(4E,6E,8E,10Z,12Z,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-23,27,29,31,33,35,37-heptahydroxy-38-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-19-[4-hydroxy-1-methyl-6-[4-(methylamino)phenyl]-6-oxo-hexyl]-18-methyl-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-21,25-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4E,6E,8E,10Z,12Z,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-23,27,29,31,33,35,37-heptahydroxy-38-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-19-[4-hydroxy-1-methyl-6-[4-(methylamino)phenyl]-6-oxo-hexyl]-18-methyl-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-21,25-dione
• 英文别名: (19E,21E,23Z,25Z,27E,29E,31E)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,7,9,13,37-heptahydroxy-36-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-17-[5-hydroxy-7-[4-(methylamino)phenyl]-7-oxoheptan-2-yl]-18-methyl-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-11,15-dione
• 化学式: C₆₅H₉₈N₄O₁₉
• 分子量: 1239.51
• InChiKey: KOIMKAYOXWYCDO-KHHAVWKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  88
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  372
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甘氨酸 、 (4E,6E,8E,10Z,12Z,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-23,27,29,31,33,35,37-heptahydroxy-38-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-19-[4-hydroxy-1-methyl-6-[4-(methylamino)phenyl]-6-oxo-hexyl]-18-methyl-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-21,25-dione 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 生成 beta-D-Mannopyranoside, (19E,21E,23Z,25Z,27E,29E,31E)-1,3,5,7,9,13,37-heptahydroxy-36-[[4-(2-hydroxyethyl)-1-piperazinyl]carbonyl]-17-[4-hydroxy-1-methyl-6-[4-(methylamino)phenyl]-6-oxohexyl]-18-methyl-11,15-dioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaen-33-yl 3,6-dideoxy-3-[[(dimethylamino)acetyl]amino]-
  参考文献：
  名称：

  Amide derivatives of partricin A with potent antifungal activity

  摘要：

  A series of partricin A amides were synthesized using the active ester method by reaction with several amines on the carboxy group and then with some acids on the mycosamine group of partricin A. Most of the derivatives are more potent antifungals than the known reference standards, including amphotericin B, and a few are also less toxic and less hemolytic. Amides substituted with basic groups may give hydrosoluble salts, useful for injectable formulations, and two derivatives were selected for further development, namely, partricin A 2-dimethylaminoethyl amide (10, SPA-S-710) and N-dimethylaminoacetyl-partricin A 2-dimethylaminoethyl amide (22, SPA-S-752).

  DOI：

  10.1016/s0223-5234(97)86175-2
• 作为产物：
  描述：

  N-羟乙基哌嗪 、 partricin A 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 生成 (4E,6E,8E,10Z,12Z,14E,16E)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-23,27,29,31,33,35,37-heptahydroxy-38-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-19-[4-hydroxy-1-methyl-6-[4-(methylamino)phenyl]-6-oxo-hexyl]-18-methyl-20,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-21,25-dione
  参考文献：
  名称：

  Amide derivatives of partricin A with potent antifungal activity

  摘要：

  A series of partricin A amides were synthesized using the active ester method by reaction with several amines on the carboxy group and then with some acids on the mycosamine group of partricin A. Most of the derivatives are more potent antifungals than the known reference standards, including amphotericin B, and a few are also less toxic and less hemolytic. Amides substituted with basic groups may give hydrosoluble salts, useful for injectable formulations, and two derivatives were selected for further development, namely, partricin A 2-dimethylaminoethyl amide (10, SPA-S-710) and N-dimethylaminoacetyl-partricin A 2-dimethylaminoethyl amide (22, SPA-S-752).

  DOI：

  10.1016/s0223-5234(97)86175-2

文献信息

• Amide derivatives of partricin A with potent antifungal activity
  作者：T Bruzzese、C Rimaroli、A Bonabello、E Ferrari、M Signorini

  DOI：10.1016/s0223-5234(97)86175-2

  日期：1996.1

  A series of partricin A amides were synthesized using the active ester method by reaction with several amines on the carboxy group and then with some acids on the mycosamine group of partricin A. Most of the derivatives are more potent antifungals than the known reference standards, including amphotericin B, and a few are also less toxic and less hemolytic. Amides substituted with basic groups may give hydrosoluble salts, useful for injectable formulations, and two derivatives were selected for further development, namely, partricin A 2-dimethylaminoethyl amide (10, SPA-S-710) and N-dimethylaminoacetyl-partricin A 2-dimethylaminoethyl amide (22, SPA-S-752).