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Journal articles on the topic 'Quinine – Synthesis'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Igarashi, Junji, Masahiro Katsukawa, Yong-Gang Wang, Hukum P. Acharya, and Yuichi Kobayashi. "Stereocontrolled synthesis of quinine and quinidine." Tetrahedron Letters 45, no. 19 (2004): 3783–86. http://dx.doi.org/10.1016/j.tetlet.2004.03.085.

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2

Nurjaya, Intan, Muhammad Hanafi, Puspa D. N. Lotulung, Teni Ernawati, and Sri Mursiti. "The Synthesis of Quinidine Salicylate Ester Compound." Jurnal Kimia Terapan Indonesia 20, no. 2 (2019): 98–102. http://dx.doi.org/10.14203/jkti.v20i2.403.

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Quinidine a compound isolated from quinine plants, one of the species of quinine plants is (Chincona ledgereriana) From PT SIL Lembang. The purpose of this study was obtain quinidine salicylate ester through esterification reaction. In this study, the synthesis of quinidine ester compound by esterification reaction was conducted. Esterification reaction was conducted by using DCC activator and DMAP catalyst with one carboxylic acid namely salicylate acid producing new compound namely quinidine salicylate, Subsequent Quinidine salicylate was obtained in the form of oil with 97% yield. The compound obtained from the synthesis was then identified using Thin Layer Chromatography continue analyzed using with Spectrophotometer, LC-ESI-MS spectroscopy. Results show that the target compound has been successfully synthesized.

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3

Sarkar, Shaheen M., Yuko Taira, Ayako Nakano, Keisuske Takahashi, Jun Ishihara, and Susumi Hatakeyama. "Organocatalytic asymmetric synthesis of quinine and quinidine." Tetrahedron Letters 52, no. 8 (2011): 923–27. http://dx.doi.org/10.1016/j.tetlet.2010.12.066.

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4

Nair, Vijay, Rajeev S. Menon, and Sreekumar Vellalath. "Asymmetric Synthesis of Quinine: A Landmark in Organic Synthesis." Natural Product Communications 1, no. 10 (2006): 1934578X0600101. http://dx.doi.org/10.1177/1934578x0600101009.

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Ever since its isolation in 1820, Quinine has played a crucial role in the development of organic chemistry, the chemical industry and modern medicine. A total synthesis of quinine, widely regarded as an event of epochal importance, was claimed by Woodward and Doering in 1945. This work, however, heavily relied on unsubstantiated literature reports and it appears that Woodward's work fell short of a total synthesis of quinine. The first total synthesis of quinine was reported by Uskokovic in the 1970s. The first stereoselective total synthesis of quinine was accomplished only in 2001, by Stork, who incidentally is the originator of the concept of stereoselectivity in total synthesis. Apart from the stereoselectivity, Stork's synthesis of quinine is remarkable for its conceptual uniqueness and retrosynthetic novelty. Naturally, this work has been attested as a landmark in organic synthesis by leaders in the field. Subsequently, Jacobson and Kobayashi reported the catalytic asymmetric synthesis of quinine in 2003 and 2004, respectively. Both these synthesis have followed a similar approach. The present review has attempted to provide a concise account of the synthesis of quinine from a historical perspective.

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5

Sanders, Natalie G., David J. Meyers, and David J. Sullivan. "Antimalarial Efficacy of Hydroxyethylapoquinine (SN-119) and Its Derivatives." Antimicrobial Agents and Chemotherapy 58, no. 2 (2013): 820–27. http://dx.doi.org/10.1128/aac.01704-13.

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ABSTRACTQuinine and other cinchona-derived alkaloids, although recently supplanted by the artemisinins (ARTs), continue to be important for treatment of severe malaria. Quinine and quinidine have narrow therapeutic indices, and a safer quinine analog is desirable, particularly with the continued threat of antimalarial drug resistance. Hydroxyethylapoquinine (HEAQ), used at 8 g a day for dosing in humans in the 1930s and halving mortality from bacterial pneumonias, was shown to cure bird malaria in the 1940s and was also reported as treatment for human malaria cases. Here we describe synthesis of HEAQ and its novel stereoisomer hydroxyethylapoquinidine (HEAQD) along with two intermediates, hydroxyethylquinine (HEQ) and hydroxyethylquinidine (HEQD), and demonstrate comparable but elevated antimalarial 50% inhibitory concentrations (IC50) of 100 to 200 nM againstPlasmodium falciparumquinine-sensitive strain 3D7 (IC50, 56 nM). Only HEAQD demonstrated activity against quinine-tolerantP. falciparumstrains Dd2 and INDO with IC50s of 300 to 700 nM. HEQD had activity only against Dd2 with an IC50of 313 nM. In the lethal mouse malaria modelPlasmodium bergheiANKA, only HEQD had activity at 20 mg/kg of body weight comparable to that of the parent quinine or quinidine drugs measured by parasite inhibition and 30-day survival. In addition, HEQ, HEQD, and HEAQ (IC50≥ 90 μM) have little to no human ether-à-go-go-related gene (hERG) channel inhibition expressed in CHO cells compared to HEAQD, quinine, and quinidine (hERG IC50s of 27, 42, and 4 μM, respectively). HEQD more closely resembled quininein vitroandin vivoforPlasmodiuminhibition and demonstrated little hERG channel inhibition, suggesting that further optimization and preclinical studies are warranted for this molecule.

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6

Eyal, Sara. "The Fever Tree: from Malaria to Neurological Diseases." Toxins 10, no. 12 (2018): 491. http://dx.doi.org/10.3390/toxins10120491.

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This article describes the discovery and use of the South American cinchona bark and its main therapeutic (and toxic) alkaloids, quinine and quinidine. Since the introduction of cinchona to Europe in the 17th century, it played a role in treating emperors and peasants and was central to colonialism and wars. Over those 400 years, the medical use of cinchona alkaloids has evolved from bark extracts to chemical synthesis and controlled clinical trials. At the present time, the use of quinine and quinidine has declined, to a large extent due to their toxicity. However, quinine is still being prescribed in resource-limited settings, in severe malaria, and in pregnant women, and quinidine made a limited comeback in the treatment of several cardiac and neurological syndromes. In addition, the article presents more recent studies which improved our understanding of cinchona alkaloids’ pharmacology. The knowledge gained through these studies will hopefully lead to a wider use of these drugs in precision medicine and to design of new generation, safer quinine and quinidine derivatives.

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7

Lee, Jaehoo, and David Y. K. Chen. "A Local-Desymmetrization-Based Divergent Synthesis of Quinine and Quinidine." Angewandte Chemie International Edition 58, no. 2 (2018): 488–93. http://dx.doi.org/10.1002/anie.201811530.

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8

Lee, Jaehoo, and David Y. K. Chen. "A Local-Desymmetrization-Based Divergent Synthesis of Quinine and Quinidine." Angewandte Chemie 131, no. 2 (2018): 498–503. http://dx.doi.org/10.1002/ange.201811530.

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9

Shiomi, Shinya, Remi Misaka, Mayu Kaneko, and Hayato Ishikawa. "Enantioselective total synthesis of the unnatural enantiomer of quinine." Chemical Science 10, no. 41 (2019): 9433–37. http://dx.doi.org/10.1039/c9sc03879e.

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10

Zajac, M., та R. Peters. "Quinine-Catalyzed β-Sultam Synthesis". Synfacts 2007, № 7 (2007): 0761. http://dx.doi.org/10.1055/s-2007-968630.

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11

Shiomi, Shinya, and Hayato Ishikawa. "Total Synthesis of Enantioenriched Quinine." Journal of Synthetic Organic Chemistry, Japan 79, no. 2 (2021): 145–54. http://dx.doi.org/10.5059/yukigoseikyokaishi.79.145.

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12

Zhou, Yong, and Zhi Guo Hu. "Synthesis of Chiral Amphiphilic Graft Copolymer PBTQMO-g-MPEO." Advanced Materials Research 308-310 (August 2011): 689–91. http://dx.doi.org/10.4028/www.scientific.net/amr.308-310.689.

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A new optically active amphiphilic graft copolymer bearing quinine pendants poly[3,3-bis(triazolyl-L-quinine) methyl oxetane]-g-poly(ethylene oxide) (PBTQMO-g-MPEO) was synthesized by ‘‘click’’ reaction of azido-modified PBAMO-g-MPEO diblock copolymer and 10,11-didehydro quinine. The fourier transform infrared spectrum(FTIR) and 1H nuclear magnetic resonance spectroscopy (1HNMR) were used to confirm its structure and composition.

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13

Leroux, Sébastien, Laurent Larquetoux, Marc Nicolas, and Eric Doris. "Asymmetric Synthesis of (+)-Mequitazine from Quinine." Organic Letters 13, no. 13 (2011): 3549–51. http://dx.doi.org/10.1021/ol2012567.

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14

Che, Zhiping, Jinming Yang, Di Sun, et al. "Combinatorial Synthesis of Novel 9R-Acyloxyquinine Derivatives as Insecticidal Agents." Combinatorial Chemistry & High Throughput Screening 23, no. 2 (2020): 111–18. http://dx.doi.org/10.2174/1386207323666200120112714.

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Background: It is one of the effective ways for pesticide innovation to develop new insecticides from natural products as lead compounds. Quinine, the main alkaloid in the bark of cinchona tree as well as in plants in the same genus, is recognized as a safe and potent botanical insecticide to many insects. The structural modification of quinine into 9R-acyloxyquinine derivatives is a potential approach for the development of novel insecticides, which showed more toxicity than quinine. However, there are no reports on the insecticidal activity of 9Racyloxyquinine derivatives to control Mythimna separata. Methods: Endeavor to discover biorational natural products-based insecticides, 20 novel 9Racyloxyquinine derivatives were prepared and assessed for their insecticidal activity against M. separata in vivo by the leaf-dipping method at 1 mg/mL. Results: Among all the compounds, especially derivatives 5i, 5k and 5t exhibited the best insecticidal activity with final mortality rates of 50.0%, 57.1%, and 53.6%, respectively. Conclusion: Overall, a free 9-hydroxyl group is not a prerequisite for insecticidal activity and C9- substitution is well tolerated; modification of out-ring double-bond is acceptable, and hydrogenation of double-bond enhances insecticidal activity; Quinine ring is essential and open of it is not acceptable. These preliminary results will pave the way for further modification of quinine in the development of potential new insecticides.

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15

MORIGUCHI, Takeshi, Takayoshi FUJII, Takahiro KOIKE, Masakuni YOSHIHARA, and Toshihisa MAESHIMA. "Synthesis and Applications of Quinine-Bearing Clay." Journal of Japan Oil Chemists' Society 42, no. 2 (1993): 134–39. http://dx.doi.org/10.5650/jos1956.42.134.

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16

Stork, Gilbert, Deqiang Niu, A. Fujimoto, et al. "The First Stereoselective Total Synthesis of Quinine." Journal of the American Chemical Society 123, no. 14 (2001): 3239–42. http://dx.doi.org/10.1021/ja004325r.

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17

Bhongale, Nandkumar N., V. S. Pore та Arvind A. Natu. "Synthesis of Optically Active β-Ketosulphides Catalysed by Quinine/Quinidine and Homogeneous Catalysts". Synthetic Communications 18, № 13 (1988): 1597–606. http://dx.doi.org/10.1080/00397918808081318.

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18

Jiang, Yan, Luca Deiana, Kaiheng Zhang, Shuangzheng Lin, and Armando Córdova. "Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations." European Journal of Organic Chemistry 2019, no. 35 (2019): 6016–23. http://dx.doi.org/10.1002/ejoc.201901003.

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19

Shiomi, Shinya, Remi Misaka, Mayu Kaneko, and Hayato Ishikawa. "Correction: Enantioselective total synthesis of the unnatural enantiomer of quinine." Chemical Science 10, no. 44 (2019): 10445. http://dx.doi.org/10.1039/c9sc90226k.

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20

Rowan, Stuart J., Paul A. Brady, and Jeremy K. M. Sanders. "Synthesis and kinetic cyclisation of quinine-derived oligomers." Tetrahedron Letters 37, no. 33 (1996): 6013–16. http://dx.doi.org/10.1016/0040-4039(96)01263-4.

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21

Edward, Justin A., Matthew K. Kiesewetter, Hyunuk Kim, James C. A. Flanagan, James L. Hedrick, and Robert M. Waymouth. "Organocatalytic Synthesis of Quinine-Functionalized Poly(carbonate)s." Biomacromolecules 13, no. 8 (2012): 2483–89. http://dx.doi.org/10.1021/bm300718b.

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22

Panda, Siva S., Mohamed A. Ibrahim, Hasan Küçükbay, et al. "Synthesis and Antimalarial Bioassay of Quinine - Peptide Conjugates." Chemical Biology & Drug Design 82, no. 4 (2013): 361–66. http://dx.doi.org/10.1111/cbdd.12134.

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23

Jain, Kavita, Saikat Chaudhuri, Kuntal Pal, and Kalpataru Das. "The Knoevenagel condensation using quinine as an organocatalyst under solvent-free conditions." New Journal of Chemistry 43, no. 3 (2019): 1299–304. http://dx.doi.org/10.1039/c8nj04219e.

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24

Arshad, Muhammad, M. Alejandro Fernández, Eoghan M. McGarrigle, and Varinder K. Aggarwal. "Synthesis of quinine and quinidine using sulfur ylide-mediated asymmetric epoxidation as a key step." Tetrahedron: Asymmetry 21, no. 13-14 (2010): 1771–76. http://dx.doi.org/10.1016/j.tetasy.2010.04.046.

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25

Zhang, Yongda, Sampada Chitale, Navneet Goyal, et al. "Asymmetric Synthesis of Sulfinamides Using (−)-Quinine as Chiral Auxiliary." Journal of Organic Chemistry 77, no. 1 (2011): 690–95. http://dx.doi.org/10.1021/jo201825b.

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26

Ihara, Masataka, Nobuaki Taniguchi, and Keiichiro Fukumoto. "Synthesis of chiral intermediates of quinine alkaloids and (+)-dihydroantirhine." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1997): 365–70. http://dx.doi.org/10.1039/a606952e.

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27

Stork, Gilbert, Deqiang Niu, A. Fujimoto, et al. "ChemInform Abstract: The First Stereoselective Total Synthesis of Quinine." ChemInform 32, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.200129188.

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28

Zhou, Ding, Xueting Yu, Jian Zhang, Wei Wang, and Hexin Xie. "Organocatalytic asymmetric addition of alcohols to cyclic trifluoromethyl ketimines: highly enantioselective synthesis of chiral N,O-ketals." Organic & Biomolecular Chemistry 14, no. 26 (2016): 6193–96. http://dx.doi.org/10.1039/c6ob00890a.

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29

KUMURA, Naokazu, Minoru IZUMI, Shuhei NAKAJIMA, et al. "Synthesis and Biological Activity of Fatty Acid Derivatives of Quinine." Bioscience, Biotechnology, and Biochemistry 69, no. 11 (2005): 2250–53. http://dx.doi.org/10.1271/bbb.69.2250.

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30

Igarashi, Junji, and Yuichi Kobayashi. "Improved synthesis of quinine alkaloids with the Teoc protective group." Tetrahedron Letters 46, no. 37 (2005): 6381–84. http://dx.doi.org/10.1016/j.tetlet.2005.06.171.

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31

ROWAN, S. J., P. A. BRADY, and J. K. M. SANDERS. "ChemInform Abstract: Synthesis and Kinetic Cyclization of Quinine-Derived Oligomers." ChemInform 27, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199646252.

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32

Gu, Zheng, Ji Zhou, Guo-Fang Jiang та Yong-Gui Zhou. "Synthesis of chiral γ-aminophosphonates through the organocatalytic hydrophosphonylation of azadienes with phosphites". Organic Chemistry Frontiers 5, № 7 (2018): 1148–51. http://dx.doi.org/10.1039/c7qo01158j.

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An organocatalytic enantioselective 1,4-addition of phosphites to azadienes has been successfully developed using quinine as a catalyst, providing an efficient and facile route to optically active γ-aminophosphonates with up to 94% ee.

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33

Ratnadewi, Diah. "Strictosidine Synthase Coding Gene Expression towards Quinine Biosynthesis and Accumulation: Inconsistency in Cultured Cells and Fresh Tissues of Cinchona ledgeriana." International Journal of Agriculture and Biology 26, no. 01 (2021): 131–38. http://dx.doi.org/10.17957/ijab/15.1817.

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Strictosidine synthase, encoded by the gene STR, facilitates the regeneration of strictosidine, a critical intermediate for the synthesis of many plant alkaloids. The gene has, however, never been studied in Cinchona spp. The plants produce quinine alkaloid used for malaria medication, SARS-CoV-2 treatment and other industrial purposes. Cultured cells can produce the alkaloid but only at a much lower yield than the natural tree. This study describes STR expression and quinine content in various plant materials. Bioinformatic analyses were conducted on nine species of Rubiaceae to obtain reference sequences to design conservative primers for Cinchona ledgeriana STR (ClSTR). ClSTR expression was analyzed using qRT-PCR and quinine content was determined using HPLC. A complete coding sequence (CDS) of ClSTR was deposited in NCBI GenBank under the accession number MK422544.1. ClSTR was expressed in cultured cells, young and mature leaves, and stem bark. The elicited cells have higher expression than the control and they performed since the fourth week. However, the quinine content was greater in older cells. The gene expression in young leaves was superior, but quinine was most abundant in the stem bark. Every cell of C. ledgeriana, in culture or in the plant, expressed ClSTR and was capable of synthesizing the alkaloid quinine. The alkaloid from the leaves of the plant might be translocated and accumulated in the bark. No efflux of alkaloids from the confined cultured cells might contribute in triggering feedback inhibition in the biosynthetic pathway. This study revealed a critical obstacle in cell culture as a means of secondary metabolites production that needs further development of metabolic engineering. © 2021 Friends Science Publishers

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34

Hackler, László, Márió Gyuris, Orsolya Huzián, et al. "Enantioselective Synthesis of 8-Hydroxyquinoline Derivative, Q134 as a Hypoxic Adaptation Inducing Agent." Molecules 24, no. 23 (2019): 4269. http://dx.doi.org/10.3390/molecules24234269.

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Hypoxia is a common feature of neurodegenerative diseases, including Alzheimer’s disease that may be responsible for disease pathogenesis and progression. Therefore, the hypoxia-inducible factor (HIF)1 system, responsible for hypoxic adaptation, is a potential therapeutic target to combat these diseases by activators of cytoprotective protein induction. We have selected a candidate molecule from our cytoprotective hydroxyquinoline library and developed a novel enantioselective synthesis for the production of its enantiomers. The use of quinidine or quinine as a catalyst enabled the preparation of enantiomer-pure products. We have utilized in vitro assays to evaluate cytoprotective activity, a fluorescence-activated cell sorting (FACS) based assay measuring mitochondrial membrane potential changes, and gene and protein expression analysis. Our data showed that the enantiomers of Q134 showed potent and similar activity in all tested assays. We have concluded that the enantiomers exert their cytoprotective activity via the HIF1 system through HIF1A protein stabilization.

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35

Zhou, Yu-Hao, Yu-Zu Zhang, Zhu-Lian Wu, Tian Cai, Wei Wen, and Qi-Xiang Guo. "Organocatalytic Asymmetric Aldol Reaction of Arylglyoxals and Hydroxyacetone: Enantioselective Synthesis of 2,3-Dihydroxy-1,4-diones." Molecules 25, no. 3 (2020): 648. http://dx.doi.org/10.3390/molecules25030648.

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A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities.

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36

Ekawati, Linda, Bambang Purwono, and Muhammad Idham Darussalam Mardjan. "Synthesis N-Phenyl Pyrazoline from Dibenzalacetone and Heme Polymeration Inhibitory Activity (HPIA) Assay." Key Engineering Materials 840 (April 2020): 245–50. http://dx.doi.org/10.4028/www.scientific.net/kem.840.245.

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The synthesis of 1,5-diphenyl-3-styryl-4,5-dihydro-1H-pyrazole (B1) and 5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-1-phenyl-4,5-dihydro-1H-pyrazole (B2) have been conducted from 1,5-diphenylpenta-1,4-dien-3-on (A1) and 1,5-bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one (A2). Heme polymerization inhibitory activity (HPIA) assay of the synthesized compounds has also been carried out. The first step of reaction was Claisen-Schmidt condensation of benzaldehyde derivatives and acetone using NaOH 20% and ethanol as solvent. Dibenzalacetone derivatives were reacted with phenylhydrazine using acetic acid to form N-phenylpyrazoline. The structure of products was characterized by FT-IR, GC-MS, DI-MS, 1H- and 13C-NMR The result of heme polymerization inhibitory activity assay showed that IC50 of B1 and B2 1.26 and 0.79 mM while quinine 1.26 mM. The result indicated that compound B2 was more potent as antimalarial than quinine.

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37

IHARA, M., N. TANIGUCHI, and K. FUKUMOTO. "ChemInform Abstract: Synthesis of Chiral Intermediates of Quinine Alkaloids and (+)- Dihydroantirhine." ChemInform 28, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.199729215.

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38

Van Bruggen, Craig, David Punihaole, Allison R. Keith, et al. "Quinine copolymer reporters promote efficient intracellular DNA delivery and illuminate a protein-induced unpackaging mechanism." Proceedings of the National Academy of Sciences 117, no. 52 (2020): 32919–28. http://dx.doi.org/10.1073/pnas.2016860117.

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Polymeric vehicles that efficiently package and controllably release nucleic acids enable the development of safer and more efficacious strategies in genetic and polynucleotide therapies. Developing delivery platforms that endogenously monitor the molecular interactions, which facilitate binding and release of nucleic acids in cells, would aid in the rational design of more effective vectors for clinical applications. Here, we report the facile synthesis of a copolymer containing quinine and 2-hydroxyethyl acrylate that effectively compacts plasmid DNA (pDNA) through electrostatic binding and intercalation. This polymer system poly(quinine-co-HEA) packages pDNA and shows exceptional cellular internalization, transgene expression, and low cytotoxicity compared to commercial controls for several human cell lines, including HeLa, HEK 293T, K562, and keratinocytes (N/TERTs). Using quinine as an endogenous reporter for pDNA intercalation, Raman imaging revealed that proteins inside cells facilitate the unpackaging of polymer–DNA complexes (polyplexes) and the release of their cargo. Our work showcases the ability of this quinine copolymer reporter to not only facilitate effective gene delivery but also enable diagnostic monitoring of polymer–pDNA binding interactions on the molecular scale via Raman imaging. The use of Raman chemical imaging in the field of gene delivery yields unprecedented insight into the unpackaging behavior of polyplexes in cells and provides a methodology to assess and design more efficient delivery vehicles for gene-based therapies.

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39

Salahuddin, Salahuddin, Rahmana Emran K, Muhammad Hanafi, et al. "Sintesis dan Evaluasi Antimalaria In Vitro Turunan Kinin Terhadap Plasmodium falciparum." Jurnal Kefarmasian Indonesia 11, no. 2 (2021): 109–20. http://dx.doi.org/10.22435/jki.v11i2.3923.

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Nowadays kinin is the most effective antimalarial drug and its used as an alternative in malaria treatment. However, toxicity of quinine restrict its use as an antimalarial drug. Lipophilicity and long half-life (t½) of quinine that reach 10-20 hours are responsible for its toxicity. The aim of this research is to obtain more polar quinine derivatives by means of hydrogen peroxide reactions to reduce the toxicity. The reactions using hydrogen peroxyde is performed analogously to the procedures reported in the literature. Extract of pure anhydrous kinin is purified in coloumn chromatography followed by structure elucidation. Synthetic product is tested in vitro against Plasmodium falciparum. The characterization of reaction products is performed with proton (1H) and carbon 13 (13C) nuclear magnetic resonance (NMR) spectroscopy. It showed that the reaction using reagents led to epoxidation of vinyl substituents of chinuclidine ring with 61,08% yields. Antimalarial test against Plasmodium falciparum obtained 1.250-2.500 μg/mL of IC50 value. The IC50 values indicated that the synthesis products were not potential for malaria treatment.

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40

Ninomiya, Ichiya, Takeaki Naito, and Okiko Miyata. "Alkaloid Synthesis Using Furopyridone as Synthon —Synthesis of Key Intermediates for the Syntheses of (±)-Quinine, (±)-Ajmalicine, and (±)-7-Demethyltecomanine—." HETEROCYCLES 27, no. 6 (1988): 1321. http://dx.doi.org/10.3987/com-88-4520.

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41

Liu, Qiang, Kun Zhao, Ying Zhi, Gerhard Raabe, and Dieter Enders. "Squaramide-catalyzed domino Michael/aza-Henry [3 + 2] cycloaddition: asymmetric synthesis of functionalized 5-trifluoromethyl and 3-nitro substituted pyrrolidines." Organic Chemistry Frontiers 4, no. 7 (2017): 1416–19. http://dx.doi.org/10.1039/c7qo00161d.

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The diastereo- and enantioselective Michael/aza-Henry [3 + 2] cycloaddition reaction of trifluoromethyl-substituted iminomalonate and nitroalkenes has been developed employing 10 mol% of a quinine-squaramide catalyst.

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42

Kumar, Krishna, Bhuvnesh Singh, Soumyadip Hore, and Ravi P. Singh. "Catalytic enantioselective synthesis of chiral 4-hydroxy 4′-substituted pyrazolones by the vinylogous aldol reaction of pyrazole-4,5-diones with 3-alkylidene-2-oxindoles." New Journal of Chemistry 45, no. 31 (2021): 13747–50. http://dx.doi.org/10.1039/d0nj05886f.

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43

Pradines, B., F. Ramiandrasoa, L. K. Basco, L. Bricard, G. Kunesch, and J. Le Bras. "In vitro activities of novel catecholate siderophores against Plasmodium falciparum." Antimicrobial Agents and Chemotherapy 40, no. 9 (1996): 2094–98. http://dx.doi.org/10.1128/aac.40.9.2094.

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The activities of novel iron chelators, alone and in combination with chloroquine, quinine, or artemether, were evaluated in vitro against susceptible and resistant clones of Plasmodium falciparum with a semimicroassay system. N4-nonyl,N1,N8-bis(2,3-dihydroxybenzoyl) spermidine hydrobromide (compound 7) demonstrated the highest level of activity: 170 nM against a chloroquine-susceptible clone and 1 microM against a chloroquine-resistant clone (50% inhibitory concentrations). Compounds 6, 8, and 10 showed antimalarial activity with 50% inhibitory concentrations of about 1 microM. Compound 7 had no effect on the activities of chloroquine, quinine, and artemether against either clone, and compound 8 did not enhance the schizontocidal action of either chloroquine or quinine against the chloroquine-resistant clone. The incubation of compound 7 with FeCI3 suppressed or decreased the in vitro antimalarial activity of compound 7, while no effect was observed with incubation of compound 7 with CuSO4 and ZnSO4. These results suggest that iron deprivation may be the main mechanism of action of compound 7 against the malarial parasites. Chelator compounds 7 and 8 primarily affected trophozoite stages, probably by influencing the activity of ribonucleotide reductase, and thus inhibiting DNA synthesis.

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Bucher, Christoph, Christof Sparr, W. Bernd Schweizer, and Ryan Gilmour. "Fluorinated Quinine Alkaloids: Synthesis, X-ray Structure Analysis and Antimalarial Parasite Chemotherapy." Chemistry - A European Journal 15, no. 31 (2009): 7637–47. http://dx.doi.org/10.1002/chem.200900505.

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Nakano, Ayako, Mina Ushiyama, Yoshiharu Iwabuchi та Susumi Hatakeyama. "Synthesis of an Enantiocomplementary Catalyst of β-Isocupreidine (β-ICD) from Quinine". Advanced Synthesis & Catalysis 347, № 14 (2005): 1790–96. http://dx.doi.org/10.1002/adsc.200505138.

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Panda, Siva S., Kiran Bajaj, Marvin J. Meyers, Francis M. Sverdrup, and Alan R. Katritzky. "Quinine bis-conjugates with quinolone antibiotics and peptides: synthesis and antimalarial bioassay." Organic & Biomolecular Chemistry 10, no. 45 (2012): 8985. http://dx.doi.org/10.1039/c2ob26439k.

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Sahu, Adarsh, Ram Kishore Agrawal, and RajKishor Pandey. "Synthesis and systemic toxicity assessment of quinine-triazole scaffold with antiprotozoal potency." Bioorganic Chemistry 88 (July 2019): 102939. http://dx.doi.org/10.1016/j.bioorg.2019.102939.

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Faidallah, Hassan M., Siva S. Panda, Juan C. Serrano, et al. "Synthesis, antimalarial properties and 2D-QSAR studies of novel triazole-quinine conjugates." Bioorganic & Medicinal Chemistry 24, no. 16 (2016): 3527–39. http://dx.doi.org/10.1016/j.bmc.2016.05.060.

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Li, Jun-Hua, and Da-Ming Du. "Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives." Organic & Biomolecular Chemistry 13, no. 37 (2015): 9600–9609. http://dx.doi.org/10.1039/c5ob01211b.

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An efficient protocol for the construction of enantiomerically enriched tetrahydro-6H-benzo[c]chromenes by the cascade double Michael addition of 3-nitro-2H-chromenes and α,β-unsaturated ketones catalyzed by a quinine-derived primary amine has been developed.

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Haslberger, A., C. Romanin, and R. Koerber. "Membrane potential modulates release of tumor necrosis factor in lipopolysaccharide-stimulated mouse macrophages." Molecular Biology of the Cell 3, no. 4 (1992): 451–60. http://dx.doi.org/10.1091/mbc.3.4.451.

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Lipopolysaccharide (LPS)-mediated synthesis of macrophage gene products such as tumor necrosis factor (TNF) is controlled by different signaling pathways. We investigated intracellular free Ca2+ (Ca2+ic) and the membrane potential as early cellular responses to LPS and their role in the synthesis and release of TNF. In peritoneal macrophages and in the RAW 269 mouse macrophage cell line, LPS and its biologically active moiety lipid A stimulated TNF synthesis but exerted no significant effects on these early cellular responses using Fura-2/Indo-1 to measure Ca2+ic and bis-oxonol, as well as the patch-clamp technique to monitor membrane potential. In contrast, the platelet-activating factor transiently induced both an increase in Ca2+ic and cell membrane depolarization but no significant TNF release. Increased extracellular K+ concentrations or K(+)-channel blockers, such as quinine, tetraethylammonium, or barium chloride, inhibited the LPS-stimulated release of TNF alpha, as well as the accumulation of cell-associated TNF alpha as found by enzyme-linked immunosorbent assay analysis, but did not inhibit TNF alpha mRNA accumulation. Concentrations of quinine (greater than 125 microM) or of enhanced extracellular K+ (25-85 mM) required to inhibit TNF production both significantly depolarized macrophages. These results indicate a lack of ion transport activities as early cellular responses of macrophages to LPS but suggest an important regulatory role of the membrane potential on the posttranscriptional synthesis and release of TNF in macrophages.

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