(R)-2-(9-(1H-imidazol-1-yl)nonyl)-2,5,7,8-tetramethylchroman-6-ol | 1071461-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R)-2-(9-(1H-imidazol-1-yl)nonyl)-2,5,7,8-tetramethylchroman-6-ol
• 英文别名: (2R)-2-(9-imidazol-1-ylnonyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol
• CAS: 1071461-00-1
• 化学式: C₂₅H₃₈N₂O₂
• 分子量: 398.589
• InChiKey: MLGXSNGGDPGAOF-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  C₃₁H₅₂N₂O₂Si 在 盐酸 作用下， 以260 mg的产率得到(R)-2-(9-(1H-imidazol-1-yl)nonyl)-2,5,7,8-tetramethylchroman-6-ol
  参考文献：
  名称：

  Inhibition of oxidative metabolism of tocopherols with ω-N-heterocyclic derivatives of vitamin E

  摘要：

  The oxidative metabolism of tocopherols and tocotrienols by monooxygenases is a key factor in the plasma and tissue clearance of forms of vitamin E other than alpha-tocopherol. It is well known that a commonly ingested form of vitamin E, gamma-tocopherol, has greatly reduced plasma half-life (faster clearance) than alpha-tocopherol. The tocotrienols are metabolized even faster than gamma-tocopherol. Both gamma-tocopherol and alpha- and delta-tocotrienol possess intriguing biological activities that are different from alpha-tocopherol, making them potentially of interest for therapeutic use. Unfortunately, the fast clearance of non-alpha-tocopherols from animal tissues is a significant hurdle to maximizing their effect(s) as dietary supplements. We report here the design and synthesis of N-heterocycle-containing analogues of alpha-tocopherol that act as inhibitors of Cyp4F2, the key monooxygenase responsible for omega-hydroxylation of the side chain of tocols. In particular, an omega-imidazole containing compound, 1, [(R)-2-(9-(1H-imidazol-1-yl)nonyl)-2,5,7,8-tetramethylchroman-6-ol] had an ED50 for inhibition of gamma-CEHC production from c-tocopherol of similar to 1 nM when tested in HepG2 cells in culture. Furthermore, feeding of 1 to mice along with rapidly metabolized delta-tocopherol, resulted in a doubling of the delta-tocopherol/alpha-tocopherol ratio in liver ( P<0.05). Thus, 1 may be a useful adjuvant to the therapeutic use of non-alpha-tocopherols. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.020

文献信息

• Tocopherol derivatives and uses thereof
  申请人：Atkinson Jeffrey

  公开号：US20080293792A1

  公开（公告）日：2008-11-27

  Tocopherol derivatives having the general formula: wherein n is an integer of 6 to 13, R 1 is hydrogen, a silyl ether or acetate, R 2 is an optionally substituted nitrogen-containing heterocycle or a polycyclic nitrogen-containing heterocycle; and pharmaceutically acceptable salts thereof are provided. A method for synthesizing the compounds is also provided. The tocopherol derivatives are capable of inhibiting the primary enzyme responsible for the metabolism of the tocopherols and tocotrienols compounds of vitamin E, namely tocopherol-ω-hydroxylase, and thus increase the amount and prolong the availability of these compounds in plasma and tissue.

  提供具有一般公式的生育酚衍生物：其中n是6到13的整数，R1是氢，硅醚或醋酸酯，R2是一个可选择地取代的含氮杂环或多环含氮杂环；以及其药用可接受的盐。还提供了一种合成这些化合物的方法。这些生育酚衍生物能够抑制生育酚和生育三烯酚（维生素E化合物）的代谢的主要酶，即生育酚-ω-羟基化酶，从而增加这些化合物在血浆和组织中的含量并延长其可用性。
• THERAPEUTIC SULFATED POLYSACCHARIDES, COMPOSITIONS THEREOF, AND METHODS FOR TREATING PATIENTS
  申请人：Daniels, Bruce A.

  公开号：EP2766025A1

  公开（公告）日：2014-08-20
• SKIN CARE COMPOSITIONS
  申请人：FLAVIN Dana

  公开号：US20130164265A1

  公开（公告）日：2013-06-27

  This invention provides compositions and methods of manufacturing such compositions that employ GRAS compounds which can act to promote the generation of stem, epidermal or other skin cells in the epidermis, activation of collagen synthesis, activation of hyaluronic acid synthesis, enhanced skin hydration, and dermal healing by stimulating stem cell and fibroblast migration to sites of needed repair. These compositions and methods are useful for rejuvenating the skin and for treating some skin-related aging or other dermal damaging conditions, including wrinkle reduction and treatment of minor dermal wounds.
• Therapeutic Sulfated Polysaccharides, Compositions Thereof, and Methods for Treating Patients
  申请人：Daniels Bruce A.

  公开号：US20130273096A1

  公开（公告）日：2013-10-17

  Disclosed are methods and compositions for the treatment of a variety of disorders in subjects by affecting the glycocalyx of a subject in need of such treatment. The methods comprise administering to a subject an effective amount of a sulfated polysaccharide (SP) or analogue thereof, the SP being a non-animal based (e.g., plant, or bacteria derived) sulfated polysaccharide. The SPs can be administered as single agents, or in combination with one another, or with other medications to promote efficacy. Pharmaceutical compositions and comestibles including such SPs are also described.
• TOPICAL COMPOSITIONS
  申请人：FLAVIN Dana

  公开号：US20140328952A1

  公开（公告）日：2014-11-06

  This invention provides compositions and methods of manufacturing such compositions that employ GRAS compounds which can act to promote the generation of stem, epidermal or other skin cells in the epidermis, activation of collagen synthesis, activation of hyaluronic acid synthesis, enhanced skin hydration, and dermal healing by stimulating stem cell and fibroblast migration to sites of needed repair. These compositions and methods are useful for rejuvenating the skin and for treating some skin-related aging or other dermal damaging conditions, including wrinkle reduction and treatment of minor dermal wounds.