(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane | 1016232-57-7

• 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: (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane
• 英文别名: (8S,20S)-des-A,B-8-benzoyloxy-20-[(4S)-hydroxy-pent-(1E)-en-yl]pregnane；(8S,20S)-de-A,B-8-benzoyloxy-20-[(4S)-hydroxy-pent-(1E)-en-yl]pregnane；(8S,20S)-des-A,B-8-benzoyloxy-20-[(4S)-hydroxy-pent-(1E)-enyl]pregnane；[(1R,3aR,4S,7aR)-1-[(E,2S,6S)-6-hydroxyhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 1016232-57-7
• 化学式: C₂₄H₃₄O₃
• 分子量: 370.532
• InChiKey: YXSVMGOGJXOSAQ-HRVTUAEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'S)-hydroxy-pent-(1'E)-en-yl]-pregnane 在 2,6-二甲基吡啶 、 sodium hydroxide 、 乙醇 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (8S,20S)-de-A,B-20-[(4S)-tert-butyldimethylsilyloxy-pent-(1E)-en-yl]pregnan-8-ol
  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 、 正丁基锂 、 pyridine-SO3 complex 、 四丁基氢氧化铵 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 66.83h， 生成 (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

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。
• Removal of the 26-Methyl Group from 19-nor-1α,25-Dihydroxyvitamin D₃ Markedly Reduces in Vivo Calcemic Activity without Altering in Vitro VDR Binding, HL-60 Cell Differentiation, and Transcription
  作者：Pawel Grzywacz、Grazia Chiellini、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1021/jm1010447

  日期：2010.12.23

  Twelve new analogues of 19-nor-1 alpha,25-dihydroxyvitamin D-3 (5-16) were prepared by convergent syntheses, employing the Wittig-Horner reaction. The necessary Grundmann type ketones (45-48), possessing fixed configurations of the hydroxyl group at C-25, were obtained by a multistep procedure from commercial vitamin D-2 and enantiomers of 1,3-butanediol (23 and 24). We have examined the influence of removal of one of the methyl groups located at C-25 on the biological in vitro and in vivo activity. The in vivo tests showed that the synthesized vitamin D compounds (5-16) exhibit reduced calcemic activity both in bone and in the intestine. However, in vitro potency of 2-methylene and 2 alpha-methyl compounds (5-10, 13, and 14) remained similar or enhanced as compared to that of 1 alpha,25-(OH)(2)D-3.
• 26-Desmethyl-2-methylene-22-ene-19-nor-1α,25-dihydroxyvitamin D3 compounds selectively active on intestine
  作者：Grazia Chiellini、Pawel Grzywacz、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1016/j.steroids.2014.01.012

  日期：2014.5

  Six new analogs of 2-methylene-19-nor-1 alpha,25-dihydroxyvitamin D-3, 6-7 and 8a,b-9a,b, have been synthesized. All compounds are characterized by a trans double bond located in the side chain between C-22 and C-23. While compounds 6 and 7 possess C-26 and C-27 methyls, compounds 8a,b and 9a,b lack one of these groups. A Lythgoe-based synthesis, employing the Wittig-Horner reaction was used for these preparations. Two different types of Delta E-22-25-hydroxy Grundmann's ketone, having either only one stereogenic center located at position C-20 (20 and 21), or two stereogenic centers located at 20- and 25-positions (24a,b-25a,b) were obtained by a multi-step procedure from commercial vitamin D-2. The introduction of a double bond at C-22 appeared to lower biological activity in vitro and in vivo. Further removal of a 26-methyl in these analogs had little effect on receptor binding, HL-60 differentiation and CYP24A expression but markedly diminished or eliminated in vivo activity on bone calcium mobilization while retaining activity on intestinal calcium transport. (C) 2014 Elsevier Inc. All rights reserved.
• US8114859B2
  申请人：——

  公开号：US8114859B2

  公开（公告）日：2012-02-14