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Relevant bibliographies by topics / Quinine – Synthesis

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Academic literature on the topic 'Quinine – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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Journal articles on the topic "Quinine – Synthesis"

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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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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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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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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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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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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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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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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Dissertations / Theses on the topic "Quinine – Synthesis"

1

Hunt, Thomas. "Application of phosphorus-centred radicals towards the synthesis of (-)-quinine and related analogues." Thesis, University of York, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.428405.

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2

Ji, An. "Mn-mediated radical coupling toward synthesis of alpha, alpha-disubstituted alpha-amino esters and formal synthesis of quinine." Diss., University of Iowa, 2011. https://ir.uiowa.edu/etd/1150.

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Chiral alpha-branched amines are common substructures of bioactive synthetic targets such as alkaloids and amino acids. Direct asymmetric amine synthesis by addition to the C=N bond of carbonyl imino derivatives is promising and efficient to introduce the stereogenic center and carbon-carbon bond in one step. Furthermore, disconnection of either C-C bond at the amine stereogenic center would be the most versatile method to achieve this objective; we could make the choice depending on the different synthetic strategies, such as the availability of precursors and the presence of complicating structural features. In our group, we disclosed that manganese carbonyl mediates stereoselective photolytic radical addition of alkyl iodides to chiral imino acceptors, which is a powerful tool to form a new C-C bond and generate a chiral center. Qualitative mechanistic studies confirm the importance of free radicals, imply that this is a nonchain (or short chain length) free-radical process, and reveal that organomanganese compounds are not a viable source of alkyl radical for the addition reactions under the conditions in our lab. In my thesis, we have extended the application of our methodology. At the beginning of my research, our Mn-mediated addition methodology was first applied to accomplish the couplings of iodides and ketone N-acylhydrazones, generating quaternary carbon stereocenters and offering access to a variety of alpha-alkylated alanine analogs. These radical additions complement enolate alkylation methodologies, as they occur under nonbasic conditions and permit introduction of both primary and secondary alkyl groups with relative ease. The versatility with respect to the iodide is a distinguishing feature of the Mn-mediated coupling that foreshadows application to more complex targets. Secondly, a Mn-mediated radical-ionic annulation strategy was validated as a synthetic route to quinine. Intermolecular radical addition to C=N bonds has rarely been applied as a strategic bond construction in natural product synthesis; this synthesis of quinine offers the strongest demonstration yet of the utility of such reactions in application toward complex multifunctional targets.

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Oosthuizen, Francois Jacobus. "Syntheses of the Enantiopure Quinones A and A' and Their C-1 Epimers." Murdoch University, 2002. http://wwwlib.murdoch.edu.au/adt/browse/view/adt-MU20040820.123649.

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The 3,4-dihydro-1H-naphtho[2,3-c]pyran ring system is found in many natural products as the 5,10- or 6,9-quinones. These compounds have been synthesized by various research groups as a result of their wide range of biological activities. This thesis describes several investigations directed towards syntheses of compounds in this general area. Quinone A (16) and quinone A(17), derived from the naturally occurring aphid insect pigments protoaphin-fb and protoaphin-sl respectively, were of particular interest. The first chapter describes the previous syntheses of some naphtho[c]pyrans including those relating to the aphid pigment derivatives, followed by the isolation and identification of the aphid pigments. Also described was the ability of these naphthopyranquinones to act as potential bioreductive alkylating or dealkylating agents. The latter part of the chapter deals with the syntheses of the racemates of the aphid pigment derivatives quinones A and A and deoxyquinone as well as model studies toward the non-quinonoid cleavage product, glucoside B. The chapter concludes with the progress made towards the first asymmetric synthesis of these compounds. Chapter 2 reports the establishment of conditions which led to ortho or para regioselectivity in the intramolecular cyclisation of tethered lactaldehydes to form benzo[c]pyrans. This regioselectivity depended on whether either benzyl or tbutyldimethylsilyl was used as protecting group. This chapter also described a model for the control of stereochemistry leading to quinone A. Chapter 3 describes the syntheses of naphthalenes as potential precursors to the naphthopyranquinones derived from the aphid insect pigments. This followed after problems were encountered in previous work with inappropriate protection in the oxidation of halogenated benzopyrans. Chapter 4 develops the first successful syntheses of enantiopure quinone A and quinine A with the correct absolute stereochemistry. This involved the regioselective addition of 1,3-bis(trimethylsilyloxy)-1-methoxybuta-1,3-diene toselectively halogenated benzopyranquinones. The latter were obtained through complementary series of highly diastereoselective transformations based on 2,5- dihydroxyacetophenone as starting material and (R)-lactate from the chiral pool as the source of asymmetry.

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Arshad, Muhammad. "Syntheses of quinine and quinidine using sulfur ylide epoxidation reaction as a key step." Thesis, University of Bristol, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.535226.

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Rafipoor, Fereshteh. "Synthesis of oxindole quinones and carboline quinones." Thesis, Brunel University, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.292445.

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6

Cossette, Michael Vernie. "The Synthesis of Quinone-Capped Cyclodextrins." W&M ScholarWorks, 1988. https://scholarworks.wm.edu/etd/1539625451.

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7

Moya, Eduardo. "Ortho-quinone methides from the pyrolysis of substituted benzyltriphenylphosphonium compounds." Thesis, University of Kent, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.235694.

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Chilloux, Aurelie Amelia. "Synthesis of anticancer heterocyclic quinones." Thesis, University of Nottingham, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.537637.

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9

Barr, Stephen Alexander. "Quinoline alkaloids : synthesis and stereochemistry." Thesis, Queen's University Belfast, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.333796.

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10

Jacob, Aouregan MicheÌ€le Marguerite Simone. "Synthesis of naturally occurring quinones." Thesis, University of Nottingham, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.437087.

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Books on the topic "Quinine – Synthesis"

1

1961-, Doherty Annette M., ed. Polyquinane chemistry: Syntheses and reactions. Springer-Verlag, 1987.

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Ronne, Erik. Synthesis of imidazoazaarenes. Swedish University of Agricultural Sciences, Dept. of Chemistry, 1994.

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3

Greer, Robert James. Studies in the synthesis of quinoline alkaloids. The Author), 1987.

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4

Neville, Charles Frederick. The synthesis and biosynthesis of quinoline alkaloids. The Author], 1989.

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Rafipoor, Fereshteh. Synthesis of oxindole quionones and carboline quinones. Brunel University, 1991.

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6

Thomas, R. D. Synthetic studies using quinones and related compounds. University of East Anglia, 1987.

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Erickson, W. Randal. Studies on advanced intermediates in the biosynthesis of streptonigrin. 1987.

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8

Raghvani, Dinesh V. Studies of 1,2-quinone monooximes and their use in synthesis. 1999.

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Chakrabarti, Jayatibha. Metal complexes of 1,2-quinone monooximes and their applications in organic synthesis. 1995.

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Badahdah, Khadija Omer. Studies of quinone monooximes and of their metal complexes and synthetic applications. 1999.

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Book chapters on the topic "Quinine – Synthesis"

1

Li, Jie Jack. "Pfitzinger quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_221.

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Li, Jie Jack. "Skraup quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_266.

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Li, Jie Jack. "Combes quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_60.

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Li, Jie Jack. "Friedländer quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_102.

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Jack Li, Jie. "Skraup quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_237.

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Li, Jie Jack. "Camps quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_44.

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Li, Jie Jack. "Combes quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_58.

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Li, Jie Jack. "Doebner quinoline synthesis." In Name Reactions. Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_83.

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Li, Jie Jack. "Friedländer quinoline synthesis." In Name Reactions. Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_110.

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Li, Jie Jack. "Skraup quinoline synthesis." In Name Reactions. Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_254.

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Conference papers on the topic "Quinine – Synthesis"

1

Silva, Wanderson Amaral da, Vinícius Rangel Campos, Angela Cristina P. B. dos Santos, et al. "The Ultrasound-accelerated Synthesis of New 7- Aminocarbohydrate-isoquinoline-5,8-quinone Derivatives." In 14th Brazilian Meeting on Organic Synthesis. Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0253-2.

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Carneiro, Paula F., Alice S. B. Rocha, Guilherme C. Lechuga, et al. "Synthesis of oxirane from quinones against T. cruzi." In 15th Brazilian Meeting on Organic Synthesis. Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013820205350.

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Barbosa, Luiz C. A., Carmindo R. Borel, Sergio A. Fernandes, and Célia R. A. Maltha. "Povarov reaction for the synthesis of 2-(2-pyridyl)quinoline." In 15th Brazilian Meeting on Organic Synthesis. Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013816161848.

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Xiao Hong Yin, K. Kobayashi, T. Kawai, M. Ozaki, K. Yoshino, and Qingquan Lei. "Electrical properties of polymer composites: conducting polymerpolyacene quinone radical polymer." In International Conference on Science and Technology of Synthetic Metals. IEEE, 1994. http://dx.doi.org/10.1109/stsm.1994.835422.

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Musiol, Robert, Josef Jampilek, Katarina Kralova, et al. "New Quinoline Derivatives Possessing Herbicidal Activity." In The 9th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01508.

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Yano, J., Y. Matsufuji, and K. Ogura. "Multicolor-expressible ECD materials consisted of polyanilines, and an anionic quinone." In International Conference on Science and Technology of Synthetic Metals. IEEE, 1994. http://dx.doi.org/10.1109/stsm.1994.836068.

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Saraiva, Maiara, Roberta Krüger та Diego Alves. "Synthesis of Quinoline-Triazoil Carboxylates by Organocatalytic Cycloaddition of β-Ketoesters and 4-Azido-7-Chloroquinoline". У 15th Brazilian Meeting on Organic Synthesis. Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013811191913.

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Bittner, Shmuel, and Thida Win. "Direct Nitration of 3-Arylamino-2-Chloro-1,4-Naphthoquinones; Novel Quinone Derivatives." In The 9th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01473.

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Rahatgaonkar, Anjali Milind. "Synthesis of Chitosan-Quinoline Biocomposites for Solvent Extraction Applications." In SAE 2010 World Congress & Exhibition. SAE International, 2010. http://dx.doi.org/10.4271/2010-01-0429.

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Jampilek, Josef, Katarina Kralova, Pavel Bobal, et al. "Preparation and Herbicidal Properties of Substituted Quinoline-2-carboxanilides." In The 15th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00588.

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Reports on the topic "Quinine – Synthesis"

1

Galleguillos, R., M. Litt, and S. E. Rickert. Friedel Craft's synthesis and characterization of some acene quinone compounds. Office of Scientific and Technical Information (OSTI), 1987. http://dx.doi.org/10.2172/6631885.

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