CAS: 19545-26-7; (1S,6Br,9As,11R,11Br)-1-(Methoxymethyl)-9A,11B-Dimethyl-3,6,9-Trioxo-1,6,6B,7,8,9,9A,10,11,11B-Decahydro-3H-Furo[4,3,2-De]Indeno[4,5-H]Isochromen-11-Yl Acetate

该化合物是一种强效和选择性抑制磷化硅基酶(PI3Ks)的抑制剂,对酶的催化子单元具有不可逆转的约束力,显示出PI3K等形,特别是PI3K-α,PI3K-β和PI3K-γ的高度特异性,其IC50值在低纳米分子范围内.Wortmannin 被广泛用于生物化学和细胞研究,以调查PI3K中介信号路径,包括细胞扩散,生存和车辆贩运.它能够有效地跨过细胞膜,使之成为体外和外活性研究的宝贵工具.然而,由于水溶液的不稳定性,必须小心处理.研究人员赞成Wortmannin 的精密操作机制,以及调节PI3K活动的可靠性.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号58053-83-1 17β-hydroxy Wor... | CAS号382-44-5 4-雄烯-11β-醇-3,17-二酮 | CAS号1035-69-4 9-去氢雄烯二酮 | CAS号2899-95-8 20-hydroxycortisol | CAS号58053-83-1 17β-hydroxy Wor...

合成工艺路线路线简述

  • 合成目标产物 Wortmannin 主要起始原料 Androst-4-Ene-3,17-Dione, 9,11-Epoxy-, (11α)-
  • (文献来源)合成步骤主要原料 Androst-4-Ene-3,17-Dione, 9,11-Epoxy-, (11α)-
4-雄烯-11β-醇-3,17-二酮置于吡啶,三乙烯二胺,盐酸,甲醇,Sodium Periodate,四氧化锇,三丁基膦,三(二甲氨基)甲烷,敌草腈,Camphor-10-Sulfonic Acid,双氧水,碘,4-甲基苯磺酸吡啶,碳酸氢钠,Potassium Carbonate,Potassium Hydrogencarbonate,对甲苯磺酸,甲基磺酰氯,三乙胺,N,N-二异丙基乙胺,对苯二酚,间氯过氧苯甲酸,Pyridinium Chlorochromate,2,3-二氯-5,6-二氰基-1,4-苯醌,柠檬酸,Silver(L) Oxide,Tetramethylammonium Triacetoxyborohydride体系中,用 四氢呋喃,1,4-二氧六环,甲醇,二氯甲烷,氯仿,水,溶剂黄146,乙腈,苯 用作溶剂,化学反应 316.83H,反应生成渥曼青霉素
参考文献:从氢化可的松开始的第一个化学合成渥曼青霉素的方法
标题:从氢化可的松开始的第一个化学合成渥曼青霉素的方法
摘要:渥曼青霉素(一种有效且特异性的pi 3激酶抑制剂)的第一个化学合成是通过从市售的光学纯氢化可的松开始进行的.
Doi:10.1016/0040-4039(96)01332-9

海关参考信息

专利信息


专利号:US-12383499-B2
优先权日:2018-01-01
标题:Scale up synthesis of silicasome nanocarriers
发明人:NEL ANDRE E; MENG HUAN; LIU XIANGSHENG
权利人:UNIV CALIFORNIA
摘要:In order to facilitate the approval and commercialization of silicasome drug delivery systems (e.g. irinotecan silicasomes) it is necessary to scale up synthesis of the drug-loaded silicasomes. In this regard, it was discovered that the synthesis protocols used for laboratory synthesis of drug-loaded silicasomes (e.g., 500 mg/batch) do not scale to large scale silicasome production, because the resulting products were too heterogeneous for use as pharmaceuticals. Accordingly, new methods are provided herein that effectively afford the large-scale production of mesoporous silica nanoparticles (MSNPs) and lipid bilayer coated MSNPs (silicasomes).

专利号:US-2006246505-A1
优先权日:2003-09-02
标题:Modulation of the synthesis of insulin
发明人:WALTHER REINHARD
权利人:WALTHER REINHARD
摘要:The invention particularly relates to the use of substances, which modulate the activity of the proteins casein kinase II (CK II) and 14-3-3 epsilon and/or of the PcG protein EED or which influence the binding of the proteins casein kinase II (CK II) and 14-3-3 epsilon, of the PcG protein EED and/or of a fragment thereof with the protein pancreatic duodenal homeobox-1 (PDX-1) that plays a decisive roll in the glucose-induced biosynthesis of insulin, for influencing the synthesis of insulin or the provision of insulin.

专利号:EP-1546732-B1
优先权日:2002-09-03
标 题:Modulation of the synthesis of insulin
发明人:WALTHER REINHARD
权利人:UNIV ERNST MORITZ ARNDT
摘要:The invention particularly relates to the use of substances, which modulate the activity of the proteins casein kinase II (CK II) and 14-3-3 epsilon and/or of the PcG protein EED or which influence the binding of the proteins casein kinase II (CK II) and 14-3-3 epsilon, of the PcG protein EED and/or of a fragment thereof with the protein pancreatic duodenal homeobox-1 (PDX-1) that plays a decisive roll in the glucose-induced biosynthesis of insulin, for influencing the synthesis of insulin or the provision of insulin.

专利号:US-12391691-B2
优先权日:2018-11-16
标题:Synthesis of key intermediate of KRAS G12C inhibitor compound
发明人:PARSONS ANDREW THOMAS; COCHRAN BRIAN MCNEIL; POWAZINIK IV WILLIAM; CAPORINI MARC ANTHONY
权利人:AMGEN INC
摘要:The present invention relates to an improved, efficient, scalable process to prepare intermediate compounds, such as compound 5M, having the structure n nuseful for the synthesis of compounds that target KRAS G12C mutations, such as

专利号:US-2025206736-A1
优先权日:2019-11-14
标题 :Synthesis of kras g12c inhibitor compound
发明人:CORBETT MICHAEL THOMAS; CAILLE SEBASTIEN
权利人:AMGEN INC
摘要:The present disclosure relates to an improved, efficient, scalable process to prepare intermediate compounds, such as 2-isopropyl-4-methylpyridin-3-amine, useful for the synthesis of compounds, such as Compound 9, for the treatment of KRAS G12C mutated cancers.

专利号:US-10905769-B2
优先权日:2015-11-13
标 题:Peptide and peptide mimetic binding antagonists of polo-like kinase 1 polo box domain and methods of use
发明人:BURKE JR TERRENCE R; HYMEL DAVID T; TSUJI KOHEI
权利人:THE US SECRETARY DEPARTMENT OF HEALTH & HUMAN SERVICES
摘要:The description provides novel compounds that may serve as anticancer therapeutics. The compounds of the description bind to polo-like kinases through the polo-box domain. The peptide derivatives of the description have achieved improved efficacy in biochemical assays against Plk1. Exemplary compounds of the description include macrocyclic peptidomimetics with high affinity and selectivity for polo-like kinases, which may provide the basis for a new genre of anticancer therapeutics. Other exemplary compounds of the description include bi-valent compounds with that bind to polo-like kinases through both kinase domain and polo-box domain simultaneously by incorporating additional moieties that target Plk1 kinase domain, which significantly enhances affinitity relative and may provide the basis for a new genre of anticancer therapeutics. The description also provides methods of use, methods of preparation, compositions, and kits thereof. Further, the description provides a novel method of design and/or synthesis of phosphoryl-derived peptide derivatives useful as therapeutic agents.
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1: Pérez-Castro MÁ, Hernández-Rasco F, Alonso-Bellido IM, Letrán-Sánchez MS, Pérez-Villegas EM, Vitallé J, Real LM, Ruiz-Mateos E, Venero JL, Tabares L, Carrión ÁM, Armengol JÁ, Bachiller S, Ruiz R. HERC1 E3 Ubiquitin Ligase Is Necessary for Autophagy Processes and for the Maintenance and Homeostasis of Vesicles in Motor Nerve Terminals, but Not for Proteasomal Activity. Int J Mol Sci. 2025 Jan 18;26(2):793. doi: 10.3390/ijms26020793.
2: Zhang W, Sunami K, Liu S, Triana D, Tachrim ZP, Kikuchi R, Taniguchi T, Monde K, Takehara T, Zhou DY, Suzuki T, Hashidoko Y, Hashimoto M, Murai Y. Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens. Sci Rep. 2025 Jan 24;15(1):3110. doi: 10.1038/s41598-025-87070-z.
3: Meng NN, Xia LZ, Gong YQ, Lu PR. Autophagy serves as a protective effect against inflammatory injury of oxidative stress in ARPE-19 cell. Int J Ophthalmol. 2025 Jan 18;18(1):28-38. doi: 10.18240/ijo.2025.01.04.

合成参考文献


参考文献:10.4049/jimmunol.0903170
摘要:Antignano F, Ibaraki M, Kim C, Ruschmann J, Zhang A, Helgason CD, Krystal G. SHIP is required for dendritic cell maturation. J Immunol. 2010 Mar 15;184(6):2805–13. doi: 10.4049/jimmunol.0903170.
参考文献:10.1152/ajpheart.01330.2008
摘要:Tsubokawa T, Yagi K, Nakanishi C, Zuka M, Nohara A, Ino H, Fujino N, Konno T, Kawashiri M, Ishibashi-Ueda H, Nagaya N, Yamagishi M. Impact of anti-apoptotic and anti-oxidative effects of bone marrow mesenchymal stem cells with transient overexpression of heme oxygenase-1 on myocardial ischemia. American Journal of Physiology-Heart and Circulatory Physiology. 2010 May;298(5):H1320–9. doi: 10.1152/ajpheart.01330.2008.
参考文献:10.1093/eurjhf/hfq011
摘要:Shyu KG, Wang BW, Chen WJ, Kuan P, Hung CR. Mechanism of the inhibitory effect of atorvastatin on endoglin expression induced by transforming growth factor-beta1 in cultured cardiac fibroblasts. Eur J Heart Fail. 2010 Mar;12(3):219–26. doi: 10.1093/eurjhf/hfq011.
参考文献:10.4196/kjpp.2008.12.2.37
摘要:Kong PJ, Byun JS, Lim SY, Lee JJ, Hong SJ, Kwon KJ, Kim SS. Melatonin Induces Akt Phosphorylation through Melatonin Receptor- and PI3K-Dependent Pathways in Primary Astrocytes. Korean J Physiol Pharmacol. 2008 Apr;12(2):37–41.
参考文献:10.18632/aging.100045
摘要:Currais A, Hortobágyi T, Soriano S. The neuronal cell cycle as a mechanism of pathogenesis in Alzheimer's disease. Aging (Albany NY). 2009 Apr 28;1(4):363–71.
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