tert-butyl N-[(2S)-1-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl-[3-(dimethylamino)propyl]amino]-1-oxopropan-2-yl]carbamate | 181636-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[(2S)-1-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl-[3-(dimethylamino)propyl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 181636-80-6
• 化学式: C₄₄H₇₈N₄O₁₀
• 分子量: 823.124
• InChiKey: MUTTXFSEYNCEMH-XOMUMKKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  58.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  167.41
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl-[3-(dimethylamino)propyl]amino]-1-oxopropan-2-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以97%的产率得到CP-163,505
  参考文献：
  名称：

  Repromicin Derivatives with Potent Antibacterial Activity against Pasteurella multocida

  摘要：

  Reductive amination of repromicin with polyfunctional amines has led to new macrolide antibacterial agents, some of which are highly potent against the Gram-negative pathogen Pasteurella multocida both in vitro and in a mouse infection model. A key element in this discovery was the recognition that among certain known macrolides increasing lipophilicity results in diminished in vivo activity. One repromicin derivative, 20-{N-[3-(dimethylamino)propyl] -N-L-alanylamino}-20-deoxorepromicin (35), was selected for advanced evaluation. At 5 mg/kg, a single subcutaneous dose was found to control induced pasteurellosis in swine and induced respiratory disease in cattle.

  DOI：

  10.1021/jm960435q
• 作为产物：
  描述：

  去环氧蔷薇霉素 在 sodium cyanoborohydride 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.67h， 生成 tert-butyl N-[(2S)-1-[2-[(4R,5S,6S,7R,9R,11E,13E,15S,16R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]ethyl-[3-(dimethylamino)propyl]amino]-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Repromicin Derivatives with Potent Antibacterial Activity against Pasteurella multocida

  摘要：

  Reductive amination of repromicin with polyfunctional amines has led to new macrolide antibacterial agents, some of which are highly potent against the Gram-negative pathogen Pasteurella multocida both in vitro and in a mouse infection model. A key element in this discovery was the recognition that among certain known macrolides increasing lipophilicity results in diminished in vivo activity. One repromicin derivative, 20-{N-[3-(dimethylamino)propyl] -N-L-alanylamino}-20-deoxorepromicin (35), was selected for advanced evaluation. At 5 mg/kg, a single subcutaneous dose was found to control induced pasteurellosis in swine and induced respiratory disease in cattle.

  DOI：

  10.1021/jm960435q