(7R,7aa,14ab)-十二氢-7a,14a-甲桥-2H,6H-二吡啶并[1,2-a:1',2'-e][1,5]二氮杂环辛四烯-6,11-二酮 | 4697-83-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 中文名称: (7R,7aa,14ab)-十二氢-7a,14a-甲桥-2H,6H-二吡啶并[1,2-a:1',2'-e][1,5]二氮杂环辛四烯-6,11-二酮
• 英文名称: (+)-2,17-dioxosparteine
• 英文别名: 2,17-dioxosparteine；(+)-17-oxolupanine；17-oxolupanine；decahydro-7,14-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocine-4,13-dione；(7S)-(7at,14ac)-decahydro-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocine-4,13-dione；(7S)-(7at,14ac)-Decahydro-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-4,13-dion；(1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane-6,16-dione
• CAS: 4697-83-0
• 化学式: C₁₅H₂₂N₂O₂
• 分子量: 262.352
• InChiKey: HBYSMHYHSFSCED-QNWHQSFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7R,7aa,14ab)-十二氢-7a,14a-甲桥-2H,6H-二吡啶并[1,2-a:1',2'-e][1,5]二氮杂环辛四烯-6,11-二酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以75%的产率得到(+)-2-thiono-17-oxosparteine
  参考文献：
  名称：

  V. Thioanalogues of sparteine lactams. (+)-2-Thiono-17-oxosparteine and (+)-2,17-dithionosparteine

  摘要：

  The X-ray and spectroscopic results clearly indicate that the (+)-2-thiono-17-oxosparteine (1) and (+)-2,17-ditihionosparteine (2) are conformationally rigid. In order to analyze deviations of lactam/thiolactam groups from planarity induced by ring constraints, the Dunitz-Winkler approach has been used. The lactam and thiolactam groups are close to planarity, only the lactam group in one of the two independent molecules of 1 is markedly non-planar. The bond angles in the thiolactam and lactam groups are highly diverse. Rings A and C adopt a distorted sofa conformation in both compounds. The distortions in the molecules of 2 as compared with those in the related monothiolactams correspond to the unusual chemical shifts of H5(eq), H5(ax) and H11, as well as to the extremely low J(5ax-6) and extremely large J(5eq-6) coupling constants. Also chemical shifts show a similar regularity being extremely high and low for C2 and C 17, respectively. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.10.034
• 作为产物：
  描述：

  羽扇豆鹼 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 生成 (7R,7aa,14ab)-十二氢-7a,14a-甲桥-2H,6H-二吡啶并[1,2-a:1',2'-e][1,5]二氮杂环辛四烯-6,11-二酮
  参考文献：
  名称：

  17-HYDROXYLUPANINE AND 17-OXYLUPANINE

  摘要：

  氧化银已被证明可以将卢帕宁氧化为17-羟基卢帕宁。该碱产生的无水高氯酸铵与Marion和Leonard的“脱氢卢帕宁（NBS）”高氯酸铵相同。描述了17-氧基卢帕宁，并根据它可被催化还原为氧基斯帕尔汀的观察，推断了阿菲林和氧基斯帕尔汀的立体化学。讨论了三级碳醇胺的碱性强度。

  DOI：

  10.1139/v54-031

文献信息

• BOCZON, WLADYSLAW, BULL. POL. ACAD. SCI. CHEM., 36,(1988) N-12, C. 407-415
  作者：BOCZON, WLADYSLAW

  DOI：——

  日期：——
• Intranasal administration of modulators of hypothalamic ATP-sensitive potassium channels
  申请人：Herlands Louis

  公开号：US20070026079A1

  公开（公告）日：2007-02-01

  Provided are methods of increasing K ATP channel activity in the hypothalamus of a mammal, methods of reducing glucose production in a mammal, methods of reducing peripheral glucose levels in a mammal, methods of reducing triglyceride levels in a mammal, methods of reducing very low density lipoprotein (VLDL) levels in a mammal, methods of methods of reducing gluconeogenesis in the liver of a mammal, methods of treating metabolic disorders such as diabetes, hyperglycemia, insulin resistance, glucose intolerance, metabolic syndrome and/or obesity, and methods of increasing glucose production and peripheral glucose levels in a mammal. Also provided are methods of treating heart failure, ischemia, coronary heart disease, familial lipoprotein lipase deficiency, hypopituitarism, hyperlipidemia, hypertriglyceridemia, hyperVLDLemia, atherosclerosis, hypercholesterolemia, hypertension, polycystic ovary syndrome, gonadotropin deficiency and/or amenorrhea.
• Modulation of Hypothalamic Atp-Sensitive Potassium Channels
  申请人：Rossetti Luciano

  公开号：US20090012067A1

  公开（公告）日：2009-01-08

  Provided are methods of increasing K ATP activity in the hypothalamus of a mammal, methods of reducing glucose production and peripheral blood glucose levels in a mammal, methods of inhibiting gluconeogenesis in the liver of a mammal, and methods of increasing glucose production and peripheral blood glucose levels in a mammal.
• [EN] MODULATION OF HYPOTHALAMIC ATP-SENSITIVE POTASSIUM CHANNELS<br/>[FR] MODULATION DE CANAUX POTASSIQUES SENSIBLES A ATP HYPOTHALAMIQUES
  申请人：VERSITY ALBERT EINSTEIN COLLEG

  公开号：WO2006088798A2

  公开（公告）日：2006-08-24

  [EN] Provided are methods of increasing K_ATP channel activity in the hypothalamus of a mammal, methods of reducing glucose production in a mammal, methods of reducing peripheral blood glucose levels in a mammal, methods of reducing triglyceride levels in a mammal, methods of reducing very low density lipoprotein (VLDL) levels in a mammal, methods of treating metabolic disorders such as diabetes, hyperglycemia, insulin resistance, glucose intolerance, metabolic syndrome and/or obesity, and methods of increasing glucose production and peripheral blood glucose levels in a mammal. Also provided are methods of treating heart failure, ischemia, coronary heart disease, familial lipoprotein lipase deficiency, hypopituitarism, hyperlipidemia, hypertriglyceridemia, hyperVLDLemia, atherosclerosis, hypercholesterolemia, hypertension, polycystic ovary syndrome, gonadotropin deficiency and/or amenorrhea.
  [FR] Procédés d'augmentation de l'activité du canal ATP dans l'hypothalamus d'un mammifère, procédés de réduction de la production de glucose chez un mammifère, procédés de réduction des niveaux périphériques de glucose dans le sang chez un mammifère, procédés de réduction des niveaux de triglycéride chez un mammifère, procédés de réduction de niveaux de lipoprotéines à très faible densité (VLDL) chez un mammifère, méthodes de traitement de troubles métaboliques, notamment le diabète, l'hyperglycémie, l'insulinorésistance, l'intolérance au glucose, le syndrome métabolique et/ou l'obésité, et procédés d'augmentation de la production de glucose et des niveaux périphériques de glucose dans le sang chez un mammifère. Méthodes de traitement d'insuffisance cardiaque, d'ischémie, de maladies coronariennes, de déficience de lipase de lipoprotéine familiale, d'hypopituitarisme, d'hyperlipidémie, d'hypertriglycéridémie, d'hyperVLDLémie, d'athérosclérose, d'hypercholestérolémie, d'hypertension, de syndrome des ovaires polycystiques, de déficience de la gonadotropine et/ou de l'aménorrhée.
• 17-HYDROXYLUPANINE AND 17-OXYLUPANINE
  作者：O. E. Edwards、F. H. Clarke、Bryce Douglas

  DOI：10.1139/v54-031

  日期：1954.3.1

  Silver oxide has been shown to oxidize lupanine to 17-hydroxylupanine. This base gives an anhydronium perchlorate identical with the "dehydrolupanine (NBS)" perchlorate of Marion and Leonard. 17-Oxylupanine is described, and, from the observation that it can be reduced catalytically to oxysparteine, the stereochemistry of aphylline and oxysparteine is deduced. The basic strength of tertiary carbinolamines is discussed.

  氧化银已被证明可以将卢帕宁氧化为17-羟基卢帕宁。该碱产生的无水高氯酸铵与Marion和Leonard的“脱氢卢帕宁（NBS）”高氯酸铵相同。描述了17-氧基卢帕宁，并根据它可被催化还原为氧基斯帕尔汀的观察，推断了阿菲林和氧基斯帕尔汀的立体化学。讨论了三级碳醇胺的碱性强度。