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Journal articles on the topic 'Indéno[1,2-b]indole'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Villemson, Elena V., Ekaterina M. Budynina, Olga A. Ivanova, Dmitriy A. Skvortsov, Igor V. Trushkov, and Mikhail Ya Melnikov. "Concise approach to pyrrolizino[1,2-b]indoles from indole-derived donor–acceptor cyclopropanes." RSC Advances 6, no. 66 (2016): 62014–18. http://dx.doi.org/10.1039/c6ra11233a.

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2

Haidar, Samer, Christelle Marminon, Dagmar Aichele, et al. "QSAR Model of Indeno[1,2-b]indole Derivatives and Identification of N-isopentyl-2-methyl-4,9-dioxo-4,9-Dihydronaphtho[2,3-b]furan-3-carboxamide as a Potent CK2 Inhibitor." Molecules 25, no. 1 (2019): 97. http://dx.doi.org/10.3390/molecules25010097.

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Casein kinase II (CK2) is an intensively studied enzyme, involved in different diseases, cancer in particular. Different scaffolds were used to develop inhibitors of this enzyme. Here, we report on the synthesis and biological evaluation of twenty phenolic, ketonic, and para-quinonic indeno[1,2-b]indole derivatives as CK2 inhibitors. The most active compounds were 5-isopropyl-1-methyl-5,6,7,8-tetrahydroindeno[1,2-b]indole-9,10-dione 4h and 1,3-dibromo-5-isopropyl-5,6,7,8-tetrahydroindeno[1,2-b]indole-9,10-dione 4w with identical IC50 values of 0.11 µM. Furthermore, the development of a QSAR mo

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3

Hazra, Somjit, Biplab Mondal, Rajendra Narayan De, and Brindaban Roy. "Pd-catalyzed dehydrogenative C–H activation of iminyl hydrogen with the indole C3–H and C2–H bond: an elegant synthesis of indeno[1,2-b]indoles and indolo[1,2-a]indoles." RSC Advances 5, no. 29 (2015): 22480–89. http://dx.doi.org/10.1039/c4ra16661b.

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4

Fraser, Heidi L., and Gordon W. Gribble. "A synthesis of 6,11-disubstituted benzo[b]carbazoles." Canadian Journal of Chemistry 79, no. 11 (2001): 1515–21. http://dx.doi.org/10.1139/v01-127.

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Sequential regioselective addition of organolithium reagents to indolo[1,2-b]isoquinoline-6,11-quinone (7) followed by sodium borohydride reduction of the intermediate diol 10, which is not isolated, affords 6,11-disubstituted 5H-benzo[b]carbazoles 11. The tandem combination of methyllithium and lithium triethylborohydride (Super Hydride) gives 6-methylbenzo[b]carbazole (24).Key words: benzo[b]carbazole, organolithiums, indolo[1,2-b]isoquinoline-6,11-quinone, ellipticine, indole.

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5

Zhang, Heng, Xu-Kai Guan, Dong-Yang Sun, et al. "Asymmetric syntheses of spiro[benzofuro-cyclopenta[1,2-b]indole–indoline] scaffolds via consecutive cyclization." Chemical Communications 57, no. 18 (2021): 2313–16. http://dx.doi.org/10.1039/d0cc08083g.

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Highly diastereo- and enantioselective spiro[benzofuro-cyclopenta[1,2-b]indole–indoline] scaffolds with five successive stereogenic centers and two spiroheterocycles were synthesized via consecutive cyclization.

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6

Jordon, Jason A., Jeanese C. Badenock, Gordon W. Gribble, Jerry P. Jasinski, and James A. Golen. "3,3-Dimethyl-1,2,3,4-tetrahydrocyclopenta[b]indole-1,2-dione (bruceolline E)." Acta Crystallographica Section E Structure Reports Online 68, no. 2 (2012): o364—o365. http://dx.doi.org/10.1107/s1600536812000517.

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7

Chahboun, S., M. Gelbcke, G. van de Vliedt, and D. F. Smith. "Synthèse de 2,3,4,4a,9,9a-hexahydro-1h-indéno[1,2-b]pyrazines, analogues rigides de 3-méthyl-2-phénylpiperazines et antidépresseurs potentiels." Bulletin des Sociétés Chimiques Belges 105, no. 5 (2010): 287–96. http://dx.doi.org/10.1002/bscb.19961050511.

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8

Zhang, Guo-Ning, Xia Yuan, Weiping Niu, Mei Zhu, Juxian Wang, and Yucheng Wang. "An Efficient Synthesis of Acenaphtho[1,2-b]indole Derivatives via Domino Reaction." Molecules 23, no. 11 (2018): 3045. http://dx.doi.org/10.3390/molecules23113045.

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A concise and efficient synthesis of acenaphtho[1,2-b]indole derivatives via the domino reactions of enaminones with acenaphthoquinone catalyzed by l-proline has been developed. This protocol has the advantages of good yields, operational convenience and high regioselectivity.

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9

Hu, Fangdong, Huanhuan Liu, Jiong Jia, and Chen Ma. "Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement." Organic & Biomolecular Chemistry 14, no. 47 (2016): 11076–79. http://dx.doi.org/10.1039/c6ob02098d.

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10

Asquith, Christopher, Stephen Hilton, Lidia Konstantinova, et al. "Exploration and Development of a C–H-Activated Route to Access the [1,2]Dithiolo[4,3-b]indole-3(4H)-thione Core and Related Derivatives." Synlett 30, no. 02 (2018): 156–60. http://dx.doi.org/10.1055/s-0037-1611692.

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11

Solymár, Magdolna, Márta Palkó, Tamás Martinek, and Ferenc Fülöp. "Synthesis of Imidazo[1′,5′:1,2]pyrido[3,4-b]indole Derivatives." Monatshefte f�r Chemie / Chemical Monthly 133, no. 11 (2002): 1423–30. http://dx.doi.org/10.1007/s007060200114.

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12

Shakoori, Alireza, John B. Bremner, Mohammed K. Abdel-Hamid, Anthony C. Willis, Rachada Haritakun, and Paul A. Keller. "Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo." Beilstein Journal of Organic Chemistry 11 (April 15, 2015): 481–92. http://dx.doi.org/10.3762/bjoc.11.54.

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Diversity-directed synthesis based on the cascade allylation chemistry of indigo, with its embedded 2,2’-diindolic core, has resulted in rapid access to new examples of the hydroxy-8a,13-dihydroazepino[1,2-a:3,4-b']diindol-14(8H)-one skeleton in up to 51% yield. Additionally a derivative of the novel bridged heterocycle 7,8-dihydro-6H-6,8a-epoxyazepino[1,2-a:3,4-b']diindol-14(13H)-one was produced when the olefin of the allylic substrate was terminally disubstituted. Further optimisation also produced viable one-pot syntheses of derivatives of the spiro(indoline-2,9'-pyrido[1,2-a]indol)-3-one

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13

Noé, Eric, Denis Séraphin, Qiang Zhang, et al. "Synthesis of the new (cyclopenta [b]pyrrolo[1,2-d])azepino[4,5-b]indole ring system." Tetrahedron Letters 37, no. 32 (1996): 5701–4. http://dx.doi.org/10.1016/0040-4039(96)01215-4.

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14

Perron, Julien, Benoı̂t Joseph, and Jean-Yves Mérour. "First synthesis of pyrrolo[1,2:1′,2′]azepino[5,6-b]indole derivatives." Tetrahedron Letters 44, no. 35 (2003): 6553–56. http://dx.doi.org/10.1016/s0040-4039(03)01703-9.

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15

Sanz, Roberto, José M. Ignacio, M. Pilar Castroviejo, and Francisco J. Fañanás. "Synthesis of new indolo[1,2-b]isoquinoline derivatives from N-(2-bromobenzyl)indole." Arkivoc 2007, no. 4 (2006): 84–91. http://dx.doi.org/10.3998/ark.5550190.0008.408.

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16

Al Chab, Faten, Bernard Fenet, Marc Le Borgne, et al. "1H and13C NMR assignments of bioactive indeno[1,2-b]indole-10-one derivatives." Magnetic Resonance in Chemistry 51, no. 12 (2013): 837–41. http://dx.doi.org/10.1002/mrc.4016.

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17

Giri, Venkatachalam S., Sankar K. Das, Parasuraman Jai Sankar, James N. Shoolery, and Paul Keifer. "Unusual formation of a novel pyrrolo[1′,2′:1,2]pyrido[3,4-b]indole." Journal of Heterocyclic Chemistry 29, no. 4 (1992): 767–69. http://dx.doi.org/10.1002/jhet.5570290415.

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18

Jiang, Bo, Qiu-Yun Li, Shu-Jiang Tu, and Guigen Li. "Three-Component Domino Reactions for Selective Formation of Indeno[1,2-b]indole Derivatives." Organic Letters 14, no. 20 (2012): 5210–13. http://dx.doi.org/10.1021/ol3023038.

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19

Butera, John A., Schuyler A. Antane, Bradford Hirth, et al. "Synthesis and potassium channel opening activity of substituted 10H-Benzofuro[3,2-b]indole- and 5,10-Dihydro-indeno[1,2-b]indole-1-carboxylic acids." Bioorganic & Medicinal Chemistry Letters 11, no. 16 (2001): 2093–97. http://dx.doi.org/10.1016/s0960-894x(01)00385-7.

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20

GUEVEN, A., and R. A. JONES. "ChemInform Abstract: Potentially Tautomeric 1,2-Dihydro-1-oxo-5H-pyridazino(4,5-b)indole and 3,4-Dihydro-4-oxo-5H-pyridazino(4,5-b)indole." ChemInform 24, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199352197.

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21

Kumar, Nakul, Chhagan Lal, Bijendra Singh, and Angik K. Patel. "Synthesis and Biological Activities of Some Novel Spiro Heterocyclic Pyrrolizidine Derivatives of 11H-indeno[1,2-b]quinoxaline through 1,3-Dipolar Cycloaddition." Asian Journal of Chemistry 32, no. 5 (2020): 1255–58. http://dx.doi.org/10.14233/ajchem.2020.22630.

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The synthesis of spiropyrrolidines by the Knoevenagel condensation has been reported as highly bioactive natural and synthetic organic products. The synthesis was initiated by Knoevenagel condensation of indole-2-one with an appropriate benzaldehyde in presence of L-proline to afford spiropyrrolidines. Herein, a design and pathway of syntheses of a library of spiropyrrolidines bearing spiro heterocyclic indeno[1,2-b]quinoxaline-11-one motifs were reported, which also demonstrated an exceptional inhibitory activity against the anticancer cells. A novel series of dispiroindenoquinoxaline pyrroli

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22

El-Awaad, Ehab, Robin Birus, Christelle Marminon, et al. "Broad-Spectrum Anticancer Activity and Pharmacokinetic Properties of a Prenyloxy-Substituted Indeno[1,2-b]indole Derivative, Discovered as CK2 Inhibitor." Pharmaceuticals 14, no. 6 (2021): 542. http://dx.doi.org/10.3390/ph14060542.

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Protein kinase CK2 is involved in regulating cellular processes, such as cell cycle, proliferation, migration, and apoptosis, making it an attractive anticancer target. We previously described a prenyloxy-substituted indeno[1,2-b]indole (5-isopropyl-4-(3-methylbut-2-enyloxy)-5,6,7,8-tetrahydroindeno[1,2-b]indole-9,10-dione (4p)) as a very potent inhibitor of CK2 holoenzyme (IC50 = 25 nM). Here, we report the broad-spectrum anticancer activity of 4p and provide substantial progress on its pharmacokinetic properties. Using a cell-based CK2 activity assay and live-cell imaging of cultured A431, A

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23

KUEHMCAUBERE, C., P. CAUBERE, B. JAMARTGREGOIRE, et al. "Novel thiopyrano[3,2-b] and cycloalkeno[1,2-b]indole derivatives with high inhibitory properties in LTB4 production." European Journal of Medicinal Chemistry 34, no. 1 (1999): 51–61. http://dx.doi.org/10.1016/s0223-5234(99)80040-3.

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24

NOE, E., D. SERAPHIN, Q. ZHANG, et al. "ChemInform Abstract: Synthesis of the New (Cyclopenta(b)pyrrolo(1,2-d))azepino(4,5-b)indole Ring System." ChemInform 27, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199646188.

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25

Bhattacharya, Gautam, Tsann-Long Su, Chih-Ming Chia, and Kuo-Tung Chen. "Synthesis and Autoxidation of New Tetracyclic 9H,10H-Indolizino[1,2-b]indole-1-ones." Journal of Organic Chemistry 66, no. 2 (2001): 426–32. http://dx.doi.org/10.1021/jo001020m.

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26

Kuehm-Caubere, Catherine, Paul Caubere, Brigitte Jamart-Gregoire, et al. "Novel Indole-2-carboxamide and Cycloalkeno[1,2-b]indole Derivatives. Structure−Activity Relationships for High Inhibition of Human LDL Peroxidation." Journal of Medicinal Chemistry 40, no. 8 (1997): 1201–10. http://dx.doi.org/10.1021/jm960542k.

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27

Wanner, Klaus Th, та Ulrich Weber. "Oxazolo[3′,2′ :1,2]pyrido[3,4-b]indole und [1,3]-Oxazino [3′,2′ :1,2]pyrido[3,4-b]indole durch eine einfache Kondensationsreaktion von 3,4-Dihydro-β-carbolin mit α- bzw. β-Hydroxycarbonsäuren". Synthesis 1994, № 04 (1994): 387–90. http://dx.doi.org/10.1055/s-1994-25483.

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28

Southwick, Philip L., and Daniel S. Sullivan, Iii. "Strain-Barrier Stabilized Products from the Fischer Indole Synthesis. Compounds Containing the 4H-Imidazo[1,2-a]pyrrolo[3,4-b]indole and Dipyrrolo [3,4-b:3′,4′-b′][1,3]diazeto[1,2-a:3,4-a′]diindole Ring Systems." Synthesis 1986, no. 09 (1986): 731–35. http://dx.doi.org/10.1055/s-1986-31758.

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29

Mérour, Jean-Yves, Benoît Joseph, Virginie Chapellier, and Stéphane Léonce. "Synthesis and Antitumoral Evaluation of 12-Substituted 6,7-Dihydrobenzo[4,5]-cyclohept[1,2-b]indole Derivatives." HETEROCYCLES 48, no. 7 (1998): 1423. http://dx.doi.org/10.3987/com-98-8178.

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30

Ryabova, Svetlana Yu, Lyudmila M. Alekseeva, and Vladimir G. Granik. "A New Approach to the Synthesis of 1,2- and 1,4-Dihydropyrido[3,2-b]indole Derivatives." Mendeleev Communications 5, no. 3 (1995): 107–9. http://dx.doi.org/10.1070/mc1995v005n03abeh000480.

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31

GIRI, V. S., S. K. DAS, P. J. SANKAR, J. N. SHOOLERY, and P. KEIFER. "ChemInform Abstract: Unusual Formation of a Novel Pyrrolo(1′,2′:1,2)pyrido(3,4-b)indole." ChemInform 23, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199250196.

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32

Maleque, M. A., P. K. Adhikary, S. Pavuluri, P. Kopsombut, and H. K. Rucker. "Potentiation of cholinergic activity with pyridino[1,2-a]imidazo[5,4-b]indole: In vitro studies." General Pharmacology: The Vascular System 21, no. 2 (1990): 199–203. http://dx.doi.org/10.1016/0306-3623(90)90901-w.

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33

Jiang, Bo, Qiu-Yun Li, Shu-Jiang Tu, and Guigen Li. "ChemInform Abstract: Three-Component Domino Reactions for Selective Formation of Indeno[1,2-b]indole Derivatives." ChemInform 44, no. 8 (2013): no. http://dx.doi.org/10.1002/chin.201308119.

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34

Kuehm-Caubere, Catherine, Paul Caubere, Brigitte Jamart-Gregoire, et al. "ChemInform Abstract: Novel Thiopyrano[3,2-b] and Cycloalkeno[1,2-b]indole Derivatives with High Inhibitory Properties in LTB4 Production." ChemInform 30, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.199922119.

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35

Shertzer, H. G., and M. Sainsbury. "Intrinsic acute toxicity and hepatic enzyme inducing properties of the chemoprotectants indole-3-carbinol and 5,10-dihydroindeno[1,2-b]indole in mice." Food and Chemical Toxicology 29, no. 4 (1991): 237–42. http://dx.doi.org/10.1016/0278-6915(91)90020-8.

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36

Butera, John A., Schuyler A. Antane, Bradford Hirth, et al. "ChemInform Abstract: Synthesis and Potassium Channel Opening Activity of Substituted 10H-Benzo[4,5]furo[3,2-b]indole- and 5,10-Dihydro-indeno[1,2-b]indole-1-carboxylic Acids." ChemInform 32, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.200145132.

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37

Muratov, A. V., Yu V. Berestneva, S. Yu Zinchenko, et al. "NMR 1H Spectra of the [1,2]Diazepino[4,5-b]Indole Derivatives: Experimental versus GIAO calculated Data." International Journal of Chemistry and Research 1, no. 1 (2019): 9–12. http://dx.doi.org/10.18689/ijcr-1000102.

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38

Hemmerling, Hans-Jörg, та Guido Reiss. "Partially Saturated Indeno[1,2-b]indole Derivatives via Deoxygenation of Heterocyclic α-Hydroxy-N,O-hemiaminals". Synthesis 2009, № 06 (2009): 985–99. http://dx.doi.org/10.1055/s-0028-1087983.

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39

Balenko, S. K., V. P. Rybalkin, E. N. Shepelenko, et al. "Synthesis and photochromic properties of fulgides based on naphtho[1,2-b]furan and benzo[g]indole." Russian Journal of Organic Chemistry 42, no. 12 (2006): 1861–63. http://dx.doi.org/10.1134/s1070428006120190.

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40

MACCHIA, M., C. MANERA, S. NENCETTI, A. ROSSELLO, G. BROCCALI, and D. LIMONTA. "ChemInform Abstract: Synthesis and Antimicrobial Activity of Benzo(a)dihydrocarbazole and Benzotetrahydrocyclohept(1,2-b)indole Derivatives." ChemInform 27, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199627147.

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41

RYABOVA, S. YU, L. M. ALEKSEEVA, and V. G. GRANIK. "ChemInform Abstract: New Approach to the Synthesis of 1,2- and 1,4-Dihydropyrido(3,2-b) indole Derivatives." ChemInform 26, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199538191.

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42

Hundsdörfer, Claas, Hans-Jörg Hemmerling, Claudia Götz, et al. "Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors." Bioorganic & Medicinal Chemistry 20, no. 7 (2012): 2282–89. http://dx.doi.org/10.1016/j.bmc.2012.02.017.

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43

Balenko, S. K., N. I. Makarova, V. P. Rybalkin, et al. "Structures and photochromic properties of fulgides based on naphtho[1,2-b]furan and benzo[g]indole." Russian Chemical Bulletin 59, no. 5 (2010): 954–59. http://dx.doi.org/10.1007/s11172-010-0189-x.

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44

Dai, Pan-Pan, Yi-Zhou Zhu, Qing-Long Liu, Yi-Qiao Yan, and Jian-Yu Zheng. "Novel indeno[1,2-b]indole-spirofluorene donor block for efficient sensitizers in dye-sensitized solar cells." Dyes and Pigments 175 (April 2020): 108099. http://dx.doi.org/10.1016/j.dyepig.2019.108099.

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45

Qian, Xing, Rucai Yan, Yongjie Hang, et al. "Indeno[1,2- b ]indole-based organic dyes with different acceptor groups for dye-sensitized solar cells." Dyes and Pigments 139 (April 2017): 274–82. http://dx.doi.org/10.1016/j.dyepig.2016.12.028.

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46

Bhattacharya, Gautam, Tsann-Long Su, Chih-Ming Chia, and Kuo-Tung Chen. "ChemInform Abstract: Synthesis and Autoxidation of New Tetracyclic 9H,10H-Indolizino[1,2-b]indole-1-ones." ChemInform 32, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.200124056.

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47

Govindan, E., P. S. Yuvaraj, B. S. R. Reddy, S. Bangaru Sudarsan Alwar, and A. SubbiahPandi. "(4S)-3-Methyl-5,6,7,8-tetrahydro-4H-spiro[[1,2]oxazolo[5,4-b]quinoline-4,3′-indole]-2′,5-dione." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (2014): o168. http://dx.doi.org/10.1107/s1600536814000130.

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In the title compound, C18H15N3O3, the dihedral angle between the mean planes of the quinoline and indole ring systems [r.m.s. deviations = 0.189 (2) and 0.027 (2) Å, respectively] is 88.65 (5)°. The cyclohexene ring of the quinoline ring system adopts an envelope conformation with the central –CH2– C atom as the flap. In the crystal, molecules are linked by two pairs of N—H...O hydrogen bonds, forming inversion dimers, and enclosingR22(14) ring motifs. This arrangement results in the formation of chains propagating along [100].

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48

Nagarajan, Rajagopal, and K. Prakash. "Synthesis of Azepino[4,5-b]indole Analogues via 7-endo-Selective Cyclization of Isocyanoacetates and Indole-1,2-alkynylaldehydes: An Approach towards the Chromoazepinone Core." Synlett 26, no. 16 (2015): 2318–22. http://dx.doi.org/10.1055/s-0035-1560460.

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49

Konstantinova, Lidia S., Kirill A. Lysov, Stanislav A. Amelichev, Natalia V. Obruchnikova, and Oleg A. Rakitin. "A one-pot synthesis and 1,3-dipolar cycloaddition of [1,2]dithiolo[4,3-b]indole-3(4H)-thiones." Tetrahedron 65, no. 11 (2009): 2178–83. http://dx.doi.org/10.1016/j.tet.2009.01.069.

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50

Stephanidou-Stephanatou, Julia, Dimitra Hatzimimikou, Despina Livadiotou, and Constantinos Tsoleridis. "One-Step Synthesis of [1,2]Diazepino[4,5-b]indole Derivatives from the Reaction of Pyranoindolones with Methylhydrazine." Synlett 2008, no. 12 (2008): 1773–76. http://dx.doi.org/10.1055/s-2008-1078511.

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