DCPLA甲酯 | 56687-67-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: DCPLA甲酯
• 英文名称: methyl 8-(2-((2-pentylcyclopropyl)methyl)cyclopropyl)octanoate
• 英文别名: Methyl 8-[2-[(2-pentylcyclopropyl)methyl]cyclopropyl]octanoate
• CAS: 56687-67-3
• 化学式: C₂₁H₃₈O₂
• 分子量: 322.532
• InChiKey: WSVAMWHCPDAWFM-UHFFFAOYSA-N

物化性质

• 沸点：
  376.7±10.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：15.62 mg/ml（48.43 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  -20°C，密封保存于干燥处

制备方法与用途

生物活性：DCPLA-ME（DCPLA 甲酯）是 DCPLA 的甲酯形式，是一种有效的 PKCε 激活剂。它可用于研究神经退行性疾病。

靶点

• PKCε

反应信息

• 作为反应物：
  描述：

  DCPLA甲酯 在 lithium aluminium tetrahydride 、 草酰氯 、 三氯化硼 、 二甲基亚砜 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design and synthesis of protein kinase C epsilon selective diacylglycerol lactones (DAG-lactones)

  摘要：

  DAG-lactones afford a synthetically accessible, high affinity platform for probing structure activity relationships at the Cl regulatory domain of protein kinase C (PKC). Given the central role of PKC isoforms in cellular signaling, along with their differential biological activities, a critical objective is the design of isoform selective ligands. Here, we report the synthesis of a series of DAG-lactones varying in their side chains, with a particular focus on linoleic acid derivatives. We evaluated their selectivity for PKC epsilon versus PKC alpha both under standard lipid conditions (100% phosphatidylserine, PS) as well as in the presence of a nuclear membrane mimetic lipid mixture (NML). We find that selectivity for PKC epsilon versus PKC alpha tended to be enhanced in the presence of the nuclear membrane mimetic lipid mixture and, for our lead compound, report a selectivity of 32-fold. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.025
• 作为产物：
  描述：

  二碘甲烷 、 亚油酸甲酯 在 diethylzinc 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到DCPLA甲酯
  参考文献：
  名称：

  Design and synthesis of protein kinase C epsilon selective diacylglycerol lactones (DAG-lactones)

  摘要：

  DAG-lactones afford a synthetically accessible, high affinity platform for probing structure activity relationships at the Cl regulatory domain of protein kinase C (PKC). Given the central role of PKC isoforms in cellular signaling, along with their differential biological activities, a critical objective is the design of isoform selective ligands. Here, we report the synthesis of a series of DAG-lactones varying in their side chains, with a particular focus on linoleic acid derivatives. We evaluated their selectivity for PKC epsilon versus PKC alpha both under standard lipid conditions (100% phosphatidylserine, PS) as well as in the presence of a nuclear membrane mimetic lipid mixture (NML). We find that selectivity for PKC epsilon versus PKC alpha tended to be enhanced in the presence of the nuclear membrane mimetic lipid mixture and, for our lead compound, report a selectivity of 32-fold. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.025

文献信息

• [EN] PKC ACTIVATORS AND COMBINATIONS THEREOF<br/>[FR] ACTIVATEURS DE PKC ET DES COMBINAISONS DE CEUX-CI
  申请人：BRNI NEUROSCIENCES INST

  公开号：WO2013071282A1

  公开（公告）日：2013-05-16

  The present disclosure relates to PKC activators and combinations thereof. The disclosure further relates to compositions, kits, uses, and methods thereof.

  本公开涉及PKC激活剂及其组合物。本公开进一步涉及其组成物、试剂盒、用途和方法。
• [EN] ESTERS OF DCPLA AND METHODS OF TREATMENT USING THE SAME<br/>[FR] ESTERS DE DCPLA ET MÉTHODES DE TRAITEMENT LES UTILISANT
  申请人：BRNI NEUROSCIENCES INST

  公开号：WO2013071281A1

  公开（公告）日：2013-05-16

  The present disclosure relates to esters of 8-[2-(2-pentyl- cyclopropylmethyl)cyclopropyl]-octanoic acid ("DCPLA"). The disclosure further relates to compositions, kits, and methods for treatment using the esters.

  本公开涉及8-[2-(2-戊基-环丙基甲基)环丙基]-辛酸酯（"DCPLA"）的酯类化合物。该公开还涉及使用这些酯类化合物进行治疗的组合物、试剂盒和方法。
• PKC activators and combinations thereof
  申请人：Cognitive Research Enterprises, Inc.

  公开号：US10821079B2

  公开（公告）日：2020-11-03

  The present disclosure relates to PKC activators and combinations thereof. The disclosure further relates to compositions, kits, uses, and methods thereof.

  本公开涉及PKC激活剂及其组合物。该公开进一步涉及这些组合物的组成、试剂盒、用途和方法。
• [EN] HALOGENATED ESTERS OF CYCLOPROPANATED UNSATURATED FATTY ACIDS FOR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] ESTERS HALOGÉNÉS D'ACIDES GRAS INSATURÉS CYCLOPROPANÉS POUR UTILISATION DANS LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：BRNI NEUROSCIENCES INST

  公开号：WO2015058191A1

  公开（公告）日：2015-04-23

  The present disclosure describes novel PKC-ε activators chosen from halogenated esters of unsaturated fatty acids and derivatives thereof, including halogenated esters of both polyunsaturated and monunsaturated fatty acids and derivatives thereof. The disclosure further relates to compositions, kits, and methods for treatment using the halogenated esters.

  本公开描述了从卤代酯类不饱和脂肪酸及其衍生物中选择的新型PKC-ε激活剂，包括多不饱和脂肪酸和单不饱和脂肪酸的卤代酯及其衍生物。该公开还涉及使用这些卤代酯的组合物、试剂盒和治疗方法。
• [EN] CARBOXYLIC ACID COMPOUND HAVING CYCLOPROPANE RING<br/>[FR] COMPOSE D'ACIDE CARBOXYLIQUE AYANT UN CYCLE DE CYCLOPROPANE
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2002050013A1

  公开（公告）日：2002-06-27

  A carboxylic acid compound having cyclopropane ring(s) of the formula (I): wherein R is alkyl or alkenyl optionally having one or more 1,2-cyclopropylene in a carbon chain and/or optionally having cyclopropyl at the end of a chain,X is a single bond or alkylene, wherein the total number of carbon less the number of cyclopropane ring is 10-25, and a pharmaceutically acceptable salt thereof are provided. The compound (I) shows an LTP-like potentiation of synaptic transmission, allows slow metabolism in the living body, shows a stable LTP-like potentiation of synaptic transmission, and is useful as an agent for LTP-like potentiation of synaptic transmission, a cognition-enhancing drug or an agent for the prophylaxis and treatment of dementia, a learning and memory disorder and a neurotransmitter release disorder.

  提供一种具有环丙烷环的羧酸化合物的公式（I）：其中R是烷基或烯基，可选地具有一个或多个1,2-环丙烯基在碳链中和/或在链的末端可选地具有环丙基，X是单键或烷基，其中碳数减去环丙烷环的数量为10-25，并提供其药学上可接受的盐。化合物（I）表现出类似LTP的突触传递增强作用，可以在活体内缓慢代谢，表现出稳定的类似LTP的突触传递增强作用，并且可用作LTP样突触传递增强剂、增强认知药物或预防和治疗痴呆、学习和记忆障碍以及神经递质释放障碍的药剂。