8,8'-imino-di-octanoic acid | 101434-84-8

• 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: 8,8'-imino-di-octanoic acid
• 英文别名: Bis-(7-carboxy-heptyl)-amin；8,8'-Imino-di-octansaeure；8-(7-Carboxyheptylamino)octanoic acid
• CAS: 101434-84-8
• 化学式: C₁₆H₃₁NO₄
• 分子量: 301.426
• InChiKey: VWNPUEAYRIUTTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8,8'-imino-di-octanoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 8-{tert-Butoxycarbonyl-[7-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-heptyl]-amino}-octanoic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Hydrophobicity versus activity in crosslinked interfacial peptide inhibitors of HIV-1 protease

  摘要：

  Crosslinked peptides with amino functionality incorporated within the tethering moiety 2a-c, 3a-c were synthesized and tested as interfacial inhibitors of HIV-1 protease. As part of a strategy to develop the novel method of dissociative inhibition as a viable pharmacological approach, compounds were made to test hydrophobicity and size requirements of the tethering moiety. In the case of crosslinked interfacial peptide inhibitors of HIV-1 protease, hydrophilic 2a-c and bulky hydrophobic 3a-c tethers decreased effectiveness by approximately 10- and 2-fold, respectively. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00572-7
• 作为产物：
  描述：

  8-溴辛酸乙酯 在 sodium hydroxide 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 8,8'-imino-di-octanoic acid
  参考文献：
  名称：

  Hydrophobicity versus activity in crosslinked interfacial peptide inhibitors of HIV-1 protease

  摘要：

  Crosslinked peptides with amino functionality incorporated within the tethering moiety 2a-c, 3a-c were synthesized and tested as interfacial inhibitors of HIV-1 protease. As part of a strategy to develop the novel method of dissociative inhibition as a viable pharmacological approach, compounds were made to test hydrophobicity and size requirements of the tethering moiety. In the case of crosslinked interfacial peptide inhibitors of HIV-1 protease, hydrophilic 2a-c and bulky hydrophobic 3a-c tethers decreased effectiveness by approximately 10- and 2-fold, respectively. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00572-7

文献信息

• IONIZABLE CATIONIC LIPID FOR RNA DELIVERY
  申请人：Arcturus Therapeutics, Inc.

  公开号：US20150141678A1

  公开（公告）日：2015-05-21

  What is described is a compound of formula (1) wherein R 1 and R 2 are the same or different, each a linear or branched alkyl with 1-9 carbons, or an alkenyl or alkynyl with 2 to 11 carbon atoms; L 1 and L 2 are the same or different, each a linear alkyl having 5 to 18 carbon atoms, or form a heterocycle with N; X 1 is a bond, or is —CO—O— whereby L 2 -CO—O—R 2 is formed; X 2 is S or O; L 3 is a bond or a lower alkyl, or form a heterocycle with N; R 3 is a lower alkyl; and R 4 and R 5 are the same or different, each a lower alkyl; or a pharmaceutically acceptable salt thereof.

  所描述的化合物为公式（1）的化合物，其中R1和R2相同或不同，均为具有1-9个碳原子的线性或支链烷基，或具有2到11个碳原子的烯基或炔基；L1和L2相同或不同，均为具有5到18个碳原子的线性烷基，或与N形成杂环；X1为键或为—CO—O—，从而形成L2-CO—O—R2；X2为S或O；L3为键或较低烷基，或与N形成杂环；R3为较低烷基；R4和R5相同或不同，均为较低烷基；或其药学上可接受的盐。
• SYMMETRIC IONIZABLE CATIONIC LIPID FOR RNA DELIVERY
  申请人：Arcturus Therapeutics, Inc.

  公开号：US20150239834A1

  公开（公告）日：2015-08-27

  What are described are compounds of formulas II, III, and IV. The compound of formula II consists of a compound in which R 1 and R 2 are both a linear alkyl consisting of 1 to 12 carbons, an alkenyl or alkynyl consisting of 2 to 12 carbons; L 1 and L 2 both consist of a linear alkylene or alkenylene consisting of 5 to 18 carbons, or forming a heterocycle with N; X is S; L 3 consists of a bond or a linear alkylene consisting of 1 to 6 carbons, or forming a heterocycle with N; R 3 consists of a linear or branched alkylene consisting of 1 to 6 carbons; and R 4 and R 5 are the same or different, each consisting of hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons. The compound of formulas III and IV consists of a compound in which R 1 consists of a branched alkyl with 12 to 20 carbons; R 2 consists of a linear alkyl with 5 to 10 carbons or a branched alkyl with 12 to 20 carbons; L 1 and L 2 each consists of a bond or a linear alkyl having 1 to 3 carbon atoms; X consists of S or O; L 3 consists of a bond or a lower alkyl; R 3 consists of a lower alkyl; and R 4 and R 5 are the same or different, each consisting of a lower alkyl. The compound of formulas II, III and IV may comprise a pharmaceutically acceptable salt thereof.

  所描述的是II、III和IV式化合物。式I的化合物由化合物组成，其中R1和R2都是由1到12个碳组成的直链烷基、由2到12个碳组成的烯基或炔基；L1和L2都由由5到18个碳组成的直链烷基或烯基组成，或与N形成杂环；X为S；L3由键或由1到6个碳组成的直链烷基组成，或与N形成杂环；R3由由1到6个碳组成的直链或支链烷基组成；R4和R5相同或不同，分别由氢或由1到6个碳组成的直链或支链烷基组成。式III和IV的化合物由化合物组成，其中R1由由12到20个碳组成的支链烷基组成；R2由由5到10个碳组成的直链烷基或由12到20个碳组成的支链烷基组成；L1和L2分别由键或由1到3个碳组成的直链烷基组成；X为S或O；L3由键或由低碳的烷基组成；R3由低碳的烷基组成；R4和R5相同或不同，分别由低碳的烷基组成。II、III和IV式化合物可以包括其药学上可接受的盐。
• ASYMMETRIC IONIZABLE CATIONIC LIPID FOR RNA DELIVERY
  申请人：Arcturus Therapeutics, Inc.

  公开号：US20150239926A1

  公开（公告）日：2015-08-27

  What is described is a compound of formula I wherein R 1 consists of a linear or branched alkyl consisting of 1-18 carbons, an alkenyl or alkynyl consisting of 2 to 12 carbons, or a cholesteryl; R 2 consists of a linear or branched alkyl or an alkenyl consisting of 1 to 18 carbons; L 1 consists of a linear alkyl consisting of 5 to 9 carbons or, when R 1 consists of a cholesteryl then L 1 consists of a linear alkylene or alkenyl consisting of 3 to 4 carbons; X 1 consists of —O—(CO)— or —(CO)—O—; X 2 consists of S or O; L 2 consists of a bond or a linear alkylene of 1 to 6 carbons; R 3 consists of a linear or branched alkylene with 1 to 6 carbons; and R 4 and R 5 are the same or different, each consisting of a linear or branched alkyl of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.

  描述的是一种I式化合物，其中R1由1-18个碳原子的线性或支链烷基、2-12个碳原子的烯基或炔基，或胆固醇基组成；R2由1-18个碳原子的线性或支链烷基或烯基组成；L1由5-9个碳原子的线性烷基组成，或者当R1由胆固醇基组成时，L1由3-4个碳原子的线性烷基或烯基组成；X1由—O—(CO)—或—(CO)—O—组成；X2由S或O组成；L2由键或1-6个碳原子的线性烷基组成；R3由1-6个碳原子的线性或支链烷基组成；R4和R5相同或不同，均由1-6个碳原子的线性或支链烷基组成；或其药学上可接受的盐。
• LIPID PARTICLES WITH ASYMMETRIC CATIONIC LIPIDS FOR RNA DELIVERY
  申请人：Arcturus Therapeutics, Inc.

  公开号：US20160244761A1

  公开（公告）日：2016-08-25

  What is described is a lipid particle comprising the compound of formula I wherein R 1 consists of alkyl, alkenyl, alkynyl, or cholesteryl; R 2 consists of alkyl or alkenyl; L 1 consists of alkyl, alkylene or alkenyl; X 1 consists of —O—(CO)— or —(CO)—O—; X 2 consists of S or O; L 2 consists of a bond or alkylene; R 3 consists of alkylene; and R 4 and R 5 are the same or different, each consisting of alkyl; or a pharmaceutical preparation thereof.

  描述的是一种脂质颗粒，包括化合物I的公式，其中R1由烷基，烯基，炔基或胆固醇基组成；R2由烷基或烯基组成；L1由烷基，烷基烯基或烯基组成；X1由—O—（CO）—或—（CO）—O—组成；X2由S或O组成；L2由键或烷基烷基组成；R3由烷基烷基组成；R4和R5相同或不同，均由烷基组成；或其制备的药物制剂。
• Ionizable cationic lipid for RNA delivery
  申请人：Arcturus Therapeutics, Inc.

  公开号：US10399937B2

  公开（公告）日：2019-09-03

  What is described herein are cationic lipids that facilitate the intracellular delivery of biologically active molecules, comprising a compound of formula I wherein R1 is a linear alkyl, alkenyl, or alkynyl of 2 to 12 carbons, or a branched alkyl with 7-25 R2 is a branched alkenyl with 7-25 carbons, L1 and L2 are independently a linear alkenylene with 2-18 carbons, X is S or O, L3 is a bond, and R3 R4, and R5 are each a linear or branched alkylene with 1-6 carbons.

  本文所述的阳离子脂质可促进生物活性分子在细胞内的传递，由式 I 的化合物组成 其中 R1 是碳原子数为 2-12 的直链烷基、烯基或炔基，或碳原子数为 7-25 的支链烷基；R2 是碳原子数为 7-25 的支链烯基；L1 和 L2 独立地是碳原子数为 2-18 的直链烯基；X 是 S 或 O；L3 是键；R3、R4 和 R5 分别是碳原子数为 1-6 的直链或支链烯基。