4-(5-methoxymethoxy-8-hydroxynaphthalen-1-yloxy)naphth-1-ol | 728033-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(5-methoxymethoxy-8-hydroxynaphthalen-1-yloxy)naphth-1-ol
• 英文别名: 8-(4-Hydroxynaphthalen-1-yl)oxy-4-(methoxymethoxy)naphthalen-1-ol
• CAS: 728033-34-9
• 化学式: C₂₂H₁₈O₅
• 分子量: 362.382
• InChiKey: JVIMTGHCKDTMMG-UHFFFAOYSA-N

物化性质

• 沸点：
  622.7±55.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-methoxymethoxy-8-hydroxynaphthalen-1-yloxy)naphth-1-ol 在 4 A molecular sieve 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.75h， 生成 8-Hydroxyspiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-3,4'-naphthalene]-1'-one
  参考文献：
  名称：

  Natural product based inhibitors of the thioredoxin–thioredoxin reductase system

  摘要：

  斯匹罗酮缩萘并十氢化萘可通过基于巴顿碱的乌尔曼联萘醚偶联反应、达金反应和超氧化碘螺环化反应方便地组装。核心结构可通过烯酮加成和斯蒂尔偶联反应进一步多样化。通过这种方法制备了纳摩尔级的硫氧还/硫氧还还原酶氧化还原控制系统抑制剂，并与一系列天然产物分离物进行了比较。在MCF-7细胞试验中的细胞毒性范围从IC50的1.6到>100 μM。

  DOI：

  10.1039/b402431a
• 作为产物：
  描述：

  4,8-二羟基萘-1-甲醛 在 sodium tetrahydroborate 、 2-叔丁基-1,1,3,3-四甲基胍 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 20.5h， 生成 4-(5-methoxymethoxy-8-hydroxynaphthalen-1-yloxy)naphth-1-ol
  参考文献：
  名称：

  Natural product based inhibitors of the thioredoxin–thioredoxin reductase system

  摘要：

  斯匹罗酮缩萘并十氢化萘可通过基于巴顿碱的乌尔曼联萘醚偶联反应、达金反应和超氧化碘螺环化反应方便地组装。核心结构可通过烯酮加成和斯蒂尔偶联反应进一步多样化。通过这种方法制备了纳摩尔级的硫氧还/硫氧还还原酶氧化还原控制系统抑制剂，并与一系列天然产物分离物进行了比较。在MCF-7细胞试验中的细胞毒性范围从IC50的1.6到>100 μM。

  DOI：

  10.1039/b402431a

文献信息

• Small molecules against cancer
  申请人：Biokine Therapeutics Ltd.

  公开号：US10646465B2

  公开（公告）日：2020-05-12

  Compounds capable of, or usable in, killing cancer cells, and/or modulating a biological activity of a chemokine, and/or inhibiting a kinase, and/or treating diseases and disorders associated with a biological activity of a chemokine and/or cell migration, and/or treating disease and disorders such as cancer and inflammatory diseases and disorders, are provided herein. The compounds are listed in Tables 2, 4 and 5, and/or are represented by Formulae I, IV, V and VI, as defined in the specification. Methods utilizing these compounds are also provided.

  本文提供的化合物能够或可用于杀死癌细胞，和/或调节趋化因子的生物活性，和/或抑制激酶，和/或治疗与趋化因子的生物活性和/或细胞迁移相关的疾病和紊乱，和/或治疗疾病和紊乱，如癌症和炎症性疾病和紊乱。这些化合物列于表 2、表 4 和表 5 中，和/或由式 I、式 IV、式 V 和式 VI 表示，如说明书中所定义。还提供了利用这些化合物的方法。
• SMALL MOLECULES AGAINST CANCER
  申请人：Biokine Therapeutics Ltd.

  公开号：US20190240188A1

  公开（公告）日：2019-08-08

  Compounds capable of, or usable in, killing cancer cells, and/or modulating a biological activity of a chemokine, and/or inhibiting a kinase, and/or treating diseases and disorders associated with a biological activity of a chemokine and/or cell migration, and/or treating disease and disorders such as cancer and inflammatory diseases and disorders, are provided herein. The compounds are listed in Tables 2, 4 and 5, and/or are represented by Formulae I, IV, V and VI, as defined in the specification. Methods utilizing these compounds are also provided.
• [EN] SMALL MOLECULES AGAINST CANCER<br/>[FR] PETITES MOLÉCULES CONTRE LE CANCER
  申请人：BIOKINE THERAPEUTICS LTD

  公开号：WO2017103931A1

  公开（公告）日：2017-06-22

  Compounds capable of, or usable in, killing cancer cells, and/or modulating a biological activity of a chemokine, and/or inhibiting a kinase, and/or treating diseases and disorders associated with a biological activity of a chemokine and/or cell migration, and/or treating disease and disorders such as cancer and inflammatory diseases and disorders, are provided herein. The compounds are listed in Tables 2, 4 and 5, and/or are represented by Formulae I, IV, V and VI, as defined in the specification. Methods utilizing these compounds are also provided.
• Natural product based inhibitors of the thioredoxin–thioredoxin reductase system
  作者：Peter Wipf、Stephen M. Lynch、Anne Birmingham、Giselle Tamayo、Allan Jiménez、Nefertiti Campos、Garth Powis

  DOI：10.1039/b402431a

  日期：——

  Spiroketal naphthodecalins are readily assembled by Barton's base mediated Ullmann binaphthyl ether coupling, Dakin reactions and hypervalent iodine spirocyclization. The core structures can be further diversified by enone addition and Stille coupling reactions. Nanomolar inhibitors for the Trx/TrxR redox control system were prepared by this approach and compared to series of natural product isolates. Cytotoxicity in MCF-7 cell assays ranged from an IC50 of 1.6 to >100 µM.

  斯匹罗酮缩萘并十氢化萘可通过基于巴顿碱的乌尔曼联萘醚偶联反应、达金反应和超氧化碘螺环化反应方便地组装。核心结构可通过烯酮加成和斯蒂尔偶联反应进一步多样化。通过这种方法制备了纳摩尔级的硫氧还/硫氧还还原酶氧化还原控制系统抑制剂，并与一系列天然产物分离物进行了比较。在MCF-7细胞试验中的细胞毒性范围从IC50的1.6到>100 μM。