CAS: 83729-01-5; Methyl (2S,4Ar,6Ar,7R,9S,10As,10Br)-9-Acetyloxy-2-(Furan-3-yl)-6A,10B-Dimethyl-4,10-Dioxo-2,4A,5,6,7,8,9,10A-Octahydro-1H-Benzo[f]Isochromene-7-Carboxylate

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CAS号108-24-7 乙酸酐 | CAS号92545-30-7 Salvinorin B | CAS号865438-59-1 epi-salvinorin B | CAS号64-19-7 冰醋酸 | CAS号92545-30-7 Salvinorin B

合成工艺路线路线简述

  • 合成目标产物 Salvinorin A 主要起始原料 Acetic Anhydride And Sanguinarine (Rg)
  • (文献来源)合成步骤主要原料 Acetic Anhydride 和 Sanguinarine (Rg)
📜(2S,6As,7R,9S,10As,10Br)-7-(Dimethoxymethyl)-2-(Furan-3-yl)-5-Hydroxy-6A,10B-Dimethyl-9-(Phenylmethoxymethoxy)-2,6,7,8,9,10A-Hexahydro-1H-Benzo[f]Isochromene-4,10-Dione置于palladium Diacetate 吡啶,三乙基硅烷,4-二甲氨基吡啶,1,1'-双(二苯基膦)二茂铁,Sodium Chlorite,Sodium Dihydrogenphosphate,Lithium Tetrafluoroborate,2-甲基-2-丁烯,L-Selectride,Sodium Hydride,Potassium Carbonate体系中,用 四氢呋喃,甲醇,正己烷,水,N,N-二甲基甲酰胺,丙酮,乙腈,叔丁醇,苯 作为反应溶剂,化学反应 10.25H,反应生成 丹酚 A
参考文献:Asymmetric Synthesis Of Salvinorin A,A Potent K Opioid Receptor Agonist
标题:Asymmetric Synthesis Of Salvinorin A,A Potent K Opioid Receptor Agonist
摘要:The Stereoselective Synthesis Of Salvinorin A Is Described. A Macrocyclic Bis-Michael Reaction Cascade Provides The Requisite Tricyclic Skeleton As A Single Diastereomer.
DOI:10.1021/ja073590A

海关参考信息

专利信息


专利号:US-11512075-B2
优先权日:2017-06-14
标 题:Synthesis of 20-nor-salvinorin A
发明人:SHENVI RYAN; ROACH JEREMY; SASANO YUSUKE; BOHN LAURA; SCHMID CULLEN
权利人:SCRIPPS RESEARCH INST
摘要:The invention provides 20-nor-salvinorin A, an analog of the kappa-opioid agonist salvinorin A. The 20-nor-salvinorin A is an active kappa-opioid modulator and can be used for treatment of medical conditions wherein modulation of the kappa-opioid receptor is medically indicated, such as pain, pruritis, depression, or inflammation, or conditions implicating perception and consciousness. 20-nor-salvinorin A can be less additive when used in treatment compared to a mu-opioid receptor agonist, and 20-nor-salvinorin A is more stable in vivo than is parent compound salvinorin A. The invention further provides synthetic intermediates and procedures for preparation of 20-nor-salvinorin A.

专利号:US-8778958-B2
优先权日:2008-07-10
标题 :Synthesis of metabolically stable agents for alcohol and drug abuse
发明人:CASHMAN JOHN R
权利人:CASHMAN JOHN R
摘要:The disclosed opioid-related compounds and pharmaceutical compositions thereof, are useful in a variety of applications relating to the modulation of receptors and receptor signaling within and outside the nervous system. For example, the compounds and compositions are useful in methods for the treatment of addictions and other CNS-related disorders. The disclosed compounds can be delivered or administered to a mammal including humans, alone in the form of a pharmaceutically acceptable salt or hydrolysable precursor thereof, or in the form of a pharmaceutical composition, wherein a therapeutically effective amount of a compound is mixed with suitable carriers or excipients.

专利号:US-11434195-B2
优先权日:2017-07-20
标题:Compositions and methods for treatment of central nervous system tumors
发明人:SVETLOV STANISLAV IGOREVICH
权利人:UNIV FLORIDA
摘要:Compounds, pharmaceutical compositions, and methods for treating cancer, in particular brain cancer, are provided, including amphiphilic fatty acid/alcohol ethers (AIPs) comprising endocannabinoid and FABP motifs covalently linked to a beta-adrenoreceptor antagonist motif in one molecule. The invention includes methods for inhibiting growth of brain cancer cells by contacting the compound(s) with brain cancer cells. The invention provides a method for treating both brain cancer and brain cancer metastases, and for suppression of regrowth of brain cancer cells after radiation, surgical treatment, or chemotherapy of brain cancer. The invention also comprises an optimized chemical synthesis of the AIP compounds and methods of using the compounds, alone or in combination with another agent, for suppressing the growth of brain cancer cells, and enhancing survival of normal CNS cells, or improving recuperation from radiation, surgical or chemotherapy.

专利号:WO-2024226703-A3
优先权日:2023-04-27
标题 :Asymmetric synthesis and diversification of a stabilized salvinorin a scaffold
发明人:HILL SARAH; DAI NATHAN; SHENVI RYAN; BOHN LAURA
权利人:SCRIPPS RESEARCH INST; THE UNIV OF FLORIDA RESEARCH FOUNDATION
摘要:Described herein are short asymmetric syntheses that serve as routes that allow divergent access to focused libraries of salvinorins that include multiple analogs that exceed the potency, selectivity, stability and functional bias of salvinorin A itself.

专利号:US-12194020-B2
优先权日:2017-12-22
标 题:Reversing baldness through cannabinoid receptor activation
发明人:POSTREL RICHARD
权利人:POSTREL RICHARD
摘要:This invention reverses male pattern baldness by shocking dormant hair follicles out of their androgen induced hibernation phase back to the active hair-growing anagenic phase. The invention integrates two functions: 1) It blocks synthesis of compounds holding the follicles in the telogenic/hibernating phase and 2) It stimulates synthesis of compounds animating the hair-growing/anagenic phase in the follicular activity cycle. One preferred embodiment comprises an enzyme inhibitor blocking the conversion of testosterone to dihydrotestosterone (DHT), a flavonoid simultaneously increasing synthesis of prostaglandins alternative to prostaglandin D2, and a selected cannabinoid compound stimulating restore the hair follicle to its normal growth cycle. This novel trimodal therapy restores the hair follicles to their normal cycling processes and maintains these restorative properties so long as this rebalance in maintained.

专利号:US-2020131162-A1
优先权日:2017-06-14
标题:Synthesis of 20-nor-salvinorin a

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品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献


1: Kivell BM, Paton KF, Kumar N, Morani AS, Culverhouse A, Shepherd A, Welsh SA, Biggerstaff A, Crowley RS, Prisinzano TE. Kappa Opioid Receptor Agonist Mesyl Sal B Attenuates Behavioral Sensitization to Cocaine with Fewer Aversive Side-Effects than Salvinorin A in Rodents. Molecules. 2018 Oct 11;23(10). pii: E2602. doi: 10.3390/molecules23102602.
2: Wang Y, Metz P. Total Synthesis of the Neoclerodane Diterpene Salvinorin A via an Intramolecular Diels-Alder Strategy. Org Lett. 2018 Jun 1;20(11):3418-3421. doi: 10.1021/acs.orglett.8b01357. Epub 2018 May 22. doi: 10.1590/1414-431X20176714.
4: Hirasawa S, Cho M, Brust TF, Roach JJ, Bohn LM, Shenvi RA. O6C-20-nor-salvinorin A is a stable and potent KOR agonist. Bioorg Med Chem Lett. 2018 Sep 1;28(16):2770-2772. doi: 10.1016/j.bmcl.2018.01.055. Epub 2018 Jan 31.

合成参考文献


参考文献:10.1016/j.biopsych.2011.05.021
摘要:Potter DN, Damez-Werno D, Carlezon WA, Cohen BM, Chartoff EH. Repeated Exposure to the κ-Opioid Receptor Agonist Salvinorin A Modulates Extracellular Signal-Regulated Kinase and Reward Sensitivity. Biological Psychiatry. 2011 Oct;70(8):744–53. doi: 10.1016/j.biopsych.2011.05.021.
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