4,4'-(naphthalene-1,4-diyl)bis(butan-1-ol) | 1417745-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,4'-(naphthalene-1,4-diyl)bis(butan-1-ol)
• 英文别名: 4-[4-(4-Hydroxybutyl)naphthalen-1-yl]butan-1-ol；4-[4-(4-hydroxybutyl)naphthalen-1-yl]butan-1-ol
• CAS: 1417745-47-1
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: XQMOVIGHRNZOCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-(naphthalene-1,4-diyl)bis(butan-1-ol) 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到naphthalene-1,4-diylbis(butane-4,1-diyl)bis(4-methylbenzenesulfonate)
  参考文献：
  名称：

  New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation

  摘要：

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).

  DOI：

  10.1021/jm3014585
• 作为产物：
  描述：

  1,4-二溴代萘 在 copper(l) iodide 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4,4'-(naphthalene-1,4-diyl)bis(butan-1-ol)
  参考文献：
  名称：

  New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation

  摘要：

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).

  DOI：

  10.1021/jm3014585

文献信息

• NOVEL MONOMERS FROM BIOMASS
  申请人：SIBI Mukund P.

  公开号：US20170233325A1

  公开（公告）日：2017-08-17

  Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.

  从生物质中提取的化合物，例如纤维素和木质素，以及形成这些化合物和聚合物以及使用这些化合物形成的产品的方法。
• Monomers from biomass
  申请人：Sibi Mukund P.

  公开号：US11220475B2

  公开（公告）日：2022-01-11

  Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.

  从生物质（如纤维素和木质素）中提取的化合物、形成此类化合物的方法以及使用此类化合物形成的聚合物和产品。
• [EN] NOVEL MONOMERS FROM BIOMASS<br/>[FR] NOUVEAUX MONOMÈRES DÉRIVÉS DE BIOMASSE
  申请人：SIBI MUKUND P

  公开号：WO2016022943A2

  公开（公告）日：2016-02-11

  Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.
• New Bis-thiazolium Analogues as Potential Antimalarial Agents: Design, Synthesis, and Biological Evaluation
  作者：Sergio A. Caldarelli、Siham El Fangour、Sharon Wein、Christophe Tran van Ba、Christian Périgaud、Alain Pellet、Henri J. Vial、Suzanne Peyrottes

  DOI：10.1021/jm3014585

  日期：2013.1.24

  Bis-thiazolium salts are able to inhibit phosphatidylcholine biosynthesis in Plasmodium and to block parasite proliferation in the low nanomolar range. However, due to their physicochemical properties (i.e., permanent cationic charges, the flexibility, and lipophilic character of the alkyl chain), the oral bioavailability of these compounds is low. New series of bis-thiazolium-based drugs have been designed to overcome this drawback. They feature linker rigidification via the introduction of aromatic rings and/or a decrease in the overall lipophilicity through the introduction of heteroatoms. On the basis of the structure-activity relationships, a few of the promising compounds (9, 10, and 11) were found to exhibit potent antimalarial in vitro and in vivo activities (EC50 < 10 nM and ED50 ip < 0.7 mg/kg).