CAS: 82-02-0; 4,9-Dimethoxy-7-Methyl-5H-Furo[3,2-G]Chromen-5-One

该化合物是一种自然产生的化合物,产自Ammi ifnaga植物,通常称为牙签草,被归类为furanocumarin, 一种有机化合物,其结构为superanocumarin和coumarin.Khellin以其药理特性而著称,特别是其作为血管活体抑制器的能力,它可以帮助改善血液流和减少血压.还研究了其在治疗哮喘和肾结石等病方面的潜在治疗效果.该化合物一般是白色的到黄色晶状的固体,在乙醇和氯仿等有机溶剂中溶解,但水中的溶解度有限.Khellin的行动机制涉及某些酶的抑制和钙渠道的调节,这对其生物影响有帮助.由于它的自然起源和潜在健康利益,Khellin对传统医学和现代医学都感兴趣.然而,还需要进一步研究,以充分了解临床应用中的功效和安全性.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报REACH预注册

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CAS号484-51-5 凯林酮 | CAS号98362-17-5 1-(6-ethoxy-4,7... | CAS号37833-19-5 6-hydroxy-4,7-d... | CAS号2159-83-3 4,9-Dihydroxy-7... | CAS号4481-60-1 5-norvisnagin | CAS号141-78-6 乙酸乙酯 | CAS号481-71-0 7-Methyl-4H-fur... | CAS号3380-63-0 4,9-dimethoxy-7... | CAS号34959-30-3 阿匹氯铵 | CAS号75884-10-5 1-(4-ethoxy-6-h... | CAS号76301-19-4 替美呋酮 | CAS号668-10-0 阿米醇 | CAS号68094-07-5 6-hydroxy-4,7-d... | CAS号85518-13-4 6-acetyl-4,9-di... | CAS号86397-42-4 9-ethoxy-4-hydr... | CAS号86397-43-5 4,9-二乙氧基-7-甲基呋喃... | CAS号87145-72-0 methyl 6-hydrox...

合成工艺路线路线简述

  • 37833-19-5 = 82-02-0
    反应条件:1.1 Reagents: Hydrochloric Acid
    标题:Structure Of Khellin
    作者:Geissman,T. A.
    参考文献:Journal Of The American Chemical Society 日期:1949 卷标:71]

    98362-16-4 = 82-02-0
    反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Dimethylformamide2.1 Reagents: 2′-Deoxycytidine-5′-Monophosphate Solvents: Dichloromethane3.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane4.1 Reagents: Sodium Hydride4.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    98362-14-2 = 82-02-0
    反应条件:1.1 Reagents: Methyl Iodide,Sodium Hydride Solvents: Tetrahydrofuran,Hexamethylphosphoramide2.1 Reagents: Tetrabutylammonium Fluoride Solvents: Dimethylformamide3.1 Reagents: 2′-Deoxycytidine-5′-Monophosphate Solvents: Dichloromethane4.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane5.1 Reagents: Sodium Hydride5.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    34741-93-0 = 82-02-0
    反应条件:1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran2.1 Reagents: Methyl Iodide,Sodium Hydride Solvents: Tetrahydrofuran,Hexamethylphosphoramide3.1 Reagents: Tetrabutylammonium Fluoride Solvents: Dimethylformamide4.1 Reagents: 2′-Deoxycytidine-5′-Monophosphate Solvents: Dichloromethane5.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane6.1 Reagents: Sodium Hydride6.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    481-71-0 = 82-02-0 + 478-00-2
    反应条件:1.1 Reagents: Hydrochloric Acid,Sulfurous Acid,Sodium Salt Solvents: Water1.2 Reagents: Methyl Iodide,Potassium Carbonate Solvents: Acetone
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    98362-20-0 = 82-02-0 + 478-00-2
    反应条件:1.1 Reagents: Ceric Ammonium Nitrate Solvents: Acetonitrile,Water1.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water2.1 Reagents: Hydrochloric Acid,Sulfurous Acid,Sodium Salt Solvents: Water2.2 Reagents: Methyl Iodide,Potassium Carbonate Solvents: Acetone
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    98362-19-7 = 82-02-0 + 478-00-2
    反应条件:1.1 Reagents: 2′-Deoxycytidine-5′-Monophosphate Solvents: Dichloromethane2.1 Reagents: Ceric Ammonium Nitrate Solvents: Acetonitrile,Water2.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water3.1 Reagents: Hydrochloric Acid,Sulfurous Acid,Sodium Salt Solvents: Water3.2 Reagents: Methyl Iodide,Potassium Carbonate Solvents: Acetone
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    = 82-02-0
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Metalation In Organic Synthesis. Part 2. Reaction Of Tert-Butyl Lithioacetate With Ortho-Hydroxyphenones To Give 2-Methylchromones. An Easy Access To Khellin
    作者:Nagasawa,Kazuo; Et Al
    参考文献:Heterocycles 日期:1988 卷标:27(5) 页码:1159-62]

    484-51-5 = 82-02-0
    反应条件:1.1 Reagents: Sodium Hydride1.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    119138-95-3 + 484-51-5 = 82-02-0
    反应条件:1.1 Solvents: Toluene1.2 Reagents: Ammonium Chloride Solvents: Water2.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Metalation In Organic Synthesis. Part 2. Reaction Of Tert-Butyl Lithioacetate With Ortho-Hydroxyphenones To Give 2-Methylchromones. An Easy Access To Khellin
    作者:Nagasawa,Kazuo; Et Al
    参考文献:Heterocycles 日期:1988 卷标:27(5) 页码:1159-62]

    98362-17-5 = 82-02-0
    反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane2.1 Reagents: Sodium Hydride2.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    53503-61-0 + 582-24-1 = 82-02-0
    反应条件:1.1 Solvents: Toluene1.2 Reagents: Ammonium Chloride Solvents: Water2.1 Solvents: Toluene2.2 Reagents: Ammonium Chloride Solvents: Water3.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Metalation In Organic Synthesis. Part 2. Reaction Of Tert-Butyl Lithioacetate With Ortho-Hydroxyphenones To Give 2-Methylchromones. An Easy Access To Khellin
    作者:Nagasawa,Kazuo; Et Al
    参考文献:Heterocycles 日期:1988 卷标:27(5) 页码:1159-62]

    98393-99-8 = 82-02-0
    反应条件:1.1 Reagents: 2′-Deoxycytidine-5′-Monophosphate Solvents: Dichloromethane2.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane3.1 Reagents: Sodium Hydride3.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    98362-18-6 = 82-02-0 + 478-00-2
    反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Dimethylformamide2.1 Reagents: 2′-Deoxycytidine-5′-Monophosphate Solvents: Dichloromethane3.1 Reagents: Ceric Ammonium Nitrate Solvents: Acetonitrile,Water3.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water4.1 Reagents: Hydrochloric Acid,Sulfurous Acid,Sodium Salt Solvents: Water4.2 Reagents: Methyl Iodide,Potassium Carbonate Solvents: Acetone
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4]

    98362-15-3 = 82-02-0 + 478-00-2
    反应条件:1.1 Reagents: Methyl Iodide,Sodium Hydride Solvents: Tetrahydrofuran,Hexamethylphosphoramide2.1 Reagents: Tetrabutylammonium Fluoride Solvents: Dimethylformamide3.1 Reagents: 2′-Deoxycytidine-5′-Monophosphate Solvents: Dichloromethane4.1 Reagents: Ceric Ammonium Nitrate Solvents: Acetonitrile,Water4.2 Reagents: Hydrochloric Acid Solvents: Methanol,Water5.1 Reagents: Hydrochloric Acid,Sulfurous Acid,Sodium Salt Solvents: Water5.2 Reagents: Methyl Iodide,Potassium Carbonate Solvents: Acetone
    标题:Total Synthesis Of Khellin Via A Chromium Carbene Complex
    作者:Yamashita,Ayako
    参考文献:Journal Of The American Chemical Society 日期:1985 卷标:107(20) 页码:5823-4
6-Hydroxy-4,7-Dimethoxy-5-(3'-Trifluoroacetyloxybut-2'-(E)-Enoyl)Benzofuran 以 乙醚 作为反应溶剂,化学反应生成 凯林
参考文献:Al-Farhan,Emile; Keehn,Philip M.; Stevenseon,Robert,Organic Preparations And Procedures International,1991,Vol. 23,# 5,P. 665-667
标题:Al-Farhan,Emile; Keehn,Philip M.; Stevenseon,Robert,Organic Preparations And Procedures International,1991,Vol. 23,# 5,P. 665-667

海关参考信息

专利信息


专利号:US-4459420-A
优先权日:1982-05-17
标题 :Pyrogallol synthesis of anti-atherogenic furochromones
发明人：GAMMILL RONALD B
权利人:UPJOHN CO
摘要:The present invention provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof from pyrogallol. Pyrogallol is converted to 3,6,7-benzofurantriol triacetate using zinc chloride and chloracetanitrile, then catalytically reduced and deactoxylated at the 3 position to yield the corresponding 2,3-dihydrofuran. This substance is subjected to a Fries rearrangement to the corresponding diol, the phenolic hydroxyl group of which is then selectively alkylated. This yields 6-hydroxy-7-alkoxy-5-benzofuranyl methyl ketone, a known intermediate for the production of 4-desmethoxy khellin and analogs thereof. This compound is then selectively alkoxylated at the 4 position using lead tetraacetate or thallium (III) nitrate in an alkanol solvent to yield known chemical intermediates in the preparation of khellin and analogs thereof.

专利号:US-10925977-B2
优先权日:2006-10-05
标 题 :Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications
发明人：YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S
权利人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S; CEIL POINT LLC; UNIV TEXAS
摘要:Novel methods of synthesis of chelator-targeting ligand conjugates, compositions comprising such conjugates, and therapeutic and diagnostic applications of such conjugates are disclosed. The compositions include chelator-targeting ligand conjugates optionally chelated to one or more metal ions. Methods of synthesizing these compositions in high purity are also presented. Also disclosed are methods of imaging, treating and diagnosing disease in a subject using these novel compositions, such as methods of imaging a tumor within a subject and methods of diagnosing myocardial ischemia.

专利号:US-2002022022-A1
优先权日:2000-05-19
标题 :Inhibition of cell proliferation and matrix synthesis by antioxidants and NAD(P)H oxidase inhibitors
发明人：SHI YI; ZALEWSKI ANDREW
摘要:The present invention is directed to a method for the prophylactic and therapeutic treatment of diseases or disorders associated with the abnormal proliferation and extracellular matrix synthesis of smooth muscle cells (SMC) and fibroblasts due to activation of NAD(P)H and/or increased ROS generation. The method involves the administration of an NAD(P)H oxidase inhibitor(s) and/or antioxidant(s) to a mammal in an amount sufficient to treat the disease or disorder prophylactically or therapeutically. The NAD(P)H oxidase inhibitor inhibits the synthesis or translocation of NAD(P)H subunits, thereby blocking the generation of intracellular reactive oxygen species (ROS) and thus the proliferation and extracellular matrix synthesis of SMC and fibroblasts. Similarly, the administration of antioxidants blocks the generation of intracellular ROS, thereby inhibiting SMC and fibroblast proliferation and extracellular matrix synthesis. In addition to the prevention and treatment of vascular disease, such as atherosclerosis, graft disease, and restenosis, NAD(P)H oxidase inhibitors and antioxidants may be useful for the prevention and treatment of other conditions by decreasing cell proliferation and extracellular matrix synthesis associated therewith. These conditions include arthritis, keloid formation, cancer, tissue and organ fibrosis, and complications related to organ transplantation, metabolic syndrome, and radiation therapy.

专利号:US-8906425-B2
优先权日:2003-06-13
标 题:Stimulation of the synthesis of the activity of an isoform of lysyl oxidase-like LOXL for stimulating the formation of elastic fibers
发明人：PERRIER ERIC; CENIZO VALÉRIE; BOUEZ CHARBEL; SOMMER PASCAL; DAMOUR ODILE; GLEYZAL CLAUDINE; ANDRE VALÉRIE; REYMERMIER CORINNE
权利人:PERRIER ERIC; CENIZO VALÉRIE; BOUEZ CHARBEL; SOMMER PASCAL; DAMOUR ODILE; GLEYZAL CLAUDINE; ANDRE VALÉRIE; REYMERMIER CORINNE; BASF BEAUTY CARE SOLUTIONS F; CENTRE NAT RECH SCIENT
摘要:The invention relates to the stimulation of the synthesis and of the activity of an isoform of lysyl oxidase, and more particularly of the LOXL (lysyl oxidase-like) isoform. The invention relates notably to a method of identifying an active principle which stimulates the formation of elastic fibers. The aim of the invention is mainly to provide such a method of identification so as to provide compositions which enable stimulating the formation of elastic fibers.

专利号:US-2003157061-A1
优先权日:2001-12-05
标 题 :Combinations of a cyclooxygenase-2 selective inhibitor and a TNFalpha antagonist and therapeutic uses therefor
发明人：BENNETT DENNIS A
权利人:PHARMACIA CORP
摘要:A method for the prevention, treatment, or inhibition of pain, inflammation, or inflammation-related disorder and for the prevention, treatment, or inhibition of a cardiovascular disease or disorder in a subject that is in need of such prevention, treatment or inhibition, involves the administration to the subject of a cyclooxygenase-2 selective inhibitor or prodrug thereof and a TNFα antagonist. A method can also involve the treatment, prevention, or inhibition of cancer in a subject in need of such treatment, prevention, or inhibition, by administering to the subject a cyclooxygenase-2 selective inhibitor or prodrug thereof and a TNFα antagonist which is selected from the group consisting of a compound that affects the synthesis of TNFα, a compound that inhibits the binding of TNFα with a receptor specific for TNFα, and a compound that interferes with intracellular signaling triggered by TNFα binding with a receptor. Compositions, pharmaceutical compositions and kits that can be used with the methods are also described.

专利号:US-7339065-B2
优先权日:2003-07-21
标题 :Design and synthesis of optimized ligands for PPAR
发明人：AVERY MITCHELL A; PERSHADSINGH HARRIHAR A
权利人:BETHESDA PHARMACEUTICALS INC; UNIV MISSISSIPPI
摘要:This invention provides new chemical entities useful for treating a variety of clinical disorders including those that are influenced by the activity of peroxisome proliferator activated receptors (PPAR). The structures of the compounds and methods to design, make and use the compounds are provided. Compounds and methods for administering therapeutic compositions comprising the compounds in cases of the disease psoriasis are provided. An exemplary compound having the formula compound is 5adamantan-2-yl-pentanoic acid {2-[4-(2,4-dioxo-thiazolidin-5-yl-methyl)-phenoxy]-ethyl}-methyl-amide is provided.

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主要参考文献


1: Fenniche S, Hammami H, Zaouak A. Association of khellin and 308-nm excimer lamp in the treatment of severe alopecia areata in a child. J Cosmet Laser Ther. 2017 Oct
11:1-3. doi: 10.1080/14764172.2017.1383617. [Epub ahead of print] doi: 10.1021/acs.jafc.6b02462. Epub 2016 Dec 12. doi: 10.4103/0975-7406.168033.
4: Bagherani N. The efficacy of 308 nm UV excimer light as monotherapy and combination therapy with topical khellin 4% and/or tacrolimus 0.1% in the treatment of vitiligo. Dermatol Ther. 2016 Mar;29(2):137-8. doi: 10.1111/dth.12274. Epub 2015 Aug 17. doi: 10.1080/14786419.2014.945170. Epub 2014 Aug 11. doi: 10.1371/journal.pone.0074917. eCollection 2013.

合成参考文献


参考文献:10.1186/2047-783x-14-s4-78
摘要:Franova S, Joskova M, Novakova E, Adamicova K, Sutovska M, Nosal S. Effects of Flavin7 on allergen induced hyperreactivity of airways. European Journal of Medical Research. 2009 Dec 07;14(Suppl 4):78. doi: 10.1186/2047-783x-14-s4-78.
参考文献:10.1155/2011/403623
摘要:Jordao L, Vieira OV. Tuberculosis: New Aspects of an Old Disease. International Journal of Cell Biology. 2011;2011():1–13. doi: 10.1155/2011/403623.
参考文献:10.1016/j.pbiomolbio.2011.06.016
摘要:Kimura T, Niki I. Rab27a in pancreatic beta-cells, a busy protein in membrane trafficking. Progress in Biophysics and Molecular Biology. 2011 Nov;107(2):219–23. doi: 10.1016/j.pbiomolbio.2011.06.016.
参考文献:10.1186/1471-2156-12-63
摘要:Cabras S, Castellanos ME, Biino G, Persico I, Sassu A, Casula L, del Giacco S, Bertolino F, Pirastu M, Pirastu N. A strategy analysis for genetic association studies with known inbreeding. BMC Genomic Data. 2011 Jul 18;12(1):63. doi: 10.1186/1471-2156-12-63.
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