4-(hexadecyloxycarbonylamino)-4-methylheptanedioic acid | 1310081-48-1

• 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: 4-(hexadecyloxycarbonylamino)-4-methylheptanedioic acid
• 英文别名: 4-(Hexadecoxycarbonylamino)-4-methyl-heptanedioic acid；4-(hexadecoxycarbonylamino)-4-methylheptanedioic acid
• CAS: 1310081-48-1
• 化学式: C₂₅H₄₇NO₆
• 分子量: 457.651
• InChiKey: SZMMRWYIOBJRHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  32
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  di-tert-butyl 4-amino-4-methylheptanedicarboxylate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.25h， 生成 4-(hexadecyloxycarbonylamino)-4-methylheptanedioic acid
  参考文献：
  名称：

  Comparing micellar, hemolytic, and antibacterial properties of di- and tricarboxyl dendritic amphiphiles

  摘要：

  Homologous dicarboxyl dendritic amphiphiles-RCONHC(CH(3))(CH(2)CH(2)COOH)(2), 4(n); and ROCO-NHC(CH(3))(CH(2)CH(2)COOH)(2), 5(n), where R = n-C(n)H(2n+1) and n = 13-22 carbon atoms-were synthesized. Critical micelle concentrations (CMCs) in aqueous triethanolamine solutions and at pH 7.4 were measured along with hemolytic activity (effective concentrations, EC(10)) in phosphate-buffered saline (PBS). Log CMC showed a linear dependence on chain length (n); the longest chain in each series had the lowest CMC-in triethanolamine: 4(21), 180 mu M and 5(22), 74 mu M and at pH 7.4: 4(21), 78 mu M and 5(22), 33 mu M. These two series, 4(n) and 5(n), and three series of homologous tricarboxyl dendritic amphiphiles-RCONHC(CH(2)CH(2)COOH)(3), 1(n); ROCONHC(CH(2)CH(2)COOH)(3), 2(n); RNHCONHC(CH(2)CH(2)COOH)(3), 3(n), where R = n-C(n)H(2n+1) and n = 13-22 carbon atoms-were tested for growth inhibition of Staphylococcus aureus strain ATCC 6358 and methicillin-resistant S. aureus (MRSA) strain ATCC 43330 by microdilution in 0.1-strength brain heart infusion broth (BHIB). Amphiphiles 4(19), 4(21), 5(18), and 5(20) showed the strongest antibacterial activity (2.2-3.4 mu g/mL) against S. aureus (vancomycin, MIC = 0.25 mu g/mL). These four plus 1(21), 2(20), 2(22), and 3(20) exhibited the strongest antibacterial activity (1.7-6.8 mu g/mL) against MRSA (vancomycin, MIC = 0.25 mu g/mL). The MICs of these amphiphiles against six clinical MRSA were similar to those against the ATCC strain. In PBS, EC(10)s of the most active homologues ranged from 7 to 18 mu g/mL and 18 to 220 mu g/mL for di- and tricarboxyl dendritic amphiphiles, respectively. To assess the potential safety of using dendritic amphiphiles as drugs, measurements of micellar and hemolytic properties were conducted in the same medium (full-strength BHIB) that was used for antibacterial activity. The CMCs (9-36 mu g/mL, similar to 18-72 mu M) of ten amphiphiles were measured by microdilution (log 2 progression) with dye-covered beads. The EC10s were similar to those in PBS. The MICs of most amphiphiles (14-72 mu g/mL) and vancomycin (1.1-2.2 mu g/mL) against both S. aureus and MRSA increased significantly compared to the MICs measured in 0.1-strength BHIB. The one exception, 5(18), had an MIC against S. aureus of 1.1 mu g/mL compared to vancomycin (2.2 mu g/mL). With CMC (9-18 mu g/mL) and EC10 (16 mu g/mL) values higher than the MIC, 5(18) was discovered as a lead for further development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.036

文献信息

• Comparing micellar, hemolytic, and antibacterial properties of di- and tricarboxyl dendritic amphiphiles
  作者：Bhadreshkumar B. Maisuria、Marcelo L. Actis、Shauntrece N. Hardrict、Joseph O. Falkinham、Michael F. Cole、Ronald L. Cihlar、Stephen M. Peters、Richard V. Macri、Eko W. Sugandhi、André A. Williams、Michael A. Poppe、Alan R. Esker、Richard D. Gandour

  DOI：10.1016/j.bmc.2011.03.036

  日期：2011.5

  Homologous dicarboxyl dendritic amphiphiles-RCONHC(CH(3))(CH(2)CH(2)COOH)(2), 4(n); and ROCO-NHC(CH(3))(CH(2)CH(2)COOH)(2), 5(n), where R = n-C(n)H(2n+1) and n = 13-22 carbon atoms-were synthesized. Critical micelle concentrations (CMCs) in aqueous triethanolamine solutions and at pH 7.4 were measured along with hemolytic activity (effective concentrations, EC(10)) in phosphate-buffered saline (PBS). Log CMC showed a linear dependence on chain length (n); the longest chain in each series had the lowest CMC-in triethanolamine: 4(21), 180 mu M and 5(22), 74 mu M and at pH 7.4: 4(21), 78 mu M and 5(22), 33 mu M. These two series, 4(n) and 5(n), and three series of homologous tricarboxyl dendritic amphiphiles-RCONHC(CH(2)CH(2)COOH)(3), 1(n); ROCONHC(CH(2)CH(2)COOH)(3), 2(n); RNHCONHC(CH(2)CH(2)COOH)(3), 3(n), where R = n-C(n)H(2n+1) and n = 13-22 carbon atoms-were tested for growth inhibition of Staphylococcus aureus strain ATCC 6358 and methicillin-resistant S. aureus (MRSA) strain ATCC 43330 by microdilution in 0.1-strength brain heart infusion broth (BHIB). Amphiphiles 4(19), 4(21), 5(18), and 5(20) showed the strongest antibacterial activity (2.2-3.4 mu g/mL) against S. aureus (vancomycin, MIC = 0.25 mu g/mL). These four plus 1(21), 2(20), 2(22), and 3(20) exhibited the strongest antibacterial activity (1.7-6.8 mu g/mL) against MRSA (vancomycin, MIC = 0.25 mu g/mL). The MICs of these amphiphiles against six clinical MRSA were similar to those against the ATCC strain. In PBS, EC(10)s of the most active homologues ranged from 7 to 18 mu g/mL and 18 to 220 mu g/mL for di- and tricarboxyl dendritic amphiphiles, respectively. To assess the potential safety of using dendritic amphiphiles as drugs, measurements of micellar and hemolytic properties were conducted in the same medium (full-strength BHIB) that was used for antibacterial activity. The CMCs (9-36 mu g/mL, similar to 18-72 mu M) of ten amphiphiles were measured by microdilution (log 2 progression) with dye-covered beads. The EC10s were similar to those in PBS. The MICs of most amphiphiles (14-72 mu g/mL) and vancomycin (1.1-2.2 mu g/mL) against both S. aureus and MRSA increased significantly compared to the MICs measured in 0.1-strength BHIB. The one exception, 5(18), had an MIC against S. aureus of 1.1 mu g/mL compared to vancomycin (2.2 mu g/mL). With CMC (9-18 mu g/mL) and EC10 (16 mu g/mL) values higher than the MIC, 5(18) was discovered as a lead for further development. (C) 2011 Elsevier Ltd. All rights reserved.