4-benzooxazol-2-ylmethyl-phenol | 135135-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 4-benzooxazol-2-ylmethyl-phenol
• 英文别名: 2-(4-hydroxybenzyl)benzoxazole；4-(1,3-Benzoxazol-2-ylmethyl)phenol
• CAS: 135135-47-6
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: NXLLFCMGJXLFKO-UHFFFAOYSA-N

物化性质

• 沸点：
  412.5±28.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzooxazol-2-ylmethyl-phenol 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 3-(1-(3-(4-(benzo[d]oxazol-2-ylmethyl)phenoxy)propyl)piperidin-4-yl)-6-fluoro-benzo[d]isoxazole
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of piperidine (piperazine)-substituted benzoxazole derivatives as multi-target antipsychotics

  摘要：

  The present study describes the optimization of a series of novel benzoxazole-piperidine (piperazine) derivatives combining high dopamine D-2 and serotonin 5-HT1A, 5-HT2A receptor affinities. Of these derivatives, the pharmacological features of compound 29 exhibited high affinities for the DA D-2, 5-HT1A and 5-HT2A receptors, but low affinities for the 5-HT2C and histamine H-1 receptors and human ether-a-go-go-related gene (hERG) channels. Furthermore, compound 29 reduced apomorphine-induced climbing and 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI)-induced head twitching without observable catalepsy, even at the highest dose tested. Thus, compound 29 is a promising candidate as a multi-target antipsychotic treatment. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.045
• 作为产物：
  描述：

  在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 4-benzooxazol-2-ylmethyl-phenol
  参考文献：
  名称：

  LTA4H modulators and uses thereof

  摘要：

  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。

  公开号：

  US20080194630A1

文献信息

• [EN] BENZIMIDAZOLE, BENZTHIAZOLE AND BENZOXAZOLE DERIVATIVES AND THEIR USE AS LTA4H MODULATORS<br/>[FR] DERIVES DE BENZIMIDAZOLE, DE BENZTHIAZOLE ET DE BENZOXAZOLE ET UTILISATION DE CEUX-CI COMME MODULATEURS LTA4H
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005012296A1

  公开（公告）日：2005-02-10

  Leukotriene A4 hydrolase (LTA4H) inhibitors of formula I, compositions containing them, and their use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation, wherein X is selected from the group consisting of NR5, O, and S, with R5 being one of the H and CH3; Y is selected from the group consisting of CH2 and O; R4 is selected from the group consisting of H, OCH3, Cl, F, Br, I, OH, NH2, CN, CF3.

  白三烯A4水解酶（LTA4H）的抑制剂I式，含有它们的组合物，以及它们用于抑制LTA4H酶活性和治疗、预防或抑制炎症和/或与炎症相关疾病的用途，其中X从NR5、O和S组成的组中选择，其中R5是H和CH3中的一个；Y从CH2和O组成的组中选择；R4从H、O 、Cl、F、Br、I、OH、NH2、CN、CF3组成的组中选择。
• Heterocyclic compound
  申请人：Mitsubishi Kasei Corporation

  公开号：US05206255A1

  公开（公告）日：1993-04-27

  A novel heterocyclic compound represented by the following formula (I): ##STR1## wherein X represents an oxygen atom or sulfur atom; R.sup.1 represents a hydrogen atom or halogen atom; R.sup.2 represents a C.sub.4 -C.sub.6 alkyl group, C.sub.2 -C.sub.10 alkoxyalkyl group, C.sub.3 -C.sub.15 alkenyl group, C.sub.7 -C.sub.12 aralkyl group, C.sub.8 -C.sub.18 aralkyloxyalkyl group, C.sub.7 -C.sub.12 aryloxyalkyl group, C.sub.3 -C.sub.10 alkynyl group, C.sub.4 -C.sub.12 alkadienyl group, C.sub.6 -C.sub.18 alkatrienyl group, C.sub.6 -C.sub.12 alkadiynyl group, or C.sub.6 -C.sub.12 alkatriynyl group, said aryloxyalkyl group, alkynyl group, alkadienyl group, alkatrienyl group, alkadiynyl group and alkatriynyl group being capable of having at least one substituent selected from the group consisting of halogen atoms, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 halogenated alkyl group, phenyl group, hydroxyl group and C.sub.1 -C.sub.4 alkoxy group; and each of R.sup.3 and R.sup.4 independently represents a hydrogen atom, C.sub.1 -C.sub.6 alkyl group, phenyl group or tolyl group, or R.sup.3 and R.sup.4 may be combined together to from a benzene ring which may have at least one halogen atom; or a pharmaceutically acceptable salt thereof. The compound according to the present invention has an effect of inhibiting lipoxygenase and suppresses the formation of leukotrienes and, accordingly, useful for the prevention and treatment of inflammation, rheumatism and various allergic diseases.

  一种新的杂环化合物，其化学式如下（I）：##STR1## 其中X代表氧原子或硫原子；R.sup.1代表氢原子或卤原子；R.sup.2代表C.sub.4 -C.sub.6烷基，C.sub.2 -C.sub.10烷氧烷基，C.sub.3 -C.sub.15烯基，C.sub.7 -C.sub.12芳基烷基，C.sub.8 -C.sub.18芳基氧烷基，C.sub.7 -C.sub.12芳氧烷基，C.sub.3 -C.sub.10炔基，C.sub.4 -C.sub.12烷二烯基，C.sub.6 -C.sub.18烷三烯基，C.sub.6 -C.sub.12烷二炔基或C.sub.6 -C.sub.12烷三炔基，其中所述芳氧烷基，炔基，烷二烯基，烷三烯基，烷二炔基和烷三炔基能够具有至少一个取代基，所述取代基选择自卤原子，C.sub.1 -C.sub.4烷基，C.sub.1 -C.sub.4卤代烷基，苯基，羟基和C.sub.1 -C.sub.4烷氧基；每个R.sup.3和R.sup.4独立地代表氢原子，C.sub.1 -C.sub.6烷基，苯基或对甲苯基，或R.sup.3和R.sup.4可以结合在一起形成一个苯环，该苯环可以具有至少一个卤原子；或其药学上可接受的盐。根据本发明的化合物具有抑制脂氧合酶并抑制白三烯形成的作用，因此对于预防和治疗炎症、风湿病和各种过敏疾病非常有用。
• [EN] BENZIMIDAZOLE, BENZTHIAZOLE AND BENZOXAZOLE DERIVATIVES AND THEIR USE AS LTA4H MODULATORS<br/>[FR] DERIVES DE BENZIMIDAZOLE, BENZTHIAZOLE AND BENZOXAZOLE ET LEUR UTILISATION EN TANT QUE MODULATEURS DE LTA4H
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005012297A1

  公开（公告）日：2005-02-10

  Leukotriene A4 hydrolase (LTA4H) inhibitors of Formula (I), compositions containing them, and their use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation. Wherein X is selected from the group consisting of NR5, O, and S, with R5 being on of H and CH3; Y is selected from the group consisting; W is selected from the group consisting Of CH2 and CHR1-CH2, with R1 being one H and OH, wherein R1-attached carbon member in said CHR1-CH2 is not directly attached; R4 is selected from the group consisting of H, OCH3, CI, F Br, OH, NH2, CN, CF3 and CH3; R6 is H or F; and R2 and R3 are each independently selected from various groups.

  Leukotriene A4水解酶（LTA4H）的Formula（I）抑制剂，含有它们的组合物以及它们用于抑制LTA4H酶活性和治疗、预防或抑制炎症和/或与炎症相关疾病的用途。其中X选择自NR5，O和S组，其中R5是H和CH3之一; Y选择自组中，W选择自CH2和CHR1- 组，其中R1是H和OH之一，其中所述CHR1- 中的R1-连接碳成员不直接连接; R4选择自H，O ，CI，F Br，OH，NH2，CN，CF3和 组; R6是H或F; R2和R3各自独立地选择自各种组。
• LTA4H Modulators
  申请人：Axe U. Frank

  公开号：US20050043379A1

  公开（公告）日：2005-02-24

  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.

  Leukotriene 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/或与炎症相关的病症的使用方法。
• LTA4H modulators
  申请人：Axe U. Frank

  公开号：US20050043378A1

  公开（公告）日：2005-02-24

  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.

  Leukotriene 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使用方法。