(3β)-胆甾-5-烯-3,7-二醇 | 16840-37-2

• 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
• 中文名称: (3β)-胆甾-5-烯-3,7-二醇
• 英文名称: 7β-hydroxycholesterol
• 英文别名: 7-hydroxycholesterol；7-OH cholesterol；cholest-5-ene-3β,7ξ-diol；(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]phenanthrene-3,7-diol
• CAS: 16840-37-2
• 化学式: C₂₇H₄₆O₂
• 分子量: 402.661
• InChiKey: OYXZMSRRJOYLLO-UOQFGJKXSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  515.3±38.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3β)-胆甾-5-烯-3,7-二醇 在 十八胺 作用下， 以 various solvent(s) 为溶剂， 生成 5-胆甾烯-3β-醇-7-酮
  参考文献：
  名称：

  Kinetic Studies of Cholesterol Oxidation as Inhibited by Stearylamine during Heating

  摘要：

  The formation of cholesterol oxidation products (COPs) during heating in the presence of stearylamine at 140 degreesC was analyzed by high-performance liquid chromatography (HPLC) and kinetically studied by use of nonlinear regression models. Results indicated that the COPs concentration increased with increasing heating time, and stearylamine was shown to reduce both oxidation and degradation rates of cholesterol. Without stearylamine, the highest rate constant (per hour) was observed for epoxidation (545.4), followed by free radical chain reaction (251.0), reduction (147.3), dehydration (95.8), triol dehydrogenation (4.7), degradation (0.34), triol formation (0.31), and dehydrogenation (0.13). With stearylamine, the epoxidation and free radical chain reaction rates could be reduced by about 800- and 3.4-fold, respectively, and triol formation during oxidation could be completely inhibited. In addition, the reactions for reduction, dehydration, degradation, and dehydrogenation could proceed slower in the presence of stearylamine. The kinetic model developed in this study can be used to predict the inhibition of COPs formation by stearylamine during heating of cholesterol.

  DOI：

  10.1021/jf048951+
• 作为产物：
  描述：

  7-hydroperoxycholesterol 在 十二烷醇 、 氧气 作用下， 以 乙醇 为溶剂， 生成 (3β)-胆甾-5-烯-3,7-二醇
  参考文献：
  名称：

  Kinetic Model for Studying the Effect of Quercetin on Cholesterol Oxidation during Heating

  摘要：

  Inhibition of the heat-induced cholesterol oxidation at 150 degrees C by incorporation of quercetin was kinetically studied. Results showed that without quercetin, the cholesterol oxidation products (COPs) concentration increased with increasing heating time. A low amount (0.002%, w/w) of quercetin was effective in inhibiting the formation of COPs during the initial heating period (<= 30 min) at 150 degrees C. However, after prolonged heating (30-120 min), a low antioxiclant activity was observed because of the degradation of quercetin. When using nonlinear regression models for kinetic study of cholesterol oxidation in the absence of quercetin, the epoxidation showed the highest rate constant (h(-1) = 683.1), followed by free radical chain reaction (h(-1) = 453.5), reduction (h(-1) = 290.3), dehydration (h(-1) = 155.5), triol dehydrogenation (h(-1) = 5.35), dehydrogenation (h(-1) = 0.68), thermal degradation (h(-1) = 0.66), and triol formation (h(-1) = 0.38). However, in the presence of quercetin, the reaction rate constants (h(-1)) for epoxidation (551.4), free radical chain reaction (111.7), and thermal degradation (0.28) were reduced greatly. The kinetic model developed in this study can be used to predict the inhibition of COPs by quercetin during the heating of cholesterol.

  DOI：

  10.1021/jf052529r

文献信息

• Pyrrolo sulfonamide compounds for modulation of orphan nuclear receptor RAR-related orphan receptor-gamma (RORgamma, NR1F3) activity and for the treatment of chronic inflammatory and autoimmune diseases
  申请人：Phenex Pharmaceuticals AG

  公开号：EP2511263A1

  公开（公告）日：2012-10-17

  The invention provides modulators for the orphan nuclear receptor RORγ and methods for treating RORγ mediated diseases by administrating these novel RORγ modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo sulfonamide compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof.

  本发明提供了针对孤儿核受体RORγ的调节剂，以及通过向需要的人类或哺乳动物施用这些新型RORγ调节剂来治疗RORγ介导的疾病的方法。具体而言，本发明提供了式(1)的吡咯磺酰胺化合物及其对映体、非对映体、互变异构体、溶剂化物和药用可接受的盐。
• [EN] PYRROLO SULFONAMIDE COMPOUNDS FOR MODULATION OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORGAMMA, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASES<br/>[FR] COMPOSÉS PYRROLOSULFONAMIDES POUR LA MODULATION DE L'ACTIVITÉ DU RÉCEPTEUR ORPHELIN GAMMA APPARENTÉ AU RÉCEPTEUR NUCLÉAIRE ORPHELIN RAR (ROR-GAMMA, NR1F3) ET POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES CHRONIQUES ET AUTO-IMMUNES
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2012139775A1

  公开（公告）日：2012-10-18

  The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administrating these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo sulfonamide compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof.

  本发明提供了针对孤儿核受体RORγ的调节剂，以及通过向需要的人类或哺乳动物施用这些新型的RORγ调节剂来治疗RORγ介导的疾病的方法。具体而言，本发明提供了式(1)的吡咯磺酰胺化合物及其对映体、非对映体、互变异构体、溶剂化物和药用可接受的盐。
• [EN] PROCESS FOR PREPARATION OF 7-DEHYDROCHOLESTEROL<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 7-DÉSHYDROCHOLESTÉROL
  申请人：FERMENTA BIOTECH LTD

  公开号：WO2015170341A1

  公开（公告）日：2015-11-12

  The invention discloses an improved cost-effective process for preparation of 7-Dehydrocholesterol of formula I with good yield and purity, comprising:a) epimerizing 7(alpha+beta) bromo protected cholesterol in presence of tetrabutyl ammonium bromide in toluene or a ketonic solvent or combinations thereof to obtain predominantly 7.alpha-bromo 3-protected cholesterol; b) Reacting 7.apha-bromo 3- protected cholesterol with substituted or unsubstituted thiophenol or its salts in presence of a liquor ammonia to obtain predominantly 7.beta.-thiophenyl)-3-protected cholesterol; c) Oxidizing 7. beta. - thiophenyl 3-protected cholesterol in presence of Cumene hydrogen peroxide and Titanium tetraisopropoxide to obtain 7. beta. -phenyl sulfoxide 3-protected cholesterol; d) Converting 7. beta. -phenyl sulfoxide 3-protected cholesterol into 7-Dehydro 3-protected cholesterol in presence of base; e) purifying 7-Dehydro 3-protected cholesterol by suspending in a suitable organic solvent; and f) Deprotecting the 7-Dehydro 3-protected cholesterol by treating with alkali in presence of methanol to obtain 7-Dehydrocholesterol followed by purification of 7-Dehydrocholesterol from an organic solvent.

  该发明揭示了一种改进的经济有效的制备式I的7-去氢胆固醇的过程，具有良好的产率和纯度，包括：a)在甲苯或酮溶剂或它们的组合物中存在四丁基溴化铵的情况下，使7（α+β）溴保护的胆固醇发生对映异构化，以获得主要为7α-溴3-保护的胆固醇；b)在液氨存在下，将7α-溴3-保护的胆固醇与取代或未取代的硫酚或其盐反应，以获得主要为7β-硫酚基）-3-保护的胆固醇；c)在顺酚过氧化氢和四异丙氧基钛存在下，氧化7β-硫酚基3-保护的胆固醇，以获得7β-苯基亚砜3-保护的胆固醇；d)在碱存在下，将7β-苯基亚砜3-保护的胆固醇转化为7-去氢3-保护的胆固醇；e)通过悬浮在适当的有机溶剂中纯化7-去氢3-保护的胆固醇；f)在甲醇存在下，通过用碱处理来去保护7-去氢3-保护的胆固醇，以获得7-去氢胆固醇，然后从有机溶剂中纯化7-去氢胆固醇。
• [EN] CARBOXAMIDE OR SULFONAMIDE SUBSTITUTED THIAZOLES AND RELATED DERIVATIVES AS MODULATORS FOR THE ORPHAN NUCLEAR RECEPTOR ROR[GAMMA]<br/>[FR] THIAZOLES SUBSTITUÉS PAR CARBOXAMIDE OU SULFONAMIDE ET DÉRIVÉS APPARENTÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR NUCLÉAIRE ORPHELIN ROR[GAMMA]
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2013178362A1

  公开（公告）日：2013-12-05

  The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administering these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides carboxamide or sulfonamide containing cyclic compounds of Formula (1), (1'), (100), (100'), (200) and (200') and the enantiomers, diastereomers, tautomers, /V-oxides, solvates and pharmaceutically acceptable salts thereof.

  这项发明提供了用于孤儿核受体RORγ的调节剂，以及通过向需要的人类或哺乳动物投与这些新型RORγ调节剂来治疗RORγ介导的疾病的方法。具体而言，本发明提供了含有环状化合物的羧酰胺或磺酰胺的化合物的公式（1）、（1'）、（100）、（100'）、（200）和（200'）及其对映体、二对映体、互变异构体、/V-氧化物、溶剂合物和药用可接受盐。
• [EN] CARBOXAMIDE OR SULFONAMIDE SUBSTITUTED NITROGEN-CONTAINING 5-MEMBERED HETEROCYCLES AS MODULATORS FOR THE ORPHAN NUCLEAR RECEPTOR ROR GAMMA<br/>[FR] HÉTÉROCYCLES À 5 CHAÎNONS CONTENANT DE L'AZOTE SUBSTITUÉS PAR CARBOXAMIDE OU SULFONAMIDE EN TANT QUE MODULATEURS POUR LE RÉCEPTEUR NUCLÉAIRE ORPHELIN ROR GAMMA
  申请人：PHENEX PHARMACEUTICALS AG

  公开号：WO2014023367A1

  公开（公告）日：2014-02-13

  The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administering these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides carboxamide containing cyclic compounds of Formula (1) to Formula (5) and the enantiomers, diastereomers, tautomers, /V-oxides, solvates and pharmaceutically acceptable salts thereof.

  本发明提供了针对孤儿核受体RORγ的调节剂，以及通过向需要的人类或哺乳动物施用这些新型的RORγ调节剂来治疗RORγ介导的疾病的方法。具体而言，本发明提供含有羧酰胺的环状化合物，其化学式从公式(1)到公式(5)，以及它们的对映异构体、非对映异构体、互变异构体、N-氧化物、溶剂化物和药用可接受的盐。