bromoacetyl 5α-cholestan-3β-oate

• 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: bromoacetyl 5α-cholestan-3β-oate
• 英文别名: (10S)-3c-Bromacetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；bromoacetic acid-(5α-cholestanyl-(3β)-ester)；Bromessigsaeure-(5α-cholestanyl-(3β)-ester)；3β-Bromacetoxy-5α-cholestan；[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-bromoacetate
• 化学式: C₂₉H₄₉BrO₂
• 分子量: 509.611
• InChiKey: VJBCNYHZXKGYLM-DVNBGNEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二甲基正辛胺 、 bromoacetyl 5α-cholestan-3β-oate 以 乙腈 为溶剂， 反应 2.0h， 以95%的产率得到N,N-dimethyl-(3β-acetate-5β-cholestan)-N-octylammonium bromide
  参考文献：
  名称：

  甾醇新季烷基铵共轭物的合成、光谱和半经验研究

  摘要：

  通过甾醇（麦角甾醇、胆固醇、二氢胆固醇）与溴乙酸溴化物的两步反应，然后用长链叔烷基胺进行双分子亲核取代，获得了新的类固醇季烷基铵缀合物。通过光谱（1H-NMR、13C-NMR和FT-IR）分析、质谱和PM5半经验方法确认了产物的结构。已在物质活性谱预测 (PASS) 的基础上估计了合成化合物的药物治疗潜力。

  DOI：

  10.3390/molecules181214961
• 作为产物：
  描述：

  胆固醇 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 60.0 ℃ 、500.01 kPa 条件下， 反应 2.75h， 生成 bromoacetyl 5α-cholestan-3β-oate
  参考文献：
  名称：

  钌修饰的脂质囊泡：[Ru(terpy)(bpy)(OH2)]2+ 的光诱导释放和热背配位

  摘要：

  静电力在大型过渡金属络合物和脂质双层之间的相互作用中起着重要作用。在这项工作中，合成了硫醚-胆甾醇杂化配体 (4)，它通过其硫原子与钌 (II) 配位，并通过其非极性尾部嵌入脂质双层。通过将其钌络合物 [Ru(terpy)(bpy)(4)](2+) (terpy = 2,2';6',2''-terpyridine; bpy = 2,2'-bipyridine) 与带负电荷的脂质二肉豆蔻酰磷脂酰甘油 (DMPG) 或两性离子脂质二肉豆蔻酰磷脂酰胆碱 (DMPC)，形成用钌多吡啶复合物装饰的大单层囊泡。在可见光照射下，钌-硫配位键被选择性破坏，将钌片段释放为游离水络合物 [Ru(terpy)(bpy)(OH(2))](2+)。在蓝光照射 (452 nm) 下, DMPG 囊泡的光化学量子产率为 0.0074(8), DMPC 囊泡 (25°C) 为 0.0073(8), 这与类似的均质系统没有显着差异。动态光散射和低温

  DOI：

  10.1021/ja105025m

文献信息

• Photochemical α-carboxyalkylation of tryptophols and tryptamines <i>via</i> C–H functionalization
  作者：Zhiqiang Pan、Yuchang Liu、Fengchi Hu、Qinglong Liu、Wenbin Shang、Chengfeng Xia

  DOI：10.1039/d0cc00847h

  日期：——

  strategy activated the C-Br bonds of α-bromo-alkylcarboxylic esters to provide carbon-centered radicals under the catalysis of Ir(iii) photocatalyst and coupled with indole derivatives. This methodology displayed wide functional group tolerance and excellent regioselectivity, and was applied to the late-stage functionalization and preparation of indole-containing hybrids.

  已经开发了在可见光照射下通过CH键的官能化使色酚和色胺的α-羧烷基化的方法。该光化学策略在Ir（iii）光催化剂的催化下并与吲哚衍生物偶联，活化了α-溴代烷基羧酸酯的C-Br键以提供以碳为中心的自由基。该方法显示出宽泛的官能团耐受性和优异的区域选择性，并应用于后期功能化和含吲哚杂种的制备。
• Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols
  作者：Bogumił Brycki、Hanna Koenig、Iwona Kowalczyk、Tomasz Pospieszny

  DOI：10.3390/molecules19079419

  日期：——

  New dimeric quaternary alkylammonium conjugates of sterols were obtained by two step reactions of ergosterol, cholesterol and cholestanol with bromoacetic acid bromide, followed by bimolecular nucleophilic substitution with N, N, N', N'-tetramethyl-1,3-propanediamine, N, N, N', N'', N''-pentamethyldiethylenetriamine and 3,3'-iminobis-(N, N-dimethylpropylamine). The product structures were confirmed

  通过麦角甾醇、胆固醇和胆甾醇与溴乙酸溴化物的两步反应，然后用 N, N, N', N'-四甲基-1,3-丙二胺、N、 N, N', N", N" - 五甲基二亚乙基三胺和 3,3'-亚氨基双-(N, N-二甲基丙胺)。产物结构通过光谱（ 1 H-NMR、 13 C-NMR、 FT-IR）分析、质谱（ESI-MS）和PM5半经验方法确定。此外，还根据物质活性谱预测 (PASS) 对合成化合物进行了计算机模拟研究。
• LIGHT INDUCED DRUG RELEASE
  申请人：Bonnet Sylvestre

  公开号：US20140148425A1

  公开（公告）日：2014-05-29

  Photosensitive compounds for use in a method of treating a disease or condition are described. The photosensitive compounds have the formula R—Y, wherein R is a ruthenium complex and Y is at least one sulphur-containing photoreleasable group, and the compounds comprise at least one ruthenium-sulphur bond; or a pharmaceutically acceptable salt, solvate, ester or amide, such that upon influence of visible or near infra-red light (400-1400 nm) in vivo, said at least one ruthenium-sulphur bond is broken, thereby generating a pharmacologically active compound.

  描述了用于治疗疾病或症状的一种方法中使用的光敏化合物。这些光敏化合物具有R—Y的化学式，其中R是一个钌配合物，Y是至少一个含硫光释放基团，这些化合物包括至少一个钌-硫键；或者是药用可接受的盐、溶剂合物、酯或酰胺，因此，在体内受到可见光或近红外光（400-1400纳米）的影响时，所述至少一个钌-硫键被断裂，从而产生一种药理活性化合物。
• Synthesis, spectroscopy, theoretical and biological studies of new gramine-steroids salts and conjugates
  作者：Weronika Kozanecka、Lucyna Mrówczyńska、Tomasz Pospieszny、Beata Jasiewicz、Mateusz Gierszewski

  DOI：10.1016/j.steroids.2015.03.003

  日期：2015.6

  New gramine connections with bile acids (lithocholic, deoxycholic, cholic) and sterols (cholesterol, cholestanol) were synthesized. The structures of products were confirmed by spectral (NMR, FT-IR) analysis, mass spectrometry (ESI-MS) as well as PMS semiempirical methods. Unexpectedly, the products of the reaction of gramine with cholesterol and cholestanol were symmetrical compounds consisting of two molecules of sterols connected by N(CH3)(2) group. All new synthesized compounds interact in vitro with the human erythrocyte membrane and alter discoid erythrocyte shape inducing stomatocytosis or echinocytosis. Increase in the incorporation of the fluorescent dye merocyanine 540 (MC540) into the erythrocyte membrane indicates that new compounds at sublytic concentrations are capable of disturbing membrane phospholipids asymmetry and loosening the molecular packing of phospholipids in the bilayer. Gramine significantly decreases the membrane partitioning properties as well as haemolytic activity of lithocholic acid in its new salt. Moreover, both deoxycholic and cholic acids completely lost their membrane perturbing activities in the gramine salts. On the other hand, the capacity of new gramine-sterols connections to alter the erythrocyte membrane structure and its permeability is much higher in comparison with sterols alone. The dual effect of gramine on the bile acid and sterols cell membrane partitioning activity observed in our study should not be neglected in vivo. (C) 2015 Elsevier Inc. All rights reserved.
• Ruthenium-Decorated Lipid Vesicles: Light-Induced Release of [Ru(terpy)(bpy)(OH₂)]²⁺ and Thermal Back Coordination
  作者：Sylvestre Bonnet、Bart Limburg、Johannes D. Meeldijk、Robertus J. M. Klein Gebbink、J. Antoinette Killian

  DOI：10.1021/ja105025m

  日期：2011.1.19

  bilayers. In this work, a thioether-cholestanol hybrid ligand (4) was synthesized, which coordinates to ruthenium(II) via its sulfur atom and intercalates into lipid bilayers via its apolar tail. By mixing its ruthenium complex [Ru(terpy)(bpy)(4)](2+) (terpy = 2,2';6',2''-terpyridine; bpy = 2,2'-bipyridine) with either the negatively charged lipid dimyristoylphosphatidylglycerol (DMPG) or with the zwitterionic

  静电力在大型过渡金属络合物和脂质双层之间的相互作用中起着重要作用。在这项工作中，合成了硫醚-胆甾醇杂化配体 (4)，它通过其硫原子与钌 (II) 配位，并通过其非极性尾部嵌入脂质双层。通过将其钌络合物 [Ru(terpy)(bpy)(4)](2+) (terpy = 2,2';6',2''-terpyridine; bpy = 2,2'-bipyridine) 与带负电荷的脂质二肉豆蔻酰磷脂酰甘油 (DMPG) 或两性离子脂质二肉豆蔻酰磷脂酰胆碱 (DMPC)，形成用钌多吡啶复合物装饰的大单层囊泡。在可见光照射下，钌-硫配位键被选择性破坏，将钌片段释放为游离水络合物 [Ru(terpy)(bpy)(OH(2))](2+)。在蓝光照射 (452 nm) 下, DMPG 囊泡的光化学量子产率为 0.0074(8), DMPC 囊泡 (25°C) 为 0.0073(8), 这与类似的均质系统没有显着差异。动态光散射和低温