N-(4-叠氮基苯甲酰基)-N-去苯甲酰基紫杉醇 | 153695-19-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: N-(4-叠氮基苯甲酰基)-N-去苯甲酰基紫杉醇
• 英文名称: azidotaxol
• 英文别名: N-(4-azidobenzoyl)-N-debenzoyltaxol；3'-(p-azidobenzamido)taxol；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-[(4-azidobenzoyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 153695-19-3
• 化学式: C₄₇H₅₀N₄O₁₄
• 分子量: 894.932
• InChiKey: GVICBXRQYJAMJC-MZXODVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  65
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  236
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-(4-叠氮基苯甲酰基)-N-去苯甲酰基紫杉醇 在 超重氢 、 [Ir(1,5-COD)(P(C6H5)3)2]BF4 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-[(4-azido-2,6-ditritiobenzoyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Direct, efficient and selective tritiations of paclitaxel and photoaffinity taxoids

  摘要：

  Radiolabeled paclitaxel and three photophore-bearing derivatives were prepared by organoiridium-mediated direct tritium exchange under both catalytic and stoichiometric conditions. The resulting tritiated taxoids had specific activities ranging from 53 to 195 Ci/mmol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01652-x
• 作为产物：
  描述：

  4-叠氮基苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 N-(4-叠氮基苯甲酰基)-N-去苯甲酰基紫杉醇
  参考文献：
  名称：

  Direct, efficient and selective tritiations of paclitaxel and photoaffinity taxoids

  摘要：

  Radiolabeled paclitaxel and three photophore-bearing derivatives were prepared by organoiridium-mediated direct tritium exchange under both catalytic and stoichiometric conditions. The resulting tritiated taxoids had specific activities ranging from 53 to 195 Ci/mmol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01652-x

文献信息

• Synthesis of taxol, analogs and intermediates with variable A-nng side chains
  申请人：BRYN MAWR COLLEGE

  公开号：EP1260507A1

  公开（公告）日：2002-11-27

  An efficient protocol for the synthesis of taxol, taxol analogs, and their intermediates is described. The process includes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, calphalomanninne and various analogs, including photoaffinity labeling candidates.

  本文介绍了一种有效的紫杉醇、紫杉醇类似物及其中间体的合成协议。该过程包括将紫杉醇A环侧链连接到紫杉醇前体baccatin III上，以及用具有可变A环侧链结构的化合物合成紫杉醇和紫杉醇类似物。通过快速高效的酯化反应，将O保护的异丝氨酸和3-苯基异丝氨酸酸与N-苄氧羰基基团连接到7-O保护的baccatin III的C-13羟基上，然后进行去保护-酰化序列，制备紫杉醇、卡法洛曼宁和各种类似物，包括光亲和标记候选物。
• Characterization of Two Taxol Photoaffinity Analogs Bearing Azide and Benzophenone-Related Photoreactive Substituents in the A-Ring Side Chain
  作者：Charles S. Swindell、Julia M. Heerding、Nancy E. Krauss、Susan Band Horwitz、Srinivasa Rao、Israel Ringel

  DOI：10.1021/jm00036a009

  日期：1994.5

  Taxol is a structurally novel and clinically effective antitumor drug, which, unlike other antimitotic agents, induces the assembly of tubulin into microtubules. To characterize the binding site(s) of taxol on the microtubule, taxol-based photoaffinity reagents 1 and 2 bearing photoreactive groups on the A-ring side chain were prepared and evaluated. Taxol analogue 1 exhibits better microtubule assembly

  紫杉酚是一种结构新颖且在临床上有效的抗肿瘤药物，与其他抗有丝分裂剂不同，它可诱导微管蛋白组装成微管。为了表征紫杉醇在微管上的结合位点，制备并评估了在A环侧链上带有光反应性基团的基于紫杉醇的光亲和试剂1和2。紫杉醇类似物1与类似物2相比，表现出更好的微管组装活性，对J774.2细胞的更大细胞毒性以及微管蛋白的β亚基更特异性和更有效的光标记。因此，看来1是更理想的针对进一步研究的对象在微管上的紫杉醇结合位点的表征。
• Dasgupta; Park; Harriman, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2976 - 2980
  作者：Dasgupta、Park、Harriman、Georg、Himes

  DOI：——

  日期：——
• Direct, efficient and selective tritiations of paclitaxel and photoaffinity taxoids
  作者：Arthur Y.L Shu、J.Richard Heys

  DOI：10.1016/s0040-4039(00)01652-x

  日期：2000.11

  Radiolabeled paclitaxel and three photophore-bearing derivatives were prepared by organoiridium-mediated direct tritium exchange under both catalytic and stoichiometric conditions. The resulting tritiated taxoids had specific activities ranging from 53 to 195 Ci/mmol. (C) 2000 Elsevier Science Ltd. All rights reserved.