6-甲基麦角灵-8β-甲醇 | 18051-16-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 中文名称: 6-甲基麦角灵-8β-甲醇
• 中文别名: 9,10-二氢麦角醇；6-甲基麦角灵-8Β-甲醇
• 英文名称: 9,10-dihydrolysergol
• 英文别名: D-6-methyl-8β-hydroxymethyl-ergoline；Dihydrolysergol；[(6aR,9R,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol
• CAS: 18051-16-6
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: UFKTZIXVYHGAES-WDBKCZKBSA-N

物化性质

• 熔点：
  >265°C (dec)
• 沸点：
  444.8±40.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微量）、甲醇（微量）、吡啶（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-甲基麦角灵-8β-甲醇 在 TEA*SO₃ 、 TEA 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以82%的产率得到6-Methyl-8-β-formyl-ergoline
  参考文献：
  名称：

  Synthesis and in vitro and in vivo evaluation of dopaminergic ergoline derivatives

  摘要：

  A series of ergoline-amides was synthesised in the discovery of new dopaminomimetic agents. Several compounds exhibited in vivo high prolactin lowering activity (indirectly measured by the nidation test) in rats. For the most active, the potential anti-Parkinson activity was evaluated by observation of the contralateral turning behaviour in 6-OH-DA lesioned rats. The acute toxicity by oral route in mice was also studied. (C) 1998 Elsevier Science S.A.

  DOI：

  10.1016/s0014-827x(97)00009-8
• 作为产物：
  描述：

  9,10-dihydrolysergic acid methyl ester 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 6-甲基麦角灵-8β-甲醇
  参考文献：
  名称：

  Zur Kenntnis der Triterpene。140. Mitteilung。弗雷德林斯大学

  摘要：

  1.达芬斯C 30 H 50 O（I）左旋弗里德伦丁C 29 H 44 O 2（II）乙氧基（IV）-乙酸酯在Eisessiglösungdas-Friedelen-disäure-中的Wasserstoffperoxyd酸酐C 29 H 44 O 3（III），微熔剂zu einemgesättigten，四环酮Keton C 25 H 42 O（VI），阿布巴特·乌尔德（abgebaut wurde）。

  DOI：

  10.1002/hlca.19490320413

文献信息

• Robust Kalman filtering for continuous-time systems with norm-bounded nonlinear uncertainties
  作者：P. Shi、Y. Kaya

  DOI：10.1093/imamci/17.4.363

  日期：2000.12.1

  In this paper we study the problem of robust Kalman filtering for a class of uncertain linear continuous-time systems. The system under consideration is subjected to time-varying, norm-bounded, nonlinear parameter uncertainties in state and measurement equations. Stability of the above system is analyzed. A state estimator is designed such that the covariance of the estimation error is guaranteed to be within a certain bound for all admissible uncertainties, which is in terms of solutions of two algebraic Riccati equations.

  本文研究了一类不确定线性连续时间系统的稳健卡尔曼滤波问题。所考虑的系统在状态和测量方程中受到时变、范数有界的非线性参数不确定性的影响。对上述系统的稳定性进行了分析。设计了一种状态估计器，使得对于所有可容许的不确定性，估计误差的协方差保持在某个界限之内，这涉及到两个代数Riccati方程的解。
• New and efficient process for the preperation of cabergoline and its intermediates
  申请人：Wang Zhi-Xian

  公开号：US20080275240A1

  公开（公告）日：2008-11-06

  This invention relates to a new and efficient process for the production of dopamine agonists such as Cabergoline and the intermediates thereof.

  这项发明涉及一种用于生产多巴胺激动剂（如卡贝哌酮）及其中间体的新型高效工艺。
• Naturally Occurring Clavines: Antagonism/Partial Agonism at 5-HT_2AReceptors and Antagonism at α₁-Adrenoceptors in Blood Vessels
  作者：H. Pertz

  DOI：10.1055/s-2006-957922

  日期：1996.10

  The interaction of eight typical representatives of naturally occurring clavines (agroclavine, costaclavine, dihydrolysergol-I, elymoclavine, festuclavine, lysergene, lysergol, and pyroclavine) with 5-HT2A receptors and α1-adrenoceptors was studied in rat tail artery and aorta, respectively. Clavines antagonized 5-HT-induced contractions with calculated pKB values (pKP values for partial agonists) of 4.84-7.81 and (R)-phenylephrine-induced contractions with calculated pKB values of 5.34-7.09. Specificity of clavines at 5-HT2A receptors relative to α1 adrenoceptors was rather low. Low affinity for costaclavine at both 5-HT2A receptors (pKP = 4.84 ± 0.06) and α1-adrenoceptors (pKB = 5.34 ± 0.05) indicates that the trans-junction of ring C and D of the ergoline pharmacophore is crucial for the binding of ergolines to these sites. Lysergol, lysergene, and costaclavine produced non-parallel displacements of the 5-HT concentration-response curve in the rat tail artery and caused small contractions by themselves. Lysergol contracted the rat tail artery with a pEC50 of 6.36 ± 0.04 and an intrinsic activity of 0.18 ± 0.03 with respect to 5-HT. Lysergol-induced contractile responses were surmountably antagonized by ketanserin (10 nM) with a pKB of 9.1 which is consistent with an interaction of lysergol with 5-HT2A receptors. The pKP for the lysergol-5-HT2A receptor complex calculated from concentration-response curves to lysergol was 6.88 ± 0.07 and did not match the pKP of 7.66 ± 0.02 calculated from antagonism by lysergol of the contractile response to 5-HT. This suggests that lysergol and 5-HT possibly bind in two slightly different orientations at the 5-HT2A receptor. It is concluded that partial agonism and pure antagonism at 5-HT2A receptors on the one side and antagonism at α1-adrenoceptors on the other side may contribute to the noxious effects of naturally occurring clavines.

  研究了大鼠尾动脉和主动脉中八种自然产生的clavines（田麦角碱、肋麦角碱、二氢麦角考宁-I、elymoclavine、festuclavine、麦角胺、麦角醇和吡咯clavine）与5-HT2A受体和α1-肾上腺素受体的相互作用。Clavines拮抗了5-HT引发的收缩，计算的pKB值（部分激动剂的pKP值）为4.84-7.81，以及（R）-苯肾上腺素引发的收缩，计算的pKB值为5.34-7.09。在5-HT2A受体相对于α1肾上腺素受体方面，clavines的特异性相当低。肋麦角碱对5-HT2A受体（pKP = 4.84 ± 0.06）和α1-肾上腺素受体（pKB = 5.34 ± 0.05）的低亲和力表明，ergoline药效团的C环和D环的反式连接对于ergolines与这些位点的结合至关重要。麦角醇、麦角胺和肋麦角碱在鼠尾动脉中产生了非平行的5-HT浓度-反应曲线位移，并自身引起轻微的收缩。麦角醇使鼠尾动脉收缩，pEC50为6.36 ± 0.04，相对于5-HT的内在活性为0.18 ± 0.03。麦角醇引发的收缩反应可以被酮舍林（10 nM）以pKB为9.1的值所拮抗，这与麦角醇与5-HT2A受体的相互作用一致。从麦角醇的浓度-反应曲线计算出的麦角醇-5-HT2A受体复合物的pKP为6.88 ± 0.07，与从麦角醇对5-HT收缩反应的拮抗作用计算出的pKP 7.66 ± 0.02不符。这表明麦角醇和5-HT可能在5-HT2A受体上有两种稍微不同的取向。总之，部分激动和纯拮抗5-HT2A受体，以及α1-肾上腺素受体的拮抗作用，可能有助于自然产生的clavines的有害效应。
• Alkylation of ergoline derivatives at position N(1)
  作者：Jan Šmidrkal、Miroslav Semonský

  DOI：10.1135/cccc19820622

  日期：——

  N₍₁₎-Alkyl-8β-ergolines I-XII were prepared by alkylation of 8β-ergoline derivatives XIII to XVIII with alkyl halides in dimethyl sulphoxide in the presence of potassium hydroxide. The compounds I-XII exhibited weak inhibition effects on the secretion of prolactin

  N₍₁₎-烷基-8β-麦角酸衍生物 I-XII 通过在二甲基亚砜中存在氢氧化钾的情况下，用烷基卤化物烷基化8β-麦角酸衍生物 XIII 至 XVIII 制备而成。化合物 I-XII 对催乳素分泌表现出弱的抑制作用
• Synthese von Glycosiden und Zuckerorthoestern des 9,10-Dihydrolysergols
  作者：Karlheinz Seifert、Siegfried Johne

  DOI：10.1002/ardp.19843170702

  日期：——

  Die Glycosylierung von 9,10‐Dihydrolysergol in Gegenwart von Fétizon‐Reagens (Ag2CO3 auf Celite) ergibt die Glycoside 4, 8, 12, 15 und die Orthoester 6, 10, 14, 17.

  在 Fétizon 试剂（硅藻土上的 Ag2CO3）存在下，9,10-二水解麦角醇的糖基化得到糖苷 4、8、12、15 和原酸酯 6、10、14、17。