- Reactions of 1,2-bis(1H-indol-2-yl)ethane: Formation of indolo[2,3- c]carbazole and cyclohept[1,2-b:5,4-b']bisindole derivatives
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1,2-Bis(1H-indol-2-yl)ethane (9) has been prepared find converted into indolo[2,3-c]carbazole (8) using palladium acetate in refluxing acetic acid. Reaction of 9 with CoF3 in hot TFA led to isolation of cyclohept[1,2-b:5,4- b']bisindole derivatives 11 and 12, which could be elaborated into further derivatives. Treatment of 9 with orthoesters, aldehydes and ketones under acidic conditions afforded additional bisindoles containing a seven-membered ring. (C) 2000 Elsevier Science Ltd.
- Bergman, Jan,Janosik, Tomasz,Yudina, Larisa,Desarbre, Eric,Lidgren, G.?ran,Venemalm, Lennart
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Read Online
- Carboline derivative/analogue as well as preparation method and application thereof
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The invention belongs to the field of chemical medicines, and provides a compound shown as a formula I or pharmaceutically acceptable salt thereof. The invention also provides analogues of the compound as shown in the formula I in the specification. Biological experiments show that the compound disclosed by the invention has anti-tumor activity and serves as a good tubulin inhibitor; the compound91b has excellent antitumor activity, can effectively promote degradation of tubulin; drug resistance caused by overexpression of beta-tubulin III and P-gp can be eliminated, and a new choice is provided for clinical medication.
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Paragraph 0098-0099; 0102; 0103
(2020/07/13)
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- Copper-catalyzed arene amination in pure aqueous ammonia
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A simple protocol for copper-catalyzed arene amination using aqueous ammonia without any additional ligands and organic coordinating solvents has been developed. The reaction pathway via a Cu(i)/Cu(iii) mechanism is proposed based on the results of control experiments as well as DFT calculations.
- Takagi, Mio,Watanabe, Ayako,Murata, Shigeo,Takita, Ryo
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supporting information
p. 1791 - 1795
(2019/02/20)
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- Synthesis of Novel 3-N-substituted Carbazole Derivatives and Evaluation of their Abilities to Inhibit Platelet Aggregation
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The carbazole moiety exhibits various biological activities, including anticancer, antiviral, anti-inflammatory, and antimicrobial activities; some compounds containing the moiety also inhibit platelet aggregation. In the present study, we synthesized a series of 3-N-substituted carbazole derivatives and evaluated their abilities to inhibit in vitro platelet aggregation induced by collagen (5 μg/mL). Of the synthesized compounds, compound 5q (JSCa15), with a urea linkage within the carbazole framework, exhibited the strongest inhibitory activity (98.25% at 30 μM). Interestingly, reduction of the nitro group of compound 5q to an amine exhibited significantly decreased activity (compound 5r, 5.18% at 30 μM). Also, substitution of the urea moiety of compound 5q with a carbamate moiety resulted in a considerable loss of activity (compound 8a, 5.91% at 30 μM). These results suggest that the urea moieties and nitro groups of 3-N-substituted carbazole derivatives may play key roles in inhibiting in vitro platelet aggregation induced by collagen.
- Kim, Jiseon,Jung, Sang-Hyuk,Yun, Eunju,Cho, Soo-Hyun,Yuseok,Kim, Ji-Eun,Kim, Young-Ho,Myung, Chang-Seon,Song, Gyu-Yong
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supporting information
p. 726 - 728
(2018/05/14)
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- Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
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An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.
- Dalvi, Bhakti A.,Lokhande, Pradeep D.
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p. 2145 - 2149
(2018/05/08)
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- A amino carbazole compound synthesis method (by machine translation)
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The invention discloses amino carbazole compound of preparation method, which belongs to the field of organic synthesis. The method in order to Fe (acac)3 As the catalyst, hydrazine hydrate as the reducing agent, in the alcohol solvent 100 °C -180 °C reduction triazo carbazole compounds prepared amino carbazole compound. The method is simple, easy to control the reaction to ease, less the amount of the catalyst, the catalytic effect is good, few by-products, high reduction efficiency, reduction efficiency up to 86% or more, and the Fe3 O4 With magnetic, it is easy to clean; and has a good industrial application value. (by machine translation)
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Paragraph 0018; 0019
(2017/07/11)
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- Novel functional triamine monomer containing carbazole structure and preparation method and application thereof
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The invention discloses a novel functional triamine monomer containing a carbazole structure and a preparation method and application thereof. Starting from carbazole, the novel functional triamine monomer containing carbazole is prepared through a nitration reaction, a Ullmann coupling reaction, a reduction reaction and other reactions; or starting from mono-halogenated carbazole or dihalogenated carbazole, the novel functional triamine monomer containing carbazole is prepared through a Ullmann coupling reaction, a Suzuki reaction, a reduction reaction and other reactions. The novel functional triamine monomer containing carbazole is simple in synthesis method and technology, high in yield and easy to purify, and therefore the novel functional triamine monomer containing carbazole is suitable for industrial production. The novel functional triamine monomer can be used for synthesizing hyperbranched and functional polyamide, polyimide, polyamide imide, polyester imide and other polymers.
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Paragraph 0105; 0106; 0107
(2016/10/09)
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- Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives
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In this Letter, we investigated the barrier protective effects of 3-N-(MeO)n-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)3-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.
- Ku, Sae-Kwang,Lee, Jee-Hyun,Yuseok,Lee, Wonhwa,Song, Gyu-Yong,Bae, Jong-Sup
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supporting information
p. 4304 - 4307
(2015/11/03)
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- Carbazole N-substituent effect upon DTMA: Stabilizing and photochromic modulating
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Dithienylmaleimide derivatives 7-27 were synthesized by introducing N-substituted carbazole for photo-stabilizing purpose, and the structures were fully confirmed. The photochromism and photo-stability were recorded via UV-vis spectra. Only ortho compounds 8-17 with N-substituents on carbazole moiety showed escalated photochromic change, while compound 7 and the para counterparts 18-27 showed no appreciable photochromism. Additionally, compounds 8-18 exhibited good photo-stability except 17 under 254 nm irradiation. The unstability of 17 may probably due to overrunning hindrance. These photochromic patterns indicated that hindrance and electronic effect mutually paid a decisive influence on the photochromism and photo-stability, which potentially exploited a new way to construct novel photochromic materials with regulable and conceivable performance.
- Huo, Zhiming,Li, Zhipeng,Wang, Tingting,Zeng, Heping
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supporting information
p. 8964 - 8973
(2013/09/23)
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- NEW SUBSTITUTED ARYLSULPHONYLGLYCINES, THE PREPARATION THEREOF AND THE USE THEREOF AS PHARMACEUTICAL COMPOSITIONS
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The present invention relates to substituted arylsulphonylglycines of general formula (I) wherein R, X, Y and Z are defined as in claim 1, the tautomers, enantiomers, diastereomers, mixtures thereof and salts thereof, which have valuable pharmacological properties, particularly the suppression of the interaction of glycogen phosphorylase a with the GL subunit of glycogen-associated protein phosphatase 1 (PP1 ), and their use as pharmaceutical compositions.
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Page/Page column 93; 95
(2008/12/07)
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- Photoreduction of nitro arenes by formic acid in acetonitrile at room temperature
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The formic acid-mediated photoreduction of aromatic nitro compounds in room temperature acetonitrile solutions was investigated. This mild photoreduction can be accomplished in high yield, with wide functional group tolerance and short reaction times (30 min to 1 h), and allows a very clean method for the conversion of nitro arenes to amines. Also, the photoreduction, as a convenient, versatile and general method, applies efficiently to polycyclic and heterocyclic nitro arenes.
- Cors, Ariel,Bonesi, Sergio M.,Erra-Balsells, Rosa
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p. 1555 - 1558
(2008/09/19)
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- Synthesis and alkylation of indolo[3,2-b]carbazoles
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Double Fischer cyclisation was used to prepare indolo[3,2-b]carbazole and its 2,8-di-OMe, OH, Br and F-derivatives. N-monosubstituted derivatives of indolo[3,2-b]carbazole (methyl, hydroxymethyl, dimethylaminoethyl) were obtained starting from 5,11-di-Boc
- Yudina, Larisa N.,Bergman, Jan
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p. 1265 - 1275
(2007/10/03)
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- Alkali-induced Formation of ortho-Semidines from 3-Nitro- and 3-Azocarbazoles - Synthesis of 8,16-Dialkyldiindolo[3,2-a,d]phenazines
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The ortho-semidines 9-alkyl-4-(9-alkylcarbazol-3-ylamino)-3-aminocarbazoles (2a-d) are formed either by reduction of 9-alkyl-3-nitro-carbazoles (1a-d) or of the azo-(6) or the azoxycarbazoles (7) with zinc in alkaline alcoholic solution. It could be shown by cross experiments that the semidines 2 result from an intramolecular rearrangement. The compounds 2a-d are oxidized by air or H2O2 to the 8,16-dialkyldiindolo[3,2-a,d]phenazines (3a-d). Reduction of 1a-c with Raney-alloy affords the 9-alkyl-3-azoxycarbazoles 7a-c in good yields.
- Fanghaenel,Chtcheglov
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p. 731 - 737
(2007/10/03)
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- 2,4-Dimethyl-6H-pyrido[3,2-b]carbazole, an isomer of the antitumor alkaloid ellipticine via the Combes-Beyer reaction
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The synthesis of 2,4-dimethyl-6H-pyrido[3,2-b]carbazole (2a) and of its 9-methoxy (2b) and 9-hydroxy (2c) derivatives via the Combes-Beyer reaction is described. Pyridocarbazole 2a has been obtained by two different routes. In the course of the synthesis of 2b either a partial or a total demethoxylation has been observed depending on the route employed.
- Alunni-Bistocchi,Orvietani,Bittoun,Ricci,Lescot
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p. 817 - 820
(2007/10/02)
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- N-METHYL DERIVATIVES OF 3-AMINOCARBAZOLE
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Methylation of 3-aminocarbazole in presence of sodium hydrogencarbonate yields carbazolyl-3-trimethylammonium iodide, in alkaline media the fourth methyl group is introduced. 3-(N,N-Dimethylamino)-carbazoles were obtained from corresponding methiodides by lithium aluminium hydride reduction or by thermal decomposition.Synthesis of 3-(N-methylamino)-carbazole via tosylamide failed because of 3-(N-methyltosylamino)-9-tosylcarbazole cleaved only one sulfonamide bond.The method involving formylation of 3-aminocarbazole and reduction of the amide gave satisfactory results.
- Kyziol, Janusz B.,Daszkiewicz, Zdzislaw
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p. 839 - 847
(2007/10/02)
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