4-(2-(1-哌啶)乙氧基)苯酚 | 100238-42-4

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(2-(1-哌啶)乙氧基)苯酚
• 英文名称: 4-(2-piperidin-1-yl-ethoxy)-phenol
• 英文别名: 4-(2-(1-piperidinyl)ethoxy)-phenol；4-<2-(1-piperidinyl)ethoxy>phenol；4-(2-(piperidin-1-yl)ethoxy)phenol；4-(2-piperidin-1-ylethoxy)phenol；4-(2-piperidinylethoxy)phenol；4-(2-piperidinoethoxy)phenol
• CAS: 100238-42-4
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD06410831
• 分子量: 221.299
• InChiKey: XGMJHNYRDUELOH-UHFFFAOYSA-N

物化性质

• 沸点：
  372.7±22.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 储存条件：
  存储条件：2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  4-(2-(1-哌啶)乙氧基)苯酚 在 palladium diacetate 、 palladium dihydroxide 甲酸铵 、 三溴化硼 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 cesium fluoride 、 三环己基膦 作用下， 反应 4.0h， 生成 6-(4-methanesulfonyl-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol
  参考文献：
  名称：

  Structure–activity relationships of SERMs optimized for uterine antagonism and ovarian safety

  摘要：

  Structure-activity relationship studies are described, which led to the discovery of novel selective estrogen receptor modulators (SERMs) for the potential treatment of uterine fibroids. The SAR studies focused on limiting brain exposure and were guided by computational properties. Compounds with limited impact on the HPO axis were selected using serum estrogen levels as a biomarker for ovarian stimulation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.044
• 作为产物：
  描述：

  4-苄氧基苯酚 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 、 caesium carbonate 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 50.0h， 生成 4-(2-(1-哌啶)乙氧基)苯酚
  参考文献：
  名称：

  Discovery and Synthesis of [6-Hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]- 2-(4-hydroxyphenyl)]benzo[b]thiophene:  A Novel, Highly Potent, Selective Estrogen Receptor Modulator

  摘要：

  Raloxifene,[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone hydrochloride (2), is representative of a class of compounds known as selective estrogen receptor modulators (SERMs) that possess estrogen agonist-like actions on bone tissues and serum lipids while displaying potent estrogen antagonist properties in the breast and uterus. As part of ongoing SAR studies with raloxifene, we found that replacement of the carbonyl group with oxygen ([6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(4-hydroxyphenyl)]benzo[b]thiophene hydrochloride, 4c) resulted in a substantial (10-fold) increase in estrogen antagonist potency relative to raloxifene in an in vitro estrogen dependent cell proliferation assay (IC50 = 0.05 nM) in which human breast cancer cells (MCF-7) were utilized. In vivo, 4c potently inhibited the uterine proliferative response to exogenous estrogen in immature rats following both sc and oral dosing (ED50 of 0.006 and 0.25 mg/kg, respectively). In ovariectomized aged rats, 4c produced a significant maximal decrease (45%) in total cholesterol at 1.0 mg/kg (po) and showed a protective effect on bone relative to controls with maximal efficacy at 1.0 mg/kg (po). These data identify 4c as a novel SERM with greater potency to antagonize estrogen in uterine tissue and in human mammary cancer cells compared to raloxifene, tamoxifen or ICI-182,780.

  DOI：

  10.1021/jm970167b
• 作为试剂：
  描述：

  2-苄氧基-1-溴-6-甲氧基萘 、 4-(2-(1-哌啶)乙氧基)苯酚 在 4-(2-(1-哌啶)乙氧基)苯酚 作用下， 以30的产率得到1-{2-[4-(2-benzyloxy-6-methoxynaphthalen-1-yloxy)phenoxy]ethyl}piperidine
  参考文献：
  名称：

  J. Med. Chem. 2005, 48, 6772-6775

  摘要：

  DOI：

文献信息

• LTA4H modulators and uses thereof
  申请人：Barchuk William T.

  公开号：US20080194630A1

  公开（公告）日：2008-08-14

  Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation.

  白三烯A4水解酶（LTA4H）抑制剂，含有它们的组合物，以及用于抑制LTA4H酶活性和治疗、预防或抑制炎症和/或与炎症相关疾病的方法。
• [EN] SELECTIVE ESTROGEN RECEPTOR MODULATORS CONTAINING A PHENYLSULFONYL GROUP<br/>[FR] MODULATEURS SELECTIFS DES RECEPTEURS OESTROGENIQUES CONTENANT UN GROUPE PHENYLSULFONYLE
  申请人：LILLY CO ELI

  公开号：WO2004009086A1

  公开（公告）日：2004-01-29

  The present invention relates to a selective estrogen receptor modulator of formula I or a pharmaceutical acid addition salt thereof; useful, e.g., for treating endometriosis and/or uterine leiomyoma/leiomyomata.

  本发明涉及式I的选择性雌激素受体调节剂或其药用酸盐加合物；例如，用于治疗子宫内膜异位症和/或子宫平滑肌瘤。
• Phenyl and pyridyl LTA4H modulators
  申请人：Butler R. Christopher

  公开号：US20060223792A1

  公开（公告）日：2006-10-05

  Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and inflammatory conditions.

  白三烯A4水解酶（LTA4H）抑制剂，含有它们的组合物，以及用于抑制LTA4H酶活性和治疗、预防或抑制炎症和炎症症状的方法。
• Benzothiophene compounds, intermediates, compositions, and methods
  申请人：Eli Lilly and Company

  公开号：US05919800A1

  公开（公告）日：1999-07-06

  The present invention provides a method for inhibiting endometriosis comprising administering to a woman an effective amount of a compound of formula I ##STR1## wherein R.sup.1a is --H or --OR.sup.7a in which R.sup.7a is --H or a hydroxy protecting group; R.sup.2a is --H, halo, or --OR.sup.8a in which R.sup.8a is --H or a hydroxy protecting group; R.sup.3 is 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; n is 2 or 3; and Z is --O-- or --S--; or a pharmaceutically acceptable salt thereof.

  本发明提供了一种抑制子宫内膜异位症的方法，包括向女性施用化合物I的有效量##STR1##其中R.sup.1a为--H或--OR.sup.7a，其中R.sup.7a为--H或羟基保护基；R.sup.2a为--H，卤素或--OR.sup.8a，其中R.sup.8a为--H或羟基保护基；R.sup.3为1-哌啶基，1-吡咯啉基，甲基-1-吡咯啉基，二甲基-1-吡咯啉基，4-吗啉基，二甲胺基，二乙胺基，二异丙胺基，或1-己亚甲基亚胺基；n为2或3；Z为--O--或--S--；或其药学上可接受的盐。
• Benzothiophene Selective Estrogen Receptor Modulators with Modulated Oxidative Activity and Receptor Affinity
  作者：Zhihui Qin、Irida Kastrati、R. Esala P. Chandrasena、Hong Liu、Ping Yao、Pavel A. Petukhov、Judy L. Bolton、Gregory R. J. Thatcher

  DOI：10.1021/jm070079j

  日期：2007.5.1

  SERMs. Using computational modeling methods and measurements of antioxidant activity and estrogen receptor (ER) ligand binding, this SERM family was shown to provide both a range of ERalpha/ERbeta selectivity from 1.2- to 67-fold and a range of redox activity. Antioxidant activity was successfully modulated by varying a substituent remote from the OH group; the source of the antioxidant capacity. An efficient

  选择性雌激素受体调节剂（SERM）的雌激素和抗雌激素作用的调节被认为是其临床应用的基础。大多数SERM是易氧化为醌的氧化代谢的聚芳族苯酚，被认为具有遗传毒性。相反，SERMs的氧化还原反应性可能有助于抗氧化剂和化学预防机制，为改善SERMs的治疗性能提供了一种新方法。开发了改进的合成策略以产生苯并噻吩SERM家族。使用计算建模方法和抗氧化剂活性和雌激素受体（ER）配体结合的测量结果，表明该SERM家族既可提供1.2-67倍的ERalpha / ERbeta选择性，又可提供一定范围的氧化还原活性。通过改变远离OH基团的取代基可以成功地调节抗氧化活性。抗氧化能力的来源。报道了一种有效的合成方法，该方法产生了苯并噻吩SERM，其中氧化还原活性和ER亲和力得到调节。