1-Benzyloxy-4-hydroxynaphthalene | 73661-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Benzyloxy-4-hydroxynaphthalene
• 英文别名: 1-Benzyloxy-4-hydroxynaphthalin；4-(benzyloxy)naphthalen-1-ol；4-(benzyloxy)-1-naphthol；4-Benzyloxy-1-naphthol；4-benzyloxynaphth-1-ol；4-benzyloxy-naphthalen-1-ol；4-phenylmethoxynaphthalen-1-ol
• CAS: 73661-06-0
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: SUCPNTQKGBIXHL-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  454.9±20.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Benzyloxy-4-hydroxynaphthalene 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 4-[2-羟基-3-[4-(2-甲氧基苯基)哌嗪-1-基]丙氧基]萘-1-醇
  参考文献：
  名称：

  Identification of HUHS190, a human naftopidil metabolite, as a novel anti-bladder cancer drug

  摘要：

  We carried out structure-activity relationship study on anti-cancer effects of naftopidil (1) and its metabolites, resulted in identification of 1-(4-hydroxy-2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy) propan-2-ol (2, HUHS190), a major human metabolite of 1, which exhibited the most selective toxicities between against normal and cancer cells (Table 1). 2 was more hydrophilic compared to 1, was enough to be prepared in high concentration solution of more than 100 mu M in saline for an intravesical instillation drug. Moreover, serum concentration of 2 was comparable to that of 1, an oral preparation drug, after oral administration at 32 mg/kg (Fig. 3). Both of 1 and 2 showed broad-spectrum anti-cancer activities in vitro, for example, 1 and 2 showed inhibitory activity IC50 = 21.1 mu M and 17.2 mu M for DU145, human prostate cancer cells, respectively, and IC50 = 18.5 mu M and 10.5 mu M for T24 cells, human bladder cancer cells. In this study, we estimated anticancer effects of 2 in a bladder cancer model after intravesical administration similar to clinical cases. A single intravesical administration of 2 exhibited the most potent inhibitory activities among the clinical drugs for bladder cancers, BCG and Pirarubicin, without obvious side effects and toxicity (Fig. 4). Thus, HUHS190 (2) can be effective for patients after post-TURBT therapy of bladder cancer without side effects, unlike the currently available clinical drugs.

  DOI：

  10.1016/j.bmcl.2019.126744
• 作为产物：
  描述：

  1,4-二羟基萘 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 水 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 1-Benzyloxy-4-hydroxynaphthalene
  参考文献：
  名称：

  Synthesis of enantiomeric 4-hydroxypropranolols from 1,4-dihydroxynaphthalene

  摘要：

  Both (R)- and (S)-enantiomes of 4-hydroxypropranolol were effectively prepared from 1,4-dihydroxynaphthalene in eight steps. The overall yields were around 30%. (C) 2001 Elsevier Science Ltd. All rights, reserved.

  DOI：

  10.1016/s0957-4166(01)00122-7

文献信息

• One step hair coloring compositions using salts
  申请人：Unilever Home & Personal Care USA, Division of Conopco, Inc.

  公开号：US20040019980A1

  公开（公告）日：2004-02-05

  A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.

  一种染发组合物，包括以下两种组分，这两种组分在涂抹到头发之前混合： (a) 包括水溶性过氧化氧化剂的组合物；和 (b) 包括从芳香二胺、氨基酚、萘酚、多羟基酚、邻苯二酚和它们的混合物中选择的一种或多种氧化染发剂的组合物；其中包括一种或多种氧化染发剂的组合物进一步包括至少一种水溶性碳酸盐释放盐；和可选地一种水溶性铵盐。
• Synthese von potentiellen Naftopidil-Metaboliten
  作者：Bernhard Kutscher、Jürgen Engel、Ilona Fleischhauer、Georg Niebch

  DOI：10.1002/ardp.19933261007

  日期：——

  Es wird über die Synthese von vier potentiellen Metaboliten [Desmethyl‐Naftopidil (1), 4‐(Phenyl)‐hydroxy‐Naftopidil (2), 4‐(Naphthyl)‐hydroxy‐Naftopidil (3), Desanaphthyl‐Naftopidil (4)] des selektiven α1‐Antagonisten Naftopidil berichtet.

  它是通过四种潜在代谢物的合成来描述的 [desmethyl-naftopidil (1), 4- (phenyl)-hydroxy-naftopidil (2), 4- (naphthyl)-hydroxy-naftopidil (3), desanaphthyl-naftopidil (4) ] 选择性 α1 拮抗剂萘哌地尔。
• Piperazine derivatives, uses thereof and pharmaceutical compositions
  申请人：Boehringer Mannheim GmbH

  公开号：US05037828A1

  公开（公告）日：1991-08-06

  The present invention provides compounds of the general formula: ##STR1## wherein R.sub.1 is a hydroxyl group or a methoxy radical, R.sub.2 is a hydrogen atom or a hyroxyl group and R.sub.3 is a hydrogen atom or a hydroxyl group, with the proviso that R.sub.2 and R.sub.3 are not simultaneously hydrogen atoms when R.sub.1 is a methoxy radical; and the pharmacologically acceptable salts thereof. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them.

  本发明提供了一类通式为##STR1##的化合物，其中R1是羟基或甲氧基，R2是氢原子或羟基，R3是氢原子或羟基，但条件是当R1为甲氧基时，R2和R3不同时为氢原子；以及这些化合物的药学上可接受的盐。本发明还提供了制备这些化合物的方法和含有这些化合物的药物组合物。
• Enhanced color deposition for hair with sequestering agents
  申请人：Unilever Home & Personal Care USA, Division of Conopco, Inc.

  公开号：US20030135935A1

  公开（公告）日：2003-07-24

  Hair coloring compositions which comprise: (A) non-nitrogenous chelating agents from the group consisting of polyphosphate; phosphonates; hydroxycarboxylates; polyacrylates; zeolite; and mixtures thereof; (B) an oxidative dye primary intermediate; and (C) an oxidative dye coupler; (D) and water are described. The present invention also relates to a method for coloring hair which comprises contacting said hair with a hair coloring composition as described above.

  描述了包括以下成分的染发配方：(A) 来自聚磷酸盐、膦酸盐、羟基羧酸盐、聚丙烯酸盐、沸石及其混合物等组成的非氮螯合剂；(B) 一种氧化染料的主要中间体；和(C) 一种氧化染料偶联剂；(D) 以及水。本发明还涉及一种染发方法，该方法包括将头发与上述描述的染发配方接触。
• Benzannelated derivatives, their manufacture and use as pharmaceutical agents
  申请人：Ackermann Jean

  公开号：US20050096336A1

  公开（公告）日：2005-05-05

  There are presented compounds of the formula wherein R 6 and R 7 is R 4 and R 5 or R 5 and R 6 together with the carbon atoms to which they are attached, form a ring as defined in the description and X 1 , X 2 , Y 1 to Y 4 , R 1 to R 13 and n are as specified in the description, and to all enantiomers and pharmaceutically acceptable salts and/or esters thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by PPARδ and/or PPARα agonists.

  提供了式中的化合物，其中R6和R7是R4和R5或R5和R6连同它们所连接的碳原子形成一个如描述中定义的环，并且X1、X2、Y1至Y4、R1至R13和n如描述中所指定的，并且包括所有的对映体和药用可接受的盐和/或酯。本发明还涉及含有这类化合物的药物组合物，以及用于治疗和/或预防由PPARδ和/或PPARα激动剂调节的疾病的方法。