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: 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
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.
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
摘要:Toxicology and Applied Pharmacology., 17(1), 1970 [] 参考文献:10.1016/j.bmc.2008.03.032 摘要:da Silva Júnior EN, de Souza MCBV, Fernandes MC, Menna-Barreto RFS, Pinto MDCFR, de Assis Lopes F, de Simone CA, Andrade CKZ, Pinto AV, Ferreira VF, de Castro SL. Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones. Bioorganic & Medicinal Chemistry. 2008 May;16(9):5030–8. doi: 10.1016/j.bmc.2008.03.032. 参考文献:10.1007/s00436-020-06787-0 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. 参考文献:10.1021/np058036y 摘要:Kumar US, Tiwari AK, Reddy SV, Aparna P, Rao RJ, Ali AZ, Rao JM. Free-Radical-Scavenging and Xanthine Oxidase Inhibitory Constituents from Stereospermum personatum. J. Nat. Prod. 2005 Oct 29;68(11):1615–21. doi: 10.1021/np058036y. 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.