(20S)-des-A,B-20-butylpregnan-8-one | 852658-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (20S)-des-A,B-20-butylpregnan-8-one
• 英文别名: (20S)-de-A,B-20-butyl-pregnan-8-one；(1R,3aR,7aR)-1-[(2S)-hexan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 852658-82-3
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: QTIROIGGKAZETC-KNCOVGOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (20S)-des-A,B-20-butylpregnan-8-one 在 四丁基氟化铵 、 苯基锂 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 25.5h， 生成 (20S)-2-methylene-19,26,27-trinor-1α,25-dihydroxyvitamin D₃
  参考文献：
  名称：

  Vitamin D analogs for obesity prevention and treatment

  摘要：

  治疗和预防肥胖的方法，抑制脂肪细胞分化，抑制增加的SCD-1基因转录，和/或减少受试者体脂肪的方法包括向需要的受试者施用至少一种1α,25-二羟基维生素D3或1α,25-二羟基维生素D2的类似物或包含这种类似物的药物组合物。该类似物可以是19-去甲基维生素D类似物，如式IA的化合物，式IB的化合物，或其中的混合物，其中变量R1、R2和R3具有此处描述的值。

  公开号：

  US20050119242A1
• 作为产物：
  描述：

  维生素D2 在 nickel dichloride 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 四丁基氢氧化铵 、 碘 、 三氧化硫吡啶 、 4-甲基苯磺酸吡啶 、 氟化氢吡啶 、 臭氧 、 三乙胺 、 对甲苯磺酰氯 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 163.99h， 生成 (20S)-des-A,B-20-butylpregnan-8-one
  参考文献：
  名称：

  Vitamin D analogs for obesity prevention and treatment

  摘要：

  治疗和预防肥胖的方法，抑制脂肪细胞分化，抑制增加的SCD-1基因转录，和/或减少受试者体脂肪的方法包括向需要的受试者施用至少一种1α,25-二羟基维生素D3或1α,25-二羟基维生素D2的类似物或包含这种类似物的药物组合物。该类似物可以是19-去甲基维生素D类似物，如式IA的化合物，式IB的化合物，或其中的混合物，其中变量R1、R2和R3具有此处描述的值。

  公开号：

  US20050119242A1

文献信息

• 2alpha-Methyl and 2beta-methyl analogs of 19,26,27-trinor-(20S)-1alpha-hydroxyvitamin D3 and their uses
  申请人：DeLuca F. Hector

  公开号：US20060116352A1

  公开（公告）日：2006-06-01

  This invention discloses 2α-methyl and 2β-methyl analogs of 19,26,27-trinor-(20S) -1α-hydroxyvitamin D 3 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19,26,27-三去（20S）-1α-羟基维生素D3的2α-甲基和2β-甲基类似物及其药用。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。这些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病。这些化合物还可用于肥胖的治疗或预防。
• [EN] 2-METHYLENE-19,26,27-TRINOR-(20S)-1a-ALPHA-HYDROXYVITAMIN D3 AND ITS USES<br/>[FR] 2-METHYLENE-19,26,27-TRINOR-(20S)-1?-ALPHA-HYDROXYVITAMINE D3 ET SES UTILISATIONSITS USES
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2006057886A3

  公开（公告）日：2006-06-29
• 26- and 27-Methyl groups of 2-substituted, 19-nor-1α,25-dihydroxylated vitamin D compounds are essential for calcium mobilization in vivo
  作者：Pawel Grzywacz、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1016/j.bioorg.2013.01.001

  日期：2013.4

  Twelve new analogs of 19-nor-1 alpha,25-dihydroxyvitamin D-3 6-17, were prepared by a multi-step procedure from known alcohols 18 and 19. We have examined the influence of removing two methyl groups located at C-25, as well as the 25-hydroxy group, on the biological in vitro and in vivo biological activity. Surprisingly, removal of the 26- and 27-methyl groups from either the 2 alpha-methyl or 2-methylene-19-nor-1 alpha,25-dihydroxyvitamin D-3 reduced vitamin D receptor binding, HL-60 differentiation, and 25-hydroxylase transcription in vitro only slightly to moderately (compounds 6-13). However, these compounds were devoid of in vivo bone mobilization activity and had markedly reduced activity on intestinal calcium transport. The analogs 14-17 with a 2 beta-methyl substitution had little or no activity in vitro and in vivo as expected from previous work. (C) 2013 Elsevier Inc. All rights reserved.
• 2-METHYLENE-19,26,27-TRINOR-(20S)-1-ALPHA-HYDROXYVITAMIN D3 AND ITS USES
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP1828113B1

  公开（公告）日：2010-05-12
• 2-Methylene-19,26,27-Trinor-(20S)-1Alpha-Hydroxyvitamin D3 and Its Uses
  申请人：DeLuca F. Hector

  公开号：US20070249567A1

  公开（公告）日：2007-10-25

  This invention discloses 2-methylene-19,26,27-trinor-(20S)-vitamin D analogs, and specifically 2-methylene-19,26,27-trinor-(20S)-1α-hydroxyvitamin 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.