7-trichloroacetyl-3'-(1-cyclopentenoyl)-3'-debenzoylpaclitaxel | 502626-25-7

• 英文名称: 7-trichloroacetyl-3'-(1-cyclopentenoyl)-3'-debenzoylpaclitaxel
• CAS: 502626-25-7
• 化学式: C₄₈H₅₂Cl₃NO₁₅
• 分子量: 989.298
• InChiKey: BJADFYNEFZXQKS-MIDYMNAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  67.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  227.36
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  7-trichloroacetyl-3'-(1-cyclopentenoyl)-3'-debenzoylpaclitaxel 在 乙酸铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3'-N-(1-cyclopentenecarbonyl)-3'-N-debenzoylpaclitaxel
  参考文献：
  名称：

  Structure–activity relationship study at the 3′-N-position of paclitaxel: synthesis and biological evaluation of 3′-N-acyl-paclitaxel analogues

  摘要：

  A series of 3'-N-acyl-paclitaxel analogues la-v were synthesized and their cytotoxicities in vitro against several human tumor cell lines examined. It has been shown that distinct correlation between activity and N-acyl-substituent. The appropriate size of N-acyl group was indispensable for cytotoxicity, and moreover, the presence of beta-substituted conjugated double and triple bond to N-carbonyl generally resulted in increase of cytotoxicities. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00218-3
• 作为产物：
  描述：

  7-trichloroacetylbaccatin III 在 吡啶 、 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 7-trichloroacetyl-3'-(1-cyclopentenoyl)-3'-debenzoylpaclitaxel
  参考文献：
  名称：

  Structure–activity relationship study at the 3′-N-position of paclitaxel: synthesis and biological evaluation of 3′-N-acyl-paclitaxel analogues

  摘要：

  A series of 3'-N-acyl-paclitaxel analogues la-v were synthesized and their cytotoxicities in vitro against several human tumor cell lines examined. It has been shown that distinct correlation between activity and N-acyl-substituent. The appropriate size of N-acyl group was indispensable for cytotoxicity, and moreover, the presence of beta-substituted conjugated double and triple bond to N-carbonyl generally resulted in increase of cytotoxicities. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00218-3

文献信息

• Synthesis and biology of 3′- N -acyl- N -debenzoylpaclitaxel analogues
  作者：Eun Joo Roh、Choong Eui Song、Deukjoon Kim、Hyun-Ock Pae、Hun-Taeg Chung、Kwan Sun Lee、Ki-byung Chai、Chong Ock Lee、Sang Un Choi

  DOI：10.1016/s0968-0896(99)00173-x

  日期：1999.9

  The, 3'-N-acyl-N-debenzoylpaclitaxel analogues 1a-d were synthesized and evaluated on biological systems. Some of the analogues 1a-d exhibited higher cytotoxicities (up to 20-fold) and stronger abilities to induce apoptosis than paclitaxel. In an in vivo experiment against i.p. implanted B16 melanoma, the most cytotoxic compound 1b in vitro caused tumor growth inhibition more than paclitaxel.