(1S,2S,3R,4S,5R,7R,8R,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-1,10-dihydroxy-5,20-epoxy-7-fluoro-9-oxo-13-[(triethylsilyl)oxy]tax-11-ene | 478161-75-0

• 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: (1S,2S,3R,4S,5R,7R,8R,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-1,10-dihydroxy-5,20-epoxy-7-fluoro-9-oxo-13-[(triethylsilyl)oxy]tax-11-ene
• 英文别名: [(1S,2S,3R,4S,7R,9R,10R,12R,15S)-4-acetyloxy-9-fluoro-1,12-dihydroxy-10,14,17,17-tetramethyl-11-oxo-15-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 478161-75-0
• 化学式: C₃₅H₄₉FO₉Si
• 分子量: 660.853
• InChiKey: QOPWORCZSKBEBY-GLJOQZLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4S,5R,7R,8R,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-1,10-dihydroxy-5,20-epoxy-7-fluoro-9-oxo-13-[(triethylsilyl)oxy]tax-11-ene 在 硼烷四氢呋喃络合物 、 对甲苯磺酸 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 吡啶 、 丙酮 为溶剂， 生成 [(2R,6S,7R,8R,10R,13S,14R,15S,16S,18S)-13-acetyloxy-8-fluoro-16,18-dihydroxy-4,4,7,19,20,20-hexamethyl-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 2

  摘要：

  To investigate structure-activity relationships of the 9,10-acetal-9beta-dihydro taxoids, we modified the 7-hydroxyl groups of the 9,10-acetonide-3'-(4-pyridyl) analogue to deoxy, methoxy, alpha-F, and 7beta,8beta-methano group. As a result of this study, we found that the 7-deoxy analogue was the strongest among these analogues. In addition, we found that the 7-deoxy-3'-(4-pyridyl) and 7-deoxy-3'-(2-pyridyl) analogues showed stronger activity against cell lines expressing P-glycoprotein than the corresponding 3'-phenyl analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00628-5
• 作为产物：
  描述：

  (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-6-(((benzyloxy)carbonyl)oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-9-((triethylsilyl)oxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 在 palladium on activated charcoal 二乙胺基三氟化硫 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (1S,2S,3R,4S,5R,7R,8R,10R,13S)-4-(acetoxy)-2-(benzoyloxy)-1,10-dihydroxy-5,20-epoxy-7-fluoro-9-oxo-13-[(triethylsilyl)oxy]tax-11-ene
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 2

  摘要：

  To investigate structure-activity relationships of the 9,10-acetal-9beta-dihydro taxoids, we modified the 7-hydroxyl groups of the 9,10-acetonide-3'-(4-pyridyl) analogue to deoxy, methoxy, alpha-F, and 7beta,8beta-methano group. As a result of this study, we found that the 7-deoxy analogue was the strongest among these analogues. In addition, we found that the 7-deoxy-3'-(4-pyridyl) and 7-deoxy-3'-(2-pyridyl) analogues showed stronger activity against cell lines expressing P-glycoprotein than the corresponding 3'-phenyl analogue. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00628-5

文献信息

• TAXANE COMPOUND WITH AZETIDINE RING STRUCTURE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1942109A1

  公开（公告）日：2008-07-09

  A compound represented by the general formula (1) [X1 and X2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, R1 represents a phenyl group, R2 represents an alkyl group, an alkenyl group, or an alkoxy group, R3 represents hydrogen atom, a halogen atom, hydroxyl group, or an alkoxy group, R4 represents hydrogen atom, or an alkyl group, Z1 and Z2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, Z3 represents cyano group, an alkyl group, an alkenyl group and the like, Z4 represents an alkyl group, an alkenyl group, an alkynyl group and the like, and ---- represents a single bond or a double bond], which shows high antitumor effect against cancer cells including drug resistant cells.

  一个由通式（1）表示的化合物，其中[X1和X2代表氢原子，卤素原子，羟基等，R1代表苯基，R2代表烷基，烯基或烷氧基，R3代表氢原子，卤素原子，羟基或烷氧基，R4代表氢原子或烷基，Z1和Z2代表氢原子，卤素原子，羟基等，Z3代表氰基，烷基，烯基等，Z4代表烷基，烯基，炔基等，----代表单键或双键]，对包括药物耐药细胞在内的癌细胞表现出高抗肿瘤效果。