CAS: 4747-99-3; Norlaudanosoline

该化合物是一种生物活性四氢硫基衍生物,含有多个氢氧基化合物,有助于其作为有机合成和制药研究中的关键中间体的潜力.该化合物的结构框架将四氢基苯基核心与一种乙酸基替代苯基化合物组合结合起来,表明在研究...

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CAS号68-12-2 N,N-二甲基甲酰胺 | CAS号107-05-1 氯丙烯 | CAS号51-61-6 多巴胺 | CAS号5707-55-1 Dopal | CAS号91790-53-3 2-[(3,4-dimetho... | CAS号10597-60-1 3,4-二羟基苯乙醇 | CAS号51-61-6 多巴胺 | CAS号91-22-5 喹啉 | CAS号59-31-4 2-羟基喹啉

合成工艺路线路线简述

  • 合成目标产物 Tetrahydropapaveroline 主要起始原料 4-Hydroxyphenylpyruvic Acid
  • (文献来源)合成步骤主要原料 4-Hydroxyphenylpyruvic Acid
📜羟基酪醇置于potassium Phosphate,三氧化硫吡啶,N,N-二异丙基乙胺体系中,用 二氯甲烷,水,二甲基亚砜,乙腈 作为反应溶剂,化学反应 13.0H,反应生成 四氢维洛林
参考文献:One-Pot Triangular Chemoenzymatic Cascades For The Syntheses Of Chiral Alkaloids From Dopamine
标题:One-Pot Triangular Chemoenzymatic Cascades For The Syntheses Of Chiral Alkaloids From Dopamine
摘要:一锅法,一底物,三角形化酶级联反应,包括转氨酶(tam)和诺可克洛啉合酶(ncs),可实现(S)-苄基异喹啉和(S)-四氢原咱呱啶生物碱的形成.
DOI:10.1039/c4Gc02325K

海关参考信息

专利信息


专利号:US-12091696-B2
优先权日:2022-08-10
标 题 :O-methyltransferase protein with highly specific catalytic function for multiple bias parent nuclei and encoding gene and use thereof
发明人:CHEN SHA; YU YUETONG
权利人:INST CHINESE MATERIA MEDICA CHINA ACADEMY OF CMS
摘要:The present disclosure provides an O-methyltransferase protein with a highly specific catalytic function for multiple benzylisoquinoline alkaloids (BIAs) parent nuclei and an encoding gene and use thereof. Compared with wild-type O-methyltransferase, the O-methyltransferase protein (SEQ ID NO: 2) shows an enhanced enzymatic activity and a wider substrate scope. The O-methyltransferase protein can catalyze O-methylation of backbones from three BIAs, including monobenzylisoquinolines (norcoclaurine, coclaurine, and N-methylcoclaurine), aporphines (asimilobine and N-methylasimilobine), and protoberberines (scoulerine and tetrahydrocolumbamine). Meanwhile, this O-methyltransferase protein is highly regioselective for each backbone. The O-methyltransferase protein catalyzes methylation of the monobenzylisoquinolines at 6-OH and 7-OH, is only active on 6-OH of the backbone of the aporphines, and mainly catalyzes methylation of the protoberberines at 2-OH. Moreover, the O-methyltransferase protein has a stronger catalytic activity and can be used as a biocatalyst for the semi-synthesis of related compounds.

专利号:US-8912332-B2
优先权日:2010-09-10
标题:Synthesis of trivalent flexible frameworks with ligands comprising catechol units for functionalizing surfaces
发明人:MAISON WOLFGANG; KHALIL FAIZA; FRANZMANN ELISA
权利人:MAISON WOLFGANG; KHALIL FAIZA; FRANZMANN ELISA; UNIV GIESSEN JUSTUS LIEBIG
摘要:The present invention describes tripodal catechol derivatives with a flexible basic framework for the functionalization of surfaces, and methods for their production and use. The central atom of the flexible framework is hereby a tertiary aliphatic carbon atom. The remaining fourth bridgehead position is easily suitable to be further functionalized via so-called click reactions, e.g. with biomolecules, dyes, radiomarkers, polyethylene glycol or active agents. n The compounds according to the present invention have the general formula X—C[(CH 2 ) n —YZ] 3 , wherein X stands for a group —(CH 2 ) p —R 5 , wherein p=0 to 10 and R 5 is selected from —H, —NH 2 , —NO 2 , —OH, —SH, —O—NH 2 , —NH—NH 2 , —Nâ•?Câ•?S—, —Nâ•?Câ•?O—, —CHâ•?CH 2 , —C≡CH, —COOH, —(Câ•?O)H, —(Câ•?O)R 6 Y stands for —CH 2 —, —CHâ•?CH—, —C≡C—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HCâ•?N—O—, —O—Nâ•?CH—, —NR 1 —, -Aryl-, -Heteroaryl-, —(Câ•?O)—, —O—(Câ•?O)—, —(Câ•?O)—O—, —NH—(Câ•?O)—, —(Câ•?O)—NH—, —NR 1 —(Câ•?O)—, —(Câ•?O)—NR 1 —, —NH—(Câ•?O)—NH—, —NH—(Câ•?S)—NH—, R 1 stands for an aryl group, R 6 for an alkyl, alkenyl, alkynyl, aryl or heteroaryl group, and Z stands for a catechol derivative. n The production of the compounds occurs by reacting a compound X—C[(CH 2 ) n —Y′] 3 with a reagent Y″Z to the corresponding compound X—C[(CH 2 ) n —YZ] 3 and subsequent purification of the reaction product. n Y′ and Y″ are hereby precursors of Y. The compounds according to formula (I) according to the present invention are suitable to be used in a method to functionalize surfaces. The X group of the compounds according to the present invention is suitable to be optionally coupled to an effector, for example, by means of click chemistry.

专利号:US-8785641-B2
优先权日:2010-09-10
标题 :Synthesis of tripodal catechol derivatives having an adamantyl basic framework for functionalizing surfaces
发明人:MAISON WOLFGANG; KHALIL FAIZA; FRANZMANN ELISA
权利人:MAISON WOLFGANG; KHALIL FAIZA; FRANZMANN ELISA; UNIV GIESSEN JUSTUS LIEBIG
摘要:The present invention describes tripodal catechol derivatives with an adamantyl basic framework for the functionalization of surfaces, methods for their production and use. The remaining fourth bridgehead position is easily suitable to be further functionalised via so-called click reactions, by way of example with biomolecules, dyes, radiomarkers, polyethylene glycol or active agents. n The compounds according to the present invention have the general formula X-Ad[(CH 2 ) n —YZ] 3 , wherein A stands for the adamantyl skeleton, X stands for a group —(CH 2 ) p —R 5 , wherein p=0 to 10 and R 5 is selected from —H, —NH 2 , —NO 2 , —OH, —SH, —O—NH 2 , —NH—NH 2 , —Nâ•?Câ•?S—, —Nâ•?Câ•?O—, —CHâ•?CH 2 , —C≡CH, —COOH, —(Câ•?O)H, —(Câ•?O)R 6 Y stands for —CH 2 —, —CHâ•?CH—, —C≡C—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HCâ•?N—O—, —O—Nâ•?CH—, —NR 1 —, -aryl-, -heteroaryl-, —(Câ•?O)—, —O—(Câ•?O)—, —(Câ•?O)—O—, —NH—(Câ•?O)—, —(Câ•?O)—NH—, —NR 1 —(Câ•?O)—, —(Câ•?O)—NR 1 —, —NH—(Câ•?O)—NH—, —NH—(Câ•?S)—NH—, R 1 stands for an alkyl group, R 6 for an alkyl, alkenyl, alkynyl, aryl or heteroaryl group, and Z stands for a catechol derivative. n The production of the compounds occurs by reacting a compound X-Ad[(CH 2 ) n —Y′] 3 with a reagent Y″Z to the corresponding compound X-Ad[(CH 2 ) n —YZ] 3 and subsequently purifying the reaction product. n Y′ and Y″ are hereby precursors of Y. The compounds according to formula (I) according to the present invention are suitable to be used in a method to functionalize surfaces. The X group of the compounds according to the present invention is suitable to be optionally coupled to an effector, for example, by means of click chemistry.

专利号:US-12416029-B2
优先权日:2016-06-27
标 题 :Compositions and methods for making benzylisoquinoline alkaloids, morphinan alkaloids, thebaine, and derivatives thereof
发明人:FACCHINI PETER JAMES; CHEN XUE; COLBECK JEFFREY C; TUCKER JOSEPH E
权利人:ANTHEIA INC
摘要:Disclosed herein are methods that may be used for the synthesis of benzylisoquinoline alkaloids (“BIAsâ€?) such as alkaloid morphinan. The methods disclosed can be used to produce thebaine, oripavine, codeine, morphine, oxycodone, hydrocodone, oxymorphone, hydromorphone, naltrexone, naloxone, hydroxycodeinone, neopinone, and/or buprenorphine. Compositions and organisms useful for the synthesis of BIAs, including thebaine synthesis polypeptides, purine permeases, and polynucleotides encoding the same, are provided.

专利号:EP-3137618-A1
优先权日:2014-04-29
标 题 :Improved methods for making and using polynucleotide sequences in the synthesis of alkaloid compounds

专利号:US-2013245269-A1
优先权日:2010-09-10
标 题 :Synthesis of Tripodal Catechol Derivatives Having an Adamantyl Basic Framework for Functionalizing Surfaces

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合成参考文献


参考文献:10.1016/0006-2952(80)90394-9
摘要:Melchor CL, Mueller A, Deitrich RA. Half-lives of salsolinol and tetrahydropapaveroline hydrobromide following intracerebroventricular injection. Biochem Pharmacol. 1980 Feb 15;29(4):657–8. doi: 10.1016/0006-2952(80)90394-9.
参考文献:10.1046/j.1365-2362.1999.00511.x
摘要:Surh Y. Tetrahydropapaveroline, a dopamine-derived isoquinoline alkaloid, undergoes oxidation: implications for DNA damage and neuronal cell death. Eur J Clin Invest. 1999 Jul;29(7):650–1. doi: 10.1046/j.1365-2362.1999.00511.x.
参考文献:10.1007/s11064-006-9044-8
摘要:Kobayashi H, Oikawa S, Kawanishi S. Mechanism of DNA damage and apoptosis induced by tetrahydropapaveroline, a metabolite of dopamine. Neurochem Res. 2006 Apr;31(4):523–32. doi: 10.1007/s11064-006-9044-8.
参考文献:10.1038/ncomms1327
摘要:Nakagawa A, Minami H, Kim J, Koyanagi T, Katayama T, Sato F, Kumagai H. A bacterial platform for fermentative production of plant alkaloids. Nature Communications. 2011 May 24;2(1):326. doi: 10.1038/ncomms1327.
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