benzyl ester of L-carnitine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl ester of L-carnitine
• 英文别名: L-carnitine benzyl ester；benzyl-l-carnitine；[(2R)-2-hydroxy-4-oxo-4-phenylmethoxybutyl]-trimethylazanium
• 化学式: C₁₄H₂₂NO₃
• 分子量: 252.334
• InChiKey: HYJJJTPUNRDJLK-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl ester of L-carnitine 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 naproxen-l-carnitine
  参考文献：
  名称：

  左旋肉碱药物结合物的合成及体外表征，其为靶向人Octn2的潜在前药

  摘要：

  目的是评估与左旋肉碱结合的药物作为靶向有机阳离子/肉碱转运蛋白（OCTN2）的前药的潜力。评价了二十二种左旋肉碱类似物对人类有机阳离子/肉碱转运蛋白（hOCTN2）的抑制作用；发现3'-羟基是l-肉碱上的三个官能团（即3'-羟基，胺和羧酸盐）中唯一不有助于l-肉碱与hOCTN2相互作用的官能团。因此，将1-肉碱上的3'-羟基选择为缀合物位点。合成了三种药物-1-肉碱共轭物（即丙戊酰基-1-肉碱，萘普生-1-肉碱和酮洛芬-1-肉碱）以及两个酮洛芬类似物，后者在酮洛芬和左旋肉碱（即，酮洛芬-乙醇酸-1-肉碱和酮洛芬-甘氨酸-1-肉碱）。对这些潜在的前药的体外抑制，转运和代谢特性进行了评估。三种药物-1-肉碱共轭物和酮洛芬-甘氨酸-1-肉碱均是OCTN2抑制剂，也是底物。对于丙戊基-1-肉碱，K（i）= 155±19μM，K（m）= 132±23μM，归一化J（max）= 0.467±0.028;

  DOI：

  10.1002/jps.22557
• 作为产物：
  描述：

  溴甲苯 、 左旋肉碱 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 benzyl ester of L-carnitine
  参考文献：
  名称：

  一类L-肉毒碱两亲性衍生物及其修饰的纳米 粒及其用途

  摘要：

  本发明属于药物制剂新辅料和新剂型领域，涉及一类L‑肉毒碱两亲性衍生物及其修饰的纳米粒。还涉及L‑肉毒碱衍生物及其修饰的纳米粒的制备，及其L‑肉毒碱衍生物作为药物递送载体在脑部药物递送方面的应用。本发明利用血脑屏障和脑胶质瘤表面高表达的OCTN2转运体作为靶点，合成L‑肉毒碱两亲性衍生物，采用物理镶嵌的方法修饰纳米粒使其表面携带L‑肉毒碱，以生物相容性好的高分子材料为基础载体，包载抗肿瘤药物后制成基于OCTN2转运体的脑胶质瘤靶向药物递送系统，用于提高纳米载体的脑内分布及脑胶质瘤治疗效果。所述的两亲性化合物结构如下：

  公开号：

  CN107519496B

文献信息

• 基于肠道上皮细胞顶侧OCTN2转运体的口服 靶向纳米粒
  申请人：沈阳药科大学

  公开号：CN107176911B

  公开（公告）日：2019-07-26

  本发明属于药物制剂新辅料和新剂型领域，涉及一种肠道上皮细胞顶侧OCTN2转运体的底物L‑肉毒碱的衍生物和相应靶向纳米粒的制备，及其作为口服药物载体在药物传递方面的应用。本发明所述的硬脂酰‑L肉毒碱由OCTN2转运体底物L‑肉毒碱和硬脂酸组成的两亲性化合物，是一种稳定性好的用于构建OCTN2靶向纳米药物传递系统的靶向配基。所述的硬脂酸可以为十八酸、十六酸、十四酸等长链脂肪酸。所述的两亲性化合物的结构式如下：
• Combination of <scp>l</scp>-Carnitine with Lipophilic Linkage-Donating Gemcitabine Derivatives as Intestinal Novel Organic Cation Transporter 2-Targeting Oral Prodrugs
  作者：Gang Wang、Hongxiang Chen、Dongyang Zhao、Dawei Ding、Mengchi Sun、Longfa Kou、Cong Luo、Dong Zhang、Xiulin Yi、Jinhua Dong、Jian Wang、Xiaohong Liu、Zhonggui He、Jin Sun

  DOI：10.1021/acs.jmedchem.7b00049

  日期：2017.3.23

  Novel organic cation transporter 2 (OCTN2, SLC22A5) is responsible for the uptake of carnitine through the intestine and, therefore, might be a promising molecular target for designing oral prodrugs. Poor permeability and rapid metabolism have greatly restricted the oral absorption of gemcitabine. We here describe the design of intestinal OCTN2-targeting prodrugs of gemcitabine by covalent coupling of L-carnitine to its N4-amino group via different lipophilic linkages. Because of the high OCTN2 affinity, the hexane diacid-linked prodrug demonstrated significantly improved stability (3-fold), cellular permeability (15-fold), and oral bioavailability (5-fold), while causing no toxicity as compared to gemcitabine. In addition, OCTN2-targeting prodrugs can simultaneously improve the permeability, solubility, and metabolic stability of gemcitabine. In summary, we present the first evidence that OCTN2 can act as a new molecular target for oral prodrug delivery and, importantly, the linkage carbon chain length is a key factor in modifying the affinity of the substrate for OCTN2.
• Carnitine Conjugates of Adamantanamines and Neramexane Derivatives as Dual Prodrugs for Various Uses
  申请人：Goel Om P.

  公开号：US20090246267A1

  公开（公告）日：2009-10-01

  This invention concerns compounds of adamantanamines and neramexane, including their pharmaceutically-acceptable salts, diesterioisomers, and formulations for treating Alzheimer's related dementias, depression, AIDS related dementias, as antivirals, inflammatory diseases such as rheumatoid arthritis, and cerebral ischemia, hyperlipidemia, and diabetes.
• CARNITINE CONJUGATES OF ADAMANTANAMINES DERIVATIVES AS DUAL PRODRUGS FOR VARIOUS USES
  申请人：Goel Om P.

  公开号：US20110212166A1

  公开（公告）日：2011-09-01

  This invention concerns compounds of adamantanamines and neramexane, including their pharmaceutically-acceptable salts, diesterioisomers, and formulations for treating Alzheimer's related dementias, depression, AIDS related dementias, as antivirals, inflammatory diseases such as rheumatoid arthritis, and cerebral ischemia, hyperlipidemia, and diabetes.
• USE OF GAMMA-QUATERNARY AMMONIUM BUTYRATE COMPOUND IN PREPARATION OF AN ANIMAL FEED ADDITIVE
  申请人：Peng Xianfeng

  公开号：US20220132889A1

  公开（公告）日：2022-05-05

  Provided is an application of a γ-quaternary ammonium butyrate compound having formula (I) or a racemate, a stereoisomer, a geometric isomer, a tautomer, a solvate, or a feed-acceptable salt thereof in preparing an animal feed additive, the compound being added to the daily feed of animals at a certain concentration ratio, and being capable of increasing the average daily weight gain of animals under the same food intake conditions, having no significant effect on the daily feed intake of the animals, and reducing the feed-to-meat ratio. The γ-quaternary ammonium butyrate compound disclosed herein can effectively increase the rate of daily weight gain of the animals and improve the growth performance of the animals, having no side effects on the animals, being stable and safe, and improving the production efficiency of the breeding industry whilst ensuring the health of the animals.