toshiyuki Henmi, and Takeshi Sakamoto. "A New Synthesis of 1-Hydroxyindoles and Spectra of 1-Hydroxyindole." HETEROCYCLES 44, no. 1 (1997): 157. http://dx.doi.org/10.3987/com-95-s2.

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8

Morton, D. J. "Hydroxyindole-O-methyltransferase catalyses production of methoxyindoles in rat pineal gland dependent on the concentration of hydroxy precursors and their affinity for the enzyme." Journal of Endocrinology 115, no. 3 (1987): 455–58. http://dx.doi.org/10.1677/joe.0.1150455.

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ABSTRACT Indole metabolites were separated by thin-layer chromatography following organ culture of rat pineal glands with tritiated tryptophan. Methoxyindole production was shown to differ substantially from results obtained when pineal glands were incubated with radiolabelled serotonin. The correlation between hydroxy- and corresponding methoxyindoles was, however, remarkably similar to previous results, and indicated that in the pineal gland, it is probable that production of methoxyindoles is dependent on the concentration of the various hydroxyindoles and their relative affinities for hydr

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9

HENMI, T., T. SAKAMOTO, and Y. KIKUGAWA. "ChemInform Abstract: A New Synthesis of 1-Hydroxyindoles and Spectra of 1-Hydroxyindole." ChemInform 28, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.199721127.

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10

Hanuszewska, Maria, Magdalena Prusik, and Bogdan Lewczuk. "Embryonic Ontogeny of 5-Hydroxyindoles and 5-Methoxyindoles Synthesis Pathways in the Goose Pineal Organ." International Journal of Molecular Sciences 20, no. 16 (2019): 3948. http://dx.doi.org/10.3390/ijms20163948.

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The aim of this study was to characterize the embryonic ontogeny of 5-hydroxyindoles and 5-methoxyindoles synthesis pathways in the goose pineal organ. The study was performed on embryos aged 14–28 days, which have been incubated under a 12L:12D cycle. The pineal organs were collected for measurements of indole content by HPLC every 6 h on embryonic day (ED) 14, ED 16, ED 18 and ED 22 or every 2 h on ED 24, ED 26 and ED 28. The level of tryptophan showed no significant changes during development and no day-night variations. The content of 5-hydroxytryptophan increased between ED 14 and ED 26.

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11

Somei, Masanori. "ChemInform Abstract: 1-Hydroxyindoles." ChemInform 30, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199925284.

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12

Yokoyama, Masataka, Satoshi Watanabe, and Hidekatsu Hatanaka. "Synthesis ofN-Substituted 5-Hydroxyindoles." Synthesis 1987, no. 09 (1987): 846–48. http://dx.doi.org/10.1055/s-1987-28100.

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13

Wong, Audrey, Jeffrey T. Kuethe, and Ian W. Davies. "A General Synthesis ofN-Hydroxyindoles." Journal of Organic Chemistry 68, no. 25 (2003): 9865–66. http://dx.doi.org/10.1021/jo035351l.

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14

Nudelman, Abraham, Lena Lerman, and Marta Weinstock-Rosin. "An Improved Synthesis of Hydroxyindoles." Synthesis, no. 18 (2004): 3043–46. http://dx.doi.org/10.1055/s-2004-834924.

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15

Lavrenov, S. N., A. M. Korolev, and M. N. Preobrazhenskaya. "O-GLYCOSIDES OFN-HYDROXYINDOLES[1]." Nucleosides, Nucleotides and Nucleic Acids 20, no. 10-11 (2001): 1881–89. http://dx.doi.org/10.1081/ncn-100107199.

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16

Sharapov, Ainur D., Ramil F. Fatykhov, Igor A. Khalymbadzha, et al. "Fluorescent Pyranoindole Congeners: Synthesis and Photophysical Properties of Pyrano[3,2-f], [2,3-g], [2,3-f], and [2,3-e]Indoles." Molecules 27, no. 24 (2022): 8867. http://dx.doi.org/10.3390/molecules27248867.

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This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-f]indole, pyrano[2,3-g]indole, pyrano[2,3-f]indole, and pyrano[2,3-e]indole and photophysical studies in this series. The synthesis of pyrano[3,2-f], [2,3-g], and [2,3-e]indoles involve a tandem of Bischler–Möhlau reaction of 3-aminophenol with benzoin to form 6-hydroxy- or 4-hydroxyindole followed by Pechmann condensation of these hydroxyindoles with β-ketoesters. Pyrano[2,3-f]indoles were synthesized through the Nenitzescu reaction of p-benzoquinone and ethyl aminocrotonates and subsequent Pechmann

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17

Montesinos-Magraner, Marc, Carles Lluna-Galán, Francisco Cernicharo-Toledo, Carlos Vila, Gonzalo Blay, and José R. Pedro. "Enantioselective Friedel–Crafts reaction of hydroxyarenes with nitroenynes to access chiral heterocycles via sequential catalysis." Organic & Biomolecular Chemistry 19, no. 32 (2021): 6990–94. http://dx.doi.org/10.1039/d1ob01238j.

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18

Oura, Hiromu, Yosuke Tashiro, Masanori Toyofuku, et al. "Inhibition of Pseudomonas aeruginosa Swarming Motility by 1-Naphthol and Other Bicyclic Compounds Bearing Hydroxyl Groups." Applied and Environmental Microbiology 81, no. 8 (2015): 2808–18. http://dx.doi.org/10.1128/aem.04220-14.

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ABSTRACTMany bacteria convert bicyclic compounds, such as indole and naphthalene, to oxidized compounds, including hydroxyindoles and naphthols.Pseudomonas aeruginosa, a ubiquitous bacterium that inhabits diverse environments, shows pathogenicity against animals, plants, and other microorganisms, and increasing evidence has shown that several bicyclic compounds alter the virulence-related phenotypes ofP. aeruginosa. Here, we revealed that hydroxyindoles (4- and 5-hydroxyindoles) and naphthalene derivatives bearing hydroxyl groups specifically inhibit swarming motility but have minor effects on

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19

Somei, Masanori, Masakazu Hasegawa, Mutsuko Tabata, Keiichi Satoh, and Fumio Yamada. "A Novel Dimerization of 1-Hydroxyindoles." HETEROCYCLES 43, no. 11 (1996): 2333. http://dx.doi.org/10.3987/com-96-7588.

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20

Chirkova, Zh V., M. V. Kabanova, S. I. Filimonov, A. V. Samet, G. A. Stashina, and T. N. Sudzilovskaya. "Chlorination of 2-substituted 1-hydroxyindoles." Russian Chemical Bulletin 67, no. 6 (2018): 1083–87. http://dx.doi.org/10.1007/s11172-018-2184-6.

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21

Chilin, A., P. Rodighiero, and A. Guiotto. "Isomerization of 4-Aminobenzofurans to 4-Hydroxyindoles." Synthesis 1998, no. 03 (1998): 309–12. http://dx.doi.org/10.1055/s-1998-2024.

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22

Napolitano, Alessandra, Marco d'Ischia, Giuseppe Prota, Thomas M. Schultz, and Leszek J. Wolfram. "Oxidation of 4-, 6- and 7-hydroxyindoles." Tetrahedron 45, no. 21 (1989): 6749–60. http://dx.doi.org/10.1016/s0040-4020(01)89145-6.

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23

Belley, Michel, Daniel Beaudoin, and Gabriel St-Pierre. "A New General Synthesis of N-Hydroxyindoles." Synlett 2007, no. 19 (2007): 2999–3002. http://dx.doi.org/10.1055/s-2007-990970.

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24

Chirkova, Zhanna V., Mariya V. Kabanova, Sergey I. Filimonov, et al. "The C-3 acylation of 1-hydroxyindoles." Tetrahedron Letters 58, no. 8 (2017): 755–57. http://dx.doi.org/10.1016/j.tetlet.2017.01.025.

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25

Bruni, Paolo, Liberato Cardellini, Carla Conti, Elisabetta Giorgini, and Giorgio Tosi. "Molecular interactions between arylazopyridines and N-hydroxyindoles." Monatshefte f�r Chemie Chemical Monthly 121, no. 2-3 (1990): 165–71. http://dx.doi.org/10.1007/bf00809529.

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26

Lavrenov, S. N., A. M. Korolev, and M. N. Preobrazhenskaya. "ChemInform Abstract: O-Glycosides of N-Hydroxyindoles." ChemInform 33, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.200210200.

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27

Hermans, Rebecca, Max Van Hoof, Luc Van Meervelt, and Wim Dehaen. "Exploration of the Divergent Outcomes for the Nenitzescu Reaction of Piperazinone Enaminoesters." Organics 4, no. 2 (2023): 146–63. http://dx.doi.org/10.3390/org4020012.

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The Nenitzescu reaction is a condensation reaction between an enamine and a quinone, which can give rise to a wide variety of reaction products depending on the nature of the starting material and the reaction conditions. The most commonly observed products are 5-hydroxyindoles and 5-hydroxybenzofurans. Both classes are of interest since they are known to possess a variety of promising bioactivities. Despite the high chemodivergency for this reaction, it remains an interesting synthetic strategy thanks to the mild reaction conditions, easily accessible starting materials and simple reaction pr

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28

SOMEI, Masanori. "The chemistry of 1-hydroxyindoles and their derivatives." Journal of Synthetic Organic Chemistry, Japan 49, no. 3 (1991): 205–17. http://dx.doi.org/10.5059/yukigoseikyokaishi.49.205.

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29

Wu, Wang, Zhang, and Jin. "Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins." Molecules 24, no. 21 (2019): 3944. http://dx.doi.org/10.3390/molecules24213944.

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The enantioselective transformations of indoles preferentially take place in the more-reactive azole ring. However, the methods for the enantioselective functionalization of the indole benzene ring are scarce. In this paper, a series of bifunctional (thio)urea derivatives were used to organocatalyze the enantioselective Friedel−Crafts hydroxyalkylation of indoles with isatins. The resulting products were obtained in good yields (65–90%) with up to 94% enantiomer excess (ee). The catalyst type and the substrate scope were broadened in this methodology.

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30

Ozaki, Yutaka, Kyouko Okamura, Ayako Hosoya, and Sang-Won Kim. "A New Approach to 5-Hydroxyindoles from 1,4-Cyclohexanedione." Chemistry Letters 26, no. 7 (1997): 679–80. http://dx.doi.org/10.1246/cl.1997.679.

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31

LaPorte, Matthew, Ki Bum Hong, Jie Xu, and Peter Wipf. "5-Hydroxyindoles by Intramolecular Alkynol–Furan Diels–Alder Cycloaddition." Journal of Organic Chemistry 78, no. 1 (2012): 167–74. http://dx.doi.org/10.1021/jo3022605.

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32

Wróbel, Zbigniew, and Mieczyslaw Ma̧kosza. "Synthesis of 1-hydroxyindoles and indoles from ortho-nitroarylethanes." Tetrahedron 53, no. 15 (1997): 5501–14. http://dx.doi.org/10.1016/s0040-4020(97)00208-1.

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33

Chirkova, Zhanna V., Mariya V. Kabanova, Sergey I. Filimonov, Igor G. Abramov, Alexander V. Samet, and Galina A. Stashina. "The C-3 chlorination of 2-aryl-1-hydroxyindoles." Mendeleev Communications 27, no. 5 (2017): 498–99. http://dx.doi.org/10.1016/j.mencom.2017.09.023.

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34

ACHESON, R. M. "ChemInform Abstract: 1-Hydroxypyrroles, 1-Hydroxyindoles, and 9-Hydroxycarbazoles." ChemInform 22, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199127300.

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35

Panisheva, E. K., �. S. Krichevskii, I. S. Nikolaeva, et al. "Aminoalkyl-5- and -6-hydroxyindoles and their antiviral activity." Pharmaceutical Chemistry Journal 23, no. 2 (1989): 153–55. http://dx.doi.org/10.1007/bf00764467.

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36

CHILIN, A., P. RODIGHIERO, and A. GUIOTTO. "ChemInform Abstract: Isomerization of 4-Aminobenzofurans to 4-Hydroxyindoles." ChemInform 29, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199826153.

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37

Park, Yeon Kyeong, Hyejin Kim, Dong Sun Kim, et al. "Synthesis of New 2,3-Disubstituted 4-Chloro-1-hydroxyindoles." Bulletin of the Korean Chemical Society 36, no. 8 (2015): 2095–100. http://dx.doi.org/10.1002/bkcs.10410.

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38

Chirkova, Zh V., M. V. Kabanova, S. I. Filimonov, and E. A. Smirnova. "General synthetic method for NH-indoles starting from N-hydroxyindoles." Russian Chemical Bulletin 68, no. 6 (2019): 1196–99. http://dx.doi.org/10.1007/s11172-019-2539-7.

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39

SOMEI, M. "ChemInform Abstract: The Chemistry of 1-Hydroxyindoles and Their Derivatives." ChemInform 22, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199140310.

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40

Dinda, Bidyut Kumar, Shyam Basak, and Dipakranjan Mal. "Regiospecific Synthesis of 7-Hydroxyindoles from Pyrroles by Anionic Benzannulation." European Journal of Organic Chemistry 2014, no. 25 (2014): 5521–31. http://dx.doi.org/10.1002/ejoc.201402486.

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41

Ivan, Beatrice Cristina, Mino Rodolfo Caira, and Florea Dumitrascu. "Nenitzescu Indole Synthesis: 1929-2019 Unexpected Formation of a Pyrrole-Azepine Hybrid in the Nenitzescu Indole Synthesis: A Reinvestigation." Revista de Chimie 71, no. 5 (2020): 51–57. http://dx.doi.org/10.37358/rc.20.5.8112.

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The condensation of 1,4-benzoquinones with enamines reported ninety years ago is a name reaction known as the Nenitzescu indole synthesis which has proved to be a very useful method for obtaining both 5-hydroxyindoles and nonindole derivatives. An unexpected compound containing two condensed azepine rings was isolated in 1988 from the reaction between 1,4-benzoquinone and ethyl 3-aminocinnamate performed in 1-butanol. The reinvestigation of the proposed bisazepine structure by X-ray analysis revealed instead a pyrrole-azepine hybrid having the two heterocycles rings connected by a double bond.

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42

Patil, Shivaputra, Renukadevi Patil, and Duane Miller. "Synthetic Applications of the Nenitzescu Reaction to Biologically Active 5-Hydroxyindoles." Current Organic Chemistry 12, no. 9 (2008): 691–717. http://dx.doi.org/10.2174/138527208784567223.

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43

Gostkowski, Michael L., Theodore E. Curey, Eric Okerberg, Tai Jong Kang, David A. Vanden Bout, and Jason B. Shear. "Effects of Molecular Oxygen on Multiphoton-Excited Photochemical Analysis of Hydroxyindoles." Analytical Chemistry 72, no. 16 (2000): 3821–25. http://dx.doi.org/10.1021/ac000278+.

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44

Kadiyala, Veerabhushanam, Perla Bharath Kumar, Sridhar Balasubramanian, and Galla V. Karunakar. "Gold-Catalyzed Synthesis of 6-Hydroxyindoles from Alkynylcyclohexadienones and Substituted Amines." Journal of Organic Chemistry 84, no. 18 (2019): 12228–36. http://dx.doi.org/10.1021/acs.joc.9b02023.

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45

Xiao, Mengjie, Dengfeng Xu, Weihong Liang, Wenyu Wu, Albert S. C. Chan, and Junling Zhao. "Organocatalytic Enantioselective Friedel-Crafts Alkylation/Lactonization Reaction of Hydroxyindoles with Methyleneoxindoles." Advanced Synthesis & Catalysis 360, no. 5 (2017): 917–24. http://dx.doi.org/10.1002/adsc.201701089.

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46

Player, Mark R., and J. Walter Sowell. "Synthesis of 1,3-disubstituted-2-amino-5-hydroxyindoles by reductive aromatization." Journal of Heterocyclic Chemistry 30, no. 1 (1993): 125–28. http://dx.doi.org/10.1002/jhet.5570300122.

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47

Nicolaou, K. C., Sang Hyup Lee, Anthony A. Estrada, and Mark Zak. "Construction of SubstitutedN-Hydroxyindoles: Synthesis of a Nocathiacin I Model System." Angewandte Chemie 117, no. 24 (2005): 3802–6. http://dx.doi.org/10.1002/ange.200500724.

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48

WROBEL, Z., and M. MAKOSZA. "ChemInform Abstract: Synthesis of 1-Hydroxyindoles and Indoles from ortho-Nitroarylethanes." ChemInform 28, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199730115.

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49

OZAKI, Y., K. OKAMURA, A. HOSOYA, and S. W. KIM. "ChemInform Abstract: A New Approach to 5-Hydroxyindoles from 1,4-Cyclohexanedione." ChemInform 28, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199747138.

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50

LaPorte, Matthew, Ki Bum Hong, Jie Xu, and Peter Wipf. "ChemInform Abstract: 5-Hydroxyindoles by Intramolecular Alkynol-Furan Diels-Alder Cycloaddition." ChemInform 44, no. 20 (2013): no. http://dx.doi.org/10.1002/chin.201320129.

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