16-(tritylmercapto)hexadecanoic acid | 678139-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 16-(tritylmercapto)hexadecanoic acid
• 英文别名: 16-Tritylsulfanylhexadecanoic acid
• CAS: 678139-83-8
• 化学式: C₃₅H₄₆O₂S
• 分子量: 530.815
• InChiKey: LSJALUPRPARPQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  38
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16-(tritylmercapto)hexadecanoic acid 在 三乙基硅烷 、 氯化亚砜 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 9.0h， 生成 16-Mercaptohexadecyl 2-(trimethylammonio)ethyl phosphate
  参考文献：
  名称：

  Synthesis of 16-mercaptohexadecylphosphocholine, a miltefosine analog with leishmanicidal activity

  摘要：

  The alkylphosphocholine miltefosine (n-hexadecylphosphocholine, NIT) has been introduced recently as a very effective drug for the oral treatment of human leishmaniasis. However, the parasiticidal mechanism of MT at a molecular level is far from being understood. Here we report the synthesis and biological characterization of 16-mercaptohexadecylphosphocholine, a thiol analog of MT which was designed to facilitate the search of NIT interacting targets within the parasite by a variety of analytical methods. This analog presents the same leishmanicidal effect as the parent drug against Leishmania donovani promastigotes and Leishmania pifanoi axenic amastigotes, and has been used to develop an affinity chromatography method to attempt the isolation of putative Leishmania proteins that bind to the phosphocholine part of the molecule. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.004
• 作为产物：
  描述：

  16-巯基十六烷基酸 、 三苯基氯甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以60%的产率得到16-(tritylmercapto)hexadecanoic acid
  参考文献：
  名称：

  Synthesis of 16-mercaptohexadecylphosphocholine, a miltefosine analog with leishmanicidal activity

  摘要：

  The alkylphosphocholine miltefosine (n-hexadecylphosphocholine, NIT) has been introduced recently as a very effective drug for the oral treatment of human leishmaniasis. However, the parasiticidal mechanism of MT at a molecular level is far from being understood. Here we report the synthesis and biological characterization of 16-mercaptohexadecylphosphocholine, a thiol analog of MT which was designed to facilitate the search of NIT interacting targets within the parasite by a variety of analytical methods. This analog presents the same leishmanicidal effect as the parent drug against Leishmania donovani promastigotes and Leishmania pifanoi axenic amastigotes, and has been used to develop an affinity chromatography method to attempt the isolation of putative Leishmania proteins that bind to the phosphocholine part of the molecule. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.004

文献信息

• PRODRUGS CONTAINING ALBUMIN BINDING PROBE
  申请人：Yeda Research and Development Co. Ltd.

  公开号：EP2437786B1

  公开（公告）日：2016-05-18
• [EN] PRODRUGS CONTAINING ALBUMIN BINDING PROBE<br/>[FR] PROMÉDICAMENTS CONTENANT UNE SONDE SE LIANT À L'ALBUMINE
  申请人：YEDA RES & DEV

  公开号：WO2010140148A1

  公开（公告）日：2010-12-09

  The present invention provides albumin-binding probes capable of reversibly linking to short-lived amiho-containing drugs and non-covalently associating with albumin in-vivo, thereby converting said drugs into inactive reactivable prodrugs having prolonged lifetime in-vivo. The invention further provides conjugates of said probes with amino-containing drugs, as well as pharmaceutical compositions and uses thereof.