tert-butyl N-((S)-camptothecin-20-O-ylcarbonyl)-6-aminocaproate | 754195-69-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: tert-butyl N-((S)-camptothecin-20-O-ylcarbonyl)-6-aminocaproate
• 英文别名: tert-butyl 6-[[(19S)-19-ethyl-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl]oxycarbonylamino]hexanoate
• CAS: 754195-69-2
• 化学式: C₃₁H₃₅N₃O₇
• 分子量: 561.635
• InChiKey: YRWJAQSAUHYBGY-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 tert-butyl N-((S)-camptothecin-20-O-ylcarbonyl)-6-aminocaproate 反应 0.33h， 以97%的产率得到N-((S)-camptothecin-20-O-ylcarbonyl)-6-aminocaproic acid trifluoroacetic acid salt
  参考文献：
  名称：

  Synthesis of Camptothecin Melantotransferrin (p97) Conjugate Through a Carbamate Bond

  摘要：

  Through its 20-hydroxy group and a carbamate bond, 20(S)-camptothecin (1) is chemically linked to melanotransferrin (p97). The key step to modify the steric hindered hydroxy group of camptothecin is achieved by using triphosgene/DMAP in DMF and immediately reacting with tert-butyl 6-aminohexanoate (8). The novel camptothecin conjugate 4 is a potential agent for chemotherapy of brain tumor.

  DOI：

  10.1081/scc-120039495
• 作为产物：
  描述：

  6-氨基己酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-dimethylaminopyridine 、 碳酸二异丙酯 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.83h， 生成 tert-butyl N-((S)-camptothecin-20-O-ylcarbonyl)-6-aminocaproate
  参考文献：
  名称：

  Synthesis of Camptothecin Melantotransferrin (p97) Conjugate Through a Carbamate Bond

  摘要：

  Through its 20-hydroxy group and a carbamate bond, 20(S)-camptothecin (1) is chemically linked to melanotransferrin (p97). The key step to modify the steric hindered hydroxy group of camptothecin is achieved by using triphosgene/DMAP in DMF and immediately reacting with tert-butyl 6-aminohexanoate (8). The novel camptothecin conjugate 4 is a potential agent for chemotherapy of brain tumor.

  DOI：

  10.1081/scc-120039495

文献信息

• Synthesis of Camptothecin Melantotransferrin (p97) Conjugate Through a Carbamate Bond
  作者：Qingqi Chen、Reinhard Gabathuler

  DOI：10.1081/scc-120039495

  日期：2004.1.1

  Through its 20-hydroxy group and a carbamate bond, 20(S)-camptothecin (1) is chemically linked to melanotransferrin (p97). The key step to modify the steric hindered hydroxy group of camptothecin is achieved by using triphosgene/DMAP in DMF and immediately reacting with tert-butyl 6-aminohexanoate (8). The novel camptothecin conjugate 4 is a potential agent for chemotherapy of brain tumor.