(4-溴-1,1-二甲基丁氧基)(1,1-二甲基乙基)二甲基硅烷 | 380605-59-4

• 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
• 中文名称: (4-溴-1,1-二甲基丁氧基)(1,1-二甲基乙基)二甲基硅烷
• 英文名称: (4-bromo-1,1-dimethylbutyloxy)-tert-butyldimethylsilane
• 英文别名: 5-bromo-2methyl-2[(tert-butyldimethylsilyl)oxy]-pentane；(4-Bromo-1,1-dimethyl-butoxy)-tert-butyl-dimethyl-silane；(5-bromo-2-methylpentan-2-yl)oxy-tert-butyl-dimethylsilane
• CAS: 380605-59-4
• 化学式: C₁₂H₂₇BrOSi
• 分子量: 295.335
• InChiKey: KSQAZJRLBNGMBD-UHFFFAOYSA-N

物化性质

• 沸点：
  278.5±13.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-溴-1,1-二甲基丁氧基)(1,1-二甲基乙基)二甲基硅烷 、 3β-t-butyldimethylsilyloxy-pregn-5-en-20-one 在 六甲基磷酰三胺 、 三氢化钐 、 1,2-二碘乙烷 作用下， 以 四氢呋喃 为溶剂， 以26%的产率得到3,25-di((tert-butyl(dimethyl)silyl)oxy)cholest-5-ene-20-ol
  参考文献：
  名称：

  Hedgehog 信号通路侧链氧甾醇激动剂的构效关系

  摘要：

  氧固醇 (OHC) 是胆固醇氧化的副产物，已知可激活 Hedeghog (Hh) 信号通路。虽然在整个支架中包含羟基的 OHC 是已知的，但那些充当 Hh 信号传导激动剂的 OHC 主要在烷基侧链上包含一个羟基。我们试图通过对一系列合成 OHC 进行构效关系研究，进一步探索侧链羟基化模式如何影响氧甾醇介导的 Hh 活化。最活跃的类似物 23( R )-OHC ( 35 ) 在两个依赖于 Hh 的细胞系中证明了 Hh 信号传导的有效激活（EC 50值 0.54–0.65 μM）。此外，OHC 35与肝脏 X 受体（一种也被内源性 OHC 激活的核受体）相比，对 Hh 途径的选择性约为 3 倍。最后，35在培养的细胞中诱导成骨分化和成骨细胞形成，表明 Hh 途径的功能激动。

  DOI：

  10.1021/ml300192k
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 5-bromo-2-methylpentan-2-ol 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (4-溴-1,1-二甲基丁氧基)(1,1-二甲基乙基)二甲基硅烷
  参考文献：
  名称：

  Hedgehog 信号通路侧链氧甾醇激动剂的构效关系

  摘要：

  氧固醇 (OHC) 是胆固醇氧化的副产物，已知可激活 Hedeghog (Hh) 信号通路。虽然在整个支架中包含羟基的 OHC 是已知的，但那些充当 Hh 信号传导激动剂的 OHC 主要在烷基侧链上包含一个羟基。我们试图通过对一系列合成 OHC 进行构效关系研究，进一步探索侧链羟基化模式如何影响氧甾醇介导的 Hh 活化。最活跃的类似物 23( R )-OHC ( 35 ) 在两个依赖于 Hh 的细胞系中证明了 Hh 信号传导的有效激活（EC 50值 0.54–0.65 μM）。此外，OHC 35与肝脏 X 受体（一种也被内源性 OHC 激活的核受体）相比，对 Hh 途径的选择性约为 3 倍。最后，35在培养的细胞中诱导成骨分化和成骨细胞形成，表明 Hh 途径的功能激动。

  DOI：

  10.1021/ml300192k

文献信息

• 2-Methylene-(20E)-20(22)-Dehydro-19-Nor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20100009940A1

  公开（公告）日：2010-01-14

  This invention discloses 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-(20E)-20(22)-dehydro-19-nor-1α,25-dihydroxyvitamin D 3 , and pharmaceutical uses therefor. This compound exhibits relatively high transcription activity as well as pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also shows lower activity in vivo on bone calcium mobilization and similar in vivo intestinal calcium transport activity compared to the native hormone 1α,25-dihydroxyvitamin D 3 , and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  本发明公开了2-亚甲基-(20E)-20(22)-去氢-19-去氢维生素D类似物，特别是2-亚甲基-(20E)-20(22)-去氢-19-去氢-1α,25-二羟基维生素D3，并提供了其药用用途。该化合物表现出相对较高的转录活性，以及在阻止未分化细胞增殖和诱导它们分化为单核细胞方面表现出显著活性，从而证明其作为抗癌剂以及用于治疗银屑病等皮肤疾病以及皮肤问题，如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足的用途。该化合物在体内对骨钙动员的活性较低，并且与天然激素1α,25-二羟基维生素D3相比，在体内肠钙转运活性类似，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨病。该化合物还可用于治疗或预防肥胖。
• 2-Methylene-20(21)-Dehydro-19-Nor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20100009941A1

  公开（公告）日：2010-01-14

  This invention discloses 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-20(21)-dehydro-19-nor-1α,25-dihydroxyvitamin D 3 , and pharmaceutical uses therefor. This compound exhibits relatively high transcription activity as well as pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also shows lower activity in vivo on bone calcium mobilization and similar in vivo intestinal calcium transport activity compared to the native hormone 1αa,25-dihydroxyvitamin D 3 , and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  本发明揭示了2-亚甲基-20(21)-去氢-19-去氢维生素D类似物，具体包括2-亚甲基-20(21)-去氢-19-去氢-1α,25-二羟基维生素D3，以及其药用用途。该化合物表现出相对较高的转录活性，以及在阻止未分化细胞增殖和诱导它们分化为单核细胞方面的显著活性，从而表明其用作抗癌剂以及用于治疗银屑病等皮肤疾病以及皮肤状况，如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足。该化合物在体内对骨钙动员的活性较低，并且与天然激素1α,25-二羟基维生素D3相比，在体内肠钙转运活性类似，因此可用于治疗人类的自身免疫性疾病或炎症性疾病以及肾性骨病。该化合物还可用于肥胖的治疗或预防。
• 17,20(E)-dehydro vitamin D analogs and their uses
  申请人：DeLuca F. Hector

  公开号：US20060111330A1

  公开（公告）日：2006-05-25

  This invention discloses 17,20(E)-dehydro vitamin D analogs, and specifically 17(E)-1α,25-dihydroxy-17(20)-dehydro-2-methylene-19-nor-vitamin D 3 and pharmaceutical uses therefor. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also has little, if any, calcemic activity and therefore may be used to treat autoimmune disorders and inflammatory diseases in humans as well as renal osteodystrophy and obesity.

  本发明披露了17,20（E）-去氢维生素D类似物，特别是17（E）-1α,25-二羟基-17（20）-去氢-2-亚甲基-19-去甲基维生素D3及其药物用途。该化合物表现出明显的抑制未分化细胞增殖和诱导它们分化成单核细胞的活性，因此可作为抗癌剂和治疗银屑病等皮肤疾病以及皮肤条件如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足的用途。该化合物也几乎没有钙代谢活性，因此可用于治疗人类的自身免疫性疾病和炎症性疾病，以及肾性骨营养不良和肥胖症。
• 17,20(Z)-dehydro vitamin D analogs and their uses
  申请人：DeLuca F. Hector

  公开号：US20060116351A1

  公开（公告）日：2006-06-01

  This invention discloses 17,20(Z)-dehydro vitamin D analogs, and specifically 17(Z)-1α,25-dihydroxy-17(20)-dehydro-2-methylene-19-nor-vitamin D 3 and pharmaceutical uses therefor. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also may be used to treat autoimmune disorders and inflammatory diseases in humans as well as renal osteodystrophy and obesity. This compound also has significant calcemic activity making it a therapeutic agent for the treatment or prophylaxis of osteoporosis, osteomalacia, renal osteodystrophy and hypoparathyroidism.

  本发明披露了17,20(Z)-去氢维生素D类似物，特别是17(Z)-1α,25-二羟基-17(20)-去氢-2-甲基-19-去甲基维生素D3及其药物用途。该化合物表现出明显的活性，可阻止未分化细胞的增殖并诱导它们向单核细胞分化，从而表明其可用作抗癌剂、治疗银屑病等皮肤疾病以及皮肤状况（如皱纹、松弛的皮肤、干燥的皮肤和不足的皮脂分泌）的药物。该化合物还可用于治疗人类的自身免疫性疾病和炎症性疾病，以及肾性骨营养不良和肥胖症。此化合物还具有显著的钙调节活性，因此可用作治疗或预防骨质疏松症、佝偻病、肾性骨营养不良和甲状旁腺功能减退症的治疗剂。
• 17,20(Z)-Dehydro Vitamin D Analogs and Their Uses
  申请人：DeLuca F. Hector

  公开号：US20070259838A1

  公开（公告）日：2007-11-08

  This invention discloses 17,20(Z)-dehydro vitamin D analogs, and specifically 17(Z)-1α,25-dihydroxy-17(20)-dehydro-2-methylene-19-nor-vitamin D 3 and pharmaceutical uses therefor. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also may be used to treat autoimmune disorders and inflammatory diseases in humans as well as renal osteodystrophy and obesity. This compound also has significant calcemic activity making it a therapeutic agent for the treatment or prophylaxis of osteoporosis, osteomalacia, renal osteodystrophy and hypoparathyroidism.

  本发明揭示了17,20(Z)-去氢维生素D类似物，特别是17(Z)-1α,25-二羟基-17(20)-去氢-2-甲基-19-去氢维生素D3及其药物用途。该化合物表现出明显的活性，可抑制未分化细胞的增殖并诱导它们分化为单核细胞，因此可以用作抗癌剂和治疗皮肤疾病，如牛皮癣以及皮肤状况，如皱纹、松弛皮肤、干燥皮肤和分泌不足的皮脂。此化合物还可用于治疗人类的自身免疫性疾病和炎症性疾病，以及肾性骨营养不良和肥胖症。此化合物还具有显著的钙代谢活性，可作为治疗或预防骨质疏松症、佝偻病、肾性骨营养不良和甲状旁腺功能减退症的治疗剂。