2-ethoxy-1-hexadecanol | 104548-62-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-ethoxy-1-hexadecanol
• 英文别名: (d,l)-2-ethoxyhexadecanol；2-ethoxyhexadecanol；2-Ethoxyhexadecan-1-OL
• CAS: 104548-62-1
• 化学式: C₁₈H₃₈O₂
• 分子量: 286.499
• InChiKey: PYTRBIZZZGFMSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethoxy-1-hexadecanol 在 吡啶 、 水 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 5.58h， 生成 rac-(2-ethoxyhexadec-1-yl)phosphocholine
  参考文献：
  名称：

  Antitumor activity of (2-alkoxyalkyl)- and (2-alkoxyalkenyl)phosphocolines

  摘要：

  Analogues of the synthetic antitumor phospholipid ALP (1-octadecyl-2-methyl-sn-glycero-3-phosphocholine; alkyl lysophospholipid) in which the 1-ether oxygen atom has been removed have been prepared and evaluated for in vitro and in vivo anticancer activity. Compounds are presented in which the saturated long chain varies in length from 8 to 25 carbon atoms. Sites of unsaturation are also incorporated into the framework in some examples. In particular, rac-(2-ethoxyeicosyl)phosphocholine (10) displays the best in vivo activity of the chemical series against a variety of transplanted tumors and activates murine peritoneal macrophages to express tumor cytotoxicity in vitro. However, 10 does not offer the wide spectrum of antitumor activity we feel necessary to warrant further study.

  DOI：

  10.1021/jm00162a009

文献信息

• Therapeutically active substituted saturated and mono-and
  申请人：Astra Nutrition AB

  公开号：US04046914A1

  公开（公告）日：1977-09-06

  Pharmaceutical preparations containing alkyl and alkenyl glycerol ethers substituted in the side chain and esters thereof having the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different in each is selected from the group consisting of hydrogen and aliphatic acyl groups of at most 24 carbon atoms, one of R.sup.3 and R.sup.4 being hydrogen and the other being selected from the group consisting of straight, branched, saturated and unsaturated alkoxy groups of at most seven carbon atoms, and R.sup.5 is selected from the group consisting of straight, branched, alkyl and alkenyl groups of 4-21 carbon atoms. The compounds are useful as antibiotics in the treatment of infectious diseases and for inhibiting the growth of tumors.

  含有烷基和烯基甘油醚的药物制剂，其侧链被取代的酯类具有下列一般式：##STR1## 其中R.sup.1和R.sup.2在每个分子中相同或不同，选择自羟基和最多24个碳原子的脂肪酰基组成的群体，R.sup.3和R.sup.4中的一个是氢，另一个选择自直链、支链、饱和和不饱和最多七个碳原子的烷氧基组成的群体，R.sup.5选择自4-21个碳原子的直链、支链、烷基和烯基群体组成的群体。这些化合物在治疗感染性疾病和抑制肿瘤生长方面可用作抗生素。
• US4046914A
  申请人：——

  公开号：US4046914A

  公开（公告）日：1977-09-06
• US4659859A
  申请人：——

  公开号：US4659859A

  公开（公告）日：1987-04-21
• Antitumor activity of (2-alkoxyalkyl)- and (2-alkoxyalkenyl)phosphocolines
  作者：Rosanne Bonjouklian、Michael L. Phillips、Kathy M. Kuhler、Gerlad B. Grindey、Gerald A. Poore、Richard M. Schultz、Marilyn G. Altom

  DOI：10.1021/jm00162a009

  日期：1986.12

  Analogues of the synthetic antitumor phospholipid ALP (1-octadecyl-2-methyl-sn-glycero-3-phosphocholine; alkyl lysophospholipid) in which the 1-ether oxygen atom has been removed have been prepared and evaluated for in vitro and in vivo anticancer activity. Compounds are presented in which the saturated long chain varies in length from 8 to 25 carbon atoms. Sites of unsaturation are also incorporated into the framework in some examples. In particular, rac-(2-ethoxyeicosyl)phosphocholine (10) displays the best in vivo activity of the chemical series against a variety of transplanted tumors and activates murine peritoneal macrophages to express tumor cytotoxicity in vitro. However, 10 does not offer the wide spectrum of antitumor activity we feel necessary to warrant further study.