CAS: 548-42-5; Agroclavine

该化合物是一种自然产生的碱性碱,属于被称为类化合物类的类化合物,产自真菌Claviceps purpurea,该化合物的特点是复杂的四环结构,包括一个有引信的蛋白和异硫酸盐. (-)-Agroclavin 展示一系列生物活动,包括对...

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CAS号1935-33-7 MAGR

合成工艺路线路线简述

  • 合成目标产物 Agroclavine 主要起始原料 Indole-3-Carboxaldehyde
  • (文献来源)合成步骤主要原料 Indole-3-Carboxaldehyde
📜野麥鹼置于sodium,正丁醇体系中,化学反应生成 曲麦角碱
参考文献:Yamatodani; Abe,Journal Of The Agricultural Chemical Society Of Japan,1956,Vol. 20,P. 95
标题:Yamatodani; Abe,Journal Of The Agricultural Chemical Society Of Japan,1956,Vol. 20,P. 95

海关参考信息

专利信息


专利号:US-3968112-A
优先权日:1974-08-02
标 题:Synthesis of penniclavine and elymoclavine
发明人：KORNFELD EDMUND C; BACH NICHOLAS J
权利人:LILLY CO ELI
摘要:Synthesis of penniclavine and of elymoclavine, intermediates useful therein, and novel compounds producible therefrom.

专利号:US-3923812-A
优先权日:1974-08-02
标题:Synthesis of elymoclavine
发明人：BACH NICHOLAS J; KORNFELD EDMUND C
权利人:LILLY CO ELI
摘要:Elymoclavine is prepared by oxidation of D-6-methyl-8hydroxymethyl-10 Alpha -methoxy-8-ergolene to the corresponding D-8-aldehyde followed by reduction with an active metal in acid medium.

专利号:US-4082753-A
优先权日:1976-02-17
标题:Penniclavine acetonide
发明人：KORNFELD EDMUND C; BACH NICHOLAS J
权利人:LILLY CO ELI
摘要:Synthesis of penniclavine and of elymoclavine, intermediates useful therein, and novel compounds producible therefrom.

专利号:US-4054567-A
优先权日:1975-08-11
标 题:6-Methyl-8β-hydroxymethyl-8-γ-substituted-9-ergolene compounds
发明人：KORNFELD EDMUND C; BACH NICHOLAS J
权利人:LILLY CO ELI
摘要:Synthesis of penniclavine and of elymoclavine, intermediates useful therein, and novel compounds producible therefrom.

专利号:JP-H06279406-A
优先权日:1984-02-06
标题 :Synthesis of 6-substituted-4-dialkylaminotetrahydrobenz [c, d] indoles

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主要参考文献


1: Wu N, Yao M, Xiao W, Dong T, Ma H, Du X, Wang Y, Yuan Y. Modular Pathway Compartmentalization for Agroclavine Overproduction in Saccharomyces cerevisiae. ACS Synth Biol. 2023 Apr 21;12(4):1133-1145. doi: 10.1021/acssynbio.2c00626. Epub 2023 Mar 29. 7(4):1126-1132. doi: 10.1016/j.synbio.2022.08.003.
3: Starec M, Fiserová A, Rosina J, Malek J, Krsiak M. Effect of agroclavine on NK activity in vivo under normal and stress conditions in rats. Physiol Res. 2001;50(5):513-9. 130(12):1225-1229. doi: 10.1080/00207454.2020.1732963. Epub 2020 Feb 28. 230(3):518-25. doi: 10.1016/0304-4165(71)90182-6. 80(20):6465-72. doi: 10.1128/AEM.02137-14. Epub 2014 Aug 8.
7: Matuschek M, Wallwey C, Xie X, Li SM. New insights into ergot alkaloid biosynthesis in Claviceps purpurea: an agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine. Org Biomol Chem. 2011 Jun 7;9(11):4328-35. doi: 10.1039/c0ob01215g. Epub 2011 Apr 15. 19(13):3664-3667. doi: 10.1021/acs.orglett.7b01681. Epub 2017 Jun 22. 64(2):343-4. doi: 10.1002/jps.2600640237. 8(6):569-74. doi: 10.1016/s0960-894x(98)00072-9. 223(5211):1166-8. doi: 10.1038/2231166a0. 52(2):183-8. Russian. 80(1-2):1-8. doi: 10.1016/j.brainresbull.2009.06.010. Epub 2009 Jun 25. 64(5):11-3. Russian. 41(8):1051-2. doi: 10.1007/BF01952138. 20(1):288-291. doi: 10.1021/acs.orglett.7b03683. Epub 2017 Dec 13. 13(3):316-25. 20(3):527-9. doi: 10.1530/jrf.0.0200527. 39(3):335-40. Russian. 35(2):P367-9.

合成参考文献


摘要:A2914: Mantegani S, Brambilla E, Varasi M: Ergoline derivatives: receptor affinity and selectivity. Farmaco. 1999 May 30;54(5):288-96.
摘要:L1920: Wikipedia. Ergotism. Last Updated 6 April 2010.
摘要:A2916: Kvernmo T, Hartter S, Burger E: A review of the receptor-binding and pharmacokinetic properties of dopamine agonists. Clin Ther. 2006 Aug;28(8):1065-78.
摘要:A3101: Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35.
摘要:L1921: Van den Enden, E. (2004). Illustrated Lecture Notes on Tropical Medicine. http://www.itg.be/evde/
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