6-(benzyloxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde | 847585-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(benzyloxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde
• 英文别名: 6-(Benzyloxy)-3,4-dihydro-1-methylnaphthalene-2-carbaldehyde；1-methyl-6-phenylmethoxy-3,4-dihydronaphthalene-2-carbaldehyde
• CAS: 847585-91-5
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: XWWFLXSLPQMCDU-UHFFFAOYSA-N

物化性质

• 沸点：
  444.3±45.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde 在 茴香硫醚 、 偶氮二甲酰胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-methyl-6-(3-phenylbutoxy)-3,4-dihydronaphthalene-2-carbaldehyde
  参考文献：
  名称：

  Structure–activity relationship studies of S1P agonists with a dihydronaphthalene scaffold

  摘要：

  Structure-activity relationship (SAR) of sphingosine-1-phosphate receptor agonists with a dihydronaphthalene scaffold was investigated. Compound 1 was modified to improve S1P(1) agonistic activity and in vivo peripheral lymphocyte lowering (PLL) activity without impairing selectivity over S1P(3) agonistic activity. A detailed SAR study of the terminal lipophilic part revealed that the introduction of substituents on the propylene linker and the terminal benzene ring influences in vitro and PLL activities. Compound 6n bearing a (S)-methyl group at the 2-position on the propylene linker and chlorine at the para-position on the terminal benzene ring showed potent hS1P(1) agonistic activity with excellent selectivity over hS1P(3) and in vivo PLL activity in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.048
• 作为产物：
  描述：

  6-羟基-1-四氢萘酮 在 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 6-(benzyloxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde
  参考文献：
  名称：

  TW2021/14983

  摘要：

  公开号：

文献信息

• Compound Having S1P Receptor Binding Potency and Use Thereof
  申请人：Habashita Hiromu

  公开号：US20080207584A1

  公开（公告）日：2008-08-28

  Provided are: a compound represented by formula (I): (wherein ring A and ring D each represent a cyclic group which may have a substituent(s); E and G each represent a bond or a spacer having 1 to 8 atoms in its main chain; L represents a hydrogen atom or a substituent; X represents amino which may have a substituent(s), or a heterocyclic group which contains at least one nitrogen atom and which may have a substituent(s); n represents 0 to 3, in which when n is 2 or more, a plurality of ring A's may be the same or different from one another); a salt thereof; an N-oxide form thereof; a solvate thereof, a prodrug thereof; and a medicament which includes those. The compound represented by formula (I) is capable of binding S1P receptors (in particular, EDG-1 and/or EDG-6), and useful for preventing and/or treating rejection in transplantation, autoimmune diseases, allergic diseases, etc.

  提供的是一个由式(I)表示的化合物：其中，环A和环D分别表示可以具有取代基的环状基团；E和G分别表示具有1至8个原子的主链上的键或间隔物；L表示氢原子或取代基；X表示可以具有取代基的氨基或含有至少一个氮原子且可以具有取代基的杂环基团；n表示0至3，在其中当n为2或更多时，多个环A可以相同或不同。还提供了该化合物的盐、N-氧化物形式、溶剂化物、前药和包括其的药物。该化合物能够结合S1P受体（特别是EDG-1和/或EDG-6），并用于预防和/或治疗移植排斥、自身免疫性疾病、过敏性疾病等。
• Compound capable of binding s1p receptor and pharmaceutical use thereof
  申请人：Nakade Shinji

  公开号：US20070167425A1

  公开（公告）日：2007-07-19

  A compound having an ability to bind to an S 1 P receptor (particularly EDG-6, preferably EDG-1 and EDG-6), for example, the compound represented by formula (I) of the present invention, a salt thereof, a solvate thereof or a prodrug thereof is useful for prevention and/or treatment of rejection of transplantation, graft-versus-host disease, autoimmune disease, allergic disease and the like. wherein ring A is a cyclic group; ring B is a cyclic group which may have substituent(s); X is a spacer having 1 to 8 atoms in its main chain, etc.; Y is a spacer having 1 to 10 atoms in its main chain, etc.; n is 0 or 1, wherein when n is 0, m is 1 and R 1 is a hydrogen atom or a substituent, and wherein when n is 1, m is 0 or an integer of 1 to 7 and R 1 is a substituent, and wherein m is 2 or more, R 1 s are the same or different.

  一种具有结合S1P受体的能力的化合物（特别是EDG-6，最好是EDG-1和EDG-6），例如本发明的式（I）所表示的化合物，其盐，溶剂合物或前药，对于预防和/或治疗移植排斥，移植物抗宿主病，自身免疫性疾病，过敏性疾病等是有用的。其中，环A是一个环状基团；环B是一个可能具有取代基的环状基团；X是具有1至8个原子的主链的间隔物等；Y是具有1至10个原子的主链的间隔物等；n为0或1，其中当n为0时，m为1且R1是氢原子或取代基，当n为1时，m为0或1至7的整数且R1是取代基，当m为2或更多时，R1相同或不同。
• COMPOUND HAVING S1P RECEPTOR BINDING POTENCY AND USE THEREOF
  申请人：HABASHITA Hiromu

  公开号：US20120064060A1

  公开（公告）日：2012-03-15

  Provided are: a compound represented by formula (I): (wherein ring A and ring D each represent a cyclic group which may have a substituent(s); E and G each represent a bond or a spacer having 1 to 8 atoms in its main chain; L represents a hydrogen atom or a substituent; X represents amino which may have a substituent(s), or a heterocylic group which contains at least one nitrogen atom and which may have a substituent(s); n represents 0 to 3, and when n is 2 or more, a plurality of ring A's may be the same or different from one another); a salt, an N-oxide form, a solvate, or a prodrug thereof; and a medicament which includes those. The compound of formula (I) is capable of binding S1P receptors (in particular, EDG-1 and/or EDG-6), and useful for preventing and/or treating rejection in transplantation, autoimmune diseases, allergic diseases, etc.

  提供了一个由式(I)表示的化合物：（其中，环A和环D分别表示可能具有取代基的环状基团；E和G分别表示具有1-8个原子的主链中的键或间隔物；L表示氢原子或取代基；X表示氨基，可能具有取代基，或者含有至少一个氮原子且可能具有取代基的杂环基团；n表示0-3，当n为2或更多时，多个环A可以相同或不同）。还提供了该化合物的盐、N-氧化物形式、溶剂合物或前药；以及包括这些的药物。式(I)化合物能够结合S1P受体（特别是EDG-1和/或EDG-6），用于预防和/或治疗移植排斥、自身免疫性疾病、过敏性疾病等。
• Azetidinecarboxylic acid derivative and medicinal use thereof
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP2371811A2

  公开（公告）日：2011-10-05

  A compound represented by the formula (IC-2), a salt thereof, an N-oxide form thereof, a solvate thereof, a prodrug thereof, or a number of specific compounds and pharmaceutical compositions comprising these compounds. The compound has the ability to combine with an SIP receptor (especially EDG-1, EDG-6 and/or EDG-8). It is useful for the prevention and/or treatment of rejection reactions to transplantation, graft versus host diseases, autoimmune diseases, allergic diseases, neurodegenerative diseases etc.

  由式（IC-2）代表的化合物、其盐、其 N-氧化物形式、其溶液剂、其原药或一些特定化合物以及包含这些化合物的药物组合物。该化合物具有与 SIP 受体（尤其是 EDG-1、EDG-6 和/或 EDG-8）结合的能力。它可用于预防和/或治疗移植排斥反应、移植物抗宿主疾病、自身免疫性疾病、过敏性疾病、神经退行性疾病等。
• DIHYDRONAPHTHALENE DERIVATIVE
  申请人：ONO Pharmaceutical Co., Ltd.

  公开号：EP3228615A1

  公开（公告）日：2017-10-11

  A compound shown by general formula (I) (in the formula, all of the symbols are as defined in the specification) has selective S1P5 receptor agonist activity due to having a linker from a phenyl group to a cyclic substituent in a dihydronaphthalene skeleton; i.e., due to having a short linker of one atom or less as L in general formula (I), and can therefore serve as an agent for the treatment of S1P5-mediated diseases, e.g., neurodegenerative diseases such as schizophrenia.

  通式(I)所示化合物 (式中，所有符号如说明书中所定义）具有选择性 S1P5 受体激动剂活性，这是由于在二氢萘骨架中具有从苯基到环状取代基的连接基；即由于具有通式（I）中 L 所示的一个原子或更少的短连接基，因此可作为治疗 S1P5 介导的疾病（如精神分裂症等神经退行性疾病）的药物。