cholest-5-en-3-β-yl 2-pyridyl disulfide | 136911-91-6

• 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: cholest-5-en-3-β-yl 2-pyridyl disulfide
• 英文别名: 2-pyridyl-3-cholesteryl-disulfide；2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)disulfaneyl)pyridine；(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)disulfaneyl)pyridine；3b-cholester-3-yl pyridin-2-yl disulfide；2-(((3S,10R,13R,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)disulfanyl)pyridine；2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]disulfanyl]pyridine
• CAS: 136911-91-6
• 化学式: C₃₂H₄₉NS₂
• 分子量: 511.88
• InChiKey: CIAPOLMUGQCLNV-PTHRTHQKSA-N

物化性质

• 沸点：
  589.6±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cholest-5-en-3-β-yl 2-pyridyl disulfide 在 4 A molecular sieve 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]sulfanyl]-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  A new procedure for the conversion of thiols into reactive sulfenylating agents

  摘要：

  Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with beta-diketones to afford sulfides. This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise reactive thiols.

  DOI：

  10.1021/jo00023a039
• 作为产物：
  描述：

  甲基 2-吡啶基二硫醚 在 吗啉 、 氟磺酸甲酯 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 0.17h， 生成 cholest-5-en-3-β-yl 2-pyridyl disulfide
  参考文献：
  名称：

  A new procedure for the conversion of thiols into reactive sulfenylating agents

  摘要：

  Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with beta-diketones to afford sulfides. This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise reactive thiols.

  DOI：

  10.1021/jo00023a039

文献信息

• Effect of the Nature of the Spacer on Gene Transfer Efficacies of Novel Thiocholesterol Derived Gemini Lipids in Different Cell Lines: A Structure–Activity Investigation
  作者：Avinash Bajaj、Paturu Kondaiah、Santanu Bhattacharya

  DOI：10.1021/jm7010436

  日期：2008.4.1

  A structure-activity investigation was undertaken to see the effect of the nature of the spacer on the gene transfection efficacies of thiocholesterol -derived cationic gemini lipids possessing disulfide linkage between the cationic headgroup and the thiocholesterol moiety. Three gemini cationic lipids possessing hydrophobic flexible (-(CH2)(5)-; 1), hydrophobic rigid (-C6H4-; 2), and hydrophilic flexible (-CH2-CH2-O-CH2-CH2-; 3) spacer segments were synthesized. In HeLa cells, lipid formulations 1 and 2 were found to be more effective as compared to lipid 3 formulation. In HT1080 cell line, the order of transfectability was 3 > 1 > 2. Transfection studies in HeLa and HT 1080 cell line also showed 40-50% transfection efficacy in the presence of 10% serum conditions. These formulations were also able to transfect gene across difficult cells like HaCaT. Cytotoxic studies showed the nontoxic nature of these lipid-DNA complexes at different N/P ratios used for transfection studies.
• [EN] CLEAVABLE LIPIDS<br/>[FR] LIPIDES CLIVABLES
  申请人：SHIRE HUMAN GENETIC THERAPIES

  公开号：WO2012170889A8

  公开（公告）日：2014-01-30
• [EN] LIPID AMINES<br/>[FR] AMINES LIPIDIQUES
  申请人：[en]MODERNATX, INC.

  公开号：WO2023076598A1

  公开（公告）日：2023-05-04

  Provided are lipid amine compounds which are useful in the preparation of lipid nanoparticle compositions for delivery of therapeutic or prophylactic payload into cells.
• [EN] MUCOSAL ADMINISTRATION METHODS AND FORMULATIONS<br/>[FR] MÉTHODES ET FORMULATIONS D'ADMINISTRATION PAR VOIE MUQUEUSE
  申请人：[en]MODERNATX, INC.

  公开号：WO2023154818A1

  公开（公告）日：2023-08-17

  The present disclosure provides compositions and methods for the preparation, manufacture, and therapeutic use of lipid nanoparticles comprising nucleic acid vaccines, e.g., mRNA vaccines, for delivery to mucosal surfaces.
• A new procedure for the conversion of thiols into reactive sulfenylating agents
  作者：D. H. R. Barton、Robert H. Hesse、A. C. O'Sullivan、M. M. Pechet

  DOI：10.1021/jo00023a039

  日期：1991.11

  Thiols may be converted in high yield into unsymmetrical 2-pyridyl disulfides 3. Treatment of these with alkylating agents (e.g., alkyl fluorosulfonates or oxonium salts) affords the corresponding N-alkylpyridyl disulfides 4, which are potent sulfenylating agents (Scheme II) and react smoothly with a variety of sulfur nucleophiles (e.g., thiols, thiones, thioamides, dithiocarbamates, thiocyanate, etc.) to afford disulfides, with amines to afford sulfenamides, and with beta-diketones to afford sulfides. This new method is particularly well-suited to the preparation of unsymmetrical disulfides and sulfenamides from complex and otherwise reactive thiols.