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Journal articles on the topic 'Benzo[c]phenanthridine'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Dostál, Jiří, and Milan Potáček. "Quaternary benzo[c]phenanthridine alkaloids." Collection of Czechoslovak Chemical Communications 55, no. 12 (1990): 2840–73. http://dx.doi.org/10.1135/cccc19902840.

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This review deals with the fully aromatic quaternary benzo[c]phenanthridine alkaloids in several aspects. Firstly nomenclature principles for numbering fused heterocycles are given. Then the richest botanical sources of quaternary benzo[c]phenanthridines are mentioned as well as isolation, separation and determination methods are presented. The emphasis of this survey is focused on chemical reactivity. The main pharmacological effects of quaternary benzo[c]phenanthridine alkaloids are discussed.

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2

Kim, Dae-Keun, Jae-Soon Eun, Tae-Yong Shin, Dong-Ok Eom, and Jong-Pil Lim. "Benzo[c]phenanthridine alkaloids fromCorydalis incisa." Archives of Pharmacal Research 23, no. 6 (2000): 589–91. http://dx.doi.org/10.1007/bf02975246.

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3

Pyrko, A. N. "Synthesis of new benzo[c]phenanthridine derivatives." Russian Journal of Organic Chemistry 46, no. 12 (2010): 1843–47. http://dx.doi.org/10.1134/s1070428010120134.

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4

DOSTAL, J., and M. POTACEK. "ChemInform Abstract: Quaternary Benzo(c)phenanthridine Alkaloids." ChemInform 22, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199113355.

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5

Lv, Pei, Kanglun Huang, Longguan Xie, and Xiaohua Xu. "Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: application to the total synthesis of benzo[c]phenanthridine alkaloids." Organic & Biomolecular Chemistry 9, no. 9 (2011): 3133. http://dx.doi.org/10.1039/c0ob01208d.

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6

Jarosova, Petra, Petr Paroulek, Michal Rajecky, et al. "Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes." Physical Chemistry Chemical Physics 20, no. 33 (2018): 21772–82. http://dx.doi.org/10.1039/c8cp02681e.

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In this work, the interaction of six natural benzo[c]phenanthridine alkaloids (macarpine, sanguilutine, sanguirubine, chelerythrine, sanguinarine and chelirubine) with parallel and antiparallel G-quadruplex DNA structures was studied.

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7

Marek, Radek, Jaromír Toušek, Lukáš Králík, Jirí Dostál, and Vladimír Sklenár. "Conformational Study ofC2Symmetrical Benzo[c]phenanthridine Alkaloid Derivatives." Chemistry Letters 26, no. 4 (1997): 369–70. http://dx.doi.org/10.1246/cl.1997.369.

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8

Geen, Graham R., Inderjit S. Mann, M. Valerie Mullane, and Alexander McKillop. "A versatile synthesis of benzo[c]phenanthridine alkaloids." Journal of the Chemical Society, Perkin Transactions 1, no. 14 (1996): 1647. http://dx.doi.org/10.1039/p19960001647.

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9

Ishikawa, Tsutomu. "Benzo[c]phenanthridine bases and their antituberculosis activity." Medicinal Research Reviews 21, no. 1 (2000): 61–72. http://dx.doi.org/10.1002/1098-1128(200101)21:1<61::aid-med2>3.0.co;2-f.

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10

Nakanishi, Takeshi, and Masanobu Suzuki. "Synthesis and Cytotoxic Activities of a New Benzo[c]phenanthridine Alkaloid, 7-Hydroxynitidine, and Some 9-Oxygenated Benzo[c]phenanthridine Derivatives." Organic Letters 1, no. 7 (1999): 985–88. http://dx.doi.org/10.1021/ol990775g.

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11

Lv, Pei, Kanglun Huang, Longguan Xie, and Xiaohua Xu. "ChemInform Abstract: Palladium-Catalyzed Tandem Reaction to Construct Benzo[c]phenanthridine: Application to the Total Synthesis of Benzo[c]phenanthridine Alkaloids." ChemInform 42, no. 36 (2011): no. http://dx.doi.org/10.1002/chin.201136191.

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12

Le, Thanh Nguyen, and Won-Jea Cho. "Total Synthesis of Oxyfagaronine, Phenolic Benzo[c]phenanthridine and General Synthetic Way of 2,3,7,8- and 2,3,8,9-Tetrasubstituted Benzo[c]phenanthridine Alkaloids." CHEMICAL & PHARMACEUTICAL BULLETIN 54, no. 4 (2006): 476–80. http://dx.doi.org/10.1248/cpb.54.476.

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13

Zuo, Guo Ying, Fan Yan Meng, Xiao Yan Hao, Yun Ling Zhang, Gen Chun Wang, and Gui Li Xu. "Antibacterial Alkaloids from Chelidonium Majus Linn (Papaveraceae) Against Clinical Isolates of Methicillin-Resistant Staphylococcus Aureus." Journal of Pharmacy & Pharmaceutical Sciences 11, no. 4 (2009): 90. http://dx.doi.org/10.18433/j3d30q.

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Purpose. This study describes the antibacterial effect of extracts and compounds isolated from the aerial part of Chelidonium majus Linn. (Papaveraceae) acting against clinical strains of methicillin-resistant Staphylococcus aureus (MRSA). Methods. The activities were evaluated by using the macrobroth dilution method and reported as the MICs/MBCs. Results. Bioassay-guided fractionation of the most active extract from the aerial parts (EtOAc) led to the isolation of benzo[c]phenanthridine-type alkaloids 8-hydroxydihydrosanguinarine (hhS), 8-hydroxydihydrochelerythrine (hhC), which were potently

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14

Ishikawa, Tsutomu, and Hisashi Ishii. "Recent Advances on Antitumor-active Benzo[c]phenanthridine Alkaloids." HETEROCYCLES 50, no. 1 (1999): 627. http://dx.doi.org/10.3987/rev-98-sr(h)9.

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15

Nakanishi, Takeshi, Masanobu Suzuki, Akihiro Mashiba, Keizou Ishikawa, and Takashi Yokotsuka. "Synthesis of NK109, an Anticancer Benzo[c]phenanthridine Alkaloid." Journal of Organic Chemistry 63, no. 13 (1998): 4235–39. http://dx.doi.org/10.1021/jo9718758.

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16

Pyrko, A. N. "ChemInform Abstract: Synthesis of New Benzo[c]phenanthridine Derivatives." ChemInform 42, no. 23 (2011): no. http://dx.doi.org/10.1002/chin.201123139.

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17

Hanaoka, Miyoji, Hiroshi Yamagishi, and Chisato Mukai. "Synthesis of fagaridine, a phenolic benzo (c) phenanthridine alkaloid." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 4 (1985): 1763–65. http://dx.doi.org/10.1248/cpb.33.1763.

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18

Nakanishi, Takeshi, and Masanobu Suzuki. "ChemInform Abstract: Synthesis and Cytotoxic Activities of a New Benzo[c]phenanthridine Alkaloid, 7-Hydroxynitidine, and Some 9-Oxygenated Benzo[c]phenanthridine Derivatives." ChemInform 30, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199952216.

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19

Lasák, Pavel, Kamil Motyka, Vladimír Kryštof, and Jakub Stýskala. "Synthesis, Bacteriostatic and Anticancer Activity of Novel Phenanthridines Structurally Similar to Benzo[c]phenanthridine Alkaloids." Molecules 23, no. 9 (2018): 2155. http://dx.doi.org/10.3390/molecules23092155.

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In this study, we report the synthesis, antibacterial and anticancer evaluation of 38 novel phenanthridines that were designed as analogs of the benzo[c]phenanthridine alkaloids. The prepared phenanthridines differ from the benzo[c]phenanthridines in the absence of a benzene A-ring. All novel compounds were prepared from 6-bromo-2-hydroxy-3-methoxybenzaldehyde in several synthetic steps through reduction of Schiff bases and accomplished by radical cyclization. Twelve derivatives showed high antibacterial activity against Bacillus subtilis, Micrococcus luteus and/or Mycobacterium vaccae at sing

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20

Ishikawa, Tsutomu. "Synthetic Studies on Benzo[c]phenanthridine Alkaloids and Related Compounds." Journal of Synthetic Organic Chemistry, Japan 70, no. 1 (2012): 11–23. http://dx.doi.org/10.5059/yukigoseikyokaishi.70.11.

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21

Geen, Graham R., Inderjit S. Mann, M. Valerie Mullane, and Alexander McKillop. "A versatile synthesis of fully aromatic benzo[c]phenanthridine alkaloids." Tetrahedron 54, no. 33 (1998): 9875–94. http://dx.doi.org/10.1016/s0040-4020(98)00540-7.

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22

GEEN, G. R., I. S. MANN, M. V. MULLANE, and A. MCKILLOP. "ChemInform Abstract: A Versatile Synthesis of Benzo(c)phenanthridine Alkaloids." ChemInform 27, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199643210.

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23

Marek, Radek, Jaromír Toušek, Jiří Dostál, Jiří Slavík, Roger Dommisse, and Vladimír Sklenář. "1H and13C NMR study of quaternary benzo[c]phenanthridine alkaloids." Magnetic Resonance in Chemistry 37, no. 11 (1999): 781–87. http://dx.doi.org/10.1002/(sici)1097-458x(199911)37:11<781::aid-mrc556>3.0.co;2-h.

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24

Nakanishi, Takeshi, Masanobu Suzuki, Atsuya Saimoto, and Takashi Kabasawa. "Structural Considerations of NK109, an Antitumor Benzo[c]phenanthridine Alkaloid." Journal of Natural Products 62, no. 6 (1999): 864–67. http://dx.doi.org/10.1021/np990005d.

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25

Helesbeux, Jean-Jacques, Enguerran Vanquelef, Jean Guillon, Jean-Michel Léger, and Olivier Duval. "Crystal Structure of Ethoxidine, A Synthetic Quaternary Benzo[c]phenanthridine." Journal of Chemical Crystallography 41, no. 12 (2011): 1945–48. http://dx.doi.org/10.1007/s10870-011-9986-9.

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26

Ishikawa, Tsutomu. "ChemInform Abstract: Benzo[c]phenanthridine Bases and Their Antituberculosis Activity." ChemInform 32, no. 20 (2001): no. http://dx.doi.org/10.1002/chin.200120259.

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27

Clement, Bernd, Matthias Weide, Ulrich Wolschendorf, and Ilka Kock. "A Two-Step Synthesis of Cytostatically Active Benzo[c]phenanthridine Derivatives." Angewandte Chemie International Edition 44, no. 4 (2005): 635–38. http://dx.doi.org/10.1002/anie.200461969.

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28

Ishikawa, Tsutomu, and Hisashi Ishii. "ChemInform Abstract: Recent Advances on Antitumor-Active Benzo[c]phenanthridine Alkaloids." ChemInform 30, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199920283.

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29

NAKANISHI, T., M. SUZUKI, A. MASHIBA, K. ISHIKAWA, and T. YOKOTSUKA. "ChemInform Abstract: Synthesis of NK109, an Anticancer Benzo[c]phenanthridine Alkaloid." ChemInform 29, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199845225.

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30

Clement, Bernd, and Ilka Kock. "A New Synthetic Approach to the Benzo[c]phenanthridine Ring System." Synthesis, no. 7 (2005): 1052–54. http://dx.doi.org/10.1055/s-2005-861858.

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31

Cho, Won-Jea, Su-Jeong Yoo, Byung-Ho Chung, et al. "Synthesis of benzo[c]phenanthridine derivatives and theirin vitro antitumor activities." Archives of Pharmacal Research 19, no. 4 (1996): 321–25. http://dx.doi.org/10.1007/bf02976249.

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32

Akoua Yao-Kouassi, Philomène, Catherine Caron, Harisolo Ramiarantsoa, et al. "New nitro-benzo[c]phenanthridine and indolopyridoquinazoline alkaloids from Zanthoxylum atchoum." Comptes Rendus Chimie 18, no. 8 (2015): 891–97. http://dx.doi.org/10.1016/j.crci.2015.01.005.

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33

Mandouma, Ghislain R., Tahera Nembhard, and Brittney Bender. "Synthesis of 2,3-dimethoxy-8,10-methylenedioxy benzo[c]cinnoline 7 As Potential Topoisomerase I Inhibitor." International Journal for Innovation Education and Research 4, no. 12 (2016): 56–77. http://dx.doi.org/10.31686/ijier.vol4.iss12.50.

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A novel and green synthesis of 2,3-dimethoxy-8,10-methylenedioxy benzo[c]cinnoline 7 is herein described. This compound is structurally related to benzo[i]phenanthridine, a class of potent topoisomerase I inhibitors such as nitidine. While nitidine was found to be toxic, the benzo[c]cinnoline derivative 7 may circumvent that by not being a Schiff base. A conveniently short synthetic plan was implemented involving a novel solvent- and catalyst-free cross-coupling biarylation of halogenated nitroarenes 2 and 5 using a high speed ball milling (HSBM) procedure. Indeed, using a copper vial as react

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34

Beugelmans, René, and Michèle Bois-Choussy. "A common and general access to berberine and benzo [c] phenanthridine alkaloids." Tetrahedron 48, no. 38 (1992): 8285–94. http://dx.doi.org/10.1016/s0040-4020(01)80496-8.

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35

Bisai, Vishnumaya, M. K. Saina Shaheeda, Aditi Gupta, and Alakesh Bisai. "Biosynthetic Relationships and Total Syntheses of Naturally Occurring Benzo[ c ]Phenanthridine Alkaloids." Asian Journal of Organic Chemistry 8, no. 7 (2019): 946–69. http://dx.doi.org/10.1002/ajoc.201900244.

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36

Tolkachev, O. N., A. A. Savina, V. I. Sheichenko, and V. V. Proskudina. "ChemInform Abstract: Mechanism of Thermolysis of the Benzo[c]phenanthridine Alkaloid Chelerythrine." ChemInform 30, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199945261.

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37

MACKAY, S. P., O. METH-COHN, and R. D. WAIGH. "ChemInform Abstract: Synthesis of Quaternary Benzo(c)phenanthridine Alkaloids and Their Analogues." ChemInform 28, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199720270.

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38

GEEN, G. R., I. S. MANN, M. V. MULLANE, and A. MCKILLOP. "ChemInform Abstract: A Versatile Synthesis of Fully Aromatic Benzo[c]phenanthridine Alkaloids." ChemInform 29, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199846255.

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39

Tanahashi, Takao, and Meinhart H. Zenk. "New Hydroxylated Benzo[c]phenanthridine Alkaloids from Eschscholtzia californica Cell Suspension Cultures." Journal of Natural Products 53, no. 3 (1990): 579–86. http://dx.doi.org/10.1021/np50069a007.

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40

Slaninová, Iva, Zdenka Slunská, Jiří Šinkora, Marcela Vlková, and Eva Táborská. "Screening of Minor Benzo(c.)phenanthridine Alkaloids for Antiproliferative and Apoptotic Activities." Pharmaceutical Biology 45, no. 2 (2007): 131–39. http://dx.doi.org/10.1080/13880200601113099.

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41

Janin, Yves L., Alain Croisy, Jean Francois Riou, and Emile Bisagni. "Synthesis and evaluation of new 6-amino- substituted benzo[c]phenanthridine derivatives." Journal of Medicinal Chemistry 36, no. 23 (1993): 3686–92. http://dx.doi.org/10.1021/jm00075a025.

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42

Tolkachev, O. N., A. A. Savina, V. I. Sheichenko, and V. V. Proskudina. "On the mechanism of thermolysis of the benzo[c]phenanthridine alkaloid chelerythrine." Pharmaceutical Chemistry Journal 33, no. 6 (1999): 323–25. http://dx.doi.org/10.1007/bf02509954.

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43

Iwasaki, Hironori, Takafumi Okabe, Kensaku Takara, Takayoshi Toda, Masayuki Shimatani, and Hirosuke Oku. "Tumor-selective cytotoxicity of benzo[c]phenanthridine derivatives from Toddalia asiatica Lam." Cancer Chemotherapy and Pharmacology 65, no. 4 (2009): 719–26. http://dx.doi.org/10.1007/s00280-009-1077-7.

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44

Domínguez, Esther, Raul SanMartín, Eduardo Martínez de Marigorta, and Isabel Moreno. "Novel Entry into Benzo[c]phenanthridine Systems through a Tandem Alkene Acylation-Cyclodehydration." HETEROCYCLES 45, no. 4 (1997): 757. http://dx.doi.org/10.3987/com-97-7745.

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45

VAVRECKOVA, C., and J. ULRICHOVA. "ChemInform Abstract: Biological Activity of Quaternary Benzo(c)phenanthridine Alkaloids - Sanguinarine and Chelerythrine." ChemInform 25, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199444278.

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46

Slaninová, Iva, Jiří Slanina, and Eva Táborská. "Quaternary benzo[c]phenanthridine alkaloids—novel cell permeant and red fluorescing DNA probes." Cytometry Part A 71A, no. 9 (2007): 700–708. http://dx.doi.org/10.1002/cyto.a.20423.

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47

Hutton, Susan M., Simon Paul Mackay, and Otto Meth-Cohn. "Synthesis of Dibenzo[c,h][1,6]naphthyridine, [2]Benzopyrano[4,3-c]quinoline and Benzo[i]phenanthridine Analogues of the Quaternary Benzo[c]phenanthridines." Synthesis 2000, no. 08 (2000): 1121–24. http://dx.doi.org/10.1055/s-2000-6325.

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48

HANAOKA, Miyoji, Won Jea CHO, Shuji YOSHIDA, and Chisato MUKAI. "Chemical Transformation of Protoberberines. XVII. Biomimetic Introduction of an Oxy Functionality at the C-10 Position in the Benzo(c)phenanthridine Skeleton: Synthesis of 2,3,7,8,10-Pentaoxygenated Benzo(c)phenanthridine Alkaloids, Chelilutine and Sanguilutine." CHEMICAL & PHARMACEUTICAL BULLETIN 39, no. 5 (1991): 1163–66. http://dx.doi.org/10.1248/cpb.39.1163.

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49

Iribarra, Jennyfer, David Vásquez, Cristina Theoduloz, Julio Benites, David Ríos, and Jaime A. Valderrama. "Synthesis and Antitumor Evaluation of 6-Aryl-substituted benzo[j]phenanthridine- and Benzo[g]pyrimido[4,5-c]isoquinolinequinones." Molecules 17, no. 10 (2012): 11616–29. http://dx.doi.org/10.3390/molecules171011616.

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50

Cui, Yu-Jin, Feng Su, and Wei-Jun Jin. "Structural and luminescent properties of co-crystals of tetraiodoethylene with two azaphenanthrenes." Acta Crystallographica Section E Crystallographic Communications 76, no. 3 (2020): 438–42. http://dx.doi.org/10.1107/s2056989020002182.

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Two new co-crystals, tetraiodoethylene–phenanthridine (1/2), 0.5C2I4·C13H9N (1) and tetraiodoethylene–benzo[f]quinoline (1/2), 0.5C2I4·C13H9N (2), were obtained from tetraiodoethylene and azaphenanthrenes, and characterized by IR and fluorescence spectroscopy, elemental analysis and X-ray crystallography. In the crystal structures, C—I...π and C—I...N halogen bonds link the independent molecules into one-dimensional chains and two-dimensional networks with subloops. In addition, the planar azaphenanthrenes lend themselves to π–π stacking and C—H...π interactions, leading to a diversity of supr

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