CAS: 52806-53-8; Hydroxyflutamide

该化合物是一种主要用于治疗前列腺癌的非表面抗体,主要用于治疗前列腺癌,其作用是抑制对激素敏感的肿瘤,减缓对激素敏感的肿瘤的生长速度.氟化烃的化学配方是C11H12F3N3O3,其特征为三氟甲基组,这增加了它的威力和选择性.氢氟化烃一般是口服的,以其相对较高的生物利用率而著称.其行动机制涉及对受体进行竞争性抑制和对受体有约束的机器人,导致细胞过程的减少和机器人的中介过程.该物质的特点是有机溶剂具有中等溶性,水溶性有限.副作用可能包括胃肠紊乱,肝功能改变和对脂质新陈代谢的潜在影响.由于其对受体的具体行动,氢氟化硫化物是管理前列腺癌的重要治疗剂,特别是在需要进行热处理的情况下.

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上下游产品

5-氨基-2-硝基三氟甲苯 4-Nitro-3-(Trifluoromethyl)Benzeneamine 393-11-3
2-Methyl-2-[4-Nitro-3-(Trifluoromethyl)Phenoxy]Propanamide 62100-51-0

合成工艺路线路线简述

  • 合成目标产物 Hydroxyflutamide 主要起始原料 4-Nitro-3-(Trifluoromethyl)Phenol
  • (文献来源)合成步骤主要原料 4-Nitro-3-(Trifluoromethyl)Phenol
2-甲基-2-(4-硝基-3-(三氟甲基)苯氧基)丙酸 反应生成 羟基氟他胺
参考文献:The Smiles Rearrangement Of 2-Aryloxy-2-Methylpropanamides. Synthesis Ofn-Aryl-2-Hydroxy-2-Methylpropanamides
标题:The Smiles Rearrangement Of 2-Aryloxy-2-Methylpropanamides. Synthesis Ofn-Aryl-2-Hydroxy-2-Methylpropanamides
摘要:
DOI:10.1055/s-1977-24262

海关参考信息

专利信息


专利号:US-7700654-B2
优先权日:2005-02-05
标 题:Isolation of N-butylbenzenesulfonamide, synthesis of benzenesulfonamide derivatives, and use of N-butylbenzenesulfonamide and benzenesulfonamide derivatives for treating benign prostatic hyperplasia and/or prostate carcinoma
发明人:HOFFMANN HANS-RAINER; MATUSCH RUDOLF; BANIAHMAD ARIA
权利人:LOHMANN THERAPIE SYST LTS
摘要:A process for isolating N-butylbenzenesulfonamide (NBBS) from biological material, the chemical synthesis of benzenesulfonamide derivatives, the use of NBBS and benzenesulfonamide derivatives for treating benign prostatic hyperplasia and/or prostate carcinoma, the production of medicaments for the treatment thereof, and the use of NBBS and benzenesulfonamide derivatives as a lead substance in the development of active substances for treating benign prostatic hyperplasia and/or prostate carcinoma are provided.

专利号:US-8481519-B2
优先权日:2005-02-05
标题 :Isolation of atraric acid, synthesis of atraric acid derivatives, and use of atraric acid and the derivatives thereof for the treatment of benign prostatic hyperplasia, prostate carcinoma and spinobulbar muscular atrophy
发明人:HOFFMANN HANS-RAINER; MATUSCH RUDOLF; BANIAHMAD ARIA
权利人:HOFFMANN HANS-RAINER; MATUSCH RUDOLF; BANIAHMAD ARIA; LOHMANN THERAPIE SYST LTS
摘要:A method for isolating atraric acid from biological material, atraric acid derivatives, the chemical synthesis thereof, and the use of atraric acid and the derivatives thereof for treating or producing a medicament for treating benign prostate hyperplasia, prostate carcinoma or spinobulbar muscular atrophy is provided. In addition, a basic substance for the development of other agents used for treating benign prostate hyperplasia, prostate carcinoma, or spinobulbar muscular atrophy is provided.

专利号:US-2009143466-A1
优先权日:2005-02-05
标题 :Isolation of Atraric Acid, Synthesis of Atraric Acid Derivatives, and Use of Atraric Acid and the Derivatives Thereof for the Treatment of Benign Prostatic Hyperplasia, Prostate Carcinoma and Spinobulbar Muscular Atrophy

专利号:US-2008177107-A1
优先权日:2005-02-05
标题 :Isolation of N-Butylbenzenesulfonamide, Synthesis of Benzenesulfonamide Derivatives, and Use of N-Butylbenzenesulfonamide and Benzenesulfonamide Derivatives for Treating Benign Prostatic Hyperplasia and/or Prostate Carcinoma

专利号:US-10098896-B2
优先权日:2005-03-02
标 题:C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens, in vitro biological activities, pharmacokinetics and antitumor activity
发明人:BRODIE ANGELA; NJAR VINCENT C O
权利人:THE UNIV OF MARYLAND BALTIMORE; UNIV MARYLAND
摘要:Described are steroidal C-17 benzoazoles, pyrimidinoazoles (azabenzoazoles) and diazines. Methods for their synthesis are also described, which include methods having a step of nucleophilic vinylic “addition-eliminationâ€? substitution reaction of 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene or analogs thereof and benzoazole or pyrimidinoazole nucleophiles and methods having a palladium catalyzed cross-coupling reaction of 17-iodoandrosta-5,16-dien-3β-ol or analogs thereof with tributylstannyl diazines. The compounds are potent inhibitors of human CYP17 enzyme as well as potent antagonists of both wild type and mutant androgen receptors (AR). The compounds are useful for the treatment of human prostate cancer.

专利号:AU-2006210040-B2
优先权日:2005-02-05
标 题:Isolation of N-butylbenzenesulfonamide, synthesis of benzenesulfonamide derivatives, and use of N-butylbenzenesulfonamide and benzenesulfonamide derivatives for the treatment of benign prostate hyperplasia and/or prostate carcinoma
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主要参考文献


1: Ball AL, Kamalian L, Alfirevic A, Lyon JJ, Chadwick AE. Identification of the Additional Mitochondrial Liabilities of 2-Hydroxyflutamide When Compared With its Parent Compound, Flutamide in HepG2 Cells. Toxicol Sci. 2016 Oct;153(2):341-51. doi: 10.1093/toxsci/kfw126.
2: Duda M, Grzesiak M, Knet M, Knapczyk-Stwora K, Tabarowski Z, Michna A, Slomczynska M. The impact of antiandrogen 2-hydroxyflutamide on the expression of steroidogenic enzymes in cultured porcine ovarian follicles. Mol Biol Rep. 2014 Jul;41(7):4213-22. doi: 10.1007/s11033-014-3291-6.
3: Górowska-Wójtowicz E, Hejmej A, Kamińska A, Pardyak L, Kotula-Balak M, Dulińska-Litewka J, Laidler P, Bilińska B. Anti-androgen 2-hydroxyflutamide modulates cadherin, catenin and androgen receptor phosphorylation in androgen-sensitive LNCaP and androgen-independent PC3 prostate cancer cell lines acting via PI3K/Akt and MAPK/ERK1/2 pathways. Toxicol In Vitro. 2017 Apr;40:324-335. doi: 10.1016/j.tiv.2017.01.019. doi: 10.1021/mp5002813. doi: 10.1111/rda.12097. doi: 10.1016/j.jchromb.2010.03.042. doi: 10.1016/j.repbio.2012.10.006. doi: 10.1016/j.tiv.2015.09.027. doi: 10.1016/j.theriogenology.2014.07.013. doi: 10.1158/1535-7163.MCT-14-1055-T.

合成参考文献


参考文献:10.1007/s11845-011-0714-4
摘要:Wang Y, Li J-, Shao C, Shi C-, Liu F, Yang Z-, Qiu J-, Li Y-, Fu Q, Zhang W, Xue W, Lei Y-, Gao J-, Wang J-, Gao X-, Yuan J-, Bao T-, Zhang Y-. Androgen receptor coregulators NOCR1, TIF2, and ARA70 may account for the hydroxyflutamide insensitivity of prostate cancer cells. Irish Journal of Medical Science. 2011 Jul 05;180(4):865. doi: 10.1007/s11845-011-0714-4.
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