CAS: 22668-01-5; Etanidazole

该化合物是合成化合物,主要以其应用为抗蛋白剂而闻名,特别是治疗厌氧细菌和某些原生动物引起的感染,属于硝基聚醚类,其特点是其硝基联胺菌群,其特征是附着于一个非伊迪佐尔环的硝基基联;这一结构对于其生物活动至关重要,因为它允许该化合物在厌氧条件下减少,导致生成反应性中间体,从而可能损害微生物DNA;埃坦伊达佐素通常以口服方式施用,并因人体毒性相对较低而闻闻名于人,使该物质在某些治疗环境中成为首选,该化合物溶于有机溶剂,但水中的溶性有限,可影响其致癌性;此外,必须指出,该物质与其他硝基胺蛋白质一样,可能会产生副作用,包括胃肠紊乱和与酒精的相互作用,导致异硫磷反应.总体而言,该物质的独特的化学特性和行为机制使该物质的病发性成为了宝贵的病原体.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

ethanolamine methyl 2-(2-nitro-1H-imidazole-1-yl)acetateNSC 310455 2-(2-nitro-1H-imidazol-1-yl)acetic acid methyl 2-(2-nitro-1H-imidazole-1-yl)acetate

合成工艺路线路线简述

  • 合成目标产物 Etanidazole 主要起始原料 Monoethanolamine And Methyl 2-Nitro-1-Imidazoleacetate
  • (文献来源)合成步骤主要原料 Monoethanolamine 和 Methyl 2-Nitro-1-Imidazoleacetate
📜C.I.酸性橙108,1-乙氧基甲基-1H-咪唑置于c.I.酸性橙108体系中,用62.4的收率获得依他硝唑
参考文献:2-Nitroimidazoles
标题:2-Nitroimidazoles
摘要:在1-位置上置换有一种烷基酸,烷基酸酯或n-置换的烷基酸酰胺的2-硝基咪唑,可用作杀菌剂,抗原虫剂以及治疗病原性酵母感染的药物.

海关参考信息

专利信息


专利号:US-2012177593-A1
优先权日:2009-07-20
标 题 :Synthesis of dendrimer conjugates
发明人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH
权利人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH; UNIV MICHIGAN
摘要:The present invention relates to novel methods of synthesis of therapeutic and diagnostic dendrimers. In particular, the present invention is directed to novel dendrimer conjugates, novel methods of synthesizing the same, compositions comprising the conjugates, as well as systems and methods utilizing the conjugates (e.g., in diagnostic and/or therapeutic settings (e.g., for the delivery of therapeutics, imaging, and/or targeting agents (e.g., in disease (e.g., cancer, inflammatory disease) diagnosis and/or therapy, pain therapy, etc.)). Accordingly, dendrimer conjugates of the present invention may further comprise at least two different components for targeting, imaging, sensing, and/or providing a therapeutic or diagnostic material and/or monitoring response to therapy. Furthermore, the novel synthesis methods of certain embodiments of the present invention provide significant advantages with regard to total reaction time and simplicity.

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-5886190-A
优先权日:1993-10-04
标 题:Rapid synthesis and use of 18F-fluoromisonidazole and analogs
发明人:WALLACE SIDNEY; YANG DAVID J; CHERIF ABDALLAH
摘要:The present invention involves a rapid synthesis of 18F-FMISO and analogs thereof. New precursors such as 1-(2'-nitro-1'-imidazolyl)-2-0-acetyl-3-0-tosylpropanol, glycerol-1,3-ditosylate-2-0-acetylate, 1-(2'-nitro-1'-imidazolyl)-2,3-0-diacetyl-4-0-tosylbutanol and threitol 1,4-di-tosylate-2,3-0-diacetylate, are also important aspects of the invention. A further aspect of the invention is the development of a hydrophilic PET ligand to image tumor hypoxia. Erythrotosyl analogue of 2-nitroimidazone (Ts-ETNIM) was prepared from a mixture of 2-nitromidazole, ditosylthreitol and cesium carbonate at 60 DEG C. for 1 hr. Ts-ETNIM was isolated at 70% yield. [18F]fluoroerythronitroimidazole (FETNIM) was then prepared from Ts-ETNIM and K18F/kryptofix TM . The yield for [18F]FETNIM was 26-30% (60 min, decay corrected). Results of biodistribution and PET studies indicate that [18F]FETNIM has the potential to detect tumor hypoxia and is indicated to be less neurotoxic.

专利号:US-8734846-B2
优先权日:2008-06-16
标 题 :Methods for the preparation of targeting agent functionalized diblock copolymers for use in fabrication of therapeutic targeted nanoparticles
发明人:ALI MIR M; HRKACH JEFF; ZALE STEPHEN E; ALVAREZ DE CIENFUEGOS LUIS
权利人:BIND BIOSCIENCES INC
摘要:This application provides nanoparticles and methods of making nanoparticles using pre-functionalized poly(ethylene glycol)(also referred to as PEG) as a macroinitiator for the synthesis of diblock copolymers. Ring opening polymerization yields the desired poly(ester)-poly (ethylene glycol)-targeting agent polymer that is used to impart targeting capability to therapeutic nanoparticles. This “polymerization fromâ€? approach typically employs precursors of the targeting agent wherein the reactivity of functional groups of the targeting agent is masked using protecting groups. Also described is a “coupling toâ€? that utilized the poly(ethylene glycol)-targeting agent conjugate where the targeting agent remains in its native un-protected form. This method uses “orthogonalâ€? chemistry that exhibit no cross reactivity towards functional groups typically found within targeting agents of interest.

专利号:US-2013035307-A1
优先权日:2010-01-26
标 题:Methods for treating or preventing the spread of cancer using semi-synthetic glycosaminoglycosan ethers
发明人:PRESTWICH GLENN D; KENNEDY THOMAS P
权利人:UNIV UTAH RES FOUND; PRESTWICH GLENN D; KENNEDY THOMAS P
摘要:Described herein are methods for the treatment and prevention of tumor metastasis using alkylated and fluoroalkylated semi-synthetic glycosaminoglycan ethers (“SAGEsâ€?). The synthesis of sulfated alkylated and fluoroalkylated SAGEs is also described.

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主要参考文献


1: Hurwitz SJ, Coleman CN, Riese N, Loeffler JS, Alexander E 3rd, Buswell L, Neben TY, Shargel L, Kramer RA. Distribution of etanidazole into human brain tumors: implications for treating high grade gliomas. Int J Radiat Oncol Biol Phys. 1992;22(3):573-6. doi: 10.1016/0360-3016(92)90879-m. 52(2):208-14. doi: 10.1269/jrr.10122. 20(4):723-31. doi: 10.1016/0360-3016(91)90015-v. 28(25):3724-30. doi: 10.1016/j.biomaterials.2007.04.032. Epub 2007 May 3. 29(3):545-8. doi: 10.1016/0360-3016(94)90453-7. 20(4):703-8. doi: 10.1016/0360-3016(91)90012-s. 81(3):263-80. doi: 10.1016/s0168-3659(02)00066-4. 55(5):1182-5. doi: 10.1016/s0360-3016(02)04391-2. 20(5):987-95. doi: 10.1016/0360-3016(91)90195-a. 78(4):267-74. doi: 10.1080/09553000110105695. 103(3):599-607. doi: 10.1016/j.jconrel.2004.12.012. 29(3):541-3. doi: 10.1016/0360-3016(94)90452-9. 14(2):157-83. doi: 10.1163/156856203321142597.
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17: Eschwège F, Sancho-Garnier H, Chassagne D, Brisgand D, Guerra M, Malaise EP, Bey P, Busutti L, Cionini L, N'Guyen T, Romanini A, Chavaudra J, Hill C. Results of a European randomized trial of Etanidazole combined with radiotherapy in head and neck carcinomas. Int J Radiat Oncol Biol Phys. 1997 Sep 1;39(2):275-81. doi: 10.1016/s0360-3016(97)00327-1. 29(3):535-40. doi: 10.1016/0360-3016(94)90451-0. 11(4):489-99. doi: 10.3109/02656739509022484. 81(12):929-34. doi: 10.1093/jnci/81.12.929.

合成参考文献


参考文献:10.1007/s10439-011-0349-7
摘要:Pishko GL, Astary GW, Mareci TH, Sarntinoranont M. Sensitivity Analysis of an Image-Based Solid Tumor Computational Model with Heterogeneous Vasculature and Porosity. Annals of Biomedical Engineering. 2011 Jul 13;39(9):2360. doi: 10.1007/s10439-011-0349-7.
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