CAS: 481-06-1; α-Santonin

该化合物是一种自然形成的化学化合物,主要来自阿耳特米西亚(Atemisia cina)植物,通称为虫木,主要产自亚特米西亚(Artemisia cina)植物,其特点是晶状结构,一般为白色,一般为黄色,一般为黄色,以其药性为名,特别是在传统草药中,该化合物被用作驱赶寄生虫的神话. (-)-桑托宁也因其诱发光毒性的能力而引人注目,导致阳光照射皮肤反应.在溶解性方面,该化合物一般溶解于乙醇和氯仿等有机溶剂,但在水中溶解性有限.该化合物的立体化学特性很重要,因为(-)的指定表明其具体的光学活动对其生物相互作用至关重要.由于它的潜在影响和应用,(-)-桑托宁一直是侧重于其药理学特性和行动机制的各种研究的主题.

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合成工艺路线路线简述

  • 合成目标产物 Santonin 主要起始原料 1,2-Dihydro-Alpha-Santonin
  • (文献来源)合成步骤主要原料 1,2-Dihydro-Alpha-Santonin
1,2-二氢-Alpha-山道年置于吡啶,Chromium(Vi) Oxide,Sodium Tetrahydroborate,Cerium(Iii) Chloride,五羰基铁,三甲基脲,硫酸,Potassium Carbonate,间氯过氧苯甲酸,2,3-二氯-5,6-二氰基-1,4-苯醌体系中,用 苯 作为反应溶剂,化学反应生成 山道年
参考文献:A Formal Synthesis Of L-.Alpha.-Santonin From Chiral .Alpha.,.Beta.-Epoxyeudesmanolide Via Enzyme-Cayalyzed Hydrolysis.
标题:A Formal Synthesis Of L-.Alpha.-Santonin From Chiral .Alpha.,.Beta.-Epoxyeudesmanolide Via Enzyme-Cayalyzed Hydrolysis.
摘要:通过酵母处理(+/-)-3__-,分别得到了(4S,5R)-环氧-(3S)-羟基-(10S)-7α,11βh-桉烷-6α,12-内酯4__-和(4R,5S)-环氧-(3S)-羟基-(10R)-7β,11αh-桉烷-6β,12-内酯5__-;通过脂肪酶处理(+/-)-8__-,制备了(3S)-乙酰氧基-(4S,5R)-环氧-(10S)-7α,11βh-桉烷-6α,12-内酯8__-.通过使用手性关键中间体(10S)-8__-(通过不对称水解(+/-)-8__-制备)的短步骤合成,成功完成了l-α-山道年(9)及其δ4(14)异构体(10和11)的新全合成.
DOI:10.1248/cpb.42.1160

海关参考信息

专利信息


专利号:US-2011296543-A1
优先权日:2006-06-01
标题:Nucleic acids and proteins and methods for making and using them
发明人:CHANG HWAI; MATHUR ERIC J; CAYOUETTE MICHELLE; ROBERTSON DAN E; HUGENHOLTZ PHILIP; WARNECKE FALK; LEADBETTER JARED R; IVANOVA NATALIA; LUGINBUHL PETER; HUTCHISON DON
权利人:CHANG HWAI; MATHUR ERIC J; CAYOUETTE MICHELLE; ROBERTSON DAN E; HUGENHOLTZ PHILIP; WARNECKE FALK; LEADBETTER JARED R; IVANOVA NATALIA; LUGINBUHL PETER; HUTCHISON DON; UNIV CALIFORNIA; CALIFORNIA INST OF TECHN; VERENIUM CORP
摘要:The invention provides polypeptides, including enzymes, structural proteins and binding proteins, polynucleotides encoding these polypeptides, and methods of making and using these polynucleotides and polypeptides. Polypeptides, including enzymes and antibodies, and nucleic acids of the invention can be used in industrial, experimental, food and feed processing, nutritional and pharmaceutical applications, e.g., for food and feed supplements, colorants, neutraceuticals, cosmetic and pharmaceutical needs. Polypeptides of the invention can be used in food processing, brewing, bath additives, alcohol production, peptide synthesis, enantioselectivity, hide preparation in the leather industry, waste management and animal degradation, silver recovery in the photographic industry, medical treatment, silk degumming, biofilm degradation, biomass conversion to a biofuel (e.g., a bioethanol, biomethanol, biopropanol or biobutanol, a biodiesel, etc.), biodefense, antimicrobial agents and disinfectants, personal care and cosmetics, biotech reagents, in corn wet milling and pharmaceuticals such as digestive aids and anti-inflammatory (anti-phlogistic) agents.
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主要参考文献


1: Díaz K, Espinoza L, Madrid A, Pizarro L, Chamy R. Isolation and Identification of Compounds from Bioactive Extracts of Taraxacum officinale Weber ex F. H. Wigg. (Dandelion) as a Potential Source of Antibacterial Agents. Evid Based Complement Alternat Med. 2018 Jan 1;2018:2706417. doi: 10.1155/2018/2706417. eCollection 2018.
2: Coricello A, El-Magboub A, Luna M, Ferrario A, Haworth IS, Gomer CJ, Aiello F, Adams JD. Rational drug design and synthesis of new α-Santonin derivatives as potential COX-2 inhibitors. Bioorg Med Chem Lett. 2018 Apr 1;28(6):993-996. doi: 10.1016/j.bmcl.2018.02.036. Epub 2018 Feb 22. doi: 10.1016/j.ejmech.2018.02.073. Epub 2018 Feb 23. doi: 10.1021/acs.analchem.7b05445. Epub 2018 Feb 23. doi: 10.1002/mrc.4711. Epub 2018 Feb 8. doi: 10.1002/anie.201710463. Epub 2017 Dec 20. doi: 10.1016/j.jep.2017.10.029. doi: 10.1248/bpb.b17-00170. doi: 10.1039/c7ob01394a. doi: 10.1021/acs.jmedchem.6b01829. Epub 2017 Aug 2. doi: 10.1371/journal.pone.0175088. eCollection 2017.
12: Sakipova Z, Wong NS, Bekezhanova T, Sadykova, Shukirbekova A, Boylan F. Quantification of santonin in eight species of Artemisia from Kazakhstan by means of HPLC-UV: Method development and validation. PLoS One. 2017 Mar 16;12(3):e0173714. doi: 10.1371/journal.pone.0173714. eCollection 2017. Erratum in: PLoS One. 2017 Mar 28;12 (3):e0175088.

合成参考文献


摘要:Rueda-Becerril, M.; Sammis, G. M., Science of Synthesis Knowledge Updates, (2017) 2, 219.
摘要:Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology., 52(79S), 1956
摘要:Ruskin, J.; Lectka, T., Science of Synthesis: Modern Strategies in Organofluorine Chemistry, (2025) 2.
摘要:Saha, D.; Aggarwal, T.; Sumii, Y.; Yadav, A. K.; Shibata, N., Science of Synthesis: Modern Strategies in Organofluorine Chemistry, (2025) 2.
摘要:WICHMANN G. [Contribution to the biology of santonin plants. I. Distribution of santonin & related compounds in the plant kingdom]. Pharmazie. 1958 Aug;13(8):487–98.
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