(2'R,3'S)-3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-O-deacetyl-3'-dephenyl-3'-N-debenzoyl-4-O-methoxycarbonylpaclitaxel | 355113-98-3

• 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
• 英文名称: (2'R,3'S)-3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-O-deacetyl-3'-dephenyl-3'-N-debenzoyl-4-O-methoxycarbonylpaclitaxel
• 英文别名: 3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-deacetyl-3'-dephenyl-3'-N-debenzoyl-4-O-methoxycarbonyl-paclitaxel；3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-deacetyl-3'-deacetyl-3'-dephenyl-3'-N-debenzoyl-4-O-methoxycarbonyl-paclitaxel；Bms-275183；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-acetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-4,4-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]oxy-4-methoxycarbonyloxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 355113-98-3
• 化学式: C₄₃H₅₉NO₁₆
• 分子量: 845.939
• InChiKey: AHXICHPPXIGCBN-GPWPDEGDSA-N

物化性质

• 沸点：
  896.2±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  240
• 氢给体数：
  4
• 氢受体数：
  16

ADMET

代谢

Bms_275183已知的人类代谢物包括[12-乙酰氧基-15-[2,5-二羟基-4,4-二甲基-3-[(2-甲基丙烷-2-基)氧基羰基氨基]戊酰氧基]-1,9-二羟基-4-甲氧基羰氧基-10,14,17,17-四甲基-11-氧代-6-氧杂四环[11.3.1.03,10.04,7]十七碳-13-烯-2-基]苯甲酸盐。

Bms_275183 has known human metabolites that include [12-acetyloxy-15-[2,5-dihydroxy-4,4-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]oxy-1,9-dihydroxy-4-methoxycarbonyloxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  (2'R,3'S)-3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-O-deacetyl-3'-dephenyl-3'-N-debenzoyl-4-O-methoxycarbonylpaclitaxel 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3'-tert-butyl-4-O-deacetyl-3'-dephenyl-3'-N-debenzoyl-4-O-methoxycarbonylpaclitaxel
  参考文献：
  名称：

  The discovery of BMS-275183: an orally efficacious novel taxane

  摘要：

  The evolution of 2, a C-4-methylcarbonate analogue of paclitaxel with minimal oral bioavailability and oral efficacy, into its C-3'-t-butyl-3'-N-t-butyloxycarbonyl analogue (15i), a novel taxane with oral efficacy in preclinical models that is comparable to iv administered paclitaxel, is described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00495-4
• 作为产物：
  描述：

  N-(2,2-dimethylpropylidene)-4-methoxyaniline 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 triethylamine trihydrofluoride 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~20.0 ℃ 、344.74 kPa 条件下， 反应 134.17h， 生成 (2'R,3'S)-3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-O-deacetyl-3'-dephenyl-3'-N-debenzoyl-4-O-methoxycarbonylpaclitaxel
  参考文献：
  名称：

  The discovery of BMS-275183: an orally efficacious novel taxane

  摘要：

  The evolution of 2, a C-4-methylcarbonate analogue of paclitaxel with minimal oral bioavailability and oral efficacy, into its C-3'-t-butyl-3'-N-t-butyloxycarbonyl analogue (15i), a novel taxane with oral efficacy in preclinical models that is comparable to iv administered paclitaxel, is described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00495-4

文献信息

• COMBINATION THERAPY
  申请人：Voi Maurizio

  公开号：US20080221135A1

  公开（公告）日：2008-09-11

  This invention relates to a combination of anti-cancer compounds which comprises a) an orally effective taxane, and b) a thymidylate synthase inhibitor, and optionally at least one pharmaceutically acceptable carrier for simultaneous, separate or sequential use.
• SELF-EMULSIFYING AND SELF-MICROEMULSIFYING FORMULATIONS FOR THE ORAL ADMINISTRATION OF TAXOIDS
  申请人：PERACCHIA Maria-Teresa

  公开号：US20090069411A1

  公开（公告）日：2009-03-12

  The present invention relates to novel formulations of taxoids for oral administration. More particularly, the present invention discloses and claims self-emulsifying and self-microemulsifying formulations for the oral administration of taxoids.
• The discovery of BMS-275183: an orally efficacious novel taxane
  作者：Harold Mastalerz、Donald Cook、Craig R Fairchild、Steven Hansel、Walter Johnson、John F Kadow、Byron H Long、William C Rose、James Tarrant、Mu-Jen Wu、May Quifen Xue、Guifen Zhang、Mary Zoeckler、Dolatrai M Vyas

  DOI：10.1016/s0968-0896(03)00495-4

  日期：2003.10

  The evolution of 2, a C-4-methylcarbonate analogue of paclitaxel with minimal oral bioavailability and oral efficacy, into its C-3'-t-butyl-3'-N-t-butyloxycarbonyl analogue (15i), a novel taxane with oral efficacy in preclinical models that is comparable to iv administered paclitaxel, is described. (C) 2003 Elsevier Ltd. All rights reserved.