benzoic acid-(1S,3aR,4S,7aR)-1-((S)-1-cyano-1-methyl-propyl)-7a-methyl-octahydro-inden-4-yl ester | 951777-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzoic acid-(1S,3aR,4S,7aR)-1-((S)-1-cyano-1-methyl-propyl)-7a-methyl-octahydro-inden-4-yl ester
• 英文别名: [(1S,3aR,4S,7aR)-1-[(2S)-2-cyanobutan-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 951777-92-7
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: AUHCFUWDDAFYHM-XUJOWKJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzoic acid-(1S,3aR,4S,7aR)-1-((S)-1-cyano-1-methyl-propyl)-7a-methyl-octahydro-inden-4-yl ester 在 四丙基高钌酸铵 、 四丁基氟化铵 、 水 、 二异丁基氢化铝 、 苯基锂 、 N-甲基吗啉氧化物 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二丁醚 、 甲苯 为溶剂， 反应 44.16h， 生成 1α-hydroxy-20,21-dehydro-2-methylene-19,24,25,26,27-pentanorvitamin D3
  参考文献：
  名称：

  [EN] 2-METHYLENE-20(21)-DEHYDRO-19,24,25,26,27,-PENTANOR-VITAMIN D ANALOGS
  [FR] ANALOGUES DE 2-MÉTHYLÈNE-20(21)-DÉSHYDRO-19,24,25,26,27-PENTANOR-VITAMINE D

  摘要：

  这项发明揭示了2-亚甲基-20(21)-去氢-19,24,25,26,27-五环-维生素D类似物，特别是2-亚甲基-20(21)-去氢-19,24,25,26,27-五环-1α-羟基维生素D3，以及其药用。该化合物显示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成单核细胞方面的显著活性，因此表明可用作抗癌剂，用于治疗银屑病等皮肤疾病以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况。与天然激素1α,25-二羟基维生素D3相比，该化合物在体内对骨钙动员和肠钙转运活性较低，因此可用于治疗人类的自身免疫性疾病或炎症性疾病，以及继发性甲状旁腺功能亢进和肾性骨营养不良。该化合物还可用于肥胖的治疗或预防。

  公开号：

  WO2013012644A1
• 作为产物：
  描述：

  benzoic acid (1R,3aR,4S,7aR)-1-[(S)-(2'-hydroxyimino-1'-methyl)ethyl]-7a-methyl-octahydro-inden-4-yl ester 在 正丁基锂 、 乙酸酐 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.33h， 生成 benzoic acid-(1S,3aR,4S,7aR)-1-((S)-1-cyano-1-methyl-propyl)-7a-methyl-octahydro-inden-4-yl ester
  参考文献：
  名称：

  烷基侧链缩短的2-（3'-羟基丙叉基）-1α-羟基-19-降钙素D类似物的合成和生物活性

  摘要：

  作为我们的涉及有前途的生物性质，19-norvitamins维生素d化合物的努力的延续9 - 13，具有连接到C-2和缩短的17β-烷基链的3'-羟基亚片段，合成的。一种新的合成途径提供CD-环酮20 - 24从差向异构的醛开始描述25和26。所述hydrindanones 20 - 24进行与所述氧化膦的Wittig-Horner反应14，和维生素d化合物9 - 13羟基脱保护后得到的。与1α，25-（OH）相比2 D 3（1），除20 R-化合物12外，所制备的类似物仅约。与VDR绑定的效力降低了3倍。化合物9 - 11和13展出HL-60细胞活性的5-20倍降低和转录活性约 与激素1相关的下降10倍。当在体内测试中，所有的类似物没有显示能力，动员骨钙，并且仅在高剂量的维生素观察肠钙转运活性10，12，和13。

  DOI：

  10.1021/jm200743p

文献信息

• 2-Methylene-20-Methyl-19,24,25,26,27-Pentanor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20090170822A1

  公开（公告）日：2009-07-02

  This invention discloses 2-methylene-20-methyl-19,24,25,26,27-pentanor-vitamin D analogs, and specifically 2-methylene-20-methyl-1α-hydroxy-19,24,25,26,27-pentanor-vitamin D 3 , and pharmaceutical uses therefore. This compound exhibits 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 or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  该发明披露了2-亚甲基-20-甲基-19,24,25,26,27-五缩戊-维生素D类似物，具体包括2-亚甲基-20-甲基-1α-羟基-19,24,25,26,27-五缩戊-维生素D3，以及其药用用途。该化合物表现出抑制未分化细胞增殖并诱导其分化为单核细胞的活性，从而表明其用作抗癌剂以及治疗银屑病等皮肤疾病以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的用途。该化合物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。
• 1alpha-Hydroxy-2-(3'-Hydroxypropylidene)-19-Nor-Vitamin D Compounds with a 1,1-Dimethylpropyl Side Chain
  申请人：DeLuca Hector F.

  公开号：US20070238703A1

  公开（公告）日：2007-10-11

  This invention discloses 1α-hydroxy-2-(3′-hydroxypropylidene)-19-nor-vitamin D compounds with a 1,1-dimethylpropyl side chain, and pharmaceutical uses therefor. These compounds exhibit 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. These compounds also have little, if any, calcemic activity and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. These compounds may also be used for the treatment or prevention of obesity.

  该发明揭示了具有1,1-二甲基丙基侧链的1α-羟基-2-(3′-羟丙基亚甲基)-19-去氢维生素D化合物，并揭示了其在药物上的用途。这些化合物在抑制未分化细胞的增殖和诱导它们分化为单核细胞方面表现出显著的活性，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皱纹、皮肤松弛、干燥皮肤和皮脂分泌不足等皮肤状况。这些化合物也几乎没有钙代谢活性，因此可以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。这些化合物还可以用于肥胖的治疗或预防。
• 1α-hydroxy-2-(3′-hydroxypropylidene)-19-nor-vitamin D compounds with a 1,1-dimethylpropyl side chain
  申请人：Wisconsin Alumni Research Foundation

  公开号：US07763598B2

  公开（公告）日：2010-07-27

  This invention discloses 1α-hydroxy-2-(3′-hydroxypropylidene)-19-nor-vitamin D compounds with a 1,1-dimethylpropyl side chain, and pharmaceutical uses therefor. These compounds exhibit 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. These compounds also have little, if any, calcemic activity and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. These compounds may also be used for the treatment or prevention of obesity.

  本发明揭示了具有1,1-二甲基丙基侧链的1α-羟基-2-(3'-羟基丙烯基)-19-去氢维生素D化合物及其药物用途。这些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分化为单核细胞，因此可作为抗癌剂和治疗银屑病等皮肤疾病以及皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足等皮肤状况的药物。这些化合物也几乎没有钙代谢活性，因此可用于治疗人类自身免疫性疾病或炎症性疾病以及肾性骨营养不良。这些化合物也可用于肥胖症的治疗或预防。
• 2-methylene-20-methyl-19,24,25,26,27-pentanor-vitamin D analogs
  申请人：Wisconsin Alumni Research Foundation

  公开号：US07943601B2

  公开（公告）日：2011-05-17

  This invention discloses 2-methylene-20-methyl-19,24,25,26,27-pentanor-vitamin D analogs, and specifically 2-methylene-20-methyl-1α-hydroxy-19,24,25,26,27-pentanor-vitamin D3, and pharmaceutical uses therefore. This compound exhibits 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 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-20-甲基-19,24,25,26,27-五去环维生素D类似物，具体包括2-亚甲基-20-甲基-1α-羟基-19,24,25,26,27-五去环维生素D3，以及其药用途。该化合物表现出抑制未分化细胞增殖并诱导它们分化为单核细胞的活性，因此可用作抗癌剂以及用于治疗皮肤疾病，如牛皮癣以及皮肤状况，如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足。此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或炎症性疾病以及肾性骨营养不良。此化合物也可用于治疗或预防肥胖症。
• 2-Methylene-20(21)-Dehydro-19,24,25,26,27-Pentanor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20130178449A1

  公开（公告）日：2013-07-11

  This invention discloses 2-methylene-20(21)-dehydro-19,24,25,26,27-pentanor-vitamin D analogs, and specifically 2-methylene-20(21)-dehydro-19,24,25,26,27-pentanor-1α-hydroxyvitamin 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 lower in vivo intestinal calcium transport activity as 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 secondary hyperparathyroidism and 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-19,24,25,26,27-五环维生素D类似物，特别是2-亚甲基-20（21）-去氢-19,24,25,26,27-五环-1α-羟基维生素D3及其药物用途。该化合物表现出相对较高的转录活性以及显着的抑制未分化细胞增殖并诱导其分化成单核细胞的活性，因此可作为抗癌剂和治疗皮肤病如牛皮癣以及皮肤状况如皱纹、松弛皮肤、干燥皮肤和皮脂分泌不足的药物。该化合物在体内对骨钙动员和肠道钙转运活性的活性较天然激素1α,25-二羟基维生素D3低，因此可用于治疗人类的自身免疫性疾病或炎症性疾病，以及继发性甲状旁腺功能亢进和肾性骨营养不良。该化合物还可用于治疗或预防肥胖症。