(S)-2-((1R,3aR,4S,7aR)-4-(benzoyloxy)-7a-methyloctahydro-1H-inden-1-yl)propyl benzoate | 64190-53-0

• 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: (S)-2-((1R,3aR,4S,7aR)-4-(benzoyloxy)-7a-methyloctahydro-1H-inden-1-yl)propyl benzoate
• 英文别名: De-A,B-(Benzoyloxy)-23,24-dinor-22-(benzoyloxy)cholane；[(2S)-2-[(1R,3aR,4S,7aR)-4-benzoyloxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]propyl] benzoate
• CAS: 64190-53-0
• 化学式: C₂₇H₃₂O₄
• 分子量: 420.549
• InChiKey: SKESBUYREZNFRE-WUQKEVEASA-N

物化性质

• 沸点：
  519.3±23.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((1R,3aR,4S,7aR)-4-(benzoyloxy)-7a-methyloctahydro-1H-inden-1-yl)propyl benzoate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氢氧化钾 、 重铬酸吡啶 、 正丁基锂 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 (1R,3aR,4S,7aR)-7a-Methyl-1-{(S)-1-[5-(1-methyl-1-triethylsilanyloxy-ethyl)-2H-pyrazol-3-yl]-ethyl}-octahydro-inden-4-ol
  参考文献：
  名称：

  维生素D杂环类似物。第1部分：到CD系统侧链带有吡唑环的立体选择路线

  摘要：

  有效制备两个在侧链带有吡唑环的维生素D CD环系统合成子是基于由α-炔酮形成吡唑环。

  DOI：

  10.1016/s0040-4039(02)00031-x
• 作为产物：
  描述：

  维生素D2 在 吡啶 、 4-二甲氨基吡啶 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 43.0h， 生成 (S)-2-((1R,3aR,4S,7aR)-4-(benzoyloxy)-7a-methyloctahydro-1H-inden-1-yl)propyl benzoate
  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

• [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-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。
• Analogues of the Inhoffen–Lythgoe diol with anti-proliferative activity
  作者：Albert M. DeBerardinis、Steven Lemieux、M. Kyle Hadden

  DOI：10.1016/j.bmcl.2013.07.054

  日期：2013.10

  The anti-proliferative activity of a series of ester-and amide-linked Inhoffen-Lythgoe side chain analogues is reported. Whereas the Inhoffen-Lythgoe diol was inactive in these studies, a number of aromatic and aliphatic ester-linked side chains demonstrated modest in vitro growth inhibition in two human cancepar cell lines, U87MG (glioblastoma) and HT-29 (colorectal adenocarcinoma). Structureactivity relationship (SAR) studies demonstrated the most active aromatic (13) and aliphatic (25 and 29) substituted analogues were approximately equipotent in U87MG and HT-29 cells. Further evaluation of 13, 25, and 29 indicated these analogues do not activate canonical vitamin D signaling nor antagonize Hedgehog (Hh) signaling. Thus, the cellular mechanism(s) that govern the anti-proliferative activity for this class of truncated vitamin D-based structures appears to be different from classical mechanisms previously identified for these scaffolds. (C) 2013 Elsevier Ltd. All rights reserved.
• 25-hydroxydihydrotachysterol2 an innovative synthesis of a key metabolite of dihydrotachysterol2
  作者：Jaap C. Hanekamp、Rob Boer Rookhuizen、Hendrik J.T. Bos、Lambert Brandsma

  DOI：10.1016/s0040-4020(01)85618-0

  日期：1992.1

  A new synthesis of 25-hydroxydihydrotachysterol2 is described The hydroxylated side-chain is constructed stereoselectively using a chiral Wittig reagent. The A-ring synthon is introduced utilising the Wittig-Horner method as developed by Lythgoe et al. The preparation of the metabolite is carried out in 18 steps.