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Journal articles on the topic 'Cleistenolide'

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Author: Grafiati
Published: 6 September 2023

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1

Schmidt, Bernd, Oliver Kunz, and Anne Biernat. "Total Synthesis of (−)-Cleistenolide." Journal of Organic Chemistry 75, no. 7 (April 2, 2010): 2389–94. http://dx.doi.org/10.1021/jo1002642.

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2

Ramesh, Palakuri, and H. M. Meshram. "Total synthesis of (−)-cleistenolide." Tetrahedron Letters 52, no. 19 (May 2011): 2443–45. http://dx.doi.org/10.1016/j.tetlet.2011.01.124.

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3

Chanti Babu, Dokuburra, Kankati Ashalatha, Chitturi Bhujanga Rao, Jon Paul Selvam Jondoss, and Yenamandra Venkateswarlu. "Total Synthesis of (−)-Cleistenolide." Helvetica Chimica Acta 94, no. 12 (December 2011): 2215–20. http://dx.doi.org/10.1002/hlca.201100086.

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4

Samwel, Stephen, Stephen J. M. Mdachi, Mayunga H. H. Nkunya, Beatrice N. Irungu, Mainen J. Moshi, Brian Moulton, and Brian S. Luisi. "Cleistenolide and Cleistodienol: Novel Bioactive Constituents of Cleistochlamys kirkii." Natural Product Communications 2, no. 7 (July 2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200706.

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(-)-5-Acetoxy-6-(1-benzoyloxy-2-acetoxyethyl)-pyr-3-en-2-one (cleistenolide) and (-)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enylidenemethyl benzoate (cleistodienol) were isolated as novel antimicrobial and cytotoxic constituents of Cleistochlamys kirkii (Annonaceae), together with ( Z)-(+)-5-(2,3-dihydroxy-propylidene)-5 H-furan-2-one and its acetyl and benzoyl derivatives, (-)-1,6-desoxy-β-senepoxide, pinocembrin and polycarpol. Structural determination was achieved based on spectroscopic and other physical data. The structure of cleistenolide was confirmed by single crystal X-ray crystallographic analysis.
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5

Cai, Chao, Jun Liu, Yuguo Du, and Robert J. Linhardt. "Stereoselective Total Synthesis of (−)-Cleistenolide." Journal of Organic Chemistry 75, no. 16 (August 20, 2010): 5754–56. http://dx.doi.org/10.1021/jo101059e.

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6

Chanti Babu, Dokuburra, Jondoss Jon Paul Selavam, Dorigondla Kumar Reddy, Vanam Shekhar, and Yenamandra Venkateswarlu. "Stereoselective total synthesis of (−)-cleistenolide." Tetrahedron 67, no. 21 (May 2011): 3815–19. http://dx.doi.org/10.1016/j.tet.2011.03.107.

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7

Subba Reddy, B. V., B. Phaneendra Reddy, T. Pandurangam, and J. S. Yadav. "The stereoselective total synthesis of (−)-cleistenolide." Tetrahedron Letters 52, no. 18 (May 2011): 2306–8. http://dx.doi.org/10.1016/j.tetlet.2011.02.025.

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8

Reddy, A. Bal, B. Kumara Swamy, and Jhillu Singh Yadav. "A concise total synthesis of cleistenolide." Tetrahedron: Asymmetry 27, no. 16 (September 2016): 788–90. http://dx.doi.org/10.1016/j.tetasy.2016.06.012.

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9

Mahajan, Pankaj S., Rajesh G. Gonnade, and Santosh B. Mhaske. "Protecting-Group-Free Diastereoselective Total Synthesis of (±)-6-epi-Cleistenolide and Chemoenzymatic Synthesis of (-)-6-epi-Cleistenolide." European Journal of Organic Chemistry 2014, no. 36 (October 31, 2014): 8049–54. http://dx.doi.org/10.1002/ejoc.201403123.

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10

Vijaya Kumar, T., K. Suresh Babu, and J. Madhusudana Rao. "A simple and efficient stereoselective synthesis of (−)-cleistenolide." Tetrahedron Letters 53, no. 14 (April 2012): 1823–25. http://dx.doi.org/10.1016/j.tetlet.2012.01.123.

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11

Benedeković, Goran, Mirjana Popsavin, Niko S. Radulović, Zorica Stojanović-Radić, Sándor Farkas, Jovana Francuz, and Velimir Popsavin. "Synthesis and antimicrobial activity of (−)-cleistenolide and analogues." Bioorganic Chemistry 106 (January 2021): 104491. http://dx.doi.org/10.1016/j.bioorg.2020.104491.

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12

Farkas, Sándor, Goran Benedekovic, Sladjana Stanisavljevic, Bojana Sreco-Zelenovic, Mirjana Popsavin, Velimir Popsavin, and Dimitar Jakimov. "Synthesis and antiproliferative activity of (5R)-cleistenolide and analogues." Journal of the Serbian Chemical Society, no. 00 (2023): 18. http://dx.doi.org/10.2298/jsc230126018f.

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(5R)-Cleistenolide and a few related analogues have been synthesized starting from d-glucose. The key steps of the synthesis included a Z-selective Wittig olefination and an intramolecular Mitsunobu reaction with an inversion of configuration at the C-5 position. In vitro antiproliferative activity of synthesized compounds was tested on a panel of eight human tumour cells and against a single normal cell line (MRC-5). The majority of tested compounds showed strong antiproliferative effects on certain human tumour cells and all of them showed negligible toxicity to normal foetal lung fibroblasts (MRC-5). The most active compound obtained in this work is lactone 5, which in MDA-MB 231 cell culture showed the same activity as doxorubicin (IC50 0.09 ?M). Strong antiproliferative activities of analogues 2, 5 and 6 were recorded in the K562 cell line (IC50 0.21, 0.34 and 0.33 ?M, respectively), in which they showed very similar activities to doxorubicin (IC50 0.25 ?M). A performed SAR study revealed that a change in the stereochemistry at the C-5 position may increase the activity of resulting stereoisomers.
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13

Benedeković, Goran, Mirjana Popsavin, Ivana Kovačević, Vesna Kojić, Marko Rodić, and Velimir Popsavin. "Synthesis, antiproliferative activity and SAR analysis of (−)-cleistenolide and analogues." European Journal of Medicinal Chemistry 202 (September 2020): 112597. http://dx.doi.org/10.1016/j.ejmech.2020.112597.

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14

Benedeković, Goran, Mirjana Popsavin, Ivana Kovačević, Vesna Kojić, Jelena Kesić, Sándor Farkas, and Velimir Popsavin. "Design, synthesis and cytotoxic activity of new 6-O-aroyl (−)-cleistenolide derivatives." Tetrahedron 96 (September 2021): 132385. http://dx.doi.org/10.1016/j.tet.2021.132385.

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15

Nyandoro, Stephen S., Gasper Maeda, Joan J. E. Munissi, Amra Gruhonjic, Paul A. Fitzpatrick, Sofia Lindblad, Sandra Duffy, et al. "A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii." Molecules 24, no. 15 (July 29, 2019): 2746. http://dx.doi.org/10.3390/molecules24152746.

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Phytochemical investigations of ethanol root bark and stem bark extracts of Cleistochlamys kirkii (Benth.) Oliv. (Annonaceae) yielded a new benzopyranyl cadinane-type sesquiterpene (cleistonol, 1) alongside 12 known compounds (2–13). The structures of the isolated compounds were established from NMR spectroscopic and mass spectrometric analyses. Structures of compounds 5 and 10 were further confirmed by single crystal X-ray crystallographic analyses, which also established their absolute stereochemical configuration. The ethanolic crude extract of C. kirkii root bark gave 72% inhibition against the chloroquine-sensitive 3D7-strain malaria parasite Plasmodium falciparum at 0.01 μg/mL. The isolated metabolites dichamanetin, (E)-acetylmelodorinol, and cleistenolide showed IC50 = 9.3, 7.6 and 15.2 μM, respectively, against P. falciparum 3D7. Both the crude extract and the isolated compounds exhibited cytotoxicity against the triple-negative, aggressive breast cancer cell line, MDA-MB-231, with IC50 = 42.0 μg/mL (crude extract) and 9.6–30.7 μM (isolated compounds). Our findings demonstrate the potential applicability of C. kirkii as a source of antimalarial and anticancer agents.
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16

Karier, Pol, Gheorghe C. Catrinescu, Nicolas Diercxsens, Koen Robeyns, Michael L. Singleton, and István E. Markó. "Total synthesis of (−)-cleistenolide and formal synthesis of herbarumin I via a diastereoselective modulable allylation." Tetrahedron 74, no. 51 (December 2018): 7242–51. http://dx.doi.org/10.1016/j.tet.2018.10.063.

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17

Ghogare, Ramesh S., Sachin B. Wadavrao, and A. Venkat Narsaiah. "Enantioselective construction of 6-substituted-α,β-unsaturated-δ-lactone: total synthesis of anti-bacterial agent (−)-cleistenolide." Tetrahedron Letters 54, no. 42 (October 2013): 5674–76. http://dx.doi.org/10.1016/j.tetlet.2013.07.164.

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18

Benedeković, Goran, Ivana Kovačević, Mirjana Popsavin, Jovana Francuz, Vesna Kojić, Gordana Bogdanović, and Velimir Popsavin. "New antitumour agents with α,β-unsaturated δ-lactone scaffold: Synthesis and antiproliferative activity of (−)-cleistenolide and analogues." Bioorganic & Medicinal Chemistry Letters 26, no. 14 (July 2016): 3318–21. http://dx.doi.org/10.1016/j.bmcl.2016.05.044.

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19

Sartori, Suélen, Izabel Miranda, Davi de Matos, Markus Kohlhoff, Marisa Diaz, and Gaspar Diaz-Muñoz. "Synthetic Studies toward (−)-Cleistenolide: Highly Stereoselective Synthesis of New γ-Lactone Subunits." Journal of the Brazilian Chemical Society, 2021. http://dx.doi.org/10.21577/0103-5053.20200227.

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This study describes the stereoselective synthesis of two new γ-lactones in 6 and 3 steps and 19 and 32% yield, respectively, directed toward the total synthesis of the natural product (−)-cleistenolide. The starting material was an enantiomerically pure diacetonide diol, derived from d-mannitol with the required stereocenters for (−)-cleistenolide synthesis. γ-Lactone syntheses were based on highly selective protection and deprotection of hydroxyls from d-mannitol. The formation of γ-lactone rings was the culmination of this approach, made possible by a Horner-Wadsworth-Emmons Z-olefination between diacetal aldehyde and ethyl 2-(bis(o-tolyloxy)phosphoryl)acetate to produce an unsaturated ester. The Z-isomer ester was highly favored in relation to the E-isomer (Z/E ratio of 94:6), allowing the formation of the γ-lactone ring under acid catalysis. This strategy precluded the use of chiral auxiliaries or catalysts for the control of stereocenters in the novel γ-lactones.
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20

Reddy, A. Bal, B. Kumara Swamy, and Jhillu Singh Yadav. "ChemInform Abstract: A Concise Total Synthesis of Cleistenolide." ChemInform 47, no. 48 (November 2016). http://dx.doi.org/10.1002/chin.201648210.

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21

Vukic, Vladimir R., Dajana V. Vukic, Goran Benedekovic, Vesna Kojic, and Velimir Popsavin. "(–)-cleistenolide and its Analogs as New Potential Antitumor Compounds Against PC-3 Cells." Pharmaceutical Chemistry Journal, August 17, 2022. http://dx.doi.org/10.1007/s11094-022-02686-z.

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