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Journal articles on the topic 'Isocryptolepine'

Author: Grafiati

Published: 6 September 2023

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1

Wang, Ning, Marta Świtalska, Li Wang, et al. "Structural Modifications of Nature-Inspired Indoloquinolines: A Mini Review of Their Potential Antiproliferative Activity." Molecules 24, no. 11 (2019): 2121. http://dx.doi.org/10.3390/molecules24112121.

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Cryptolepine, neocryptolepine and isocryptolepine are naturally occurring indoloquinoline alkaloids with various spectrum of biological properties. Structural modification is an extremely effective means to improve their bioactivities. This review enumerates several neocryptolepine and isocryptolepine analogues with potent antiproliferative activity against MV4-11 (leukemia), A549 (lung cancer), HCT116 (colon cancer) cell lines in vitro. Its activity towards normal mouse fibroblasts BALB/3T3 was also evaluated. Furthermore, structure activity relationships (SAR) are briefly discussed. The anticancer screening of neocryptolepine derivatives was performed in order to determine their cytotoxic and growth inhibitory activities across the JFCR39 cancer cell line panel.

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2

Murray, Paul E., Keith Mills, and John A. Joule. "A Synthesis of Isocryptolepine." Journal of Chemical Research, no. 7 (1998): 377. http://dx.doi.org/10.1039/a801313f.

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3

Pousset, Jean-Louis, Marie-Therese Martin, Akino Jossang, and Bernard Bodo. "Isocryptolepine from Cryptolepis sanguinolenta." Phytochemistry 39, no. 3 (1995): 735–36. http://dx.doi.org/10.1016/0031-9422(94)00925-j.

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4

Aksenov, Alexander V., Dmitrii A. Aksenov, Georgii D. Griaznov, Nicolai A. Aksenov, Leonid G. Voskressensky, and Michael Rubin. "Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines." Organic & Biomolecular Chemistry 16, no. 23 (2018): 4325–32. http://dx.doi.org/10.1039/c8ob00588e.

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5

Murray, Paul E., Keith Mills, and John A. Joule. "ChemInform Abstract: A Synthesis of Isocryptolepine." ChemInform 30, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199915254.

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6

Akitake, Masahiro, Shizuki Noda, Kohei Miyoshi, Motohiro Sonoda та Shinji Tanimori. "Access to γ-Carbolines: Synthesis of Isocryptolepine". Journal of Organic Chemistry 86, № 24 (2021): 17727–37. http://dx.doi.org/10.1021/acs.joc.1c02026.

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7

Kraus, George A., and Haitao Guo. "A direct synthesis of neocryptolepine and isocryptolepine." Tetrahedron Letters 51, no. 31 (2010): 4137–39. http://dx.doi.org/10.1016/j.tetlet.2010.05.141.

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8

Dubovitskii, S. V., O. S. Radchenko, and V. L. Norikov. "Synthesis of isocryptolepine, an alkaloid fromCryptolepis sanguinolenta." Russian Chemical Bulletin 45, no. 11 (1996): 2656–57. http://dx.doi.org/10.1007/bf01431136.

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9

Helgeland, Ida, and Magne Sydnes. "A Concise Synthesis of Isocryptolepine by C–C Cross-Coupling Followed by a Tandem C–H Activation and C–N Bond Formation." SynOpen 01, no. 01 (2017): 0041–44. http://dx.doi.org/10.1055/s-0036-1590807.

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Isocryptolepine (1), a potent antimalarial natural product, was prepared in three steps from 3-bromoquinoline and 2-aminophenylboronic acid hydrochloride. The key transformations were a Suzuki–Miyaura cross-coupling reaction followed by a palladium-initiated intramolecular C–H activation/C–N bond formation between an unprotected amine and an aromatic C–H group. The two key reactions can also be performed in one pot.

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10

Whittell, Louise R., Kevin T. Batty, Rina P. M. Wong, et al. "Synthesis and antimalarial evaluation of novel isocryptolepine derivatives." Bioorganic & Medicinal Chemistry 19, no. 24 (2011): 7519–25. http://dx.doi.org/10.1016/j.bmc.2011.10.037.

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11

Li, Jun-cai, Ren-xuan Wang, Yu Sun, et al. "Design, synthesis and antifungal activity evaluation of isocryptolepine derivatives." Bioorganic Chemistry 92 (November 2019): 103266. http://dx.doi.org/10.1016/j.bioorg.2019.103266.

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12

Rujimongkon, Kitiya, Mathirut Mungthin, Jumreang Tummatorn, et al. "Proteomic analysis of Plasmodium falciparum response to isocryptolepine derivative." PLOS ONE 14, no. 8 (2019): e0220871. http://dx.doi.org/10.1371/journal.pone.0220871.

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13

Grellier, Phillippe, Lobo Ramiaramanana, Valérie Millerioux, et al. "Antimalarial Activity of Cryptolepine and Isocryptolepine, Alkaloids Isolated fromCryptolepis sanguinolenta." Phytotherapy Research 10, no. 4 (1996): 317–21. http://dx.doi.org/10.1002/(sici)1099-1573(199606)10:4<317::aid-ptr858>3.0.co;2-0.

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14

DUBOVITSKII, S. V., O. S. RADCHENKO, and V. L. NOVIKOV. "ChemInform Abstract: Synthesis of Isocryptolepine, an Alkaloid from Cryptolepis sanguinolenta." ChemInform 28, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199717217.

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15

Rodphon, Warabhorn, Pavitra Laohapaisan, Nantamon Supantanapong, et al. "Synthesis of Isocryptolepine‐Triazole Adducts and Evaluation of Their Cytotoxic Activity." ChemMedChem 16, no. 24 (2021): 3750–62. http://dx.doi.org/10.1002/cmdc.202100554.

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16

Aksenov, Alexander V., Dmitrii A. Aksenov, Naila A. Orazova, et al. "One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine." Journal of Organic Chemistry 82, no. 6 (2017): 3011–18. http://dx.doi.org/10.1021/acs.joc.6b03084.

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17

T. Parvatkar, Prakash, Perunninakulath S. Parameswaran, and Santosh G. Tilve. "Isolation, Biological Activities and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine and Neocryptolepine." Current Organic Chemistry 15, no. 7 (2011): 1036–57. http://dx.doi.org/10.2174/138527211794785118.

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18

Thobokholt, Elida N., Enrique L. Larghi, Andrea B. J. Bracca, and Teodoro S. Kaufman. "Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid." RSC Advances 10, no. 32 (2020): 18978–9002. http://dx.doi.org/10.1039/d0ra03096a.

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19

Aggrey, Mike Okweesi, Hui-Hui Li, Wen-Qiong Wang, Weibin Song, Yiping Wang, and Li-Jiang Xuan. "Isocryptolepine, an indoloquinoline alkaloid from Cryptolepis sanguinolenta promotes LDL uptake in HepG2 cells." Revista Brasileira de Farmacognosia 28, no. 6 (2018): 654–57. http://dx.doi.org/10.1016/j.bjp.2018.08.008.

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20

Kraus, George, Haitao Guo, Ganesh Kumar, et al. "A Flexible Synthesis of Indoles from ortho-Substituted Anilines: A Direct Synthesis of Isocryptolepine." Synthesis 2010, no. 08 (2010): 1386–93. http://dx.doi.org/10.1055/s-0029-1218706.

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21

Kraus, George, Haitao Guo, Ganesh Kumar, Heather Carruthers, Divya Chaudhary, and Jonathan Beasley. "A Flexible Synthesis of Indoles from ortho-Substituted Anilines: A Direct Synthesis of Isocryptolepine." Synthesis 2010, no. 14 (2010): 2496. http://dx.doi.org/10.1055/s-0029-1218853.

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22

Parvatkar, Prakash T., Perunninakulath S. Parameswaran, and Santosh G. Tilve. "ChemInform Abstract: Isolation, Biological Activities, and Synthesis of Indoloquinoline Alkaloids: Cryptolepine, Isocryptolepine, and Neocryptolepine." ChemInform 42, no. 38 (2011): no. http://dx.doi.org/10.1002/chin.201138237.

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23

Aroonkit, Pasuk, Charnsak Thongsornkleeb, Jumreang Tummatorn, Suppachai Krajangsri, Mathirut Mungthin, and Somsak Ruchirawat. "Synthesis of isocryptolepine analogues and their structure–activity relationship studies as antiplasmodial and antiproliferative agents." European Journal of Medicinal Chemistry 94 (April 2015): 56–62. http://dx.doi.org/10.1016/j.ejmech.2015.02.047.

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24

Kraus, George A., Haitao Guo, Ganesh Kumar, et al. "ChemInform Abstract: A Flexible Synthesis of Indoles from ortho-Substituted Anilines: A Direct Synthesis of Isocryptolepine." ChemInform 41, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.201035120.

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25

Murugan, Arumugavel, Shinde Vidyacharan, Ruma Ghosh, and Duddu S. Sharada. "Metal-Free Regioselective Dual C-H Functionalization in a Cascade Fashion: Access to Isocryptolepine Alkaloid Analogues." ChemistrySelect 2, no. 12 (2017): 3511–15. http://dx.doi.org/10.1002/slct.201700263.

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26

Håheim, Katja S., Emil Lindbäck, Kah Ni Tan, et al. "Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioisomers for Antimalarial, Antiproliferative and Antimicrobial Activities." Molecules 26, no. 11 (2021): 3268. http://dx.doi.org/10.3390/molecules26113268.

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A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 µM; 9b: MBIC = 100 µM).

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27

Hayashi, Kaori, Tominari Choshi, Kyoko Chikaraishi, et al. "A novel total synthesis of isocryptolepine based on a microwave-assisted tandem Curtius rearrangement and aza-electrocyclic reaction." Tetrahedron 68, no. 22 (2012): 4274–79. http://dx.doi.org/10.1016/j.tet.2012.03.055.

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28

Håheim, Katja S., Ida T. Urdal Helgeland, Emil Lindbäck, and Magne O. Sydnes. "Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers." Tetrahedron 75, no. 21 (2019): 2949–57. http://dx.doi.org/10.1016/j.tet.2019.04.026.

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29

Hingane, Dattatray G., та Radhika S. Kusurkar. "An efficient new route towards biologically active isocryptolepine and γ-carboline derivatives using an intramolecular thermal electrocyclization strategy". Tetrahedron Letters 52, № 28 (2011): 3686–88. http://dx.doi.org/10.1016/j.tetlet.2011.05.049.

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30

Chen, Chen, Yuebo Wang, Xiaonan Shi, et al. "Palladium-Catalyzed C-2 and C-3 Dual C–H Functionalization of Indoles: Synthesis of Fluorinated Isocryptolepine Analogues." Organic Letters 22, no. 11 (2020): 4097–102. http://dx.doi.org/10.1021/acs.orglett.0c01159.

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31

Uchuskin, Maxim G., Arkady S. Pilipenko, Olga V. Serdyuk, Igor V. Trushkov, and Alexander V. Butin. "From biomass to medicines. A simple synthesis of indolo[3,2-c]quinolines, antimalarial alkaloid isocryptolepine, and its derivatives." Organic & Biomolecular Chemistry 10, no. 36 (2012): 7262. http://dx.doi.org/10.1039/c2ob25836f.

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32

Chen, Xuebing, Peng Sun, Jinyi Xu, et al. "Construction of indoloquinolinones via Pd(II)-catalyzed tandem CC/CN bond formation: application to the total synthesis of isocryptolepine." Tetrahedron Letters 55, no. 51 (2014): 7114–17. http://dx.doi.org/10.1016/j.tetlet.2014.11.008.

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33

Hostyn, Steven, Bert U. W. Maes, Luc Pieters та ін. "Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine". Tetrahedron 61, № 6 (2005): 1571–77. http://dx.doi.org/10.1016/j.tet.2004.11.073.

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34

Agarwal, Piyush K., Devesh Sawant, Sunil Sharma, and Bijoy Kundu. "New Route to the Synthesis of the Isocryptolepine Alkaloid and Its Related Skeletons Using a Modified Pictet-Spengler Reaction." European Journal of Organic Chemistry 2009, no. 2 (2009): 292–303. http://dx.doi.org/10.1002/ejoc.200800929.

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35

Mahajan, Pankaj S., Vivek T. Humne, Subhash D. Tanpure, and Santosh B. Mhaske. "Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C–H Activation." Organic Letters 18, no. 14 (2016): 3450–53. http://dx.doi.org/10.1021/acs.orglett.6b01634.

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36

Aksenov, Nicolai A., Alexander V. Aksenov, Alexander Kornienko, et al. "A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities." RSC Advances 8, no. 64 (2018): 36980–86. http://dx.doi.org/10.1039/c8ra08155g.

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37

Indu, Satrajit, Parthasarathi Subramanian, and Krishna P. Kaliappan. "Transition-Metal-Catalyzed Selective Cyclization Strategy to 2-Substituted Benzofurans and Indoles en Route to the Oxa Analogues of Isocryptolepine." European Journal of Organic Chemistry 2014, no. 32 (2014): 7193–202. http://dx.doi.org/10.1002/ejoc.201402869.

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38

Uchuskin, Maxim G., Arkady S. Pilipenko, Olga V. Serdyuk, Igor V. Trushkov, and Alexander V. Butin. "ChemInform Abstract: From Biomass to Medicines. A Simple Synthesis of Indolo[3,2-c]quinolines, Antimalarial Alkaloid Isocryptolepine, and Its Derivatives." ChemInform 44, no. 8 (2013): no. http://dx.doi.org/10.1002/chin.201308150.

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39

Indu, Satrajit, Parthasarathi Subramanian, and Krishna P. Kaliappan. "ChemInform Abstract: Transition-Metal-Catalyzed Selective Cyclization Strategy to 2-Substituted Benzofurans and Indoles en Route to the Oxa Analogues of Isocryptolepine." ChemInform 46, no. 16 (2015): no. http://dx.doi.org/10.1002/chin.201516147.

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40

Chen, Xuebing, Peng Sun, Jinyi Xu, et al. "ChemInform Abstract: Construction of Indoloquinolinones via Pd(II)-Catalyzed Tandem C-C/C-N Bond Formation: Application to the Total Synthesis of Isocryptolepine." ChemInform 46, no. 18 (2015): no. http://dx.doi.org/10.1002/chin.201518218.

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41

Wang, Ning, Kathryn J. Wicht, Kento Imai та ін. "Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11". Bioorganic & Medicinal Chemistry 22, № 9 (2014): 2629–42. http://dx.doi.org/10.1016/j.bmc.2014.03.030.

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42

Kirsch, Gilbert, Eslam El-Sawy, and Ahmed Abdelwahab. "Utilization of 1H-Indole-3-carboxaldehyde as a Precursor for the Synthesis of Bioactive Indole Alkaloids." Synthesis 50, no. 23 (2018): 4525–38. http://dx.doi.org/10.1055/s-0037-1610288.

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Indole alkaloids constitute a large class of natural products and their diverse and complex structures have been attributed to potent biological activities such as anticancer, anti-inflammatory, antimicrobial, antimalarial, antiplasmodial and protein kinase inhibition. The isolation of bioactive compounds from natural sources is difficult, costly and an extremely time-consuming process, therefore synthetic pathways are more convenient than natural separation to deliver such compounds in considerable amounts. In this respect, this review provides comprehensive information on the structures and the synthesis of bioactive indole alkaloids utilizing 1H-indole-3-carboxaldehyde and its derivatives as starting compounds. 1 Overview2 Phytoalexins2.1 Brassinin, Cyclobrassinin and Brassitin2.2 1-Methoxybrassinin, 1-Methoxyspirobrassinol and 1-Methoxyspirobrassinin2.3 4-Methoxybrassinin and 4-Methoxycyclobrassinin2.4 Cyclobrassinone2.5 Brassilexin2.6 (S)-(–)-Spirobrassinin2.7 Camalexin3 Bis(indole) Alkaloids: Rhopaladines A–D4 Coscinamides A and B5 α-Cyclopiazonic Acid6 Dipodazine7 Isocryptolepine8 Apparicine9 Carbazole Alkaloids: Mukonine and Clausine E10 Indolmycin11 Conclusion

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43

Schendera, Eva, Lisa‐Natascha Unkel, Phung Phan Huyen Quyen, et al. "Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines." Chemistry – A European Journal 26, no. 1 (2019): 269–74. http://dx.doi.org/10.1002/chem.201903921.

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44

Jonckers, Tim H. M., Bert U. W. Maes, Guy L. F. Lemiere, et al. "Synthesis of Isocryptolepine via a Pd-Catalyzed “Amination—Arylation” Approach." ChemInform 34, no. 30 (2003). http://dx.doi.org/10.1002/chin.200330227.

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45

Morozov, Vyacheslav, and Yurii Shklyaev. "Metal‐Free Rapid Diastereoselective Construction of Isocryptolepine Core via Elecrophilic Dearomatization ‐ Inramolecular Michael Addition Sequence." ChemistrySelect 7, no. 23 (2022). http://dx.doi.org/10.1002/slct.202201709.

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46

Hostyn, Steven, Bert U. W. Maes, Luc Pieters та ін. "Synthesis of the Benzo-β-Carboline Isoneocryptolepine: The Missing Indoloquinoline Isomer in the Alkaloid Series Cryptolepine, Neocryptolepine and Isocryptolepine." ChemInform 36, № 23 (2005). http://dx.doi.org/10.1002/chin.200523212.

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47

Agarwal, Piyush K., Devesh Sawant, Sunil Sharma, and Bijoy Kundu. "ChemInform Abstract: New Route to the Synthesis of the Isocryptolepine Alkaloid and Its Related Skeletons Using a Modified Pictet-Spengler Reaction." ChemInform 40, no. 20 (2009). http://dx.doi.org/10.1002/chin.200920188.

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48

Mahajan, Pankaj S., Vivek T. Humne, Subhash D. Tanpure, and Santosh B. Mhaske. "ChemInform Abstract: Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation." ChemInform 47, no. 48 (2016). http://dx.doi.org/10.1002/chin.201648028.

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49

Verma, Kanchan, Yogesh Kumar Tailor, Sarita Khandelwal, et al. "Synthesis and characterization of terbium doped TiO 2 nanoparticles and their use as recyclable and reusable heterogeneous catalyst for efficient and environmentally sustainable synthesis of spiroannulated indolo[3,2‐ c ]quinolines‐ mimetic scaffolds of isocryptolepine." Applied Organometallic Chemistry 34, no. 10 (2020). http://dx.doi.org/10.1002/aoc.5836.

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