CAS: 82-08-6; (E)-1-(6-(3-Acetyl-2,4,6-Trihydroxy-5-Methylbenzyl)-5,7-Dihydroxy-2,2-Dimethyl-2H-Chromen-8-yl)-3-Phenylprop-2-En-1-One

该化合物是马洛托斯花生植物产生的自然产生的化合物,被归类为氟氯素,以其独特的黄色闻名.罗特林展示了一系列生物活动,包括抗炎,抗氧化剂和潜在的抗癌特性.其行动机制主要归功于其抑制蛋白质血酶C(PKC)的能力,C(PKC)在包括细胞生长和分化在内的各种细胞过程中发挥着关键作用.此外,罗特林已经研究过它对各种信号路径的影响,使其成为药理学研究的热点.该化合物溶解于有机溶剂,但水溶解性有限,可能影响其生物利用率和治疗应用.由于它具有多种生物影响,正在探索罗特林在治疗各种疾病方面的潜在用途,尽管需要进行进一步的研究,以充分了解其在临床环境中的效力和安全性.

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欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号501-52-0 3-苯丙酸 | CAS号619-89-6 4-硝基肉桂酸 | CAS号552-16-9 2-硝基苯甲酸 | CAS号62-23-7 对硝基苯甲酸 | CAS号612-41-9 邻硝基肉桂酸 | CAS号88-03-9 2,4,6-三羟基甲苯 | CAS号108-73-6 间苯三酚 | CAS号621-82-9 肉桂酸 | CAS号64-19-7 冰醋酸 | CAS号65-85-0 苯甲酸

合成工艺路线路线简述

  • 2657-28-5 + 1812196-98-7 = 82-08-6
    反应条件:1.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin: The Sequel
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Natural Products 日期:2019 卷标:82(5) 页码:1190-1199]

    2657-28-5 + 1812196-97-6 = 82-08-6
    反应条件:1.1 Reagents: Lanthanum Triflate Solvents: Ethanol,Water; 10 H,Rt
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    62018-55-7 = 82-08-6
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; Rt; Rt -> 50 °C1.2 Reagents: Mercury Alloy,Nonbase,Hg,Zn; 5 Min,50 °C2.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(21) 页码:10668-10674]

    900811-51-0 + 100-52-7 = 82-08-6
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 0 °C; 28 H,Rt2.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Rt3.1 Solvents: Chloroform; 1 H,Reflux
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    900811-51-0 + 100-52-7 = 82-08-6
    反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Methanol; 10 H,Rt2.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Reflux3.1 Solvents: Chloroform; 0.5 H,Reflux4.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(21) 页码:10668-10674]

    480-66-0 = 82-08-6
    反应条件:1.1 Reagents: Phosphorus Oxychloride Solvents: Ethyl Acetate; 0 °C; 1 H,Rt2.1 Reagents: Hydrochloric Acid,Sodium Cyanoborohydride Solvents: Tetrahydrofuran,Water; 4 H,Ph 4,Rt; 15 H,Rt; 2 H,Rt3.1 Reagents: Lanthanum Triflate Solvents: Ethanol,Water; 10 H,Rt
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    107-86-8 + 139140-13-9 = 82-08-6
    反应条件:1.1 Reagents: Ethylenediaminediacetic Acid Solvents: Chloroform; 10 Min,Rt2.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 5 Min,0 °C2.2 2 H,Rt2.3 Reagents: Water; 30 Min,Rt3.1 Solvents: Chloroform; 0.5 H,Reflux4.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin: The Sequel
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Natural Products 日期:2019 卷标:82(5) 页码:1190-1199]

    18162-48-6 + 480-66-0 = 82-08-6
    反应条件:1.1 Reagents: Imidazole Solvents: Dimethylformamide; 15 Min,Rt1.2 Reagents: Pyridinium P-Toluenesulfonate Solvents: Methanol; 2 H,Reflux2.1 Reagents: Ethylenediaminediacetic Acid Solvents: Chloroform; 10 Min,Rt3.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 5 Min,0 °C3.2 2 H,Rt3.3 Reagents: Water; 30 Min,Rt4.1 Solvents: Chloroform; 0.5 H,Reflux5.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin: The Sequel
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Natural Products 日期:2019 卷标:82(5) 页码:1190-1199]

    265975-36-8 = 82-08-6
    反应条件:1.1 Reagents: Pyridinium P-Toluenesulfonate Solvents: Methanol; 2 H,Reflux2.1 Reagents: Ethylenediaminediacetic Acid Solvents: Chloroform; 10 Min,Rt3.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 5 Min,0 °C3.2 2 H,Rt3.3 Reagents: Water; 30 Min,Rt4.1 Solvents: Chloroform; 0.5 H,Reflux5.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin: The Sequel
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Natural Products 日期:2019 卷标:82(5) 页码:1190-1199]

    65490-09-7 = 82-08-6
    反应条件:1.1 Reagents: Iodine Solvents: Methanol; 10 H,Rt2.1 Reagents: Acetic Acid,Ethylenediamine Solvents: Chloroform; 12 H,Reflux3.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 0 °C; 28 H,Rt4.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Rt5.1 Reagents: Lanthanum Triflate Solvents: Ethanol,Water; 10 H,Rt
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    2657-28-5 + 1812196-97-6 = 82-08-6 + 56866-12-7
    反应条件:1.1 Catalysts: Sulfuric Acid Solvents: Ethanol,Water; 18 H,Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water; Rt; Neutralized
    标题:Efficient Synthesis Of Rottlerin And Its Two Subunits
    作者:Li,Yangfeng; Et Al
    参考文献:Tetrahedron Letters 日期:2016 卷标:57(17) 页码:1856-1859]

    2657-28-5 + 1812196-98-7 = 82-08-6
    反应条件:1.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(21) 页码:10668-10674]

    2657-28-5 + 33797-51-2 + 1812196-97-6 = 82-08-6
    反应条件:1.1 Solvents: Chloroform; 1 H,Reflux
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    = 82-08-6
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Rt2.1 Solvents: Chloroform; 1 H,Reflux
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    = 82-08-6
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Reflux2.1 Solvents: Chloroform; 0.5 H,Reflux3.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(21) 页码:10668-10674]

    33797-51-2 + 1812196-97-6 = 82-08-6
    反应条件:1.1 Solvents: Chloroform; 0.5 H,Reflux2.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin: The Sequel
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Natural Products 日期:2019 卷标:82(5) 页码:1190-1199]

    33797-51-2 + 1812196-97-6 = 82-08-6
    反应条件:1.1 Solvents: Chloroform; 0.5 H,Reflux2.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(21) 页码:10668-10674]

    62018-55-7 = 82-08-6
    反应条件:1.1 Reagents: Hydrochloric Acid,Sodium Cyanoborohydride Solvents: Tetrahydrofuran,Water; 4 H,Ph 4,Rt; 15 H,Rt; 2 H,Rt2.1 Reagents: Lanthanum Triflate Solvents: Ethanol,Water; 10 H,Rt
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    1187462-02-7 + 100-52-7 = 82-08-6
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 5 Min,0 °C1.2 2 H,Rt1.3 Reagents: Water; 30 Min,Rt2.1 Solvents: Chloroform; 0.5 H,Reflux3.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin: The Sequel
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Natural Products 日期:2019 卷标:82(5) 页码:1190-1199]

    480-66-0 = 82-08-6
    反应条件:1.1 Reagents: Phosphorus Oxychloride Solvents: Ethyl Acetate; 1 H,Rt1.2 Reagents: Water2.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; Rt; Rt -> 50 °C2.2 Reagents: Mercury Alloy,Nonbase,Hg,Zn; 5 Min,50 °C3.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(21) 页码:10668-10674]

    107-86-8 + 257621-57-1 = 82-08-6
    反应条件:1.1 Reagents: Acetic Acid,Ethylenediamine Solvents: Chloroform; 12 H,Reflux2.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 0 °C; 28 H,Rt3.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Rt4.1 Solvents: Chloroform; 1 H,Reflux
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    480-66-0 = 82-08-6
    反应条件:1.1 -2.1 Reagents: Potassium Hydroxide Solvents: Methanol; 10 H,Rt3.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Reflux4.1 Solvents: Chloroform; 0.5 H,Reflux5.1 Solvents: Toluene; 0.5 H,Reflux
    标题:The Mosaic Of Rottlerin
    作者:Hong,Kenneth K. C.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2015 卷标:80(21) 页码:10668-10674]

    480-66-0 = 82-08-6
    反应条件:1.1 Catalysts: 1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Dimethylformamide; Rt; 2 H,Rt1.2 Solvents: Dimethylformamide; Rt; 14.5 H,Rt2.1 Reagents: Iodine Solvents: Methanol; 10 H,Rt3.1 Reagents: Acetic Acid,Ethylenediamine Solvents: Chloroform; 12 H,Reflux4.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 0 °C; 28 H,Rt5.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water; 4 H,Rt6.1 Reagents: Lanthanum Triflate Solvents: Ethanol,Water; 10 H,Rt
    标题:The Practical Total Synthesis Of Rottlerin And Rottlerone
    作者:Chen,Xu-Ling; Et Al
    参考文献:Chemistryselect 日期:2020 卷标:5(29) 页码:9206-9209]

    88-03-9 = 82-08-6 + 56866-12-7
    反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Acetic Acid; 3 H,Reflux2.1 Catalysts: Sulfuric Acid Solvents: Ethanol,Water; 18 H,Rt2.2 Reagents: Sodium Bicarbonate Solvents: Water; Rt; Neutralized
    标题:Efficient Synthesis Of Rottlerin And Its Two Subunits
    作者:Li,Yangfeng; Et Al
    参考文献:Tetrahedron Letters 日期:2016 卷标:57(17) 页码:1856-1859]

    = 82-08-6 + 56866-12-7
    反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 0 °C; 6 H,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Rt2.1 Catalysts: Sulfuric Acid Solvents: Ethanol,Water; 18 H,Rt2.2 Reagents: Sodium Bicarbonate Solvents: Water; Rt; Neutralized
    标题:Efficient Synthesis Of Rottlerin And Its Two Subunits
    作者:Li,Yangfeng; Et Al
    参考文献:Tetrahedron Letters 日期:2016 卷标:57(17) 页码:1856-1859
📜2,4,6-三甲氧基苯甲醛置于硫酸,三溴化硼,四氯化锡,Sodium Cyanoborohydride体系中,用 四氢呋喃,乙醇,二氯甲烷 作为反应溶剂,化学反应 36.0H,反应生成 粗糠柴苦素
参考文献:高效合成rottlerin及其两个亚基
标题:高效合成rottlerin及其两个亚基
摘要:Rottlerin是一种从菲律宾古猿(mallotus Philippensis)分离出的天然产物,具有一系列生物活性.其化学结构的特征是通过亚甲基连接的两个不同的取代间苯三酚单元.在这项研究中,我们使用酚醛缩合作为关键反应完成了rottlerin的全合成.通过我们的方法,实现了两个结构亚基的克级制备,并且在最长的八线性步骤中以20%的总收率获得了rottlerin.我们的研究提供了一种实用的解决方案,以有效的方式获得rottlerin的样品.
DOI:10.1016/j.Tetlet.2016.03.049

海关参考信息

专利信息


专利号:US-8586768-B2
优先权日:2009-11-12
标 题 :Design, synthesis and functional characterization of rottlerin analogs
发明人:KANTHASAMY ANUMANTHA G; KRAUS GEORGE A; ANANTHARAM VELLAREDDY
权利人:KANTHASAMY ANUMANTHA G; KRAUS GEORGE A; ANANTHARAM VELLAREDDY; UNIV IOWA STATE RES FOUND INC
摘要:A method of synthesizing rottlerin analogs is described. The synthesis methods described are the first known method of synthesizing rottlerin analogs from commercially-available materials to produce cost effective analogs. Rottlerin analog structures made by the synthesis methods and methods of use for treating a neurological or inflammatory response mediated by protein kinase C (PKC) are further described.

专利号:WO-9941984-A9
优先权日:1998-02-20
标 题 :INTERACTION BETWEEN THE MEC1-DEPENDENT DNA SYNTHESIS CHECKPOINT AND G1 CYCLIN FUNCTION IN $i(SACCAROMYCES CEREVISIAE)
发明人:VALLEN ELIZABETH A; CROSS FREDERICK R
权利人:HUTCHINSON FRED CANCER RES
摘要:The completion of DNA synthesis in yeast is monitored by a checkpoint that requires MEC1 and RAD53. Overexpression of the S. cerevisiae G1 cyclin CLN1 results in genomic instability and lethality of mec1-1 checkpoint-deficient cells compared to cln1 cln2 mec1-1 cells. Here we show that overexpression of CLN2 or CLB5, but not CLN3, also killed mec1-1 strains. We identified RNR1, which encodes a subunit of ribonucleotide reductase, as a high-copy suppressor of the lethality of mec1-1 GAL1-CLN1. Northern analysis demonstrated that RNR1 expression is reduced by CLN1 or CLN2 overexpression. Since limiting RNR1 expression might decrease dNTP pools, CLN1 or CLN2 may cause lethality in mec1-1 strains by causing initiation of DNA replication with inadequate dNTP pools. In MEC1 strains, a delay of S phase due to the checkpoint would occur, but in mec1-1 strains lethality would result. Consistent with this model, CLN1 overexpression did result in a prolongation of S phase in a MEC1 background. In a cln1 cln2 background, a prolonged period of expression of genes turned on at the G1-S border has been observed. Thus deletion of CLN1 and CLN2 could function similarly to overexpression of RNR1 in suppressing mec1-1 lethality. While Mec1p has been proposed to act in a linear pathway upstream of Rad53p, rad53 lethality was rescued little by deletion of CLN1 and CLN2, suggesting that Rad53p has Mec1-independent activities.

专利号:US-2007232495-A1
优先权日:2006-03-24
标题:Compositions and methods to add value to plant products, increasing the commercial quality, resistance to external factors and polyphenol content thereof
发明人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
权利人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
摘要:The invention is related to compositions and methods that naturally protect plant tissues against ultraviolet radiation and temperature, thus giving protection against sunburn to plants, plant parts, fruits and/or flowers during their development. The invention is also related to compositions and methods to naturally improve the color of plants, plant parts, fruits and/or flowers by inducing the natural synthesis of flavonoids and anthocyanins present in plants. Likewise, the present invention is directed to improving the nutritional value of plants, plant parts, fruits and/or flowers by increasing the normal levels of polyphenolic compounds, especially flavonoids, present therein. Additionally, the present invention is related to compositions and methods that give more resistance to plants, plant parts, fruits and/or flowers against pathogens as bacteria and fungi. Finally, the present invention is related to plants, plant parts, fruits, flowers and/or propagating material treated with the compositions described in the present document.

专利号:US-2025231101-A1
优先权日:2024-01-11
标 题 :Validation of natural matrices for therapeutic use on humans, animals and plants on bio-physical bases as an alternative to validation through chemically definable substances derived from said matrices by isolation and/or synthesis processes and also as an alternative to products comprising natural matrices validated on the basis of their traditional use
发明人:MERCATI VALENTINO; LUCCI JACOPO
权利人:BIOS THERAPY PHYSIOLOGICAL SYSTEMS FOR HEALTH S P A
摘要:The present invention relates to a new method for assessing acceptability ranges or cut-offs for the compliance validation of batches of products comprising or consisting of one or more natural matrix, wherein said products have an ascertained therapeutic or beneficial effect. The invention also relates to a new process for the compliance validation of one or more batches of said products.

专利号:US-2011207789-A1
优先权日:2010-02-19
标题 :Methods related to casein kinase ii (ck2) inhibitors and the use of purinosome-disrupting ck2 inhibitors for anti-cancer therapy agents
发明人:FANG YE; VERRIER FLORENCE
权利人:FANG YE; VERRIER FLORENCE
摘要:Disclosed are methods related to label-free biosensor cellular assays to classify multienzyme complex modulators in live cells. Disclosed are also methods related to the identification of purinosome disrupting Casein Kinase II (CK2) inhibitors, and methods related to the use of purinosome disrupting CK2 inhibitors as therapeutic agents for modulating CK2 activity and purine synthesis pathway, and for improving prevention and treatment of CK2 associated cancers, viral infection and inflammation conditions.

专利号:US-10335382-B2
优先权日:2013-06-14
标 题:Use of hydrogen sulfide synthesis inhibitors for cancer therapy
发明人:HELLMICH MARK; ZHOU JIA; SZABO CSABA
权利人:HELLMICH MARK; ZHOU JIA; SZABO CSABA; UNIV TEXAS
摘要:In certain aspects the methods comprise administering an inhibitor of hydrogen sulfide biosynthesis, a cystathionine-β-synthase (CBS) inhibitor, or a hydrogen sulfide neutralizing agent to a patient having a cancer associated with elevated production of hydrogen sulfide.

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1: Alav I, Pordelkhaki P, Rodriguez-Navarro J, Neo O, Kessler C, Awodipe RJ, Cliffe P, Pulavan N, Marton HL, Gibbons S, Buckner MMC. Natural products from food sources can alter the spread of antimicrobial resistance plasmids in Enterobacterales. Microbiology (Reading). 2024 Aug;170(8). doi: 10.1099/mic.0.001496. 12(7):797. doi: 10.3390/vaccines12070797.
3: Wang D, Li Y, Li G, Liu M, Zhou Z, Wu M, Song S, Bian Y, Dong J, Li X, Du Y, Zhang T, Shi Y. Inhibition of PKC-δ retards kidney fibrosis via inhibiting cGAS- STING signaling pathway in mice. Cell Death Discov. 2024 Jul 7;10(1):314. doi: 10.1038/s41420-024-02087-z.
4: Qin P, Zhou P, Huang Y, Long B, Gao R, Zhang S, Zhu B, Li YQ, Li Q. Upregulation of rate-limiting enzymes in cholesterol metabolism by PKCδ mediates endothelial apoptosis in diabetic wound healing. Cell Death Discov. 2024 May 29;10(1):263. doi: 10.1038/s41420-024-02030-2.
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