CAS: 65646-68-6; (2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-Dimethyl-9-(2,6,6-Trimethylcyclohex-1-En-1-yl)Nona-2,4,6,8-Tetraenamide

该化合物是一种合成的视质素,又称N(4-羟基苯)异丁胺,主要研究其癌症治疗和预防的潜在治疗作用,其特点是能够调节基因表达和影响细胞分化和血吸虫病,使其成为肿瘤研究感兴趣的课题;芬列丁酸是一种独特的行动机制,不同于其他视质,因为它不以同样的方式激活视质素;相反,人们认为它通过氧化性压力诱导和各种信号路径的调节来产生其效果;该化合物通常以无毒剂量的形式进行,其致癌基因的调节,其致癌作用包括吸收,分布,新陈代谢和排泄液过程,这些过程对于其效果至关重要;芬列丁酸在临床试验中表现出对某些癌症,特别是乳腺癌的许诺,并且正在研究其在其他恶性肿瘤中的潜在用途.其安全特征和副作用也是正在进行的研究中的重要考虑因素.

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欧盟法规

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上下游产品

CAS号302-79-4 维生素A酸; 视黄酸 | CAS号123-30-8 对氨基苯酚 | CAS号53839-60-4 Retinoyl chloride | CAS号75664-77-6 [4-[[(2Z,4E,6E,...

合成工艺路线路线简述

  • 合成目标产物 4-Hydroxyphenylretinamide 主要起始原料 Retinoic Acid
  • (文献来源)合成步骤主要原料 Retinoic Acid
维a酸置于三氯化磷体系中,用 苯 作为反应溶剂,化学反应 4.0H,反应生成 维甲酰酚胺
参考文献:某些13-顺式和全反式视黄酰胺的合成和性质
标题:某些13-顺式和全反式视黄酰胺的合成和性质
摘要:通过13-顺-视黄酰氯或13-顺-1-视黄基咪唑从13-顺-视黄酸合成了几种13-顺-视黄酰胺.由全反式视黄酰氯和甘氨酸乙酯制备全反式视黄酰甘氨酸.开发了用于制备其他全反式维甲酸酰胺的详细程序,以用于癌症化学预防的研究.
DOI:10.1002/jps.2600730610

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: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-2022233673-A1
优先权日:2019-06-04
标 题:METHODS OF PRODUCING SHIGA TOXIN B-SUBUNIT (STxB) MONOMERS AND OLIGOMERS, AND USES THEREOF
发明人:BILLET ANNE; SCHMIDT FRÉDÉRIC; JOHANNES LUDGER; SERVENT DENIS; MOURIER GILLES; TARTOUR ÉRIC; KAY MICHAEL; FULCHER JAMES M
权利人:INST CURIE; CENTRE NAT RECH SCIENT; INST NAT SANTE RECH MED; COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES CEA; APHP ASSIST PUBLIQUE HOPITAUX DE PARIS; UNIV PARIS; UNIV OF UTAH RESEARCH FOUDATION; UNIV UTAH RES FOUND
摘要:A method of producing a monomer of a Shiga toxin B-subunit (STxB) protein or of a variant thereof by peptide chemical synthesis, as well as to a method of producing a pentamer of the STxB protein or of the variant thereof. The methods are particularly advantageous as they overcome major issues typically observed in peptide chemical synthesis, including solubility and purity issues.
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主要参考文献


1: Potenza RL, Lodeserto P, Orienti I. Fenretinide in Cancer and Neurological Disease: A Two-Face Janus Molecule. Int J Mol Sci. 2022 Jul 4;23(13):7426. doi: 10.3390/ijms23137426.
2: Ulukaya E, Wood EJ. Fenretinide and its relation to cancer. Cancer Treat Rev. 1999 Aug;25(4):229-35. doi: 10.1053/ctrv.1999.0127. 21(11):3812. doi: 10.3390/ijms21113812.
4: Hail N Jr, Kim HJ, Lotan R. Mechanisms of fenretinide-induced apoptosis. Apoptosis. 2006 Oct;11(10):1677-94. doi: 10.1007/s10495-006-9289-3. 242(11):1178-1184. doi: 10.1177/1535370217706952. Epub 2017 Apr 21.

合成参考文献


参考文献:10.1093/jn/126.10.2474
摘要:Matsuura T, Zhao Z, Ross AC. N-(4-Hydroxyphenyl)-Retinamide Increases Lecithin:Retinol Acyltransferase Activity in Rat Liver. The Journal of Nutrition. 1996 Oct;126(10):2474–80. doi: 10.1093/jn/126.10.2474.
参考文献:10.1093/jnci/91.13.1099
摘要:Reed JC. Fenretinide: the Death of a Tumor Cell. JNCI Journal of the National Cancer Institute. 1999 Jul 07;91(13):1099–100. doi: 10.1093/jnci/91.13.1099.
参考文献:10.1093/jnci/91.13.1138
摘要:Maurer BJ, Metelitsa LS, Seeger RC, Cabot MC, Reynolds CP. Increase of Ceramide and Induction of Mixed Apoptosis/Necrosis by N-(4-Hydroxyphenyl)- retinamide in Neuroblastoma Cell Lines. JNCI Journal of the National Cancer Institute. 1999 Jul 07;91(13):1138–46. doi: 10.1093/jnci/91.13.1138.
参考文献:10.1074/jbc.c200147200
摘要:Boehm JE, Singh U, Combs C, Antonyak MA, Cerione RA. Tissue Transglutaminase Protects against Apoptosis by Modifying the Tumor Suppressor Protein p110 Rb. Journal of Biological Chemistry. 2002 Jun;277(23):20127–30. doi: 10.1074/jbc.c200147200.
参考文献:10.1038/sj.leu.2402414
摘要:Fontana JA, Rishi AK. Classical and novel retinoids: their targets in cancer therapy. Leukemia. 2002 Apr;16(4):463–72. doi: 10.1038/sj.leu.2402414.
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