di-tert-butyl 4-isocyanato-4-methylheptanedioate | 1310081-15-2

• 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: di-tert-butyl 4-isocyanato-4-methylheptanedioate
• CAS: 1310081-15-2
• 化学式: C₁₇H₂₉NO₅
• 分子量: 327.421
• InChiKey: PXTKOFJHUBNMBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  82.03
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 4-isocyanato-4-methylheptanedioate 在 三乙胺 、 三氟乙酸 作用下， 反应 25.0h， 生成 4-(docosyloxycarbonylamino)-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
• 作为产物：
  描述：

  丙烯酸叔丁酯 在 4-二甲氨基吡啶 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 20.0~40.0 ℃ 、365.43 kPa 条件下， 反应 27.25h， 生成 di-tert-butyl 4-isocyanato-4-methylheptanedioate
  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