CAS: 304-21-2; Harmaline

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合成工艺路线路线简述

  • 合成目标产物 Harmaline 主要起始原料 3-(2-Aminoethyl)-6-Methoxyindole
  • (文献来源)合成步骤主要原料 3-(2-Aminoethyl)-6-Methoxyindole
📜(7-Methoxy-2,3,4,9-Tetrahydro-1H-β-Carbolin-1-yl)-Methanol置于磷酸体系中,化学反应生成 骆驼蓬灵
参考文献:A Synthesis Of Harmaline
标题:A Synthesis Of Harmaline
摘要:通过将相应的1-羟甲基-1,2,3,4-四氢-β-咔啉脱水合成1-甲基-3,4-二氢-β-咔啉(harmalan)及其两种衍生物.harmalan也可以通过氧化脱羧1-甲基-1,2,3,4-四氢-β-咔啉-1-羧酸来获得.
DOI:10.1139/v59-272

海关参考信息

专利信息


专利号:WO-2025119975-A1
优先权日:2023-12-04
标 题:A method for synthesis of harmine
发明人:HETT ROBERT; GRAB HANUSCH; LAGOUTTE ROMAN
权利人:RECONNECT LABS AG
摘要:The invention relates to a method of synthesis of a compound of formula (I), harmine, according to the method comprising a step of transforming the compound of formula (II), into the compound of formula (I). The invention further relates to a compound of formula (II), which is an intermediate in synthesis of harmine according to the present invention.

专利号:US-11912647-B2
优先权日:2020-05-22
标 题:Diversity-oriented synthesis of N,N,O-trisubstituted hydroxylamines from alcohols and amines by N—O bond formation
发明人:CRICH DAVID; HETTIKANKANAMALAGE ASIRI; HILL JARVIS
权利人:UNIV GEORGIA
摘要:In one aspect, the disclosure relates to a method for the direct synthesis of complex N,N,O-trisubstituted hydroxylamines by N—O bond formation. In another aspect, the method can successfully be employed using a wide variety of commercially available alcohols and secondary amines and enables the construction of large fragment-based libraries of trisubstituted hydroxylamines for drug discovery purposes. Also disclosed are N,N,O-trisubstituted hydroxylamines having low basicity, high stability at ambient temperatures, and an inherent lack of reactivity towards acetylating and sulfonylating enzymes that confer mutagenicity on less-substituted hydroxylamines.

专利号:US-11578070-B2
优先权日:2020-09-01
标 题:Harmine synthesis
发明人:ZAID GENE H; DONAVALLI KRISHNA MOHAN; VERMA RAJNI
权利人:ANKH LIFE SCIENCES LTD
摘要:Methods for the synthesis of harmine comprise reacting harmaline with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in the presence of a diacid catalyst. In an embodiment, the synthesis is carried out using a reaction mixture of harmaline, DDQ, THF solvent, and succinic acid; the reaction is carried out under an inert atmosphere with refluxing for a period of 4-12 hours.

专利号:US-12419872-B2
优先权日:2020-03-05
标 题:Low-temperature synthesis of thymoquinone and harmaline compounds
发明人:ZAID GENE H; WOLF BETH ANN; ROPP RACHEL ELIZABETH; DONAVALLI KRISHNA MOHAN; VERMA RAJNI
权利人:ANKH LIFE SCIENCES LTD
摘要:Low-temperature syntheses of thymoquinone/harmaline compounds which are useful for the treatment of human diabetes and cancers, and the derivatives, solvates, prodrugs, isomers, and tautomers of such compounds.

专利号:US-11358963-B2
优先权日:2020-03-05
标 题 :Low-temperature synthesis of thymoquinone and harmaline compounds
发明人:ZAID GENE H; WOLF BETH ANN; ROPP RACHEL ELIZABETH
权利人:ANKH LIFE SCIENCES LTD
摘要:Low-temperature syntheses of thymoquinone/harmaline compounds are provided which give increased yields of desirable products having molecular weights of from about 360-380. The syntheses involve carrying out reactions between thymoquinone and harmaline and a non-interfering solvent at a temperature of less than about 10° C.

专利号:US-2024002405-A1
优先权日:2022-06-01
标题 :Antimicrobial compounds, synthesis methods, and uses thereof
发明人:VERMA RAJNI; DONAVALLI KRISHNA MOHAN; ZAID GENE H
权利人:ANKH LIFE SCIENCES LTD
摘要:Fused tricyclic compounds and novel methods of synthesizing, using, and/or administering the same. Methods of inhibiting microbial activity and/or treating a microbial infection with fused tricyclic compounds, bicyclic compounds, and other polycyclic compounds. The treatment of subjects suffering from a microbial infection comprises the step of administering to the subject one or more fused tricyclic compounds, bicyclic compounds, and other polycyclic compounds or a composition comprising one or more fused tricyclic compounds, bicyclic compounds, and other polycyclic compounds.

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主要参考文献


1: Siddiqui H, Tasneem S, Farooq S, Sami A, Rahman AU, Choudhary MI. Harmaline and its Derivatives Against the Infectious Multi-Drug Resistant Escherichia coli. Med Chem. 2017;13(5):465-476. doi: 10.2174/1573406413666170125113832. doi: 10.1080/01616412.2016.1275456. Epub 2017 Jan 18. doi: 10.1016/j.pharep.2016.01.008. Epub 2016 Feb 5.

合成参考文献


参考文献:10.1016/j.neuropharm.2011.06.029
摘要:Strick CA, Li C, Scott L, Harvey B, Hajós M, Steyn SJ, Piotrowski MA, James LC, Downs JT, Rago B, Becker SL, El-Kattan A, Xu Y, Ganong AH, Tingley FD, Ramirez AD, Seymour PA, Guanowsky V, Majchrzak MJ, Fox CB, Schmidt CJ, Duplantier AJ. Modulation of NMDA receptor function by inhibition of D-amino acid oxidase in rodent brain. Neuropharmacology. 2011 Oct;61(5-6):1001–15. doi: 10.1016/j.neuropharm.2011.06.029.
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