4-[5-(3-羟基苯基)-2-噻吩基]-2-甲基苯酚 | 1122660-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-[5-(3-羟基苯基)-2-噻吩基]-2-甲基苯酚
• 英文名称: 4-[5-(3-hydroxyphenyl)-2-thienyl]-2-methylphenol
• 英文别名: 4-(5-(3-Hydroxyphenyl)thiophen-2-yl)-2-methylphenol；4-[5-(3-hydroxyphenyl)thiophen-2-yl]-2-methylphenol
• CAS: 1122660-25-6
• 化学式: C₁₇H₁₄O₂S
• 分子量: 282.363
• InChiKey: ICDRVGLMFQWTDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基-3-甲基苯基)-5-(3-甲氧基苯基)噻吩 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到4-[5-(3-羟基苯基)-2-噻吩基]-2-甲基苯酚
  参考文献：
  名称：

  New Insights into the SAR and Binding Modes of Bis(hydroxyphenyl)thiophenes and -benzenes: Influence of Additional Substituents on 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1) Inhibitory Activity and Selectivity

  摘要：

  17 beta-Hydroxystcroid dehydrogenase type 1 (17 beta-HSD1) is responsible for the catalytic reduction of weakly active E1 to highly potent E2. E2 stimulates the proliferation of hormone-dependent diseases via activation of the estrogen receptor alpha (ER alpha). Because of the overexpression of 17 beta-HSD1 in mammary tumors, this enzyme should be an attractive target for the treatment of estrogen-dependent pathologies. Recently, we have reported on a series of potent 17 beta-HSD1 inhibitors: bis(hydroxyphenyl) azoles, thiophenes, and benzenes. In this paper, different substituents are introduced into the core structure and the biological properties of the corresponding inhibitors are evaluated. Computational methods and analysis of different X-rays of 17 beta-HSD1 lead to identification of two different binding modes for these inhibitors. The fluorine compound 23 exhibits an IC50 of 8 nM and is the most potent nonsteroidal inhibitor described so far. It also shows a high selectivity (17 beta-HSD2, ER alpha) and excellent pharmacokinetic properties after peroral application to rats.

  DOI：

  10.1021/jm901195w

文献信息

• 17BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS FOR THE TREATMENT OF HORMONE-RELATED DISEASES
  申请人：Hartmann Rolf

  公开号：US20110046147A1

  公开（公告）日：2011-02-24

  The invention relates to 17beta-hydroxysteroid dehydrogenase type 1 (17betaHSD1) inhibitors, the preparation thereof and the use thereof for the treatment and prophylaxis of hormone-related, especially estrogen-related or androgen-related, diseases.

  该发明涉及17beta-羟基类固醇脱氢酶1型（17betaHSD1）抑制剂，其制备以及用于治疗和预防激素相关疾病，特别是雌激素相关或雄激素相关疾病的用途。
• 17BETA-HYDROXYSTEROID-DEHYDROGENASE-TYP1-INHIBITOREN ZUR BEHANDLUNG HORMONABHÄNGIGER ERKRANKUNGEN
  申请人：Universität des Saarlandes

  公开号：EP2190421A2

  公开（公告）日：2010-06-02
• [DE] 17BETA-HYDROXYSTEROID-DEHYDROGENASE-TYP1-INHIBITOREN ZUR BEHANDLUNG HORMONABHÄNGIGER ERKRANKUNGEN<br/>[EN] 17BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS FOR THE TREATMENT OF HORMONE-DEPENDENT DISEASES<br/>[FR] INHIBITEURS 17BÊTA-HYDROXYSTÉROÏD-DÉHYDROGÉNASE DE TYPE 1 POUR TRAITER DES MALADIES HORMONO-DÉPENDANTES
  申请人：UNIV SAARLAND

  公开号：WO2009027346A2

  公开（公告）日：2009-03-05

  Die Erfindung betrifft 17Beta-Hydroxysteroid-Dehydrogenase-Typ1 (17betaHSD1) Inhibitoren, deren Herstellung und Verwendung zur Behandlung und Prophylaxe hormonabhängiger, insbesondere estrogenabhängiger oder androgenabhängiger Erkrankungen.
• [EN] SUBSTRATE SELECTIVE HSD17B13 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE HSD17B13 SÉLECTIFS D'UN SUBSTRAT ET UTILISATIONS DE CEUX-CI
  申请人：INIPHARM INC

  公开号：WO2021211981A1

  公开（公告）日：2021-10-21

  Described herein are substrate specific HSD17B13 inhibitors and pharmaceutical compositions comprising said inhibitors. The subject compounds and compositions are useful for the treatment of liver disease, metabolic disease, or cardiovascular disease, such as NAFLD or NASH.
• [EN] PLASMA AND TISSUE MOLECULAR MARKERS OF LIVER DISEASE AND UTILITY FOR TREATMENT<br/>[FR] MARQUEURS MOLÉCULAIRES DE PLASMA ET DE TISSU DE MALADIE DU FOIE ET UTILITÉ POUR LE TRAITEMENT
  申请人：[en]INIPHARM, INC.

  公开号：WO2022098749A1

  公开（公告）日：2022-05-12

  Provided are biomarker panels and methods of using biomarkers. Some embodiments include methods for treating a patient, methods for identifying a patient likely to benefit from treatment with an HSD17B13 inhibitor, methods for evaluating an HSD17B13 inhibitor treatment of a patient, or methods for identifying a risk that a patient has or will develop a liver disease.