Ro 23-7553 | 118694-43-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Ro 23-7553
• 英文别名: 1,25-dihydroxy-16-ene-23-yne-vitamin D₃；1α,25-dihydroxy-16-ene-23-yne-vitamin D₃；1α,25-dihydroxy-16-en-23-yne-vitamin D₃；(1α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19),16-tetraen-23-yne-1,3,25-triol；1,25-dihydroxy-16-ene-23-yne-cholecalciferol；1,25-Dihydroxy-16-ene-23-yne-vitamin D3；(1R,3S,5Z)-5-[(2E)-2-[(3aS,7aS)-1-[(2R)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-3a,5,6,7-tetrahydro-3H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS: 118694-43-2
• 化学式: C₂₇H₃₈O₃
• 分子量: 410.597
• InChiKey: JKFZMIQMKFWJAY-RQJQXFIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ro 23-7553 在 bovine adrenodoxin reductase 、 bovine adrenodoxin 、 recombinant rat cytochrome P450 24A1(Δ2-32) 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 0.08h， 生成 1α,25,26-trihydroxy-16-en-23-yne-vitamin D3
  参考文献：
  名称：

  A new insight into the role of rat cytochrome P450 24A1 in metabolism of selective analogs of 1α,25-dihydroxyvitamin D3

  摘要：

  We examined the metabolism of two synthetic analogs of 1 alpha,25-dihydroxyvitamin D-3 (1), namely 1 alpha,25-dihydroxy-16-ene-23-yne-vitamin D-3 (2) and 1 alpha,25-dihydroxy-16-ene-23-yne-26,27-dimethyl-vitamin D-3 (4) using rat cytochrome P450 24A1 (CYP24A1) in a reconstituted system. We noted that 2 is metabolized into a single metabolite identified as C26-hydroxy-2 while 4 is metabolized into two metabolites, identified as C26-hydroxy-4 and C26a-hydroxy-4. The structural modification of adding methyl groups to the side chain of 1 as in 4 is also featured in another analog, 1 alpha,25-dihydroxy-22,24-diene-24,26,27-tri-homo-vitamin D-3 (6). In a previous study, 6 was shown to be metabolized exactly like 4, however, the enzyme responsible for its metabolism was found to be not CYP24A1. To gain a better insight into the structural determinants for substrate recognition of different analogs, we performed an in silico docking analysis using the crystal structure of rat CYP24A1 that had been solved for the substrate-free open form. Whereas analogs 2 and 4 docked similar to 1,6 showed altered interactions for both the A-ring and side chain, despite prototypical recognition of the CD-ring. These findings hint that CYP24A1 metabolizes selectively different analogs of 1, based on their ability to generate discrete recognition cues required to close the enzyme and trigger the catalytic mechanism. 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2011.02.004
• 作为产物：
  描述：

  <3aR-<1(R*),3aα,7aβ>>-3,3a,5,6,7,7a-hexahydro-1-(5-hydroxy-1,5-dimethyl-3-hexynyl)-7a-methyl-1H-inden-4-one 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium tert-butylate 、 potassium acetate 、 三环己基膦 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 8.08h， 生成 Ro 23-7553
  参考文献：
  名称：

  总合成在侧链和D环上修饰的1α，25-二羟基维生素D 3类似物†

  摘要：

  在本文中，我们描述了一种合成策略，可访问在C20具有天然或非天然构型且在D环具有不饱和键的1α，25-二羟基维生素D 3（骨三醇）类似物。合成方法以两种有效的类似物为例，即1α，25-二羟基-16-en-23-炔-维生素D 3和1α，25-二羟基-20- epi -24a-homo-26,27-二甲基维生素D 3。合成策略的关键特征是通过胶束系统中的CuH物种催化α，β，γ，δ-不饱和酯的催化不对称还原，从而在C20处生成不自然的构型。

  DOI：

  10.1039/c8ob01002a

文献信息

• [EN] USE OF VITAMIN D COMPOUNDS FOR THE PREVENTION OR TREATMENT OF CHRONIC PROSTATITIS<br/>[FR] UTILISATION DE COMPOSES DE VITAMINE D POUR LA PREVENTION OU LE TRAITEMENT DE LA PROSTATITE CHRONIQUE
  申请人：BIOXELL SPA

  公开号：WO2006035075A1

  公开（公告）日：2006-04-06

  The use of a vitamin D compound in the prevention or treatment of chronic prostatitis and related methods, pharmaceutical formulations and kits.

  维生素D化合物在慢性前列腺炎的预防或治疗中的使用，以及相关方法、药物配方和工具包。
• Process for the preparation of
  申请人：Hoffmann-La Roche Inc.

  公开号：US05789607A1

  公开（公告）日：1998-08-04

  A process for preparing 1,25-dihydroxy-16-ene-23-yne cholecalciferol.

  制备1,25-二羟基-16-烯-23-炔-维生素D3的方法。
• Process for the synthesis of vitamin d compounds and intermediates for the synthesis of the compounds
  申请人：Kashiwagi Hirotaka

  公开号：US20070135394A1

  公开（公告）日：2007-06-14

  An object of the present invention is to provide a process for synthesizing a vitamin D compound by simple procedures at lower costs. The present invention provides a process for preparing a vitamin D compound and an intermediate thereof, comprising the step of: (a) mixing a ketone or aldehyde, a Wittig reagent, and a base; or (b) mixing a ketone or aldehyde and a Wittig reagent, and then adding a base to the resulting mixture.

  本发明的一个目的是提供一种通过简单程序以更低成本合成维生素D化合物的方法。本发明提供了一种制备维生素D化合物及其中间体的方法，包括以下步骤：(a)混合酮或醛、威蒂格试剂和碱；或者(b)混合酮或醛和威蒂格试剂，然后向所得混合物中加入碱。
• FMO3 inhibitors for treating pain
  申请人：Akron Molecules GmbH

  公开号：EP2674161A1

  公开（公告）日：2013-12-18

  The present invention relates to new therapies to treat pain and related diseases, as well as pharmaceutical compounds for use in said therapies.

  本发明涉及治疗疼痛和相关疾病的新疗法，以及用于上述疗法的药物化合物。
• WO2006/51106
  申请人：——

  公开号：——

  公开（公告）日：——