3-lauroylamino-1,2-propanediol | 92866-80-3

• 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: 3-lauroylamino-1,2-propanediol
• 英文别名: N-(2,3-dihydroxy-propyl)-lauramide；N-Lauroyl-β.γ-dioxy-propylamin；N-Lauroyl-(γ-amino-propylenglykol)；N-(2,3-Dihydroxy-propyl)-lauramid；3-Lauroylamino-1.2-dioxy-propan；N-(2,3-dihydroxypropyl)dodecanamide
• CAS: 92866-80-3
• 化学式: C₁₅H₃₁NO₃
• 分子量: 273.416
• InChiKey: BCBJXCMEFUOEJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-lauroylamino-1,2-propanediol 在 吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(3-hydroxy-2-octoxypropyl)dodecanamide
  参考文献：
  名称：

  Structure—activity relationships for enhancement of paracellular permeability by 2-alkoxy-3-alkylamidopropylphosphocholines across Caco-2 cell monolayers

  摘要：

  The oral route is the preferred route of delivery for a large number of drug molecules. However, the intestinal epithelium presents a formidable barrier for delivery of drugs into systemic circulation. Phospholipids are among compounds that enhance the absorption of drugs across the intestinal epithelium. In this paper, we describe structure-activity relationships for phospholipid derivatives as enhancers of paracellular permeability across Caco-2 cell monolayers. in a series of 2-alkoxy-3-alkylamidopropylphosphocholine derivatives, compounds with a long chain at C-3 (R-3) and short chain at C-2 (R-2) were potent in causing a decrease in transepithelial electrical resistance (TEER) and an increase in mannitol transport, but also showed significant cytotoxicity. Compounds with 9-11 carbons at C-3 and 6-10 carbons at C-2 provided good separation (up to 2.7-fold) between activity and cytotoxicity. Notably, a good correlation (r(2) = 0.93) was observed between EC50 (TEER) [concentration that caused a drop in TEER to 50% of its control (untreated) value] and EC10X (mannitol) [concentration that caused 10-fold increase in mannitol transport over the control (untreated) value], confirming that a decrease in TEER is associated with enhanced permeability of the hydrophilic compounds across Caco-2 cell monolayers. Compounds with medium to long carbon chains at C-2 and C-3, and the total carbons in the alkyl chains > 20, showed poor activity and no cytotoxicity.

  DOI：

  10.1021/js9900957
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 3-lauroylamino-1,2-propanediol
  参考文献：
  名称：

  Bergmann; Sabetay, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1924, vol. 137, p. 52

  摘要：

  DOI：

文献信息

• Continuous lipase-catalyzed production of pseudo-ceramides in a packed-bed bioreactor
  作者：Florian Le Joubioux、Nicolas Bridiau、Mehdi Sanekli、Marianne Graber、Thierry Maugard

  DOI：10.1016/j.molcatb.2014.08.022

  日期：2014.11

  a two-step continuous enzymatic process with immobilized Candida antarctica lipase B (Novozym® 435) in a packed-bed bioreactor. The first step involved the selective N-acylation of 3-amino-1,2-propanediol using stearic acid as the first acyl donor (i). This was followed by the selective O-acylation of the N-stearyl 3-amino-1,2-propanediol synthesized in the first step, with myristic acid as the second

  神经酰胺是鞘脂化合物，在制药和化妆品工业中作为活性成分都非常有吸引力。在这项研究中，神经酰胺类似物的合成，即所谓的伪神经酰胺，进行了使用首次与固定的两步连续酶促过程念珠菌antarcti CA脂肪酶B（诺维信®在填充床435）生物反应器。第一步涉及使用硬脂酸作为第一酰基供体（i）对3-氨基-1，2-丙二醇进行选择性N-酰化。随后是第一步中合成的N-硬脂基3-氨基-1,2-丙二醇的选择性O-酰化反应，以肉豆蔻酸作为第二个酰基供体，生成N，O-二酰基3-氨基-1，2-丙二醇型假神经酰胺，即1- O-肉豆蔻基，3- N-硬脂基3-氨基-1，2-丙二醇（ii）。首先通过评估三个因素的影响对工艺进行优化：进料流速，生物催化剂的量和底物浓度。在最佳条件下，酰胺合成产率为92％，令人满意的生产率为3.15 mmol h -1  g生物催化剂-1（1128 mg h -1  g生物催化剂-1）。第二步，N-酰基3-氨基-1
• Methods and compositions for the treatment of respiratory syncytial virus
  申请人：Kucera S. Louis

  公开号：US20050187191A1

  公开（公告）日：2005-08-25

  The invention includes compounds useful for inhibiting RSV replication and treating a host infected with RSV. The invention also includes methods of treating a host infected with RSV by administering to the host an anti-RSV effective amount of a compound of the invention.

  该发明包括用于抑制RSV复制和治疗感染RSV的宿主的化合物。该发明还包括通过向宿主施用该发明的化合物的抗RSV有效量来治疗感染RSV的宿主的方法。
• One‐Step Biocatalytic Synthesis of Sustainable Surfactants by Selective Amide Bond Formation**
  作者：Max Lubberink、William Finnigan、Christian Schnepel、Christopher R. Baldwin、Nicholas J. Turner、Sabine L. Flitsch

  DOI：10.1002/anie.202205054

  日期：2022.7.25

  route to commercially important surfactants is presented. A truncated construct of carboxylic acid reductase (CARmm-A) catalyzes amide bond formation between fatty acids and amino alcohols with no esterification observed. The wide substrate scope of the enzyme, co-factor recycling, reaction engineering and up-scaling show the feasibility of this method for synthesis.

  提出了一种获得商业上重要的表面活性剂的酶促途径。截短的羧酸还原酶构建体 (CAR mm -A) 催化脂肪酸和氨基醇之间形成酰胺键，未观察到酯化反应。该酶的广泛底物范围、辅因子回收、反应工程和放大显示了该合成方法的可行性。
• Structure—activity relationships for enhancement of paracellular permeability by 2-alkoxy-3-alkylamidopropylphosphocholines across Caco-2 cell monolayers
  作者：Dong-Zhou Liu、Susan L. Morris-Natschke、Louis S. Kucera、Khalid S. Ishaq、Dhiren R. Thakker

  DOI：10.1021/js9900957

  日期：1999.11

  The oral route is the preferred route of delivery for a large number of drug molecules. However, the intestinal epithelium presents a formidable barrier for delivery of drugs into systemic circulation. Phospholipids are among compounds that enhance the absorption of drugs across the intestinal epithelium. In this paper, we describe structure-activity relationships for phospholipid derivatives as enhancers of paracellular permeability across Caco-2 cell monolayers. in a series of 2-alkoxy-3-alkylamidopropylphosphocholine derivatives, compounds with a long chain at C-3 (R-3) and short chain at C-2 (R-2) were potent in causing a decrease in transepithelial electrical resistance (TEER) and an increase in mannitol transport, but also showed significant cytotoxicity. Compounds with 9-11 carbons at C-3 and 6-10 carbons at C-2 provided good separation (up to 2.7-fold) between activity and cytotoxicity. Notably, a good correlation (r(2) = 0.93) was observed between EC50 (TEER) [concentration that caused a drop in TEER to 50% of its control (untreated) value] and EC10X (mannitol) [concentration that caused 10-fold increase in mannitol transport over the control (untreated) value], confirming that a decrease in TEER is associated with enhanced permeability of the hydrophilic compounds across Caco-2 cell monolayers. Compounds with medium to long carbon chains at C-2 and C-3, and the total carbons in the alkyl chains > 20, showed poor activity and no cytotoxicity.
• US7344868B2
  申请人：——

  公开号：US7344868B2

  公开（公告）日：2008-03-18