2-amino-dodecanoic acid methyl ester | 135312-85-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-amino-dodecanoic acid methyl ester
• 英文别名: 2-Amino-dodecansaeure-methylester；2-Amino-laurinsaeure-methylester；Methyl 2-aminododecanoate
• CAS: 135312-85-5
• 化学式: C₁₃H₂₇NO₂
• 分子量: 229.363
• InChiKey: RVTLMGSZWNZFCA-UHFFFAOYSA-N

物化性质

• 熔点：
  241-242 °C (decomp)
• 沸点：
  293.4±13.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-dodecanoic acid methyl ester 在 sodium methylate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 2-(N-(4-(β-D-glucopyranosylamino)succinyl))amino-D,L-dodecanoic acid
  参考文献：
  名称：

  红霉素和卡那霉素抗生素与脂糖两亲性离子对的合成，表征及体外评价

  摘要：

  亲水离子削皮策略（HIP）是一种探索方法，旨在改善吸附不良的药物在细胞/组织中的吸收并优化其理化特性。在这种情况下，我们在这里描述了两种模型阳离子抗生素，红霉素（ERY）和卡那霉素A（KAN）的一些离子对的合成，其中脂糖具有不同的亲脂性和电荷水平。通过傅里叶变换红外光谱（FT-IR），差示扫描量热法（DSC）和粉末X射线衍射（PXRD）分析确认了药物-脂糖复合物的形成。 通过测量化合物对一组对母体抗生素敏感或具有抗性的细菌菌株的最小抑制浓度（MIC），来评估两亲脂糖部分对ERY和KAN抗菌活性的影响。尽管未发现MIC值降低，但离子对并未降低体外抗生素活性。实验结果将激发该离子对策略在药物设计中的未来研究，例如，允许提高亲水性抗生素在脂质基纳米载体中的包封效率，或改变其体内生物分布和药代动力学特征。

  DOI：

  10.1016/j.ejmech.2016.04.074
• 作为产物：
  描述：

  2-Brom-dodecansaeure-methylester 在 氨 、 水 作用下， 生成 2-amino-dodecanoic acid methyl ester
  参考文献：
  名称：

  CERTAIN AMINO DERIVATIVES OF LAURIC ACID

  摘要：

  DOI：

  10.1021/ja01359a026

文献信息

• Development and characterization of anionic liposaccharides for enhanced oral drug delivery
  作者：Adel S. Abdelrahim、Pavla Simerska、Istvan Toth

  DOI：10.1016/j.ijpharm.2012.04.018

  日期：2012.7

  The aim of this study was to synthesize charged amphoteric molecules, which after complexation with poorly bioavailable drugs would have the potential to improve their oral uptake. Novel anionic liposaccharide derivatives containing d-glucose and lipoamino acids were synthesized by solution phase peptide synthesis. High sensitivity isothermal titration microcalorimetry was used to determine the critical

  这项研究的目的是合成带电荷的两性分子，将其与生物利用度较差的药物复合后，有可能改善其口服吸收能力。通过溶液相肽合成法合成了含有d-葡萄糖和脂氨基酸的新型阴离子脂糖衍生物。使用高灵敏度等温滴定微量热法测定临界聚集浓度和热力学曲线。研究了脂糖的溶血和细胞毒性活性，结果表明，脂糖在口服给药的浓度下是无毒的。将模型药物妥布霉素与含有两种脂质的脂糖混合，在200 nm左右形成聚集体，从而增加妥布霉素在正辛醇/水之间的分配。
• Process for reacting a carboxylic acid ester
  申请人：Evonik Operations GmbH

  公开号：US10745721B2

  公开（公告）日：2020-08-18

  The invention provides a process for reacting a carboxylic acid ester of the formula (I) R1-A-COOR2  (I), wherein R1 is hydrogen, —CH2OH, —CHO, —COOR3, —CH2SH, —CH2OR3 or —CH2NH2, R2 is an alkyl group, R3 is hydrogen or an alkyl group, and A is a substituted, unsubstituted, linear, branched and/or cyclic alkylene, alkenylene, arylene or aralkylene radical having at least 4 carbons, in the presence of a cell. The process comprises a) contacting the cell with said carboxylic acid ester in an aqueous solution, wherein the cell is a recombinant cell which has reduced activity of a polypeptide comprising SEQ ID NO: 2 or a variant thereof over the wild-type cell.

  本发明提供了一种使式 (I) 羧酸酯发生反应的工艺 R1-A-COR2 (I)、 其中 R1 是氢、-CH2OH、-CHO、-COOR3、-CH2SH、-CH2OR3 或 -CH2NH2，R2 是烷基，R3 是氢或烷基，A 是取代的、未取代的、直链的、支链的和/或环状的亚 烷基、亚烯基、亚芳基或芳烷基，至少有 4 个碳原子。该过程包括 a) 使细胞与水溶液中的所述羧酸酯接触，其中细胞是重组细胞，与野生型细胞相比，其包含 SEQ ID NO: 2 或其变体的多肽的活性降低。
• Small molecule agents, compositions, and formulations, for internal use, displaying inhibitory activity against gram-positive and/or gram-negative organisms
  申请人：NATUREZA, INC.

  公开号：US11351134B2

  公开（公告）日：2022-06-07

  Active components comprising lauric acid, or a lauric acid derivative, are utilized independently, or in combination, to provide new and useful compositions for bacteriostatic action against susceptible pathogens. The lauric acid derivative includes one or more of 12-aminododecanoic acid, 12-amino-1-dodecanoic acid methyl ester, sucrose monolaurate, 12-(7-nitrobenzofurazan-4-ylamino) dodecanoic acid, 4-nitrophenyl dodecanoate, 1-lauroyl-rac-glycerol, 3-oxo-N-(2-oxocyclohexyl) dodecanamide, butyl laurate, benzyl laurate, isoamyl laurate, monolaurin, isopropyl laurate, pentyl laurate, and hexyl laurate. A preparation includes combining the active component with lecithin, and after an initial processing phase, coating with chitosan or a carrier. Final compositions may be or may contain particles, such as nanoparticles. Final compositions, or formulations containing said final compositions, may be utilized internally, causing one or more membrane changes (e.g., a membrane of an internal target pathogen, which may or may not be an antibiotic-resistant pathogen). At least some compositions inhibit growth of one or more Gram-positive bacterial species and one or more Gram-negative bacterial species.

  由月桂酸或月桂酸衍生物组成的活性成分可单独使用，也可组合使用，以提供对易感病原体具有抑菌作用的新型有用组合物。月桂酸衍生物包括 12-氨基十二烷酸、12-氨基-1-十二烷酸甲酯、蔗糖单月桂酸酯、12-（7-硝基苯并呋喃-4-基氨基）十二烷酸中的一种或多种、月桂酸丁酯、月桂酸苄酯、月桂酸异戊酯、月桂酸单月桂酯、月桂酸异丙酯、月桂酸戊酯和月桂酸己酯。制备方法包括将活性成分与卵磷脂结合，经过初始加工阶段后，涂上壳聚糖或载体。最终组合物可以是或可以包含颗粒，如纳米颗粒。最终组合物或含有所述最终组合物的制剂可在内部使用，引起一种或多种膜变化（例如，内部目标病原体的膜，可以是也可以不是抗生素抗性病原体）。至少有些组合物能抑制一种或多种革兰氏阳性细菌和一种或多种革兰氏阴性细菌的生长。
• Analogues of Thiolactomycin as Potential Antimalarial Agents
  作者：Simon M. Jones、Jonathan E. Urch、Marcel Kaiser、Reto Brun、John L. Harwood、Colin Berry、Ian H. Gilbert

  DOI：10.1021/jm049067d

  日期：2005.9.1

  Analogues of the natural antibiotic thiolactomycin (TLM), an inhibitor of the condensing reactions of type II fatty acid synthase, were synthesized and evaluated for their ability to inhibit the growth of the malaria parasite Plasmodium falciparum. Alkylation of the C4 hydroxyl group led to the most significant increase in growth inhibition (over a 100-fold increase in activity compared to TLM). To investigate the mode of action, the P. falciparum KASIII enzyme was produced for inhibitor assay. A number of TLM derivatives were identified that showed improved inhibition of this enzyme compared to TLM. Structure-activity relationships for enzyme inhibition were identified for some series of TLM analogues, and these also showed weak correlation with inhibition of parasite growth, but this did not hold for other series. On the basis of the lack of a clear correlation between inhibition of pfKASIII activity and parasite growth, we conclude that pfKASIII is not the primary target of TLM analogues. Some of the analogues also inhibited the growth of the parasitic protozoa Trypanosoma cruzi, T. brucei, and Leishmania donovani.
• Zeelen; Havinga, Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 267,271
  作者：Zeelen、Havinga

  DOI：——

  日期：——