ethyl (5Z,7E,23aE)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-23-hydroxy-23a-methyl-23a,23b-dihomo-9,10-secochola-5,7,10(19),23-tetraene-24-oate | 501431-51-2

• 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: ethyl (5Z,7E,23aE)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-23-hydroxy-23a-methyl-23a,23b-dihomo-9,10-secochola-5,7,10(19),23-tetraene-24-oate
• CAS: 501431-51-2
• 化学式: C₄₇H₇₆O₇SSi₂
• 分子量: 841.353
• InChiKey: ZGOWNQARBRHHOR-ANPSLTOMSA-N

物化性质

• 沸点：
  803.9±65.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.54
• 重原子数：
  57.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  99.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl (5Z,7E,23aE)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-23-hydroxy-23a-methyl-23a,23b-dihomo-9,10-secochola-5,7,10(19),23-tetraene-24-oate 在 disodium hydrogenphosphate 、 sodium amalgam 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 5.5h， 生成 (24E)-(1S)-24-dehydro-24a-homo-26,27-diethyl-1,25-dihydroxyergocalciferol
  参考文献：
  名称：

  Synthesis and antiproliferative activity of side-chain unsaturated and homologated analogs of 1,25-dihydroxyvitamin D2

  摘要：

  A series of analogs of 1,25-dihydroxyergocalciferol (1-4) was synthesized and screened for their antiproliferative activity in vitro. The structure of new analogs was designed based on biological activity of the previously obtained side-chain modified analogs of vitamin D-2 and D-3. The analogs were obtained by the Julia olefination of C-22-vitamin D sulfone 11 with side-chain aldehyde 15. The analogs were tested for their antiproliferative activity against the cells of human breast cancer lines T47D and MCF7 as well as human and mouse leukemia lines, HL-60 and WEHI-3, respectively. Analog 2 (PRI-1907) showed the strongest antiproliferative activity out of the present series of analogs of 1,25-dihydroxyvitamin D-2 with the mono homologated and double unsaturated side chain. The activity of 2 was 3-150 times stronger, depending on the cell line, than that of 1,25-dihydroxycholecalciferol (calcitriol), used as standard. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00038-7
• 作为产物：
  描述：

  (7E)-(1S,3R)-4'-phenyl-6,9-[1',2']epi[1',2',4']triazolo-1,3-bis[(t-butyldimethyl-silyl)oxy]-22,23-dinor-9,10-secochola-5(10),7-dien-24-ol-3',5'-dion 在 4-二甲氨基吡啶 、 氢氧化钾 、 正丁基锂 、 lithium carbonate 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.08h， 生成 ethyl (5Z,7E,23aE)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-22-phenylsulfonyl-23-hydroxy-23a-methyl-23a,23b-dihomo-9,10-secochola-5,7,10(19),23-tetraene-24-oate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of side-chain unsaturated and homologated analogs of 1,25-dihydroxyvitamin D2

  摘要：

  A series of analogs of 1,25-dihydroxyergocalciferol (1-4) was synthesized and screened for their antiproliferative activity in vitro. The structure of new analogs was designed based on biological activity of the previously obtained side-chain modified analogs of vitamin D-2 and D-3. The analogs were obtained by the Julia olefination of C-22-vitamin D sulfone 11 with side-chain aldehyde 15. The analogs were tested for their antiproliferative activity against the cells of human breast cancer lines T47D and MCF7 as well as human and mouse leukemia lines, HL-60 and WEHI-3, respectively. Analog 2 (PRI-1907) showed the strongest antiproliferative activity out of the present series of analogs of 1,25-dihydroxyvitamin D-2 with the mono homologated and double unsaturated side chain. The activity of 2 was 3-150 times stronger, depending on the cell line, than that of 1,25-dihydroxycholecalciferol (calcitriol), used as standard. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00038-7