金鸡纳素IB | 85022-69-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 金鸡纳素IB
• 英文名称: cinchonain Ib
• 英文别名: cinchonain Ia；(2R,3R,10S)-2,10-bis(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one
• CAS: 85022-69-1
• 化学式: C₂₄H₂₀O₉
• 分子量: 452.417
• InChiKey: LKCOZWLUAKSRQM-IBUUURQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  金鸡纳素IB 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以244 mg的产率得到(2R,3R,10S)-2,10-Bis-(3,4-dimethoxy-phenyl)-3-hydroxy-5-methoxy-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one
  参考文献：
  名称：

  Tannins and related compounds. VII. Phenylpropanoid-substituted epicatechnins, cinchonains from Cinchona succirubra. (1).

  摘要：

  通过对 Cinchona succirubra（茜草科）树皮中分子量相对较低的酚类化合物进行研究，分离出了 Cinchonains Ia (1)、Ib (2)、Ic (3) 和 Id (4)，以及咖啡酸 (5) 和 (-)-epicatechin (6)，这是一类在 A 环上被 C6-C3 单元取代的新的黄烷-3-醇。这些化合物的结构是根据化学和光谱证据确定的。此外，还实现了咖啡酸和(-)-表儿茶素的直接偶联，从而形成了金鸡纳类化合物。

  DOI：

  10.1248/cpb.30.4268
• 作为产物：
  描述：

  (2R,3S,10S)-4-Benzylsulfanyl-2,10-bis-(3,4-dihydroxy-phenyl)-3,5-dihydroxy-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one 在 镍 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以3 mg的产率得到金鸡纳素IB
  参考文献：
  名称：

  Tannins and related compounds. VIII. A new type of proanthocyanidin, cinchonains IIa and IIb from Cinchona succirubra. (2).

  摘要：

  已知原花青素B-2（7）、B-5（8）、A-2（9）和C-1（10）仅由（-）表儿茶素（C2、C3：顺式）单元组成，而辛可宁IIa和IIb则从红金鸡纳（Cinchona succirubra，茜草科）树皮中分离出来。它们是基于降解研究以及1H-和13C-NMR证据而确定的，是一种含有苯丙烷基取代基的新型原花青素二聚体。

  DOI：

  10.1248/cpb.30.4277

文献信息

• Pharmaceutical composition comprising cinchonains 1a and 1b, process for preparing an epimeric mixture of cinchonains 1a and 1b, use and method for reverting/combating ventricular fibrillation
  申请人：Laboratorio Catarinense S/A.

  公开号：EP2327405A1

  公开（公告）日：2011-06-01

  The present invention relates to the effects of certain cinchonains, especially the epimeric mixture of cinchonains Ia and Ib, on pathologies that involve alterations in the cardiovascular system, essentially in combating, preventing and reverting ventricular fibrillation in human beings and animals, especially for combating spontaneous or electric-stimulus-induced ventricular fibrillation, to revert spontaneous or electric-stimulus-induced ventricular fibrillations, for preventing ventricular fibrillation, for the treatment of ventricular fibrillation of any etiology or for the treatment of post-fibrillation to maintain normal cardiac rhythm. The present invention further relates to methods for the synthesis of an epimeric mixture of the chemical substances cinchonain Ia and Ib. The present invention also relates to the use of these chemical substances in reverting/combating ventricular fibrillation and/or in protecting against ventricular fibrillation. A pharmaceutical composition will be used for administering these chemical substances in human beings and animals.

  本发明涉及某些金鸡纳蛋白，特别是金鸡纳蛋白Ia和Ib的表聚混合物，对涉及心血管系统改变的病理学的影响，主要是在人类和动物中防治、预防和恢复心室颤动、特别是用于对抗自发的或电刺激诱发的心室颤动，恢复自发的或电刺激诱发的心室颤动，预防心室颤动，治疗任何病因引起的心室颤动或治疗颤动后维持正常心律。 本发明进一步涉及合成化学物质辛可宁 Ia 和 Ib 的表聚混合物的方法。 本发明还涉及这些化学物质在恢复/对抗心室颤动和/或防止心室颤动中的用途。一种药物组合物将用于在人类和动物体内施用这些化学物质。
• Pharmaceutical Composition Comprising Cinchonains Ia And Ib, Process For Preparing An Epimeric Mixture Of Cinchonains Ia And Ib, Use And Method For Reverting/Combating Ventricular Fibrillation
  申请人：Silva Filho Ney Osvaldo

  公开号：US20110144193A1

  公开（公告）日：2011-06-16

  The present invention relates to the effects of the epimeric mixture of cinchonains Ia and Ib on pathologies that involve alterations in the cardiovascular system, essentially in combating, preventing and reverting ventricular fibrillation in human beings and animals, especially for combating spontaneous or electric-stimulus-induced ventricular fibrillation, to revert spontaneous or electric-stimulus-induced ventricular fibrillations, for preventing ventricular fibrillation, for the treatment of ventricular fibrillation of any etiology or for the treatment of post-fibrillation to maintain normal cardiac rhythm. The present invention further relates to methods for the synthesis of an epimeric mixture of the chemical substances cinchonain Ia and Ib. The present invention also relates to the use of these chemical substances in reverting/combating ventricular fibrillation and/or in protecting against ventricular fibrillation. A pharmaceutical composition will be used for administering these chemical substances in human beings and animals.
• Pharmaceutical Composition Comprising Cinchonains Ia and Ib, Process For Preparing An Epimeric Mixture of Cinchonains Ia and Ib, Use and Method for Reverting/Combating Ventricular Fibrillation
  申请人：Laboratorio Catarinense S/A

  公开号：US20130217761A1

  公开（公告）日：2013-08-22

  The present invention relates to the effects of the epimeric mixture of cinchonains Ia and Ib on pathologies that involve alterations in the cardiovascular system, in combating, preventing and reverting ventricular fibrillation in human beings and animals, especially for combating spontaneous or electric-stimulus-induced ventricular fibrillation, to revert spontaneous or electric-stimulus-induced ventricular fibrillations, for preventing ventricular fibrillation, for the treatment of ventricular fibrillation of any etiology or for the treatment of post-fibrillation to maintain normal cardiac rhythm. The present invention further relates to methods for the synthesis of an epimeric mixture of the chemical substances cinchonain Ia and Ib. The present invention also relates to the use of these chemical substances in reverting/combating ventricular fibrillation and/or in protecting against ventricular fibrillation. A pharmaceutical composition will be used for administering these chemical substances in human beings and animals.
• [EN] PHENOLIC EXTRACTS OF UNCARIA TOMENTOSA L. (CAT'S CLAW) CONTAINING PROCYANIDINS, PROPELARGONIDINS AND FLAVONOLIGNANS, METHOD FOR THE PRODUCTION THEREOF, AND APPLICATIONS OF SAME<br/>[ES] EXTRACTOS FENÓLICOS DE UNCARIA TOMENTOSA L. (UÑA DE GATO) QUE CONTIENEN PROCIANIDINAS, PROPELARGONIDINAS Y FLAVANOLIGNANOS, PROCEDIMIENTO DE OBTENCIÓN Y SUS APLICACIONES<br/>[FR] EXTRAITS PHÉNOLIQUES DE UNCARIA TOMENTOSA L. (GRIFFE DE CHAT) CONTENANT DES PROCYANIDINES, DES PROPÉLARGONIDINES ET DES FLAVONOLIGNANES, PROCÉDÉ D'OBTENTION ET LEURS APPLICATIONS
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2014096488A1

  公开（公告）日：2014-06-26

  Esta invención se refiere a extractos fenólicos conteniendo procianidinas, propelargonidinas y flavanolignanos, con propiedades/actividades potencialmente beneficiosas para la salud humana, y obtenidos a partir de las partes aéreas y de la madera interna de la planta Uncaria tomentosa L., así como al procedimiento de obtención de dichos extractos. Estos extractos son útiles para elaborar aditivos alimentarios, composiciones cosméticas y composiciones farmacéuticas con actividad antioxidante, antimicrobiana, citotóxica y antiproliferativa.
• Tannins and related compounds. VII. Phenylpropanoid-substituted epicatechnins, cinchonains from Cinchona succirubra. (1).
  作者：GENICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.30.4268

  日期：——

  As a result of an investigation of the relatively lower-molecular-weight phenolics in the bark of Cinchona succirubra (Rubiaceae), cinchonains Ia (1), Ib (2), Ic (3) and Id (4), a new class of flavan-3-ols substituted at the A-ring with a C6-C3 unit, have been isolated, together with caffeic acid (5) and (-)-epicatechin (6). The structures of these compounds have been established on the basis of chemical and spectroscopic evidence. A direct coupling of caffeic acid and (-)-epicatechin leading to the formation of cinchonains has also been achieved.

  通过对 Cinchona succirubra（茜草科）树皮中分子量相对较低的酚类化合物进行研究，分离出了 Cinchonains Ia (1)、Ib (2)、Ic (3) 和 Id (4)，以及咖啡酸 (5) 和 (-)-epicatechin (6)，这是一类在 A 环上被 C6-C3 单元取代的新的黄烷-3-醇。这些化合物的结构是根据化学和光谱证据确定的。此外，还实现了咖啡酸和(-)-表儿茶素的直接偶联，从而形成了金鸡纳类化合物。