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Articoli di riviste sul tema "Crinane"

Autore: Grafiati

Pubblicato: 4 giugno 2021

Ultima modifica: 7 febbraio 2022

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1

van Rensburg, Elmarie, Pieter C. Zietsman, Susan L. Bonnet e Anke Wilhelm. "Alkaloids from the Bulbs of Boophone disticha". Natural Product Communications 12, n. 9 (settembre 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200911.

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Boophone disticha is widely used in South African traditional medicine. Several of its biological properties can be corroborated via its alkaloid constituents. Previous research on this plant led to the isolation of several alkaloids, mainly of the crinane alkaloid group of the Amaryllidaceae. In the present study, one new compound 1- O-acetylbuphanamine (1) and four known crinane alkaloids were isolated chromatographically from the ethanol extract of the bulbs of B. disticha. Their structures were determined via spectroscopic methods, including 1D and 2D NMR, ESI-MS, HRMS and IR data.

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2

Raghavan, Sadagopan, e Anil Ravi. "Synthesis of crinane utilizing an allylic sulfoxide for the construction of a hydroindole ring via vinylogous C–N bond formation". Organic & Biomolecular Chemistry 14, n. 43 (2016): 10222–29. http://dx.doi.org/10.1039/c6ob01966h.

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3

Das, Mrinal Kanti, Subhadip De, Shubhashish Shubhashish e Alakesh Bisai. "Concise total syntheses of (±)-mesembrane and (±)-crinane". Organic & Biomolecular Chemistry 13, n. 12 (2015): 3585–88. http://dx.doi.org/10.1039/c5ob00183h.

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A unified approach to the Amaryllidaceae alkaloids having a cis-3a-aryloctahydroindole scaffold is developed via a key Eschenmoser–Claisen rearrangement of all-carbon quaternary stereocenters present in these alkaloids. Utilizing this strategy, a concise total synthesis of (±)-mesembrane and (±)-crinane is achieved.

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4

Nair, Jerald J., Jaume Bastida, Francesc Viladomat e Johannes van Staden. "Cytotoxic Agents of the Crinane Series of Amaryllidaceae Alkaloids". Natural Product Communications 7, n. 12 (dicembre 2012): 1934578X1200701. http://dx.doi.org/10.1177/1934578x1200701234.

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In the alkaloid galanthamine, the plant family Amaryllidaceae has endowed the pharmaceutical community with a potent and selective inhibitor of the enzyme acetylcholinestersae (AChE), of prominence in the chemotherapeutic approach towards motor neuron diseases. Following on the commercial success of this prescription drug in the treatment of Alzheimer's disease, it is anticipated that other drug candidates will in future emerge from the family. In this regard, the phenanthridones, exemplified by narciclasine and pancratistatin, of the lycorine series of Amaryllidaceae alkaloids have shown much promise as remarkably potent and selective anticancer agents, with a drug target of the series destined for the clinical market within the next decade. Given these interesting biological properties and their natural abundance, plants of the Amaryllidaceae have provided a diverse and accessible platform for phytochemical-based drug discovery. The crinane series of Amaryllidaceae alkaloids are also enriched with a significant array of biological properties. As a consequence of their close structural similarity to the anticancer agents of the lycorine series, the cytotoxic potential of crinane alkaloids has been realized through structure-activity relationship (SAR) studies involving targets of both semi-synthetic and natural origin, which has identified several members as leads with promising antiproliferative profiles. As the first of its kind, this review seeks to collate such information from the past few decades in advancing the crinane group as a viable platform for anticancer drug discovery.

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5

Nair, Jerald J., Jaume Bastida, Francesc Viladomat e Johannes van Staden. "Cytotoxic Agents of the Crinane Series of Amaryllidaceae Alkaloids". Natural Product Communications 8, n. 5 (maggio 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800501.

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Abstract (sommario):

In the alkaloid galanthamine, the plant family Amaryllidaceae has endowed the pharmaceutical community with a potent and selective inhibitor of the enzyme acetylcholinestersae (AChE), of prominence in the chemotherapeutic approach towards motor neuron diseases. Following on the commercial success of this prescription drug in the treatment of Alzheimer's disease, it is anticipated that other drug candidates will in future emerge from the family. In this regard, the phenanthridones, exemplified by narciclasine and pancratistatin, of the lycorine series of Amaryllidaceae alkaloids have shown much promise as remarkably potent and selective anticancer agents, with a drug target of the series destined for the clinical market within the next decade. Given these interesting biological properties and their natural abundance, plants of the Amaryllidaceae have provided a diverse and accessible platform for phytochemical-based drug discovery. The crinane series of Amaryllidaceae alkaloids are also enriched with a significant array of biological properties. As a consequence of their close structural similarity to the anticancer agents of the lycorine series, the cytotoxic potential of crinane alkaloids has been realized through structure-activity relationship (SAR) studies involving targets of both semi-synthetic and natural origin, which has identified several members as leads with promising antiproliferative profiles. As the first of its kind, this review seeks to collate such information from the past few decades in advancing the crinane group as a viable platform for anticancer drug discovery.

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6

Koch, Michel, Genevi竣e Baudouin e Fran腔is Tillequin. "Albiflomanthine — A Crinane Alkaloid from Haemanthus albiflos (JACQ)". HETEROCYCLES 38, n. 5 (1994): 965. http://dx.doi.org/10.3987/com-93-6668.

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7

Herrera, María R., Alex K. Machocho, Reto Brun, Francesc Viladomat, Carles Codina e Jaume Bastida. "Crinane and Lycorane Type Alkaloids from Zephyranthes citrina". Planta Medica 67, n. 2 (2001): 191–93. http://dx.doi.org/10.1055/s-2001-11495.

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8

Liu, Danyang, Zhijian Zhou e Hao Liu. "The Theoretical Total Synthesis of an Aromatic Esters of the Crinane Amaryllidaceae Alkaloid Ambelline". E3S Web of Conferences 267 (2021): 02011. http://dx.doi.org/10.1051/e3sconf/202126702011.

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Abstract (sommario):

ABSTRACT. A series of crinane-type alkaloid ambelline derivatives were assessed for their potency to inhibit both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), which has been shown to be effective medicine for the treatment of Alzheimer’s disease. However, no enzyme modification has been reported total synthesis. In this work, two possible theoretical synthesis paths of Crinane-type alkaloid ambelline were discussed in this article. The major difficulty of the proposed synthesis was the synthesis of the quaternary carbon. One of the approaches emphasized on the reactions between cyclic and heterocyclic compounds and substrates on the intermediates to generate the quaternary carbon shown on the desired product. The other approach utilized series of amine reactions and Michael addition to create the precursor for the reactant in the Diels-Alder reaction and, therefore, the quaternary carbon, and finally, the desired natural product was obtained after a weak acid workup. The synthesis of ambelline has the potential to provide new pathways for treatment of Alzheimer’s disease.

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9

Gao, Ya-Ru, Da-Yu Wang e Yong-Qiang Wang. "Asymmetric Syntheses of Amaryllidaceae Alkaloids (−)-Crinane and (+)-4a-Dehydroxycrinamabine". Organic Letters 19, n. 13 (9 giugno 2017): 3516–19. http://dx.doi.org/10.1021/acs.orglett.7b01486.

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10

Cheesman, Lee, Jerald J. Nair e Johannes van Staden. "Antibacterial activity of crinane alkaloids from Boophone disticha (Amaryllidaceae)". Journal of Ethnopharmacology 140, n. 2 (marzo 2012): 405–8. http://dx.doi.org/10.1016/j.jep.2012.01.037.

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11

Hanh, Tran Thi Hong, Do Hoang Anh, Phan Thi Thanh Huong, Nguyen Van Thanh, Nguyen Quang Trung, Tran Van Cuong, Nguyen Thi Mai et al. "Crinane, augustamine, and β -carboline alkaloids from Crinum latifolium". Phytochemistry Letters 24 (aprile 2018): 27–30. http://dx.doi.org/10.1016/j.phytol.2018.01.004.

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12

Tram, Nguyen Thi Ngoc, Maya Mitova, Vassya Bankova, Nedyalka Handjieva e Simeon S. Popov. "Gc-Ms Of Crinum Latifolium L. Alkaloids". Zeitschrift für Naturforschung C 57, n. 3-4 (1 aprile 2002): 239–42. http://dx.doi.org/10.1515/znc-2002-3-407.

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Abstract (sommario):

A GC-MS analysis of underivatized alkaloids from leaves of Crinum latifolium was performed. From the identified 15 alkaloids, 9 were found for the first time in this plant. Almost all alkaloids belonged to the crinane type. Substantial changes in the methylation and oxidation pattern of the alkaloids at and after flowering were observed

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13

Das, Mrinal K., Abhinay Yadav, Satyajit Majumder e Alakesh Bisai. "Catalytic deacylative alkylations (DaA) of enolcarbonates: Total synthesis of (±)-Crinane". Tetrahedron Letters 61, n. 29 (luglio 2020): 152129. http://dx.doi.org/10.1016/j.tetlet.2020.152129.

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14

McNulty, James, Jerald J. Nair, Jaume Bastida, Siyaram Pandey e Carly Griffin. "Structure Activity Studies on the Crinane Alkaloid Apoptosis-inducing Pharmacophore". Natural Product Communications 4, n. 4 (aprile 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400408.

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The apoptosis-inducing ability of α-ethano bridged crinane alkaloids was investigated using natural and semi-synthetic derivatives uncovering novel structural requirements of this cytotoxic pharmacophore. An α-ethano bridge is required; an α- or ß-methoxy or hydroxyl H-bond acceptor are all tolerated at C-3; a small substituent (H, or OH) alone is tolerated at C-11; and a C-1 to C-2 double bond is shown to modulate, but is not a requirement for, apoptosis-inducing activity.

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15

Abou-Donia, Amina H., Masouda E. Amer, Fikria A. Darwish, Fahima F. Kassem, Hala M. Hammoda, Maged S. Abdel-Kader, Bing-Nan Zhou e David G. I. Kingston. "Two New Alkaloids of the Crinane Series from Pancratium sickenbergeri". Planta Medica 68, n. 4 (aprile 2002): 379–81. http://dx.doi.org/10.1055/s-2002-26754.

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16

Nair, Jerald J., e Johannes van Staden. "The Amaryllidaceae as a source of antiplasmodial crinane alkaloid constituents". Fitoterapia 134 (aprile 2019): 305–13. http://dx.doi.org/10.1016/j.fitote.2019.02.009.

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17

Nair, J. J., e J. Van Staden. "Caspase-inducing effects of lycorane and crinane alkaloids of the Amaryllidaceae". South African Journal of Botany 120 (gennaio 2019): 33–38. http://dx.doi.org/10.1016/j.sajb.2018.05.016.

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18

Schkeryantz, Jeffrey M., e William H. Pearson. "An efficient synthesis of (±)-crinane using an intramolecular azide-olefin cycloaddition". Tetrahedron 52, n. 9 (febbraio 1996): 3107–16. http://dx.doi.org/10.1016/0040-4020(95)01098-x.

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19

Das, Mrinal Kanti, Subhadip De, Shubhashish Shubhashish e Alakesh Bisai. "ChemInform Abstract: Concise Total Synthesis of (.+-.)-Mesembrane (I) and (.+-.)-Crinane (II)." ChemInform 46, n. 29 (luglio 2015): no. http://dx.doi.org/10.1002/chin.201529251.

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20

Das, Mrinal K., Abhinay Yadav, Satyajit Majumder, Ayan Mondal e Alakesh Bisai. "Total syntheses of (+)- and (−)-Crinane via Pd(0)-Catalyzed deacylative allylation". Tetrahedron 82 (febbraio 2021): 131928. http://dx.doi.org/10.1016/j.tet.2021.131928.

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21

Nair, Jerald J., Lucie Rárová, Miroslav Strnad, Jaume Bastida, Lee Cheesman e Johannes van Staden. "Crinane Alkaloids of the Amaryllidaceae with Cytotoxic Effects in Human Cervical Adenocarcinoma (HeLa) Cells". Natural Product Communications 9, n. 4 (aprile 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900406.

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Abstract (sommario):

The family Amaryllidaceae has a long history of usage in the traditional medicinal practices of the indigenous peoples of South Africa, with three of its species known to be used for cancer treatment. Furthermore, the Amaryllidaceae is widely recognized for its unique alkaloid constituents, several of which exhibit potent and selective cytotoxic activities. In this study, several crinane alkaloids derived from local Amaryllidaceae species were examined for cytotoxic effects against the human cervical adenocarcinoma cell line, of which distichamine was the most potent (IC50 2.2 μM).

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22

Maříková, Jana, Aneta Ritomská, Jan Korábečný, Rozálie Peřinová, Abdullah Al Mamun, Tomáš Kučera, Eliška Kohelová et al. "Aromatic Esters of the Crinane Amaryllidaceae Alkaloid Ambelline as Selective Inhibitors of Butyrylcholinesterase". Journal of Natural Products 83, n. 5 (20 aprile 2020): 1359–67. http://dx.doi.org/10.1021/acs.jnatprod.9b00561.

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23

SCHKERYANTZ, J. M., e W. H. PEARSON. "ChemInform Abstract: An Efficient Synthesis of (.+-.)-Crinane Using an Intramolecular Azide- Olefin Cycloaddition." ChemInform 27, n. 25 (5 agosto 2010): no. http://dx.doi.org/10.1002/chin.199625219.

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24

Frahm, August W., Ahmed A. Ali e Mahmoud A. Ramadan. "13C nuclear magnetic resonance spectra of amaryllidaceae alkaloids. I—alkaloids with the crinane skeleton". Magnetic Resonance in Chemistry 23, n. 10 (ottobre 1985): 804–8. http://dx.doi.org/10.1002/mrc.1260231004.

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25

Bisai, Alakesh, Mrinal Das e Subhadip De. "Concise Total Syntheses of (±)-Joubertiamine, (±)-O-Methyljoubertiamine, (±)-3′-Methoxy-4′-O-methyljoubertiamine, (±)-Mesembrane, and (±)-Crinane". Synthesis 48, n. 13 (18 marzo 2016): 2093–104. http://dx.doi.org/10.1055/s-0035-1561583.

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26

Massaro, Nicholas P., e Joshua G. Pierce. "Rapid synthesis of the core scaffold of crinane and haemanthamine through a multi-component approach". Tetrahedron Letters 75 (luglio 2021): 153201. http://dx.doi.org/10.1016/j.tetlet.2021.153201.

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27

Kohelová, Eliška, Rozálie Peřinová, Negar Maafi, Jan Korábečný, Daniela Hulcová, Jana Maříková, Tomáš Kučera et al. "Derivatives of the β-Crinane Amaryllidaceae Alkaloid Haemanthamine as Multi-Target Directed Ligands for Alzheimer’s Disease". Molecules 24, n. 7 (3 aprile 2019): 1307. http://dx.doi.org/10.3390/molecules24071307.

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Abstract (sommario):

Twelve derivatives 1a–1m of the β-crinane-type alkaloid haemanthamine were developed. All the semisynthetic derivatives were studied for their inhibitory potential against both acetylcholinesterase and butyrylcholinesterase. In addition, glycogen synthase kinase 3β (GSK-3β) inhibition potency was evaluated in the active derivatives. In order to reveal the availability of the drugs to the CNS, we elucidated the potential of selected derivatives to penetrate through the blood-brain barrier (BBB). Two compounds, namely 11-O-(2-methylbenzoyl)-haemanthamine (1j) and 11-O-(4-nitrobenzoyl)-haemanthamine (1m), revealed the most intriguing profile, both being acetylcholinesterase (hAChE) inhibitors on a micromolar scale, with GSK-3β inhibition properties, and predicted permeation through the BBB. In vitro data were further corroborated by detailed inspection of the compounds’ plausible binding modes in the active sites of hAChE and hBuChE, which led us to provide the structural determinants responsible for the activity towards these enzymes.

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28

Bao, Xu, Qian Wang e Jieping Zhu. "Palladium-Catalyzed Enantioselective Desymmetrizing Aza-Wacker Reaction: Development and Application to the Total Synthesis of (−)-Mesembrane and (+)-Crinane". Angewandte Chemie International Edition 57, n. 7 (16 gennaio 2018): 1995–99. http://dx.doi.org/10.1002/anie.201712521.

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29

Bao, Xu, Qian Wang e Jieping Zhu. "Palladium-Catalyzed Enantioselective Desymmetrizing Aza-Wacker Reaction: Development and Application to the Total Synthesis of (−)-Mesembrane and (+)-Crinane". Angewandte Chemie 130, n. 7 (16 gennaio 2018): 2013–17. http://dx.doi.org/10.1002/ange.201712521.

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30

Qing, Zhi-Xing, Jia-Lu Huang, Xue-Yi Yang, Jing-Hong Liu, Hua-Liang Cao, Feng Xiang, Pi Cheng e Jian-Guo Zeng. "Anticancer and Reversing Multidrug Resistance Activities of Natural Isoquinoline Alkaloids and their Structure-activity Relationship". Current Medicinal Chemistry 25, n. 38 (7 gennaio 2019): 5088–114. http://dx.doi.org/10.2174/0929867324666170920125135.

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The severe anticancer situation as well as the emergence of multidrug-resistant (MDR) cancer cells has created an urgent need for the development of novel anticancer drugs with different mechanisms of action. A large number of natural alkaloids, such as paclitaxel, vinblastine and camptothecin have already been successfully developed into chemotherapy agents. Following the success of these natural products, in this review, twenty-six types of isoquinoline alkaloids (a total of 379 alkaloids), including benzyltetrahydroisoquinoline, aporphine, oxoaporphine, isooxoaporphine, dimeric aporphine, bisbenzylisoquinoline, tetrahydroprotoberberine, protoberberine, protopine, dihydrobenzophenanthridine, benzophenanthridine, benzophenanthridine dimer, ipecac, simple isoquinoline, pavine, montanine, erythrina, chelidonine, tropoloisoquinoline, azafluoranthene, phthalideisoquinoline, naphthylisoquinoline, lycorine, crinane, narciclasine, and phenanthridone, were summarized based on their cytotoxic and MDR reversing activities against various cancer cells. Additionally, the structure-activity relationships of different types of isoquinoline alkaloid were also discussed. Interestingly, some aporphine, oxoaporphine, isooxoaporphine, bisbenzylisoquinoline, and protoberberine alkaloids display more potent anticancer activities or anti-MDR effects than positive control against the tested cancer cells and are regarded as attractive targets for discovery new anticancer drugs or lead compounds.

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31

Gao, Shuanhu, Yong Qiang Tu, Zhenlei Song, Aixia Wang, Xiaohui Fan e Yijun Jiang. "A General and Efficient Strategy for 7-Aryloctahydroindole andcis-3a-Aryloctahydroindole Alkaloids: Total Syntheses of (±)-γ-Lycorane and (±)-Crinane". Journal of Organic Chemistry 70, n. 16 (agosto 2005): 6523–25. http://dx.doi.org/10.1021/jo0507690.

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32

Jitsuno, Maki, Akihito Yokosuka, Ken Hashimoto, Osamu Amano, Hiroshi Sakagami e Yoshihiro Mimaki. "Chemical Constituents of Lycoris albiflora and their Cytotoxic Activities". Natural Product Communications 6, n. 2 (febbraio 2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600208.

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An alcoholic extract of Lycoris albiflora (Amaryllidaceae) showed potent cytotoxic activity against HL-60 cells with an IC50 value of 1.7 μg/mL. Phytochemical examination of the extract resulted in the isolation of 15 alkaloids, including two phenanthridine-type alkaloids (1, 2), one benzylphenethylamine-type alkaloid (3), two crinane-type alkaloids (4, 5), one pyrrolophenanthridine-type alkaloid (6), six lycorenan-type alkaloids (7–12), and three galanthamine-type alkaloids (13–15), together with three neolignans (16–18), two flavans (19, 20), and two acetophenone derivatives (21, 22). Compound 3 (hostasinine A) has not been isolated from Amaryllidaceae plants, and 1, 2, 4, 5, 7–9, 11, 12 and 14–22 are the first isolation and identification from L. albiflora. The phenanthridine-type alkaloids (1, 2), as well as the alkaloids (3–5), exhibited potent cytotoxic activities against not only HL-60 cells but also HSC-2 cells, thus leading to the conclusion that these alkaloids are mainly responsible for the cytotoxicity of the L. albiflora extract. Compound 1 (lycoricidinol), with the most potent cytotoxic activities, induced apoptosis in both HL-60 cells and HSC-2 cells. It is notable that 1 induced transient autophagy and morphological changes in mitochondria in the early stages of the apoptotic cell death process in HSC-2 cells.

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33

Lan, Ping, Martin G. Banwell e Anthony C. Willis. "Total Synthesis of (±)-Crinane from 6,6-Dibromobicyclo[3.1.0]hexane Using a 5-exo-trig Radical Cyclization Reaction to Assemble the C3a-Arylated Perhydroindole Substructure". Journal of Organic Chemistry 83, n. 15 (24 maggio 2018): 8493–98. http://dx.doi.org/10.1021/acs.joc.8b01088.

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Dasgupta, Debaprotim, e Suvakanta Dash. "EVALUATION OF IN VIVO ANTICANCER AND IMMUNOSTIMULATORY ACTIVITY OF FLOWERS OF MIMOSA PUDICA LINN. (FABACEAE)". Asian Journal of Pharmaceutical and Clinical Research 10, n. 7 (1 luglio 2017): 266. http://dx.doi.org/10.22159/ajpcr.2017.v10i7.18514.

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Abstract (sommario):

Objective: To investigate the in vivo anticancer and immunostimulatory activity of dichloromethane (DCM) extract of flowers of Mimosa pudica and its isolated compound 11β hydroxy-3 methoxy 1,2 dehydro crinane.Methods: The anticancer activity was performed on Ehrlich ascites carcinoma (EAC) cell line in Swiss albino mice. The activity was assessed by evaluating tumor volume, viable and nonviable tumor cell count, tumor weight, hematological, and histopathological parameters of EAC-bearing animals. The immunostimulatory activity was performed through carbon clearance, delayed type hypersensitivity (DTH), neutrophil adhesion and humoral antibody (HA) titer methods.Results: At the dose of 500 and 1000 mg/kg/day p.o for the extracts and 2.5 mg/kg/day p.o. for the isolated compound, significantly decrease the tumor volume (3.46±0.135 ml, 2.25±0.153 ml, and 1.84±0.012), increased the life span (59.32%, 76.39%, and 82.43%) and significantly (p<0.05) decreased tumor weight as compared with control. Hematological profiles were found to be nearly normal level in extract treated mice compared with tumor bearing control mice. The immunostimulatory activity was also found to be effective in the above dosage regimen. The results revealed that animals treated with above doses show a significant increase in the rate of carbon clearance from blood, increase in HA titer value, increase in neutrophil adhesion and significant (p<0.05) increase in mean paw edema in DTH reactions in dose-dependent manner.Conclusion: The results demonstrated that the extract is possessing dose-dependent anticancer activity and immunostimulatory activity attributed to the presence of crinane alkaloid.

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35

Zhang, Fu-Min, Yong-Qiang Tu, Jian-Dong Liu, Xiao-Hui Fan, Lei Shi, Xiang-Dong Hu, Shao-Hua Wang e Yong-Qiang Zhang. "A general approach to crinine-type Amaryllidaceae alkaloids: total syntheses of (±)-haemanthidine, (±)-pretazettine, (±)-tazettine, and (±)-crinamine". Tetrahedron 62, n. 40 (ottobre 2006): 9446–55. http://dx.doi.org/10.1016/j.tet.2006.07.027.

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36

Tam, Nguyen Thanh, Jayhyok Chang, Eun-Ju Jung e Cheon-Gyu Cho. "Total Syntheses of (±)-Crinine, (±)-Crinamine, and (±)-6a-epi-Crinamine via the Regioselective Synthesis and Diels−Alder Reaction of 3-Aryl-5-bromo-2-pyrone". Journal of Organic Chemistry 73, n. 16 (agosto 2008): 6258–64. http://dx.doi.org/10.1021/jo8008353.

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37

Stell, Geoffrey. "Crinan Canal". Archaeological Journal 164, sup1 (gennaio 2007): 55–56. http://dx.doi.org/10.1080/00665983.2007.11771004.

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38

Zuo, Xiao-Dong, Shu-Min Guo, Rui Yang, Jian-Hua Xie e Qi-Lin Zhou. "Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones". Chemical Science 8, n. 9 (2017): 6202–6. http://dx.doi.org/10.1039/c7sc02112g.

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Abstract (sommario):

A bioinspired enantioselective synthesis of crinine-type alkaloids was developed by iridium-catalyzed asymmetric hydrogenation of enones, providing 24 crinine-type alkaloids and 8 analogues with high yield and high enantioselectivity.

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39

Tu, Yong-Qiang, Jian-Dong Liu, Shao-Hua Wang, Fu-Min Zhang e Yong-Qiang Zhang. "Concise Total Synthesis of (±)-Crinine". Synlett 2009, n. 18 (13 ottobre 2009): 3040–42. http://dx.doi.org/10.1055/s-0029-1218296.

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40

Li, Ruizhi, Mrityunjay Kothari, Alexander K. Landauer, Moon-Hyun Cha, Heemin Kwon e Kyung-Suk Kim. "A New Subcritical Nanostructure of Graphene—Crinkle-Ruga Structure and Its Novel Properties". MRS Advances 3, n. 45-46 (2018): 2763–69. http://dx.doi.org/10.1557/adv.2018.432.

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AbstractHere, we report an experimental characterization of a new subcritical graphene nanostructure termed a crinkle ruga. Multilayer graphene forms crinkles as a periodic mode of buckling if the ratio of periodic buckling span to thickness is smaller than a critical value. Otherwise, it forms wrinkles. The crinkles have sawtooth-shaped profiles with their faces perfectly flat and the tips of the peaks and valleys highly curved. Our AFM measurements show that the width of the curvature focusing band at the tip is very narrow, e.g. smaller than 16 nm for a 6o crinkle, indicating a strong influence of flexoelectric coupling in crinkle formation. We also found that concavity or convexity of crinkle tips, i.e. parity of the crinkle, can be controlled. Due to the flexoelectric coupling, the concave tip at the crinkle valley is positively charged, and the convex tip at the crinkle peak negatively charged. In addition, here, we demonstrate that the charges at the crinkle tips can attract macromolecules in adsorption experiments. We show linearly-aligned adsorption of C60 along crinkle valleys on an HOPG surface. In another experiment, we exhibit period-doubled adsorption of lambda DNA on an HOPG surface, possibly caused by ion kinetics involved in the DNA adsorption along the crinkle valleys.

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41

Yang, Xiaodong, Lijuan Yang, Xuequan Wang, Zhiqiang Pan, Ming Zhou e Wen Chen. "Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine". Synlett 2011, n. 02 (23 dicembre 2010): 207–10. http://dx.doi.org/10.1055/s-0030-1259288.

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42

Castelvecchi, Davide. "Crinkle wrinkle". Science News 172, n. 5 (30 settembre 2009): 69. http://dx.doi.org/10.1002/scin.2007.5591720508.

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43

Martin, Stephen F., e Carlton L. Campbell. "Total syntheses of (±)-crinine and (±)-buphanisine". Tetrahedron Letters 28, n. 5 (gennaio 1987): 503–6. http://dx.doi.org/10.1016/s0040-4039(00)95766-6.

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44

Martin, Stephen F., e Carlton L. Campbell. "Total syntheses of (.+-.)-crinine and (.+-.)-buphanisine". Journal of Organic Chemistry 53, n. 14 (luglio 1988): 3184–90. http://dx.doi.org/10.1021/jo00249a011.

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di Valvasone, Luisa. "Cringe". XVI, 2021/1 (gennaio-marzo), n. 1 (11 gennaio 2021): 118–25. http://dx.doi.org/10.35948/2532-9006/2021.5457.

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46

Du, Kang, He Yang, Pan Guo, Liang Feng, Guangqing Xu, Qinghai Zhou, Lung Wa Chung e Wenjun Tang. "Efficient syntheses of (−)-crinine and (−)-aspidospermidine, and the formal synthesis of (−)-minfiensine by enantioselective intramolecular dearomative cyclization". Chemical Science 8, n. 9 (2017): 6247–56. http://dx.doi.org/10.1039/c7sc01859b.

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Abstract (sommario):

Palladium-catalyzed enantioselective dearomative cyclization has enabled the concise and enantioselective total syntheses of (−)-crinine and (−)-aspidospermidine, as well as a formal total synthesis of (−)-minfiensine.

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47

Banwell, Martin G., Nadia Yuqian Gao, Xinghua Ma, Laurent Petit, Lorenzo V. White, Brett D. Schwartz, Anthony C. Willis e Ian A. Cade. "gem-Dibromocyclopropanes and enzymatically derived cis-1,2-dihydrocatechols as building blocks in alkaloid synthesis". Pure and Applied Chemistry 84, n. 6 (2 ottobre 2011): 1329–39. http://dx.doi.org/10.1351/pac-con-11-07-05.

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48

Bru, Claire, e Catherine Guillou. "Total syntheses of crinine and related alkaloids". Tetrahedron 62, n. 38 (settembre 2006): 9043–48. http://dx.doi.org/10.1016/j.tet.2006.07.005.

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49

Gao, Nadia (Yuqian), Xinghua Ma, Laurent Petit, Brett D. Schwartz, Martin G. Banwell, Anthony C. Willis, Ian A. Cade e A. David Rae. "Synthetic Studies Concerning the Crinine Alkaloid Haemultine". Australian Journal of Chemistry 66, n. 1 (2013): 30. http://dx.doi.org/10.1071/ch12473.

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Abstract (sommario):

The racemic form, (±)-1, of the structure originally assigned to the crinine alkaloid haemultine has been prepared for the first time. A key step involved the conversion of compound (±)-4 into the isomeric cis-C3a-arylhexahydroindole (±)-3 using a Pd0-catalysed intramolecular Alder-ene reaction. The amino-alcohol (±)-2 derived from the latter compound reacted with paraformaldehyde in the presence of trifluoroacetic acid to give, via a Pictet–Spengler reaction, the target (±)-1. The diastereoisomeric Mosher esters 15 and 16 obtained by coupling the racemate (±)-1 with the R-form, 14, of the Mosher acid could be separated chromatographically and then reductively cleaved to give the enantiomerically pure compounds (+)-1 and (–)-1, respectively. The physical and spectroscopic data derived from the former enantiomer are consistent with the proposition that the title natural product is, in fact, a mixture of (+)-1 and its Δ2,3-double bond isomer.

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Marso, Lori. "Feminist Cringe Comedy: Dear Dick, The Joke Is on You". Politics & Gender 15, n. 1 (6 agosto 2018): 107–29. http://dx.doi.org/10.1017/s1743923x18000387.

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AbstractFeminist cringe comedies eschew the conventions of romance and sentimentality in favor of comedy that discomforts. Cringe comedies are one example of what I call feminism's visual realisms, so named for doing feminist political work by evoking laughter and the cringe. The cringe pulls us inward in our posture, while laughter opens us to others. This bodily response to cringe comedies interrupts the fantasies of the male gaze and makes space for spectators to acknowledge the excessive, complicated, and seemingly shameful realities of female desire. My primary example is Jill Soloway's television adaptation of Chris Kraus's I Love Dick, a series that builds on the feminist legacy of avant-garde director Catherine Breillat. Departing from politically correct narratives and comforting or sentimental affect, I Love Dick achieves feminist community through the appeal, the cringe, and the irruption of laughter.

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