(20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al | 115527-12-3

• 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: (20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al
• 英文别名: (8S,20R)-des-A,B-8-benzoyloxy-20-formylpregnane；(8S,20R)-des-A,B-8-benzoyloxy-20-formyl-pregnane；(8S,20R)-de-A,B-8-benzoyloxy-20-formylpregnane；[(1R,3aR,4S,7aR)-7a-methyl-1-[(2R)-1-oxopropan-2-yl]-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 115527-12-3
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: DCXYXPCMRLYABB-PIUDJOPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以52%的产率得到(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane
  参考文献：
  名称：

  2-Methylene-(20S,25S)-19,27-Dinor-(22E)-Vitamin D Analogs

  摘要：

  本发明披露了2-甲烯基-(20S,25S)-19,27-二去-(22E)-维生素D类似物，特别是2-甲烯基-(20S,25S)-19,27-二去-(22E)-1α,25-二羟基维生素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其分化为单核细胞的活性，因此可用作抗癌剂和治疗诸如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。该化合物还可用于治疗或预防肥胖症。

  公开号：

  US20080081799A1
• 作为产物：
  描述：

  维生素D2 在 吡啶 、 4-二甲氨基吡啶 、 pyridine-SO3 complex 、 四丁基氢氧化铵 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 44.83h， 生成 (20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al
  参考文献：
  名称：

  2-Methylene-(20S,25S)-19,27-Dinor-(22E)-Vitamin D Analogs

  摘要：

  本发明披露了2-甲烯基-(20S,25S)-19,27-二去-(22E)-维生素D类似物，特别是2-甲烯基-(20S,25S)-19,27-二去-(22E)-1α,25-二羟基维生素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其分化为单核细胞的活性，因此可用作抗癌剂和治疗诸如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。该化合物还可用于治疗或预防肥胖症。

  公开号：

  US20080081799A1

文献信息

• 2alpha-Methyl and 2beta-Methyl Analogs of 19,26-Dinor-1alpha,25-Dihydroxyvitamin D3 and Their Uses
  申请人：DeLuca Hector F.

  公开号：US20120283228A1

  公开（公告）日：2012-11-08

  This invention discloses 2α-methyl and 2β-methyl analogs of 19,26-dinor-1α,25-dihydroxyvitamin D 3 and pharmaceutical uses therefor. These compounds exhibit in vitro biological activities 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 have little, if any, in vivo calcemic activity and therefore may be used to treat autoimmune disorders in humans as well as secondary hyperparathyroidism and renal osteodystrophy.

  这项发明揭示了19,26-去甲基-1α,25-二羟基维生素D3的2α-甲基和2β-甲基类似物以及其药用。这些化合物在体外表现出生物活性，可作为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。这些化合物在体内几乎没有钙调节活性，因此可用于治疗人类的自身免疫性疾病，以及继发性甲状旁腺功能亢进和肾性骨病。
• 2-Methylene-(20S,25S)-19,26-Dinor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20090170821A1

  公开（公告）日：2009-07-02

  This invention discloses 2-methylene-(20S,25S)-19,26-dinor-vitamin D analogs, and specifically 2-methylene-(20S,25S)-19,26-dinor-1α,25-dihydroxyvitamin 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 or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  这项发明披露了2-亚甲基-(20S,25S)-19,26-二诺尔维生素D类似物，具体为2-亚甲基-(20S,25S)-19,26-二诺尔-1α,25-二羟基维生素D3，以及其药用。该化合物在阻止未分化细胞增殖和诱导它们向单核细胞分化方面表现出显著活性，因此可作为抗癌剂以及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的药物。该化合物在钙代谢方面几乎没有活性，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。此外，该化合物还可用于肥胖的治疗或预防。
• [EN] 2-METHYLENE-19,26-NOR-(20S)-1a-HYDROXYVITAMIN D3<br/>[FR] 2-MÉTHYLÈNE-19,26-NOR-(20S)-1?-HYDROXYVITAMINE D3
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2011066506A1

  公开（公告）日：2011-06-03

  Compounds of formula I are provided where X1 and X2 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.

  提供了化学式I的化合物，其中X1和X2可以独立地选择为H或羟基保护基团。这些化合物可用于制备药物组合物，并在治疗各种生物状况方面具有用处。
• 2-Methylene-(20S,25R)-19,26-Dinor-Vitamin D Analogs
  申请人：DeLuca Hector F.

  公开号：US20090170820A1

  公开（公告）日：2009-07-02

  This invention discloses 2-methylene-(20S,25R)-19,26-dinor-vitamin D analogs, and specifically 2-methylene-(20S,25R)-19,26-dinor-1α,25-dihydroxyvitamin 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 or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

  该发明揭示了2-亚甲基-(20S,25R)-19,26-双去-维生素D类似物，具体为2-亚甲基-(20S,25R)-19,26-双去-1α,25-二羟基维生素D3，以及其药用。该化合物在抑制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，因此可作为抗癌剂以及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的药物。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。
• 2-alkylidene-18,19-dinor-vitamin D compounds
  申请人：DeLuca F. Hector

  公开号：US20050227950A1

  公开（公告）日：2005-10-13

  2-alkylidene-18,19-dinor-vitamin D compounds are disclosed as well as pharmaceutical uses for these compounds and methods of synthesizing these compounds. These compounds are characterized by low bone calcium mobilization activity and high intestinal calcium transport activity. This results in novel therapeutic agents for the treatment and prophylaxis of diseases where bone formation is desired, particularly osteoporosis, as well as autoimmune diseases such as multiple sclerosis, diabetes mellitus and lupus. These compounds also 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. These compounds also increase both breaking strength and crushing strength of bones evidencing use in conjunction with bone replacement surgery such as hip and knee replacements.

  披露了2-烷基亚烯基-18,19-二诺尔维生素D化合物，以及这些化合物的药用途和合成这些化合物的方法。这些化合物的特点是低骨钙动员活性和高肠道钙运输活性。这导致了用于治疗和预防骨形成期望的疾病的新型治疗剂，特别是骨质疏松症，以及自身免疫疾病，如多发性硬化症、糖尿病和红斑狼疮。这些化合物还表现出明显的活性，可以阻止未分化细胞的增殖，并诱导它们分化为单核细胞，从而表明其用作抗癌剂和用于治疗银屑病等皮肤疾病。这些化合物还增加了骨骼的抗折强度和抗压强度，表明它们可与骨骼置换手术（如髋关节和膝关节置换）结合使用。