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Journal articles on the topic 'Quinolizinium'

Author: Grafiati

Published: 9 March 2023

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1

Bandaru, Siva Sankar Murthy, Darinka Dzubiel, Heiko Ihmels, Mohebodin Karbasiyoun, Mohamed M. A. Mahmoud, and Carola Schulzke. "Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions." Beilstein Journal of Organic Chemistry 14 (July 23, 2018): 1871–84. http://dx.doi.org/10.3762/bjoc.14.161.

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9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivativ

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2

Faulhaber, Katja, Anton Granzhan, Heiko Ihmels, and Giampietro Viola. "Detection of biomacromolecules with fluorescent light-up probes." Pure and Applied Chemistry 78, no. 12 (2006): 2325–31. http://dx.doi.org/10.1351/pac200678122325.

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The emission properties of selected benzo[b]quinolizinium (acridizinium) derivatives in the presence of double-stranded DNA and proteins are presented. Spectrophotometric studies and linear dichroism (LD) spectroscopic experiments reveal that benzo[b]quinolizinium derivatives bind to DNA, mainly by intercalation. In contrast to the 9-aminobenzo[b]quinolizinium, which exhibits a moderate emission quantum yield in water, the 6-aminobenzo[b]quinolizinium ion as well as N-phenyl-9-aminobenzo[b]quinolizinium derivatives are almost nonfluorescent. The low intrinsic fluorescence quantum yields of the

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3

Sato, Kiyoshi, Sadao Arai, Takamichi Yamagishi, and Tomoaki Tanase. "Quinolizinium hexafluorophosphate." Acta Crystallographica Section C Crystal Structure Communications 57, no. 2 (2001): 174–75. http://dx.doi.org/10.1107/s0108270100015742.

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4

O, Wa-Yi, Wing-Cheung Chan, Caifeng Xu, Jie-Ren Deng, Ben Chi-Bun Ko, and Man-Kin Wong. "A highly selective quinolizinium-based fluorescent probe for cysteine detection." RSC Advances 11, no. 53 (2021): 33294–99. http://dx.doi.org/10.1039/d1ra06104f.

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5

Das, Avijit Kumar, Heiko Ihmels, and Sarah Kölsch. "Diphenylaminostyryl-substituted quinolizinium derivatives as fluorescent light-up probes for duplex and quadruplex DNA." Photochemical & Photobiological Sciences 18, no. 6 (2019): 1373–81. http://dx.doi.org/10.1039/c9pp00096h.

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6

Wickhorst, Peter Jonas, Heiko Ihmels, Melanie Marianne Lammert-Baumgartner, Mareike Müller, and Holger Schönherr. "9-Nitrobenzo[b]quinolizinium as a fluorogenic probe for the detection of nitroreductase in vitro and in Escherichia coli." New Journal of Chemistry 46, no. 1 (2022): 39–43. http://dx.doi.org/10.1039/d1nj05230f.

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7

Kung, Karen Ka-Yan, Cai-fung Xu, Wa-Yi O, et al. "Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins." RSC Advances 12, no. 10 (2022): 6248–54. http://dx.doi.org/10.1039/d1ra08329e.

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8

Upadhyay, Nitinkumar Satyadev, Jayachandran Jayakumar, and Chien-Hong Cheng. "Facile one-pot synthesis of 2,3-dihydro-1H-indolizinium derivatives by rhodium(iii)-catalyzed intramolecular oxidative annulation via C–H activation: application to ficuseptine synthesis." Chemical Communications 53, no. 16 (2017): 2491–94. http://dx.doi.org/10.1039/c7cc00008a.

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9

Bortolozzi, Roberta, Sebastian von Gradowski, Heiko Ihmels, Katy Schäfer, and Giampietro Viola. "Selective ratiometric detection of H2O2 in water and in living cells with boronobenzo[b]quinolizinium derivatives." Chem. Commun. 50, no. 60 (2014): 8242–45. http://dx.doi.org/10.1039/c4cc02283a.

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10

Benner, Katja, Heiko Ihmels, Sarah Kölsch, and Phil M. Pithan. "Targeting abasic site-containing DNA with annelated quinolizinium derivatives: the influence of size, shape and substituents." Org. Biomol. Chem. 12, no. 11 (2014): 1725–34. http://dx.doi.org/10.1039/c3ob42140f.

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A comparative analysis showed that the type and degree of annelation as well as methyl or chloro-substitution are relevant structural features that determine the interactions of quinolizinium derivatives with abasic site-containing DNA.

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11

Tantipanjaporn, Ajcharapan, Karen Ka-Yan Kung, Hoi-Yi Sit, and Man-Kin Wong. "Quinolizinium-based fluorescent probes for formaldehyde detection in aqueous solution, serum, and test strip via 2-aza-Cope rearrangement." RSC Advances 12, no. 18 (2022): 11543–47. http://dx.doi.org/10.1039/d2ra01397e.

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Novel quinolizinium-based fluorescent probes were designed based on 2-aza-Cope rearrangement reaction to detect formaldehyde in aqueous solution, serum, and paper format. The use of a geminal dimethyl group allows fast response within 15 min.

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12

Yeung, Chi-Fung, Lai-Hon Chung, Sheung-Ying Tse, et al. "Conventional and unconventional alkyne activations by Ru and Os for unprecedented dimetalated quinolizinium complexes." Chemical Communications 56, no. 63 (2020): 8908–11. http://dx.doi.org/10.1039/d0cc03480k.

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Two types of unexpected quinolizinium complexes were obtained from the reactions between pyridine-functionalized propargylic alcohol HCCC(OH)(Ph)(CH<sub>2</sub>(2-py)) (L1) and cis-[M(L^L)<sub>2</sub>Cl<sub>2</sub>] (M = Ru, Os; L^L = dppm, bpy).

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13

Zacharioudakis, Emmanouil, Tatiana Cañeque, Raúl Custodio, et al. "Quinolizinium as a new fluorescent lysosomotropic probe." Bioorganic & Medicinal Chemistry Letters 27, no. 2 (2017): 203–7. http://dx.doi.org/10.1016/j.bmcl.2016.11.074.

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14

Ge, Qingmei, Bin Li, Haibin Song, and Baiquan Wang. "Rhodium(iii)-catalyzed cascade oxidative annulation reactions of aryl imidazolium salts with alkynes involving multiple C–H bond activation." Organic & Biomolecular Chemistry 13, no. 28 (2015): 7695–710. http://dx.doi.org/10.1039/c5ob00823a.

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The cascade oxidative annulation reactions of aryl imidazolium salts with alkynes proceed efficiently in the presence of [Cp*RhCl<sub>2</sub>]<sub>2</sub> and Cu(OAc)<sub>2</sub>·H<sub>2</sub>O to give substituted imidazo[1,2-a]-quinolinium salts and benzo[ij]imidazo[2,1,5-de]quinolizinium salts.

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15

Becher, Jonas, Daria V. Berdnikova, Darinka Dzubiel, Heiko Ihmels, and Phil M. Pithan. "Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state." Beilstein Journal of Organic Chemistry 13 (February 1, 2017): 203–12. http://dx.doi.org/10.3762/bjoc.13.23.

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3-Hydroxynaphtho[1,2-b]quinolizinium was synthesized by cyclodehydration route and its optical properties in different media were investigated. The absorption and emission spectra of this compound depend on the pH of the solution. Thus, at higher pH values the deprotonation yields a merocyanine-type dye that exhibits significantly red-shifted absorption bands and causes a dual emisson, i.e., a combination of emission bands of the hydroxyquinolizinium and its deprotonated form. Whereas this compound is a weak acid in the ground state (pK a = 7.9), it has a strongly increased acidity in the exci

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16

Dérand, Renaud, Laurence Bulteau-Pignoux, Yvette Mettey, et al. "Activation of G551D CFTR channel with MPB-91: regulation by ATPase activity and phosphorylation." American Journal of Physiology-Cell Physiology 281, no. 5 (2001): C1657—C1666. http://dx.doi.org/10.1152/ajpcell.2001.281.5.c1657.

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We have designed and synthesized benzo[c]quinolizinium derivatives and evaluated their effects on the activity of G551D cystic fibrosis transmembrane conductance regulator (CFTR) expressed in Chinese hamster ovary and Fisher rat thyroid cells. We demonstrated, using iodide efflux, whole cell patch clamp, and short-circuit recordings, that 5-butyl-6-hydroxy-10-chlorobenzo[c]quinolizinium chloride (MPB-91) restored the activity of G551D CFTR (EC50 = 85 μM) and activated CFTR in Calu-3 cells (EC50 = 47 μM). MPB-91 has no effect on the ATPase activity of wild-type and G551D NBD1/R/GST fusion prote

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17

Anulewicz, R., K. Woźniak, and J. A. Soroka. "(±)-7,10,12-Triphenyl-7,8-dihydroacenaphtho[4,5-c]quinolizinium perchlorate." Acta Crystallographica Section C Crystal Structure Communications 48, no. 12 (1992): 2238–40. http://dx.doi.org/10.1107/s0108270192002841.

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18

Martín, M. A., B. del Castillo, J. Ezquerra, and J. Alvarez-Builla. "Quinolizinium salts as fluorescent probes for N-nucleophiles." Analytica Chimica Acta 170 (1985): 89–94. http://dx.doi.org/10.1016/s0003-2670(00)81729-8.

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19

Arai, Sadao, Kunihisa Tabuchi, Hitoshi Arai, Takamichi Yamagishi, and Mitsuhiko Hida. "Synthesis of Benzo[c]quinolizinium Salts by Photocyclization." Chemistry Letters 20, no. 8 (1991): 1355–56. http://dx.doi.org/10.1246/cl.1991.1355.

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20

Arai, Sadao, Masuo Yamazaki, and Mitsuhiko Hida. "Synthesis and reaction of methylbenzo[a]quinolizinium salts." Journal of Heterocyclic Chemistry 27, no. 4 (1990): 1073–78. http://dx.doi.org/10.1002/jhet.5570270448.

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21

Arai, Sadao, Hitoshi Arai, Kunihisa Tabuchi, Takamichi Yamagishi, and Mitsuhiko Hida. "Synthesis and reactions of methylbenzo[c]quinolizinium salts." Journal of Heterocyclic Chemistry 29, no. 1 (1992): 215–20. http://dx.doi.org/10.1002/jhet.5570290139.

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22

G. Earley, William, John A. Dority Jr., Virendra Kumar, and John P. Mallamo. "Regiocontrolled Syntheses of Benzo[b]quinolizinium and Heteroisoquinolinium Cations." HETEROCYCLES 41, no. 2 (1995): 309. http://dx.doi.org/10.3987/com-94-6936.

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23

Cañeque, Tatiana, Ana M. Cuadro, Julio Alvarez-Builla, and Juan J. Vaquero. "Efficient functionalization of quinolizinium cations with organotrifluoroborates in water." Tetrahedron Letters 50, no. 13 (2009): 1419–22. http://dx.doi.org/10.1016/j.tetlet.2009.01.040.

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24

Schäfer, Katy, Heiko Ihmels, Cornelia Bohne, Karolina Papera Valente, and Anton Granzhan. "Hydroxybenzo[b]quinolizinium Ions: Water-Soluble and Solvatochromic Photoacids." Journal of Organic Chemistry 81, no. 22 (2016): 10942–54. http://dx.doi.org/10.1021/acs.joc.6b01991.

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25

Li, Feng, Jihee Cho, Shenpeng Tan, and Sanghee Kim. "Synthesis of Quinolizinium-Type Heteroaromatics via a Carbene Intermediate." Organic Letters 20, no. 3 (2018): 824–27. http://dx.doi.org/10.1021/acs.orglett.7b03964.

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26

Cañeque, Tatiana, Ana M. Cuadro, Julio Alvarez-Builla, et al. "Novel charged NLO chromophores based on quinolizinium acceptor units." Dyes and Pigments 101 (February 2014): 116–21. http://dx.doi.org/10.1016/j.dyepig.2013.09.031.

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27

Pingali, Subramanya, James P. Donahue, and Florastina Payton-Stewart. "Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid." Acta Crystallographica Section C Structural Chemistry 71, no. 4 (2015): 262–65. http://dx.doi.org/10.1107/s2053229615004076.

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Tetrahydroberberine (systematic name: 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. The intermolecular hydrogen bonds that play an apparent role in crystal packing are 1,3-benzodioxole –CH2...OCH3and –OCH3...OCH3interactions between neighboring molecules.

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28

Pithan, Phil M., David Decker, Manlio Sutero Sardo, Giampietro Viola, and Heiko Ihmels. "Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives." Beilstein Journal of Organic Chemistry 12 (May 2, 2016): 854–62. http://dx.doi.org/10.3762/bjoc.12.84.

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Cationic biaryl derivatives were synthesized by Suzuki–Miyaura coupling of 3-bromonaphtho[1,2-b]quinolizinium bromide with arylboronic acids. The resulting cationic biaryl derivatives exhibit pronounced fluorosolvatochromic properties. First photophysical studies in different solvents showed that the emission energy of the biaryl derivatives decreases with increasing solvent polarity. This red-shifted emission in polar solvents is explained by a charge shift (CS) in the excited state and subsequent solvent relaxation. Furthermore, the polarity of protic polar and aprotic polar solvents affects

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29

ARAI, S., K. TABUCHI, H. ARAI, T. YAMAGISHI, and M. HIDA. "ChemInform Abstract: Synthesis of Benzo(c)quinolizinium Salts by Photocyclization." ChemInform 23, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.199202228.

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30

ARAI, S., H. ARAI, K. TABUCHI, T. YAMAGISHI, and M. HIDA. "ChemInform Abstract: Synthesis and Reactions of Methylbenzo(c)quinolizinium Salts." ChemInform 23, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199232164.

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31

Jortzik, Esther, Kathleen Zocher, Antje Isernhagen, et al. "Benzo[b]quinolizinium Derivatives Have a Strong Antimalarial Activity and Inhibit Indoleamine Dioxygenase." Antimicrobial Agents and Chemotherapy 60, no. 1 (2015): 115–25. http://dx.doi.org/10.1128/aac.01066-15.

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ABSTRACTThe heme-containing enzymes indoleamine 2,3-dioxygenase-1 (IDO-1) and IDO-2 catalyze the conversion of the essential amino acid tryptophan into kynurenine. Metabolites of the kynurenine pathway and IDO itself are involved in immunity and the pathology of several diseases, having either immunoregulatory or antimicrobial effects. IDO-1 plays a central role in the pathogenesis of cerebral malaria, which is the most severe and often fatal neurological complication of infection withPlasmodium falciparum. Mouse models are usually used to study the underlying pathophysiology. In this study, w

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32

Sit, Hoi-Yi, Jie-Ren Deng, Wing-Cheung Chan, Ben Chi-Bun Ko, and Man-Kin Wong. "Quinolizinium-based tunable pH fluorescent probes for imaging in live cells." Dyes and Pigments 205 (September 2022): 110541. http://dx.doi.org/10.1016/j.dyepig.2022.110541.

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33

Arai, Sadao, Kimihiko Nagakura, Masanori Ishikawa, and Mitsuhiko Hida. "Synthesis of solvatochromic cyanine dyes having a benzo[a]quinolizinium ring." Journal of the Chemical Society, Perkin Transactions 1, no. 7 (1990): 1915. http://dx.doi.org/10.1039/p19900001915.

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34

Stratford, Fiona L. L., Malcolm M. C. Pereira, Frederic Becq, Margaret A. McPherson та Robert L. Dormer. "Benzo(c)quinolizinium drugs inhibit degradation of ΔF508-CFTR cytoplasmic domain". Biochemical and Biophysical Research Communications 300, № 2 (2003): 524–30. http://dx.doi.org/10.1016/s0006-291x(02)02883-8.

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35

García-Cuadrado, Domingo, Ana M. Cuadro, Bernardo M. Barchín, et al. "Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations." Journal of Organic Chemistry 71, no. 21 (2006): 7989–95. http://dx.doi.org/10.1021/jo060634+.

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36

Martin, M. A., B. del Castillo, and P. Prados. "13-Hydroxyacenaphato[1,2-b]quinolizinium bromide as a new flouorescence indicator." Talanta 40, no. 11 (1993): 1719–23. http://dx.doi.org/10.1016/0039-9140(93)80089-a.

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37

EARLY, W. G., J. A. JUN DORITY, V. KUMAR, and J. P. MALLAMO. "ChemInform Abstract: Regiocontrolled Syntheses of Benzo(b)quinolizinium and Heteroisoquinolinium Cations." ChemInform 26, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.199529184.

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38

Arai, Sadao, Hiroe Yoda, Kiyoshi Sato, and Takamichi Yamagishi. "ChemInform Abstract: Photocyclization of Styrylbenzo[a]quinolizinium Salts. Part 3. Novel Five-Membered Ring Formation by Oxidative Photocyclization of 4-(2-Arylvinyl)benzo[a]quinolizinium Salts." ChemInform 33, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.200238146.

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39

Dormer, Robert L., Renaud Dérand, Ceinwen M. McNeilly, et al. "Correction of delF508-CFTR activity with benzo(c)quinolizinium compounds through facilitation of its processing in cystic fibrosis airway cells." Journal of Cell Science 114, no. 22 (2001): 4073–81. http://dx.doi.org/10.1242/jcs.114.22.4073.

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A number of genetic diseases, including cystic fibrosis, have been identified as disorders of protein trafficking associated with retention of mutant protein within the endoplasmic reticulum. In the presence of the benzo(c)quinolizinium drugs, MPB-07 and its congener MPB-91, we show the activation of cystic fibrosis transmembrane conductance regulator (CFTR) delF508 channels in IB3-1 human cells, which express endogenous levels of delF508-CFTR. These drugs were without effect on the Ca2+-activated Cl– transport, whereas the swelling-activated Cl– transport was found altered in MPB-treated cell

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40

Arai, Sadao, Kiyoshi Sato, Koji Kano, Takuya Yafune, Mitsuhiko Hida, and Takamichi Yamagishi. "Synthesis of 6-Methylisoquinolino[7,8-a]quinolizinium Salt: Efficient Synthesis of 2-(2-Arylvinyl)quinolizinium Salts by Knoevenagel Condensation Using Acetonitrile as a Solvent and the Photocyclization." HETEROCYCLES 37, no. 2 (1994): 955. http://dx.doi.org/10.3987/com-93-s95.

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41

Pithan, Phil M., Sören Steup, and Heiko Ihmels. "Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates." Beilstein Journal of Organic Chemistry 16 (May 5, 2020): 904–16. http://dx.doi.org/10.3762/bjoc.16.82.

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Two new spiroindolinonaphthoxazine derivatives with an electron-accepting styrylquinolizinium or styrylcoralyne unit, respectively, were synthesized, and the influence of such an arylvinyl substituent on the chemical and photochemical properties of the compounds was investigated. Specifically, these spirooxazines turned out to be resistant towards the photoinduced merocyanine formation, and the irradiation with light mainly led to photodegradation of the substrates. However, it was shown by colorimetric and fluorimetric screening assays as well as by detailed NMR spectroscopic and mass spectro

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42

Granzhan, Anton, and Heiko Ihmels. "Synthesis of 9-amino- and 9-sulfanyl-substituted benzo[b]quinolizinium derivatives." Arkivoc 2007, no. 8 (2006): 136–49. http://dx.doi.org/10.3998/ark.5550190.0008.813.

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43

Martín, M. A., M. Ballesteros, and B. Del Castillo. "The influence of solvent polarity and viscosity on fluorescence of quinolizinium salts." Analytica Chimica Acta 170 (1985): 95–100. http://dx.doi.org/10.1016/s0003-2670(00)81730-4.

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44

Soroka, Jacek A. "Photochemistry of hemicyanines IV: Synthesis of (±) 5,6-dihydronaphto[2,1-c]-quinolizinium salts." Journal of Photochemistry and Photobiology A: Chemistry 64, no. 2 (1992): 171–82. http://dx.doi.org/10.1016/1010-6030(92)85104-3.

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45

Marcelo, Gema, Sandra Pinto, Tatiana Cañeque, et al. "Nonlinear Emission of Quinolizinium-Based Dyes with Application in Fluorescence Lifetime Imaging." Journal of Physical Chemistry A 119, no. 11 (2014): 2351–62. http://dx.doi.org/10.1021/jp507095b.

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46

Alvarez-Builla, J., G. Gonzalez Trigo, J. Ezquerra, and M. E. Fombella. "2-Methylpyridinium salts as 1,4-dinucleophiles. Quinolizinium salts from the westphal condensation." Journal of Heterocyclic Chemistry 22, no. 3 (1985): 681–85. http://dx.doi.org/10.1002/jhet.5570220313.

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47

Viola, Giampietro, Francesco Dall′Acqua, Nadia Gabellini, Stefano Moro, Daniela Vedaldi, and Heiko Ihmels. "Indolo[2,3-b]-Quinolizinium Bromide: An Efficient Intercalator with DNA-Photodamaging Properties." ChemBioChem 3, no. 6 (2002): 550. http://dx.doi.org/10.1002/1439-7633(20020603)3:6<550::aid-cbic550>3.0.co;2-z.

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48

SATO, K., K. KANO, Y. YAFUNE, M. HIDA, S. ARAI, and T. YAMAGISHI. "ChemInform Abstract: Synthesis of 6-Methylisoquinolino(7,8-a)quinolizinium Salt: Efficient Synthesis of 2-(2-Arylvinyl)quinolizinium Salts by Knoevenagel Condensation Using Acetonitrile as a Solvent and the Photocyclization." ChemInform 25, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199428205.

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49

Balu, Maiiakel P., Hiriyakkanavar Ila та Hiriyakkanavar Junjappa. "Cycloaromatization of α-oxoketene dithioacetals with 2-picolyllithium: A facile quinolizinium cation annelation". Tetrahedron Letters 28, № 26 (1987): 3023–26. http://dx.doi.org/10.1016/s0040-4039(00)96275-0.

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50

Martin, P., M. A. Martin, B. Del Castillo, and I. Cayre. "Polarity effect on fluorescence of styryl derivatives of quinolizinium salts in micellar media." Analytica Chimica Acta 205 (1988): 129–37. http://dx.doi.org/10.1016/s0003-2670(00)82322-3.

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