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Journal articles on the topic 'Carbazoles (6H)'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Singha, Raju, Atiur Ahmed, Yasin Nuree, Munmun Ghosh, and Jayanta K. Ray. "KOtBu mediated efficient approach for the synthesis of fused heterocycles via intramolecular O-/N-arylations." RSC Advances 5, no. 62 (2015): 50174–77. http://dx.doi.org/10.1039/c5ra07532g.

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2

Golubeva, I. S., N. P. Yavorskaya, L. V. Ektova, et al. "ANTITUMOR ACTIVITY OF SOME DERIVATIVES OF INDOLO[2,3-A]CARBAZOLES N-GLYCOSIDES WITH XYLOSE CARBOHYDRATE RESIDUE." Russian Journal of Biotherapy 19, no. 4 (2020): 86–93. http://dx.doi.org/10.17650/1726-9784-2020-19-4-86-93.

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Introduction. The search for new antineoplastic agents in a series of indolo[2,3-a]-carbazole derivatives is an urgent and promising direction, since compounds with antitumor activity have been found in this class. In the chemical fusion laboratory, N.N. Blokhin National Medical Research Center оf the Ministry of Health of Russia has developed an original and effective method for the synthesis of glycosides of indolo[2,3-a]-pyrrolo[3,4-c]carbazoles, which makes it possible to synthesize derivatives of N-glycosides of indolo[2,3-a]carbazoles with different substituents in the heterocyclic parts

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3

Modi, Sandeep P., Todd McComb, Abdel-Hadi Zayed, R. Christopher Oglesby, and Sydney Archer. "Synthesis of 6h-pyrido[4,3-b]carbazoles." Tetrahedron 46, no. 16 (1990): 5555–62. http://dx.doi.org/10.1016/s0040-4020(01)87753-x.

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4

MODI, S. P., T. MCCOMB, A. H. ZAYED, R. C. OGLESBY, and S. ARCHER. "ChemInform Abstract: Synthesis of 6H-Pyrido(4,3-b)carbazoles." ChemInform 22, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199101222.

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5

Yaqub, Ghazala, Abdul Hannan, Erum Akbar, et al. "Synthesis, Antibacterial, and Antifungal Activities of Novel Pyridazino Carbazoles." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/818739.

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Strategy to synthesize novel carbazole, that is, 2,3-dihydro-2-phenyl-6H-pyridazino[4, 5-b]carbazole-1,4-dione (2), is developed as key reaction. This novel compound showed ideal reactivity toward different functional groups like methyl, carboxylic, nitro, piperazine, and amine; thus series of its derivatives are synthesized sequentially with the aim to fuel up the carbazole compounds with new versatile derivatives. All compounds were investigated for their activity against bacteria (MRSA andS. typhi) and fungi (Candida albicans). Among tested compounds3,6, and8exhibited pronounced antibacteri

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6

Trécourt, François, Marc Mallet, Florence Mongin, and Guy Quéguiner. "Synthesis of 11H-Pyrido[2,3-a]carbazoles and 6H-Pyrido[3,2-b]carbazoles from 8-methoxy bromoquinolines." Tetrahedron 51, no. 43 (1995): 11743–50. http://dx.doi.org/10.1016/0040-4020(95)00726-o.

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7

Archer, Sydney, Bruce S. Ross, Livia Pica-Mattoccia, and Donato Cioli. "Synthesis and biological properties of some 6H-pyrido[4,3-b]carbazoles." Journal of Medicinal Chemistry 30, no. 7 (1987): 1204–10. http://dx.doi.org/10.1021/jm00390a014.

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8

Moinet-Hedin, V., T. Tabka, F. Sichel, et al. "In vitro cytotoxicity of carbazole derivatives. V. 9-Halogeno-substituted 5,11-dimethyl-6H-pyrido[3,2-b]carbazoles." European Journal of Medicinal Chemistry 32, no. 2 (1997): 113–22. http://dx.doi.org/10.1016/s0223-5234(97)87537-x.

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9

TRECOURT, F., M. MALLET, F. MONGIN, and G. QUEGUINER. "ChemInform Abstract: Synthesis of 11H-Pyrido(2,3-a)carbazoles and 6H-Pyrido(3,2-b) carbazoles from 8-Methoxy Bromoquinolines." ChemInform 27, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199609151.

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10

Modi, Sandeep P., Meged A. Michael, Sydney Archer, and James J. Carey. "An efficient synthesis of C-11 substituted 6H-pyrido[4,3-b]carbazoles." Tetrahedron 47, no. 33 (1991): 6539–48. http://dx.doi.org/10.1016/s0040-4020(01)82308-5.

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11

Moinet-Hedin, V., T. Tabka, P. Gauduchon, et al. "In vitro cytotoxicity of carbazole derivatives IV. 5,11-Dimethyl-6H-pyrido[3,2-b]carbazoles substituted on the pyridine ring." European Journal of Medicinal Chemistry 28, no. 9 (1993): 721–26. http://dx.doi.org/10.1016/0223-5234(93)90032-a.

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12

MOINET-HEDIN, V., T. TABKA, F. SICHEL, et al. "ChemInform Abstract: In vitro Cytotoxicity of Carbazole Derivatives. Part 5. 9-Halogeno- Substituted 5,11-Dimethyl-6H-pyrido(3,2-b)carbazoles." ChemInform 28, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199725140.

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13

Praly-Deprez, Isbelle, Christian Rivalle, Christiane Huel, Jean Belehradek, Claude Paoletti, and Emile Bisagni. "Synthesis of 11-amino-substituted-9-methoxy-5-methyl-6H-pyrido[4,3-b]-carbazoles." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (1991): 3165. http://dx.doi.org/10.1039/p19910003165.

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14

MODI, S. P., M. A. MICHAEL, S. ARCHER, and J. J. CAREY. "ChemInform Abstract: An Efficient Synthesis of C-11 Substituted 6H-Pyrido(4,3-b)carbazoles." ChemInform 22, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199148251.

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15

Hogan, Iain, Paul D. Jenkins, and Malcolm Sainsbury. "The chemistry of the pyrido[4,3-b]carbazoles part 15 the synthesis of unsymmetrically 1,4-disubstituted carbazoles and their use in the synthesis of 6H-Pyrido-[4,3-b]carbazoles." Tetrahedron 46, no. 8 (1990): 2943–64. http://dx.doi.org/10.1016/s0040-4020(01)88387-3.

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16

Molina, Pedro, Pilar M. Fresneda, and Pedro Almendros. "Fused carbazoles by tandem Aza Wittig/electrocyclic ring closure. Preparation of 6H-pyrido[4,3-b] carbazole, 11H-pyrido[4,3-a]carbazole and 11H-pyrido[3,4-a]carbazole derivatives." Tetrahedron 49, no. 6 (1993): 1223–36. http://dx.doi.org/10.1016/s0040-4020(01)85813-0.

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17

Bisagni, Emile, Marilys Rautureau, and Christiane Huel. "1-Functionalized 5,6-Dimethyl-6H-pyrido[4,3-b]carbazoles (Ellipticines) and Analogues: A New Rapid Synthesis." HETEROCYCLES 27, no. 7 (1988): 1671. http://dx.doi.org/10.3987/com-88-4543.

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18

LANCELOT, JEAN-CHARLES, JEAN-MARIE GAZENGEL, NGUYENHUY DUNG, and MAX ROBBA. "Synthesis of 3-amino-2-cyanocarbazole and 3,4-dihydro-4-oxo-6H-pyrimidino(5,4-b)carbazoles." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 2 (1985): 842–46. http://dx.doi.org/10.1248/cpb.33.842.

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19

MOLINA, P., P. M. FRESNEDA, and P. ALMENDROS. "ChemInform Abstract: Fused Carbazoles by Tandem Aza Wittig/Electrocyclic Ring Closure. Preparation of 6H-Pyrido(4,3-b)carbazole, 11H-Pyrido(4,3-a)carbazole and 11H-Pyrido(3,4-a)carbazole Derivatives." ChemInform 24, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199324193.

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20

PRALY-DEPREZ, I., C. RIVALLE, C. HUEL, J. BELEHRADEK, C. PAOLETTI, and E. BISAGNI. "ChemInform Abstract: Synthesis of 11-Amino-substituted-9-methoxy-5-methyl-6H-pyrido(4,3-b) carbazoles (XII)." ChemInform 23, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199213222.

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21

Ratcliffe, Andrew J., Malcolm Sainsbury, Andrew D. Smith, and David I. C. Scopes. "Chemistry of 6H-pyrido[4,3-b]carbazoles. Part 12. Synthesis of potential bisintercalating drugs bearing two ellipticine units." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1988): 2933. http://dx.doi.org/10.1039/p19880002933.

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22

Sainsbury, Malcolm, Andrew D. Smith, Kuok K. Vong, and David I. C. Scopes. "Chemistry of 6H-pyrido[4,3-b]carbazoles. Part 13. Syntheses of ring-A- and ring-D-substituted ellipticines." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1988): 2945. http://dx.doi.org/10.1039/p19880002945.

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23

Baeckvall, Jan E., and Niklas A. Plobeck. "New synthesis of the 6H-pyrido[4,3-b]carbazoles ellipticine and olivacine via cycloaddition of 2-phenylsulfonyl 1,3-dienes to indoles." Journal of Organic Chemistry 55, no. 15 (1990): 4528–31. http://dx.doi.org/10.1021/jo00302a013.

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24

Awasthis, Keshav K., Ruchika Chakrabarty, and Anil K. Saxena. "A CONVENIENT ROUTE FOR THE SYNTHESIS OF CIS-1-SUBSTITUTED 1,2,3,4,4a,5,11,11a-OCTAHYDRO-6H-PYRIDO[3,2-b]CARBAZOLES AND 4-SUBSTITUTED 1,2,3,4,4a,5,6,11c-OCTAHYDRO-7H-PYRIDO[2,3-c] CARBAZOLES AS POTENT DOPAMINE AGONISTS." Medicinal Chemistry Research 13, no. 8-9 (2004): 758–69. http://dx.doi.org/10.1007/s00044-004-0115-6.

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25

Nguyen, Chi Hung, Émile Bisagni, and Jean-Marc Lhoste. "Synthèse de dérivés N-5 substitués des 5H-pyrido[4,3-b]benzo[f]indoles, isomères des 6H-pyrido[4,3-b]carbazoles (ellipticines)." Canadian Journal of Chemistry 64, no. 3 (1986): 545–51. http://dx.doi.org/10.1139/v86-087.

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2-Lithio dérivatives of 1-alkyl-4-chloropyrrolo[3,2-c]pyridines react with acetophenones, giving the corresponding tertiary alcohols. After déhydration into 1,1-diarylethylenes and subsequent reduction to 1,1 -diarylethanes, the synthesis of 1-chloro-5-alkyl-5H-pyrido[4,3-b]benzo[f]indoles was achieved either by direct cyclization with dichloromethylmethylether plus stannic chloride or by formylation and cyclodehydration with polyphosphoric acid. Finally, the substitution of the chlorine atom with dialkylaminoalkylamines leads to 1-amino substituted 5-alkyl-5H-pyrido[4,3-b]benzo[f]indoles, iso

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26

BAECKVALL, J. E., and N. A. PLOBECK. "ChemInform Abstract: New Synthesis of the 6H-Pyrido(4,3-b)carbazoles Ellipticine and Olivacine via Cycloaddition of 2-Phenylsulfonyl 1,3-Dienes to Indoles." ChemInform 22, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199101339.

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27

Gazengel, Jean-Marie, Jean-Charles Lancelot, Sylvain Rault, and Max Robba. "Etude des conditions d'accés aux 6H-, 7H- et 11H-pyrimidino-[4,5-a], [4,5-b], [5,4-a] [5,4-b] et [5,4-c]carbazoles. 1." Journal of Heterocyclic Chemistry 26, no. 4 (1989): 1135–39. http://dx.doi.org/10.1002/jhet.5570260443.

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28

Jasztold-Howorko, Ryszard, Włodzimierz Doroszkiewicz, Gabriela Bugla-Płoskońska, Alain Croisy, and Daniele Carrez. "The Synthesis and Bioloqical Properties of a 1-(2-Methylpyridin-4-yl) Olivacine Derivative." Scientia Pharmaceutica 73, no. 3 (2005): 101–12. http://dx.doi.org/10.3797/scipharm.aut-05-09.

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Starting from 2-(6-methoxy-1-methyl-9H-carbazol-2-yl)ethylamine and 2-methylisonicotinic acid, 9-hydroxy-5,6-dimethyl-1-(2-methylpyridin-4-yl)-6H-pyrido[4,3-b]carbazole (5) was obtained. The new compound showed significant cytostatic activity for cultured L1210 cells and no inhibition of growth of the E. coli O56 strain was observed. The bactericidal activity of normal human serum against E. coli O56 was not affected by the examined compound 5 and its isomer 4.

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29

MEHTA, P., Y. KUMAR, A. K. SAXENA, A. K. GULATI, H. K. SINGH, and N. ANAND. "ChemInform Abstract: Synthesis of cis- and trans-1-Substituted 1,2,3,4,4a,5,11,11a- Octahydro-6H-pyrido(3,2-b)carbazoles, 4-Substituted 1,2,3,4,4a,5,6,11c- Octahydro-7H-pyrido(2,3-c)carbazoles, cis-4-Methyl-1,2,3,4,4a,5,6,12b- octahydro-7H-pyrido(2,3-c)ac." ChemInform 22, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199130200.

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30

Liu, Anyi, Qingshuai Han, Xiaofeng Zhang, Buhong Li, and Qiufeng Huang. "Transition-Metal-Controlled Synthesis of 11H-Benzo[a]carbazoles and 6-Alkylidene-6H-isoindo[2,1-a]indoles via Sequential Intermolecular/Intramolecular Cross-Dehydrogenative Coupling from 2-Phenylindoles." Organic Letters 21, no. 17 (2019): 6839–43. http://dx.doi.org/10.1021/acs.orglett.9b02476.

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31

DORMOY, J. R., and A. HEYMES. "ChemInform Abstract: Industrial Synthesis of Ellipticines. Part 2. Elaboration of a Novel Route to 6H-Pyrido(4,3-b)carbazoles and Analogues. Part B. Synthesis of Tetracyclic Structures." ChemInform 24, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199332244.

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32

DORMOY, J. R., and A. HEYMES. "ChemInform Abstract: Industrial Synthesis of Ellipticines. Part 1. Elaboration of a Novel Route to 6H-Pyrido(4,3-b)carbazoles and Analogues. Part A. Synthesis and Study of the Precursors." ChemInform 24, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199332243.

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33

Wu, Tongjing, Taeyeon Kim, Bangshao Yin, et al. "Carbazole-containing porphyrinoid and its oligomers." Chemical Communications 55, no. 76 (2019): 11454–57. http://dx.doi.org/10.1039/c9cc06114b.

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A novel carbazole-containing porphyrinoid 4H and its oligomers 6H and 7H were synthesized for the first time via the Suzuki–Miyaura cross-coupling reaction. The structures of 4H, 4Pd, 6H, and 6Zn were finally confirmed by X-ray analysis.

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34

Yanni, Amal S., Zarif H. Khalil, and Ahmed A. Timmawy. "Synthesis of some new sulfonamide derivatives of 7-chloroquinoline-5,8-dione and pyridocarbazolediones." Collection of Czechoslovak Chemical Communications 56, no. 7 (1991): 1489–94. http://dx.doi.org/10.1135/cccc19911489.

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Interaction of 6-chloroquinoline-5,8-dione hydrochloride (I) or 6,7-dichloroquinoline-5,8-dione (II) with sulfa drug in ethanol containing diethylaniline afforded 7-substituted sulfonamide-10H-pyrido[3,2-b]carbazole-5,11-dione (III), and sulfonamide derivatives of 7-chloroquinoline-5,8-diones (IV). Moreover the reaction of II with arylamine in pyridine afforded substituted 6H-pyrido[2,3-b]carbazole-5,11-dione (V). The structure of the compounds was determined by elemental and spectral analysis, and by chemical reaction.

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35

Mohamooda Sumaya, U., E. Sankar, K. Arasambattu MohanaKrishnan, K. Biruntha, and G. Usha. "Crystal structure determination, Hirshfeld surface analysis and energy frameworks of 6-phenylsulfonyl-6H-thieno[3,2-c]carbazole." Acta Crystallographica Section E Crystallographic Communications 74, no. 7 (2018): 878–83. http://dx.doi.org/10.1107/s2056989018007971.

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In the title compound, C20H13NO2S2, the carbazole ring system forms a dihedral angle of 89.08 (1)° with the sulfonyl-substituted phenyl ring. Intramolecular C—H...O hydrogen bonds involving the sulfone O atoms and the carbazole moiety result in two S(6) rings. In the crystal, molecules are linked via pairs of C—H...O hydrogen bonds forming inversion dimers with an R 2 2(12) graph-set motif. Analysis of the Hirshfeld surfaces and two-dimensional fingerprint plots was used to explore the distribution of weak intermolecular interactions in the crystal structure.

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36

Bruce S, Ross, and Archer Sydney. "Synthesis of 5-hydroxymethyl-11-methyl-6H-pyrido[4,3-b]carbazole and 5-formyl-11-methyl-6H-pyrido[4,3-b]carbazole (17-oxoellipticine)." Tetrahedron Letters 27, no. 44 (1986): 5343–46. http://dx.doi.org/10.1016/s0040-4039(00)85206-5.

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37

Modi, Sandeep P., James J. Carey, and Sydney Archer. "Synthesis of 5-methyl-6h-pyrido[4,3-b]carbazole-11-methanol." Tetrahedron Letters 31, no. 41 (1990): 5845–48. http://dx.doi.org/10.1016/s0040-4039(00)97974-7.

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38

Lancelot, Jean-Charles, Sylvain Rault, Max Robba, and Nguyen Huy Dung. "EFFICIENT SYNTHESIS OF 6H-PYRIDO [3, 2-b] CARBAZOLE DERIVATIVES FROM 3-AMINO-1, 4-DIMETHYL CARBAZOLE." CHEMICAL & PHARMACEUTICAL BULLETIN 35, no. 1 (1987): 425–28. http://dx.doi.org/10.1248/cpb.35.425.

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39

Zhang, Weifang, Weicheng Huang, Shenyuan Gao, Yuanxu Zeng, Hao Wei, and Qing Ye. "Synthesis of pyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones via addition/cyclization reactions between 3-chloro-4-indolylmaleimides and alkynes." Journal of Chemical Research 44, no. 9-10 (2020): 551–56. http://dx.doi.org/10.1177/1747519820909456.

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3-Chloro-4-indolylmaleimides and two different alkynes are used as the starting materials in a novel and highly effective Pd-catalyzed addition/C–H activation/cyclization sequence for the synthesis of pyrrolo[3,4- c]carbazole-1,3(2 H,6 H)-diones. The desired products are obtained in moderate to excellent yields. Such compounds show a wide range of biological activities.

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40

Morel, Sandrine, Gérard Boyer, Fabien Coullet, and Jean-Pierre Galy. "A Synthesis of 9-Methoxy-1-Methyl-1H,6H-Pyrazolo[4,3-c]Carbazole." Synthetic Communications 26, no. 13 (1996): 2443–47. http://dx.doi.org/10.1080/00397919608004556.

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41

MODI, S. P., J. J. CAREY, and S. ARCHER. "ChemInform Abstract: Synthesis of 5-Methyl-6H-pyrido(4,3-b)carbazole-11-methanol." ChemInform 22, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199139232.

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42

Christoffers, Jens, and Nina Wache. "Synthesis of Some New Optically Active Octahydro-6H-pyrido[4,3-b]-carbazole Derivatives." Synlett 2009, no. 18 (2009): 3016–18. http://dx.doi.org/10.1055/s-0029-1218007.

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43

Tylińska, Beata, Ryszard Jasztold-Howorko, Henryk Mastalarz, Katarzyna Szczaurska-Nowak, and Joanna Wietrzyk. "Synthesis and Anticancer Activity of New 1-Substituted-6H-pyrido[4,3-b]carbazole Derivatives." Archiv der Pharmazie 341, no. 6 (2008): 351–56. http://dx.doi.org/10.1002/ardp.200700203.

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44

Tylińska, Beata, Agnieszka Dobosz, Jan Spychała, et al. "Evaluation of Interactions of Selected Olivacine Derivatives with DNA and Topoisomerase II." International Journal of Molecular Sciences 22, no. 16 (2021): 8492. http://dx.doi.org/10.3390/ijms22168492.

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Olivacine and ellipticine are model anticancer drugs acting as topoisomerase II inhibitors. Here, we present investigations performed on four olivacine derivatives in light of their antitumor activity. The aim of this study was to identify the best antitumor compound among the four tested olivacine derivatives. The study was performed using CCRF/CEM and MCF-7 cell lines. Comet assay, polarography, inhibition of topoisomerase II activity, histone acetylation, and molecular docking studies were performed. Each tested compound displayed interaction with DNA and topoisomerase II, but did not cause

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45

MOREL, S., G. BOYER, F. COULLET, and J. P. GALY. "ChemInform Abstract: A Synthesis of 9-Methoxy-1-methyl-1H,6H-pyrazolo(4,3-c)carbazole." ChemInform 27, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199639151.

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46

Matsumura, Mio, Masatoshi Kawahata, Atsuya Muranaka, et al. "Efficient Synthesis, Structural Characterization, and Optical Properties of 6H -Dibenzo[b ,h ]carbazole and Its Derivatives." European Journal of Organic Chemistry 2019, no. 23 (2019): 3788–93. http://dx.doi.org/10.1002/ejoc.201900464.

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47

Meggers, Eric, Howard Bregman, and Douglas S. Williams. "Pyrido[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-diones: Synthesis, Cyclometalation, and Protein Kinase Inhibition." Synthesis, no. 9 (2005): 1521–27. http://dx.doi.org/10.1055/s-2005-865331.

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48

Haider, Norbert, and Eddy Sotelo. "1,5-Dimethyl-6H-pyridazino[4,5-b]carbazole, a 3-Aza Bioisoster of the Antitumor Alkaloid Olivacine." CHEMICAL & PHARMACEUTICAL BULLETIN 50, no. 11 (2002): 1479–83. http://dx.doi.org/10.1248/cpb.50.1479.

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49

Shivachev, Boris, Petar Petrov, and Malinka Stoyanova. "Synthesis and Crystal Structure of 4-Methyl-6H-pyrido[3,2,1-jk]carbazol-6-one." Journal of Chemical Crystallography 39, no. 3 (2008): 209–12. http://dx.doi.org/10.1007/s10870-008-9459-y.

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50

Kharaneko, O. I. "1,3,6-Trimethyl-6H-pyrano[4,3-b]carbazole-2-pyrylium Perchlorate. Synthesis and Mechanisms of Formation and Recyclization." Russian Journal of Organic Chemistry 54, no. 11 (2018): 1670–74. http://dx.doi.org/10.1134/s1070428018110088.

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