(2S,3R)-2-(二苄基氨基)十八烷-3-醇 | 247067-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2S,3R)-2-(二苄基氨基)十八烷-3-醇
• 英文名称: (2S,3R)-2-(dibenzylamino)octadecan-3-ol
• 英文别名: (2S,3R)-2-(N,N-Dibenzylamino)-3-octadecanol
• CAS: 247067-43-2
• 化学式: C₃₂H₅₁NO
• 分子量: 465.763
• InChiKey: AUGRPIHBMZBMKB-BHDXBOSCSA-N

物化性质

• 沸点：
  561.2±30.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(二苄基氨基)十八烷-3-醇 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以84%的产率得到1-脱氧鞘氨醇(m18：0)
  参考文献：
  名称：

  Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols

  摘要：

  An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.010
• 作为产物：
  描述：

  (S)-(+)-2-(二苄氨基)-1-丙醇 在 草酰氯 、 二甲基亚砜 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2S,3R)-2-(二苄基氨基)十八烷-3-醇
  参考文献：
  名称：

  Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols

  摘要：

  An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.010

文献信息

• Spisulosine compounds
  申请人：The Board of Trustees of the University of Illinois

  公开号：US06107520A1

  公开（公告）日：2000-08-22

  The present invention is directed to the isolation and bioactive characterization of compounds isolated from the clam Spisula polynyma. These compounds include three sphingoid-type bases, spisulosines 285, 299 and 313 (1-3), each of which shows unique cytotoxicity against L1210 murine lymphocytic leukemia cells. In addition, sphingosine (also referred to as 4-sphingenine or octadeca-4-shpingenine, 4) and two related compounds, nonadeca-4-sphingenine (a one carbon longer homolog, 5) and sphinga-4,10-diene (a dehydrosphingosine deravitive, 6) were also obtained, These compounds also contribute to the cytotoxicity of the Spisula polynyma extracts, but did not cause the morphology changes observed with compounds 1-3.

  本发明涉及从Spisula polynyma蛤蜊中分离和生物活性表征的化合物。这些化合物包括三种鞘氨醇类碱，spisulosines 285、299和313（1-3），每种化合物对L1210小鼠淋巴细胞白血病细胞表现出独特的细胞毒性。此外，还获得了鞘氨醇（也称为4-鞘氨醇或辛十八烷-4-鞘氨醇，4）和两种相关化合物，即辛十九烷-4-鞘氨醇（一种碳原子更长的同系物，5）和鞘氨醇-4,10-二烯（一种去氢鞘氨醇衍生物，6）。这些化合物也对Spisula polynyma提取物的细胞毒性有贡献，但不会引起观察到的化合物1-3的形态学变化。
• [EN] SPISULOSINE COMPOUNDS HAVING ANTITUMOUR ACTIVITY<br/>[FR] COMPOSES DE SPISULOSINE PRESENTANT UNE ACTION ANTITUMORALE
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：WO1999052521A1

  公开（公告）日：1999-10-21

  (EN) Investigation of the activity of extracts of the clam $i(Spisula polynyma) has led to antitumour long-chain, straight-chain alkane or alkene compounds which have a 2-amino group and a 3-hydroxy group.(FR) L'étude de l'activité d'extraits de la mye $i(Spisula polynyma) a permis d'identifier des composés alcanes ou alcènes à chaîne longue et ramifiée, présentant un groupe 2-amino et un groupe 3-hydroxy.

  对于蛤蜊 $i(Spisula polynyma) 提取物活性的研究已经发现了具有抗肿瘤作用的长链、直链烷或烯化合物，这些化合物具有2-氨基和3-羟基官能团。
• COMPOSITIONS AND METHODS COMPRISING LONG-CHAIN, STRAIGHT-CHAIN 2-AMINO-3- HYDROXYALKANES
  申请人：Rinehart L. Kenneth

  公开号：US20060183806A9

  公开（公告）日：2006-08-17

  Investigation of the activity of extracts of the clam Spisula polynyma has led to antitumour long-chain, straight-chain alkane or alkene compounds which have a 2-amino group and a 3-hydroxy group.

  对蛤蜊Spisula polynyma提取物活性的研究表明，含有2-氨基和3-羟基的长链、直链烷或烯化合物具有抗肿瘤活性。
• Long-chain, straight-chain 2-amino-3-hydroxyalkanes
  申请人：Rinehart L. Kenneth

  公开号：US20060235082A1

  公开（公告）日：2006-10-19

  Investigation of the activity of extracts of the clam Spisula polynyma has led to antitumor long-chain, straight-chain alkane compounds which have a 2-amino group and a 3-hydroxy group. Compositions and methods comprising an isolated and purified long-chain, straight-chain 2-amino-3-hydroxyalkane, or prodrug thereof, and a pharmaceutically acceptable carrier are also described, wherein the carbon chain in the long-chain, straight-chain 2-amino-3-hydroxyalkane is C 16 -C 24 .

  对Spisula polynyma蛤的提取物活性的研究已经发现了具有2-氨基和3-羟基的抗肿瘤长链直链烷化合物。还描述了包含分离和纯化的长链直链2-氨基-3-羟基烷或其前药及药学可接受载体的组合物和方法，其中长链直链2-氨基-3-羟基烷中的碳链为C16-C24。
• Self-assembling nanoparticles of dually hydrophobic prodrugs constructed from camptothecin analogue for cancer therapy
  作者：Yixuan Zhang、Ruijuan Yin、Guanzhao Wu、Mingming Yu、Jiannan Liu、Xueting Wang、Xuemeng Liu、Huashi Guan、Rilei Yu、Tao Jiang

  DOI：10.1016/j.ejmech.2020.112365

  日期：2020.8

  Nanomedicines have shown success in cancer therapy in recent years because of their excellent solubility in aqueous solution and drug accumulation through controlled release in tumor tissues, but the preparation of most nanomedicines still requires ionic materials, surfactants or the amphiphilic structure to maintain nanoparticle stability and function. In this study, we developed a couple of novel dually hydrophobic prodrugs (DHPs) by combining two hydrophobic compounds through different linkers and elaborated their self-assembly mechanisms by virtue of computational simulation. Importantly, without using any excipients, FL-2 NPs exhibited significantly prolonged retention in blood circulation and displayed a remarkable anti-tumor effect at very low concentration in vivo. Both DHPs consisted of camptothecin structural analogue(FL118) and a marine natural product (ES-285). Comparative experiments proved that these compounds could quickly form nanoparticles by way of simple preparation and remained relatively stable for long periods in PBS. FL-2 NPs linked with a disulphide bond could rapidly release bioactive FL118 after being triggered by endogenous reductive stimulus to exert anti-cancer effects. Overall, this study provides a new strategy for design of therapeutic nanomedicines consisting of dually hydrophobic molecules for cancer therapy. (C) 2020 Elsevier Masson SAS. All rights reserved.