N-({3-氯-4-[(4-氯苄基)磺酰基]苯基}氨基甲酰)-2,6-二氟苯甲酰胺 | 80-90-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: N-({3-氯-4-[(4-氯苄基)磺酰基]苯基}氨基甲酰)-2,6-二氟苯甲酰胺
• 中文别名: 2-呋喃乙酸,2,5-二氢-4-甲氧基-3-甲基-5-羰基-,甲基酯,(+)-
• 英文名称: UC1020
• 英文别名: 5β-pregnane-3β,20α-diol；5β-pregnan-3β,20α-diol；(20S)-5β-pregnanediol-(3β.20)；(10S)-3c-Hydroxy-10r.13c-dimethyl-17c-((S)-1-hydroxy-aethyl)-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3β-Hydroxy-10.13-dimethyl-17β-((S)-1-hydroxy-aethyl)-5β-gonan；5β-Pregnandiol-(3β.20α_F)；(3beta,5beta)-Pregnane-3,20-diol；(3S,5R,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 80-90-0
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: YWYQTGBBEZQBGO-HUTKLZKUSA-N

物化性质

• 沸点：
  435.9±18.0 °C(Predicted)
• 密度：
  1.086 g/cm3
• 保留指数：
  2622.6

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-({3-氯-4-[(4-氯苄基)磺酰基]苯基}氨基甲酰)-2,6-二氟苯甲酰胺 在 potassium phosphate 、 rabbit aldose reductase-like protein AKR₁B₁₉ 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 甲醇 为溶剂， 生成 5b-孕甾烷-20alpha-醇-3-酮
  参考文献：
  名称：

  Characterization of rabbit aldose reductase-like protein with 3β-hydroxysteroid dehydrogenase activity

  摘要：

  In this study, we isolated the cDNA for a rabbit aldose reductase-like protein that shared an 86% sequence identity to human aldo-keto reductase (AKR)(1) 1B10 and has been assigned as AKR1B19 in the AKR superfamily. The purified recombinant AKR1B19 was similar to AKR1B10 and rabbit aldose reductase (AKR1B2) in the substrate specificity for various aldehydes and alpha-dicarbonyl compounds. In contrast to AKR1B10 and AKR1B2, AKR1B19 efficiently reduced 3-keto-5 alpha/beta-dihydro-C19/C21/C24-steroids into the corresponding 3 beta-hydroxysteroids, showing K-m of 1.3-9.1 mu M and k(cat) of 1.1-7.6 min(-1). The stereospecific reduction was also observed in the metabolism of 5 alpha- and 5 beta-dihydrotestosterones in AKR1B19-overexpressing cells. The mRNA for AKR1B19 was ubiquitously expressed in rabbit tissues, and the enzyme was co-purified with 3 beta-hydroxysteroid dehydrogenase activity from the lung. Thus, AKR1B19 may function as a 3-ketoreductase, as well as a defense system against cytotoxic carbonyl compounds in rabbit tissues. The molecular determinants for the unique 3-ketoreductase activity were investigated by replacement of Phe303 and Met304 in AKR1B19 with Gln and Ser, respectively, in AKR1B10. Single and double mutations (F303Q, M304S and F303Q/M304S) significantly impaired this activity, suggesting the two residues play critical roles in recognition of the steroidal substrate. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2012.07.012
• 作为产物：
  描述：

  pregnanediol 20-monoacetate 在 chromium(VI) oxide 、 sodium hydroxide 、 氢溴酸 、 溶剂黄146 、 铂 作用下， 生成 N-({3-氯-4-[(4-氯苄基)磺酰基]苯基}氨基甲酰)-2,6-二氟苯甲酰胺
  参考文献：
  名称：

  Sterols. XXII. The Pregnandiols and Pregnanolones

  摘要：

  DOI：

  10.1021/ja01290a057

文献信息

• Human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1‒AKR1C4) of the aldo-keto reductase superfamily: functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones
  作者：Trevor M. PENNING、Michael E. BURCZYNSKI、Joseph M. JEZ、Chien-Fu HUNG、Hseuh-Kung LIN、Haiching MA、Margaret MOORE、Nisha PALACKAL、Kapila RATNAM

  DOI：10.1042/0264-6021:3510067

  日期：2000.10.1

  recombinant human 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD) isoforms of the aldo-keto reductase (AKR) superfamily. The enzymes correspond to type 1 3alpha-HSD (AKR1C4), type 2 3alpha(17beta)-HSD (AKR1C3), type 3 3alpha-HSD (AKR1C2) and 20alpha(3alpha)-HSD (AKR1C1), and share at least 84% amino acid sequence identity. All enzymes acted as NAD(P)(H)-dependent 3-, 17- and 20-ketosteroid reductases and

  动力学参数，类固醇底物特异性和反应产物的身份确定了醛-酮还原酶（AKR）超家族的四个同质重组人3α-羟基类固醇脱氢酶（3alpha-HSD）同工型。这些酶分别对应于1型3alpha-HSD（AKR1C4），2型3alpha（17beta）-HSD（AKR1C3），3型3alpha-HSD（AKR1C2）和20alpha（3alpha）-HSD（AKR1C1），并且共享至少84％氨基酸序列同一性。所有的酶都可以作为依赖NAD（P）（H）的3-，17-和20-酮类固醇还原酶以及3α-，17β-和20α-羟基类固醇氧化酶。这些同工型的功能可塑性突出了它们调节活性雄激素，雌激素和孕激素水平的能力。突出的特点是AKR1C4具有最高的催化效率，底物的k（cat）/ K（m）值比其他同工型获得的底物高10-30倍。在还原方向上，所有同工型均使5α-二氢睾丸激素（17β-羟基-5α-雄烷-3-酮；5α-D
• Pregnane steroids for use in the treatment of cns disorders
  申请人：Backstrom Torbjorn

  公开号：US20050222099A1

  公开（公告）日：2005-10-06

  Steroid compounds prossessing a hydrogen donor in 3beta position, either in the form of a hydroxy- or a sulfate group, function as efficient blockers of the 3alpha-hydroxy-pregnan-steroid action and thus have utility as therapeutic substances for the prevention and/or treatment of steroid related CNS disorders. Treatment methods based on the administration of these substances are disclosed, and these substances either alone or in combination are also suggested for the manufacture of pharmaceuticals for the treatment of many specific steroid induced CNS disorders.

  在 3beta 位具有氢供体的类固醇化合物，无论是以羟基还是硫酸基的形式，都能有效阻断 3α-羟基-孕甾醇的作用，因此可用作预防和/或治疗与类固醇有关的中枢神经系统疾病的治疗物质。已公开了基于这些物质的治疗方法，还建议将这些物质单独或组合用于制造治疗许多特定类固醇引起的中枢神经系统疾病的药物。
• Sterols. LXXXVII. Cholesterol and Sitosterol Derivatives
  作者：Russell E. Marker、Ewald Rohrmann

  DOI：10.1021/ja01860a016

  日期：1940.3
• Sapogenin transformation products and preparation of same
  申请人：PARKE DAVIS & CO

  公开号：US02352852A1

  公开（公告）日：1944-07-04
• Butenandt; Mueller, Chemische Berichte, 1938, vol. 71, p. 191,196
  作者：Butenandt、Mueller

  DOI：——

  日期：——