4-(2-硝基苯氧基)丁酸乙酯 | 112290-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-硝基苯氧基)丁酸乙酯
• 英文名称: 4-(2-nitrophenoxy)butanoic acid ethyl ester
• 英文别名: ethyl 4-(2-nitrophenoxy)-butyrate；ethyl 4-(2-nitrophenoxy) butyrate；Ethyl 4-(2-nitrophenoxy)butyrate；Ethyl 4-(2-nitrophenoxy)butanoate
• CAS: 112290-15-0
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: KCHSJDLFGWRPQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-硝基苯氧基)丁酸乙酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 生成 (+/-)-ONO-3805
  参考文献：
  名称：

  Steroid 5α-Reductase: Comparative Study of Mechanism of Inhibition by Nonsteroids ONO-3805 and LY191704

  摘要：

  Two nonsteroids, ONO-3805 and LY191704, were evaluated as inhibitors of the human and rat 5 alpha-reductases (5 alpha R). ONO-3805 was prepared in a 12-step convergent synthesis. This compound is a potent inhibitor of the human and rat 5 alpha Rs, with more potent inhibition seen against the rat enzymes. The inhibition patterns of this compound were best fit to an uncompetitive model which suggests binding in a ternary complex with enzyme and NADP(+). Apparent K-i values of 27, 31, 1, and 0.5 nM versus testosterone were obtained with human type 1, human type 2, rat type 1, and rat type 2 5 alpha R, respectively. Multiple inhibition studies with ONO-3805 and NADP(+) support synergistic binding of these two inhibitors with all isozymes. LY191704 was also evaluated as an inhibitor of the human and rat 5 alpha Rs. This compound is a selective, competitive inhibitor of human type 1 5 alpha R. Poor inhibition was observed with human type 2 and rat types 1 and 2 5 alpha R. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0033
• 作为产物：
  描述：

  硝苯酚 生成 4-(2-硝基苯氧基)丁酸乙酯
  参考文献：
  名称：

  JOENSSON N. A.; MERENYI F.; SVAHN C. M.; GYLLANDER J., ACTA CHEM. SCAND., 1978, B32, NO 5, 317-321

  摘要：

  DOI：

文献信息

• Method of treatment for benign prostatic hyperplasia
  申请人：Merck & Co., Inc.

  公开号：US05753641A1

  公开（公告）日：1998-05-19

  Disclosed is an improved treatment for men with benign prostatic hyperplasia (BPH), involving combination therapy of a 5.alpha.-reductase inhibitor, e.g. a 17.beta.-substituted 4-azasteroid, a 17.beta.-substituted non-azasteroid, 17.beta.-acyl-3-carboxy-androst-3,5-diene, benzoylaminophenoxybutanoic acid derivative, fused benz(thio)amide or cinnamoylamide derivative, aromatic 1,2-diethers or thioethers, aromatic ortho acylaminophenoxy alkanoic acids, ortho thioalkylacylaminophenoxy alkanoic acids, pharmaceutically acceptable salts and esters thereof, and particularly finasteride, in combination with an .alpha..sub.1 -adrenergic receptor blocker, i.e., terazosin. The combination provides therapy at the molecular level for the underlying cause of the disease as well as providing symptomatic relief. Pharmaceutical compositions useful for treatment are also disclosed.

  本文揭示了一种改进的治疗方法，用于治疗患有良性前列腺增生（BPH）的男性，涉及联合疗法，包括5α-还原酶抑制剂，例如17β-取代的4-氮杂类固醇，17β-取代的非氮杂类固醇，17β-酰基-3-羧基-雄烯-3,5-二烯，苯甲酰氨基苯氧丁酸衍生物，融合苯基（硫）酰胺或肉桂酰胺衍生物，芳香族1,2-二醚或硫醚，芳香族邻位酰胺基苯氧烷酸，邻位硫烷基酰胺基苯氧烷酸，其药用盐和酯，特别是非那司丁（finasteride），与α1-肾上腺能受体阻滞剂，即特拉唑辛（terazosin）结合。该组合提供了治疗疾病潜在病因的分子水平治疗，同时提供了症状缓解。还揭示了用于治疗的药物组合物。
• New sulphur containing nonsteroidal drugs as 5-alpha reductase inhibitors
  申请人：MERCK & CO. INC.

  公开号：EP0525885A1

  公开（公告）日：1993-02-03

  Described are new non-steroidal drugs for treatment of benign prostatic hyperplasia and other disorders mediated by high 5-a reductase activity, high DHT levels and other conditions of hyperandrogenic stimulation, of the formula: wherein A, D, X, R, R', R", Ra, y and z are as defined in claim 1.

  描述了一种新的非类固醇药物，用于治疗良性前列腺增生和其他由高5-a还原酶活性、高DHT水平和其他雄激素过度刺激情况介导的疾病，其化学式为：其中A、D、X、R、R'、R"、Ra、y和z如权利要求1中定义的那样。
• Method of treatment for prostatic cancer
  申请人：Merck & Co., Inc.

  公开号：US05994362A1

  公开（公告）日：1999-11-30

  Disclosed is a new treatment for men with prostatic cancer involving combination therapy of a 5.alpha.-reductase inhibitor, i.e., a 17.beta.-substituted 4-azasteroid, a 17.beta.-substituted non-azasteroid, 17.beta.-acyl-3-carboxyandrost-3,5-diene, benzoylaminophenoxybutanoic acid derivative, fused benz(thio)amide or cinnamoylamide derivative, aromatic 1,2-diethers or thioethers, aromatic ortho acylaminophenoxy alkanoic acids, ortho thioalkylacylamino-phenoxy alkanoic acids, pharmaceutically acceptable salts and esters thereof, and particularly finasteride, in combination with an antiandrogen, i.e. flutamide. Pharmaceutical compositions useful for treatment are also disclosed.

  公开了一种新的治疗前列腺癌的方法，涉及使用5α-还原酶抑制剂，即17β-取代的4-氮杂类固醇，17β-取代的非氮杂类固醇，17β-酰基-3-羧基雄烯-3,5-二烯，苯甲酰氨基苯氧丁酸衍生物，融合苯并（硫）酰胺或肉桂酰胺衍生物，芳香族1,2-二醚或硫醚，芳香族邻位酰胺基苯氧烷酸，邻位硫烷基酰氨基苯氧烷酸，以及其药学上可接受的盐和酯，特别是非那司特，与抗雄激素药物，即氟他胺结合。还公开了用于治疗的药物组合物。
• New non-steroidal agents as 5-alpha reductase inhibitors
  申请人：MERCK & CO. INC.

  公开号：EP0526093A1

  公开（公告）日：1993-02-03

  Described are new non-steroidal drugs for treatment of benign prostatic hyperplasia and other disorders mediated by high 5-alpha reductase activity, high dihydrotestosterone levels, and other conditions of hyperandrogenic stimulation, of the formula: wherein A, D, E, X, R, R′, R˝, Ra, y and z are as defined in claim 1.

  描述了一种新的非甾体药物，用于治疗良性前列腺增生和其他由高5α-还原酶活性、高二氢睾酮水平和其他雄激素过度刺激症状介导的疾病，其化学结构如下：其中A、D、E、X、R、R'、R˝、Ra、y和z的定义如权利要求书中所述。
• [EN] PHARMACEUTICAL COMBINATION FOR THE TREATMENT OF BENIGN PROSTATIC HYPERPLASIA COMTAINING A 5 ALPHA-REDUCTASE INHIBITOR
  申请人：MERCK & CO., INC.

  公开号：WO1992018132A1

  公开（公告）日：1992-10-29

  (EN) Disclosed is a new treatment for men with benign prostatic hyperplasia (BPH), involving combination therapy of a 5$g(a)-reductase inhibitor, e.g. a 17$g(b)-substituted non-azasteroid, 17$g(b)-acyl-3-carboxy-androst-3,5-diene, benzoylaminophenoxybutanoic acid derivative, fused benz(thio)amide or cinnamoylamide derivative, aromatic 1,2-diethers or thioethers, aromatic ortho acylaminophenoxy alkanoic acids, ortho thioalkylacylamino-phenoxy alkanoic acids, pharmaceutically acceptable salts and esters thereof, e.g. finsteride, in combination with an aromatase inhibitor, i.e., fadrazole, being 4-(5,6,7,8-tetra-hydroimidazo-[1,5-$g(a)]pyridin-5-yl)benzonitrile. The combination provides therapy at the molecular level for the underlying cause of the disease as well as providing symptomatic relief. Pharmaceutical compositions useful for treatment are also disclosed.(FR) On décrit un nouveau traitement destiné aux hommes souffrant d'hyperplasie prostatique bénigne (HPB), et qui comprend une thérapie d'association composée d'un inhibiteur de 5$g(a)-réductase, par exemple un dérivé d'acide benzoylaminophénoxybutanoïque, 17$g(b)-substitué non azastéroïde, 17$g(b)-acyl-3-carboxy-androst-3,5-diène, un dérivé de cinnamoylamide ou de benz(thio)amide fusionné, des thioéthers ou 1,2-diéthers aromatiques, des acides alcanoïques aromatiques d'ortho acylaminophénoxy, des acides alcanoïques d'ortho thioalkylacylamino-phénoxy, des sels et des esters pharmaceutiquement acceptables de ces éléments, par exemple de la finastéride, en association avec un inhibiteur d'aromatase, c'est-à-dire du fadrazole, étant composé de 4-(5,6,7,8-tétrahydro-imidazo-[1,5-$g(a)]pyridin-5-yle) benzonitrile. L'association constitue une thérapie au niveau moléculaire dirigée contre la cause sous-jacente de la maladie tout en produisant un soulagement symptomatique. Des compositions pharmaceutiques utilisées pour ce traitement sont aussi décrites.

  该专利公开了一种新的治疗良性前列腺增生（BPH）的方法，涉及使用5α-还原酶抑制剂的联合治疗，例如17β-取代的非阿扎斯特罗伊德类、17β-酰基-3-羧基-雄烯-3,5-二烯、苯甲酰氨基苯氧丁酸衍生物、融合苯（硫）酰胺或肉桂酰胺衍生物、芳香族1,2-二醚或硫醚、芳香族正交酰胺基苯氧基烷酸、正交硫烷基酰胺基苯氧基烷酸，以及其药学上可接受的盐和酯，例如非那雄胺，与芳香化酶抑制剂，即4-（5,6,7,8-四氢咪唑[1,5-a]吡啶-5-基）苯甲腈的联合使用。该联合疗法在分子水平上治疗疾病的根本原因，并提供症状缓解。还公开了用于治疗的药物组合。