Bibliographies thématiques / Isocryptolepine

Littérature scientifique sur le sujet « Isocryptolepine »

Auteur : Grafiati
Publié le 6 septembre 2023

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Articles de revues sur le sujet "Isocryptolepine"

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Wang, Ning, Marta Świtalska, Li Wang, Elkhabiry Shaban, Md Imran Hossain, Ibrahim El Tantawy El Sayed, Joanna Wietrzyk et Tsutomu Inokuchi. « Structural Modifications of Nature-Inspired Indoloquinolines : A Mini Review of Their Potential Antiproliferative Activity ». Molecules 24, no 11 (5 juin 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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Murray, Paul E., Keith Mills et 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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Pousset, Jean-Louis, Marie-Therese Martin, Akino Jossang et Bernard Bodo. « Isocryptolepine from Cryptolepis sanguinolenta ». Phytochemistry 39, no 3 (juin 1995) : 735–36. http://dx.doi.org/10.1016/0031-9422(94)00925-j.

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Aksenov, Alexander V., Dmitrii A. Aksenov, Georgii D. Griaznov, Nicolai A. Aksenov, Leonid G. Voskressensky et 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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Murray, Paul E., Keith Mills et John A. Joule. « ChemInform Abstract : A Synthesis of Isocryptolepine. » ChemInform 30, no 15 (16 juin 2010) : no. http://dx.doi.org/10.1002/chin.199915254.

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Akitake, Masahiro, Shizuki Noda, Kohei Miyoshi, Motohiro Sonoda et Shinji Tanimori. « Access to γ-Carbolines : Synthesis of Isocryptolepine ». Journal of Organic Chemistry 86, no 24 (6 décembre 2021) : 17727–37. http://dx.doi.org/10.1021/acs.joc.1c02026.

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

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

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Helgeland, Ida, et 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 (mars 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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Whittell, Louise R., Kevin T. Batty, Rina P. M. Wong, Erin M. Bolitho, Simon A. Fox, Timothy M. E. Davis et Paul E. Murray. « Synthesis and antimalarial evaluation of novel isocryptolepine derivatives ». Bioorganic & ; Medicinal Chemistry 19, no 24 (décembre 2011) : 7519–25. http://dx.doi.org/10.1016/j.bmc.2011.10.037.

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Thèses sur le sujet "Isocryptolepine"

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Whittell, Louise Renee'. « The synthesis and biological evaluation of novel analogues of isocryptolepine ». Thesis, Curtin University, 2011. http://hdl.handle.net/20.500.11937/2558.

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This thesis investigates the potential of the alkaloid isocryptolepine 16 as a lead compound in antimalarial drug development. Fifteen derivatives of the parent alkaloid were prepared and fully characterised, twelve of which were novel compounds. A select group of compounds were subsequently evaluated for both antimalarial activity and cytotoxicity.Three previously reported synthetic methodologies to the parent alkaloid were initially investigated; wherein two approaches were able to be reproduced or improved. These two synthetic methodologies were subsequently applied to the preparation of derivatives. The first of these methodologies, the Jonckers Method, involved two consecutive palladium catalysed coupling reactions. During the course of these investigations it was found that these two reactions could be combined into a single ‘domino’ reaction resulting in a reduction in the number of steps required to prepare the parent alkaloid. This methodology was then applied to the preparation of both ring-substituted and structural isomers. The second methodology, The Molina Method, involved a benzotriazole-mediated strategy and was applicable to preparing isocryptolepine derivatives with ring substituents on the quinoline ring. Finally a method for selective electrophilic aromatic substitution was developed and applied to the preparation of a further range of halogenated derivatives.Eight of the prepared derivatives were selected for biological evaluation. Antimalarial activity was assessed against a chloroquine sensitive and resistant strain of P. falciparum, whilst cytotoxicity was evaluated against mouse embryonic fibroblasts (3T3 cells). All compounds were found to be more active compared to the parent alkaloid against the chloroquine resistant strain of P. falciparum; specifically 8-bromo-2-chloroisocryptolepine 107 (IC[subscript]50 = 85 nM) and 8-bromo-3-chloroisocryptolepine 105 (IC[subscript]50 = 100 nM) were the most potent. Cytotoxicity evaluations revealed that ring substitution did not enhance cytotoxicity and the most potent antimalarial derivative, 8-bromo-2-chloroisocryptolepine 107 (IC[subscript]50 = 9.01 μM), displayed a 4-fold reduction in cytotoxicity.In conclusion, isocryptolepine 16 and its derivatives have significant potential as antimalarial lead compounds, with many derivatives possessing enhanced bioactivity versus the parent. This study has also identified 8-bromo-2-chloroisocryptolepine 107 to be a very promising lead compound which warrants further biological or pharmaceutical investigation.
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黃閔賢. « Optimization of Metal-Catalyzed Cascade Reaction for the Synthesis of Indolo[2,3-c]quinolinones and Total Synthesis of Isocryptolepine ». Thesis, 2018. http://ndltd.ncl.edu.tw/handle/z9m3jc.

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碩士
國立嘉義大學
應用化學系研究所
107
In this thesis, I report the optimization of a metal-catalyzed cascade reaction for the synthesis of indolo[2,3-c]quinolinone (1) using 2-(2-bromophenyl)-N-(2-cyanophenyl)acetamide (19) as the starting material. First, I studied the effect of bases including NaH, NaOH, t-BuONa, and t-BuOK on this reaction by use of CuI as the catalyst and DMF as the solvent. The results showed that NaH and t-BuONa were the most reactive bases with CuI for the reaction. Consequently, NaH and t-BuONa were combined with different copper catalysts in DMF to further optimize the reaction. The results revealed that CuI, CuBr, Cu2O, CuBr·SMe2 showed good reactivity at 110 C. By lowering the reaction temperature, I found that CuBr and t-BuONa were the best combination for the reaction. Addition of a ligand or changing the reaction solvent redcued the yield. As a result, the optimal reaction conditions for the reaction are using t-BuONa as a base, CuBr as a catalyst, and DMF as a solvent. When the reaction was carried out at 110 C for 16 h, product 1 was obtained in 96% yield. I then applied the metal-catalyzed cascade reaction to synthesize alkaloid isocryptolepine (2). By addition of a monomethylation step into the cascade, 2 can obtained in three steps with a total yield of 72% from commercially available starting materials.
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