(8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-(formylmethyl)pregnane | 300344-38-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-(formylmethyl)pregnane
• 英文别名: (8S,20R)-des-A,B-20-(formylmethyl)-8β-[(triethylsilyl)oxy]pregnane；des-A,B-8β-triethylsililoxy-24-norcholan-23-al；(3R)-3-[(1R,3aR,4S,7aR)-7a-methyl-4-triethylsilyloxy-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]butanal
• CAS: 300344-38-1
• 化学式: C₂₀H₃₈O₂Si
• 分子量: 338.606
• InChiKey: MLYTYHHSMHARHU-SWBPCFCJSA-N

物化性质

• 沸点：
  384.7±15.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-(formylmethyl)pregnane 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以1.49 g的产率得到des-A,B-8β-triethylsililoxy-24,24-dibromo-23-cholene
  参考文献：
  名称：

  钙三醇的新型炔基膦酸酯类似物在癌细胞中具有有效的抗增殖作用且缺乏钙化活性

  摘要：

  在这里，我们描述了二乙基 [(5 Z ,7 E )-(1 S ,3 R )-1,3-dihydroxy-9,10-secochola-5,7,10(19)-trien-的设计和合成23-in-24-yl] 膦酸盐（化合物10），结合了膦酸盐的低血钙特性和由于 C-24 中存在三键而减少的代谢失活，并研究了其对几种癌细胞系的体外影响及其对血钙水平的体内影响。我们证明这种化合物是一种有效的抗增殖维生素 D 类似物，在体内显示出缺乏钙血效应。

  DOI：

  10.1021/ml200034w
• 作为产物：
  描述：

  des-A,B-8β-triethylsililoxy-23,24-dinor-22-cyanocholane 在 二异丁基氢化铝 、 盐酸 、 水 作用下， 以 正己烷 、 二氯甲烷 、 乙醚 为溶剂， 反应 0.75h， 以1.28 g的产率得到(8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-(formylmethyl)pregnane
  参考文献：
  名称：

  钙三醇的新型炔基膦酸酯类似物在癌细胞中具有有效的抗增殖作用且缺乏钙化活性

  摘要：

  在这里，我们描述了二乙基 [(5 Z ,7 E )-(1 S ,3 R )-1,3-dihydroxy-9,10-secochola-5,7,10(19)-trien-的设计和合成23-in-24-yl] 膦酸盐（化合物10），结合了膦酸盐的低血钙特性和由于 C-24 中存在三键而减少的代谢失活，并研究了其对几种癌细胞系的体外影响及其对血钙水平的体内影响。我们证明这种化合物是一种有效的抗增殖维生素 D 类似物，在体内显示出缺乏钙血效应。

  DOI：

  10.1021/ml200034w

文献信息

• [EN] 1-DEOXY ANALOGS OF VITAMIN D-RELATED COMPOUNDS<br/>[FR] ANALOGUES 1-DÉSOXY DE COMPOSÉS APPARENTÉS À LA VITAMINE D
  申请人：CYTOCHROMA INC

  公开号：WO2011088209A3

  公开（公告）日：2015-09-03
• [EN] 25-SO2-SUBSTITUTED ANALOGS OF 1ALPHA, 25-DIHYDROXYVITAMIN D3 (CALCITRIOL)<br/>[FR] ANALOGUES 25-SO2-SUBSITUTES DE LA 1 DOLLAR G(A),25-DIHYDROXYVITAMINE D3
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2004054968A3

  公开（公告）日：2004-10-21
• Synthesis and biological properties of 2-methylene-19-nor-25-dehydro-1α-hydroxyvitamin D3-26,23-lactones—weak agonists
  作者：Grazia Chiellini、Pawel Grzywacz、Lori A. Plum、Rafal Barycki、Margaret Clagett-Dame、Hector. F. DeLuca

  DOI：10.1016/j.bmc.2008.08.011

  日期：2008.9

  In a continuing effort to explore the 2-methylene-1 alpha-hydroxy-19-norvitamin D-3 class of pharmacologically important vitamin D compounds, two novel 2-methylene-19-nor-25-dehydro-1 alpha-hydroxyvitamin D-3-26,23-lactones, GC-3 and HLV, were synthesized and biologically tested. Based on reports of similarly structured molecules, it was hypothesized that these compounds might act as antagonists, at least in vitro. The pathway designed to synthesize these compounds was based on two key steps: first, the Lythgoe-type Wittig-Horner coupling of Windaus-Grundmann-type ketone 18, with phosphine oxide 15, followed, later in the synthesis, by the Zn-mediated Reformasky-type allylation of aldehyde 20 with methylbromomethylacrylate 8. Our biological data show that neither compound has antagonistic activity but acts as weak agonists in vitro and in vivo. (C) 2008 Elsevier Ltd. All rights reserved.
• WO2006/74227
  申请人：——

  公开号：——

  公开（公告）日：——
• A Methylene Group on C-2 of 24,24-Difluoro-19-nor-1α,25-dihydroxyvitamin D₃ Markedly Increases Bone Calcium Mobilization in Vivo
  作者：Agnieszka Flores、Ilaria Massarelli、James B. Thoden、Lori A. Plum、Hector F. DeLuca

  DOI：10.1021/acs.jmedchem.5b01564

  日期：2015.12.24

  Four side chain fluorinated analogues of 1 alpha,25-dihydroxy-19-norvitamin D have been prepared in convergent syntheses using the Wittig-Homer reaction as a key step. Structures and absolute configurations of analogues 3 and 5 were confirmed by X-ray crystallography. All analogues showed high potency in HL-60 cell differentiation and vitamin D-24-hydroxylase (24-OHase) transcription as compared to 1 alpha,25-dihydroxyvitamin D-3 (1). Most important is that all of the 20S-configured derivatives (4 and 6) had high bone mobilizing activity in vivo. However, in the 20R series, a 2-methylene group was required for high bone mobilizing activity. A change in positioning of the 20R molecule in the vitamin D receptor when the 2-methylene group is present may provide new insight into the molecular basis of bone calcium mobilization induced by vitamin D.