CAS: 84-79-7; 2-Hydroxy-3-(3-Methylbut-2-En-1-yl)Naphthalene-1,4-Dione

该化合物是一种自然形成的环烷磺酮化合物,产自塔布伊亚树各种物种的树皮,常见于热带地区,其特点是黄色晶状表面,分子式为C15H14O3.拉帕乔尔展示了一系列生物活动,包括抗微生物,抗风泡和抗炎特性,使其对药用化学和药理感兴趣,其行动机制被认为涉及产生反应性氧物种和抑制某些酶.此外,对青蒿素的潜在抗癌作用进行了研究,特别是各种癌症细胞线,该化合物在有机溶剂中溶解,但在水中溶解性有限.由于其生物活性特性,拉帕青已引起对潜在治疗用途的关注,尽管需要进行进一步研究以充分了解其在临床环境中的功效和安全性.与许多天然产品一样,提取和净化过程会影响其供应和效力.

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CAS号83-72-7 2-羟基-1,4萘醌 | CAS号870-63-3 1-溴-3-甲基-2-丁烯 | CAS号107-86-8 异戊烯醛 | CAS号36417-25-1 4-hydroxynaphth... | CAS号78-79-5 异戊二烯 | CAS号5690-26-6 1,2,3,4-Naphtha... | CAS号556-82-1 3-甲基-2-丁烯-1-醇 | CAS号15298-01-8 1,4-Naphthalene... | CAS号111479-51-7 3-(3-chloro-3-m... | CAS号4707-32-8 β-拉帕醌 | CAS号4707-33-9 α-拉杷醌 | CAS号15297-92-4 去氢-α-拉杷醌 | CAS号74693-31-5 2-(prop-1-en-2-... | CAS号18635-24-0 2-Isopropenyl-2... | CAS号85-44-9 苯酐 | CAS号137493-02-8 sten°Carpoquinone B | CAS号32358-83-1 naphtho(1,2-b)f... | CAS号195156-48-0 2-((3,3-dimethy...

合成工艺路线路线简述

  • 605-37-8 = 84-79-7
    反应条件:1.1 Reagents: Oxalic Acid Solvents: 1,4-Dioxane; 60 H,100 °C
    标题:Synthesis Of Pharmacologically Important Naphthoquinones And Anticancer Activity Of 2-Benzyllawsone Through Dna Topoisomerase-Ii Inhibition
    作者:Kumar,Balagani Sathish; Ravi,Kusumoori; Verma,Amit Kumar; Fatima,Kaneez; Hasanain,Mohammad; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2017 卷标:25(4) 页码:1364-1373]

    107-86-8 + 83-72-7 = 84-79-7
    反应条件:1.1 Reagents: Formic Acid,Oxygen Solvents: Ethanol,Water; 3 H,200 °C; 3 - 3000 Psi
    标题:A New Method To Prepare 3-Alkyl-2-Hydroxy-1,4-Naphthoquinones: Synthesis Of Lapachol And Phthiocol
    作者:Ferreira,Sabrina Baptista; Rodrigues Da Rocha,David; Carneiro,Jose Walkimar M.; Santos,Wilson Costa; Ferreira,Vitor Francisco
    参考文献:Synlett 日期:2011 卷标:(11) 页码:1551-1554]

    83-72-7 + 870-63-3 = 84-79-7
    反应条件:1.1 Reagents: Pyridine,Sodium Iodide Solvents: Dimethyl Sulfoxide; Rt; 5 H,Rt -> 45 °C1.2 Reagents: Water; 20 Min,Cooled
    标题:Synthesis Of β-Lapachone
    作者:Sun,Min; Wei,Hong-Tao; Cai,Jin; Ji,Min
    参考文献:Zhongguo Xinyao Zazhi 日期:2008 卷标:17(18) 页码:1598-1599]

    83-72-7 + 870-63-3 = 84-79-7
    反应条件:1.1 Reagents: Potassium Iodide Solvents: Dimethyl Sulfoxide; 3 H,Rt -> 140 °C
    标题:Iron(Iii) Chloride Catalyzed Formation Of 3,4-Dihydro-2H-Pyrans From α-Alkylated 1,3-Dicarbonyls. Selective Synthesis Of α- And β-Lapachone
    作者:Watson,Rebecca B.; Golonka,Alexander N.; Schindler,Corinna S.
    参考文献:Organic Letters 日期:2016 卷标:18(6) 页码:1310-1313]

    107-86-8 + 83-72-7 = 84-79-7 [标题:Reaction Conditions
    标题:Development Of A Microemulsion Loaded With Epoxy-α-Lapachone Against Leishmania (Leishmania) Amazonensis Murine Infection
    作者:Peixoto,Juliana Figueiredo; Goncalves-Oliveira,Luiz Filipe; Souza-Silva,Franklin; Cortes,Luzia Monteiro De Castro; Dias-Lopes,Geovane; Et Al
    参考文献:International Journal Of Pharmaceutics (Amsterdam 日期:2023 卷标:636]

    83-72-7 + 5362-50-5 = 84-79-7
    反应条件:1.1 Reagents: Formic Acid Solvents: Ethanol,Water; 3 H,200 °C
    标题:Molecular Mechanism Of Action Of New 1,4-Naphthoquinones Tethered To 1,2,3-1H-Triazoles With Cytotoxic And Selective Effect Against Oral Squamous Cell Carcinoma
    作者:Cavalcanti Chipoline,Ingrid; Carolina Carvalho Da Fonseca,Anna; Ribeiro Machado Da Costa,Gabriella; Pereira De Souza,Michele; Won-Held Rabelo,Vitor; Et Al
    参考文献:Bioorganic Chemistry 日期:2020 卷标:101]

    3568-90-9 = 84-79-7
    反应条件:1.1 Reagents: Tert-Butyl Hydroperoxide Catalysts: Tetrabutylammonium Iodide Solvents: Tetrahydrofuran,Water; 24 H,120 °C1.2 Reagents: Sodium Sulfite Solvents: Water
    标题:Tetrabutylammonium Iodide Catalyzed Hydroxylation Of Naphthoquinone Derivatives With Tert-Butyl Hydroperoxide As An Oxidant
    作者:Yu,Dong; Chen,Xu-Ling; Ai,Bai-Ru; Zhang,Xiao-Mei; Wang,Ji-Yu
    参考文献:Tetrahedron Letters 日期:2018 卷标:59(40) 页码:3620-3623]

    83-72-7 + 870-63-3 = 84-79-7
    反应条件:1.1 Reagents: Triethylamine,Sodium Iodide Solvents: Dimethyl Sulfoxide; 1 H,Rt; 6 H,70 °C
    标题:Ligand-Based Design,Synthesis And Biochemical Evaluation Of Potent And Selective Inhibitors Of Schistosoma Mansoni Dihydroorotate Dehydrogenase
    作者:Calil,Felipe A.; David,Juliana S.; Chiappetta,Estela R. C.; Fumagalli,Fernando; Mello,Rodrigo B.; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2019 卷标:167 页码:357-366]

    83-72-7 + 115-18-4 = 84-79-7 + 64469-16-5
    反应条件:1.1 Catalysts: 1-Adamantanecarboxylic Acid,Tetrakis(Triphenylphosphine)Palladium; 1 H,Reflux
    标题:Palladium-Catalyzed Allylation Of 2-Hydroxy-1,4-Naphthoquinone. Application To The Preparation Of Lapachol
    作者:Kazantzi,Georgia; Malamidou-Xenikaki,Elizabeth; Spyroudis,Spyros
    参考文献:Synlett 日期:2007 卷标:(3) 页码:427-430
2-甲氧基-1,4-萘醌置于sodium Carbonate,锌体系中,用 四氢呋喃 作为反应溶剂,化学反应 24.83H,反应生成 黄钟花醌
参考文献:Kapoor,N. K.; Gupta,R. B.; Khanna,R. N.,Indian Journal Of Chemistry-Section B Organic And Medicinal Chemistry,1982,Vol. 21,# 3,P. 189-191
标题:Kapoor,N. K.; Gupta,R. B.; Khanna,R. N.,Indian Journal Of Chemistry-Section B Organic And Medicinal Chemistry,1982,Vol. 21,# 3,P. 189-191

海关参考信息

专利信息


专利号:WO-2017100796-A1
优先权日:2015-12-11
标 题 :Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
发明人:WONG CHI-HUEY; HSU TSUI-LING; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI
权利人:SINACA ACAD; WONG CHI-HUEY; HSU TSUI-LING
摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta- 4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for disgnostic and therapeutic uses.

专利号:US-2017283878-A1
优先权日:2015-12-11
标题:Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
发明人:WONG CHI-HUEY; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI; HSU TSUI-LING
权利人:ACADEMIA SINICA
摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta-4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for diagnostic and therapeutic uses.

专利号:US-10342858-B2
优先权日:2015-01-24
标题 :Glycan conjugates and methods of use thereof
发明人:WONG CHI-HUEY; WU CHUNG-YI
权利人:ACADEMIA SINICA
摘要:The present disclosure is directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA3/SSEA4/GloboH associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globo-series glycosphingolipid synthesis. The present disclosure relates to methods and compositions which can modulate the globo-series glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globo-series glycosphingolipid SSEA3/SSEA4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta-4GalNAcT-I; or beta-3GalT-V enzymes in the globo-series synthetic pathway. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions.

专利号:US-5763625-A
优先权日:1995-04-25
标 题:Synthesis and use of β-lapachone analogs
发明人:BOOTHMAN DAVID A; FRYDMAN BENJAMIN J; WITIAK DONALD T
权利人:WISCONSIN ALUMNI RES FOUND
摘要:3-Substituted-β-lapachone analogs and their use either alone or to augment chemotherapy or radiotherapy to induce programmed neoplastic cell death without exhibiting toxicity to surrounding normal cells are disclosed. In particular, 3-allyl-β-lapachones, 3-alkyl-β-lapachones and 3-halo-β-lapachones were found to be Topoisomerase (Topo I) inhibitors. When these analogs are used alone there is a reversible single-strand break in the DNA of neoplastic cells causing apoptosis and cell death in some cells. However, when these analogs are combined with chemotherapy or X-irradiation, an irreversible Topo I-mediated break is achieved. A new and more efficient chemical synthesis of the compounds is also disclosed.

专利号:WO-2023203374-A1
优先权日:2022-04-20
标 题 :[1,2]selenazolo[2,3-a]pyridin-8-ium inhibitors of pyruvate kinase isoform m2
发明人:ARSENJANS PAVELS; DIMITRIJEVS PAVELS; MAKRECKA-KUKA MARINA
权利人:LATVIAN INST ORGANIC SYNTHESIS
摘要:The present invention relates to a novel isoselenazolopyridinium salts as anticancer agents by inhibiting pyruvate kinase isoform M2 (PKM2) activity, as well as methods of their manufacturing and use in different pharmaceutical compositions for the treatment of various diseases and disorders by administration of such substances.

专利号:US-6458974-B1
优先权日:2001-01-25
标 题:Synthesis of β-lapachone and its intermediates
发明人:JIANG ZHIWEI; HOGELAND JANE
权利人:CYCLIS PHARMACEUTICALS INC
摘要:A novel process for synthesizing beta-lapachone (beta-lapachone), an agent that has demonstrated significant antineoplastic activity against human cancer lines. The process comprises the conversion of starting material, 2-hydroxy-1,4-naphothoquinone into beta-lapachone intermediate, lapachol. The lapachol is then converted to beta-lapachone by treatment with sulfuric acid and purified by recrystallization from ethanol. This novel process is extremely simple and provides beta-lapachone in excellent quality and high yield.
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主要参考文献


1: Oliveira Silva E, Cruz de Carvalho T, Parshikov IA, Alves dos Santos R, Silva Emery F, Jacometti Cardoso Furtado NA. Cytotoxicity of lapachol metabolites produced by probiotics. Lett Appl Microbiol. 2014 Jul;59(1):108-14. doi: 10.1111/lam.12251. Epub 2014 Apr 9.
3: Mata-Santos T, Pinto NF, Mata-Santos HA, De Moura KG, Carneiro PF, Carvalho Tdos S, Del Rio KP, Pinto Mdo C, Martins LR, Fenalti JM, Da Silva PE, Scaini CJ. ANTHELMINTIC ACTIVITY OF LAPACHOL, β-LAPACHONE AND ITS DERIVATIVES AGAINST Toxocara canis LARVAE. Rev Inst Med Trop Sao Paulo. 2015 May-Jun;57(3):197-204. doi: 10.1590/S0036-46652015000300003.
4: Bai L, Han Y, Yao J, Li X, Li Y, Xu P, Xue M. Structural elucidation of the metabolites of lapachol in rats by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jan 1;944:128-35. doi: 10.1016/j.jchromb.2013.11.024. Epub 2013 Nov 22. doi: 10.1016/j.jinorgbio.2014.03.009. Epub 2014 Mar 27. pii: S0074-02762013000300342. doi: 10.1590/S0074-02762013000300013.

合成参考文献


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摘要:Ghodsian S, Taghipour N, Deravi N, Behniafar H, Lasjerdi Z. Recent researches in effective antileishmanial herbal compounds: narrative review. Parasitol Res. 2020 Dec;119(12):3929–46. doi: 10.1007/s00436-020-06787-0.
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参考文献:10.1021/np068004q
摘要:de Sousa JR, Silva GDF, Miyakoshi T, Chen. Constituents of the Root Wood of Austroplenckia populnea var. ovata. J. Nat. Prod. 2006 Aug 01;69(8):1225–7. doi: 10.1021/np068004q.
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