dioncopeltine A | 60158-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: dioncopeltine A
• 英文别名: (1R,3R)-7-[5-hydroxy-2-(hydroxymethyl)-4-methoxynaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
• CAS: 60158-81-8
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: ZQSUAGVTKAZDJV-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dioncopeltine A 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 、 silver(l) oxide 作用下， 以 乙醇 、 氯仿 、 丙酮 为溶剂， 反应 7.0h， 生成 jozipeltine A
  参考文献：
  名称：

  Jozipeltine A, a Novel, Unnatural Dimer of the Highly Hydroxylated Naphthylisoquinoline Alkaloid Dioncopeltine A

  摘要：

  The synthesis of jozipeltine A (5), the 6'-coupled constitutionally symmetric dimer of the highly antimalarial naphthylisoquinoline alkaloid dioncopeltine A (4), is described. After selective protection of two of the four OH- and NH-functionalities of 4, the coupling succeeds oxidatively, with Ag2O as the reagent. Deprotection gives the target molecule 5, in only three steps from 4. Jozipeltine A is the first naphthylisoquinoline dimer with oxygen functions in the side chain of the naphthalene part. Investigations on its antiplasmodial and antiviral activities provide valuable insight into structure-activity relationships within this promising class of bioactive quateraryls. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00538-x
• 作为产物：
  描述：

  1-bromo-5-isopropoxy-4-methoxy-2-naphthoic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 lithium aluminium tetrahydride 、 草酰氯 、 氢气 、 sodium acetate 、 三氯化硼 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 0.83h， 生成 dioncopeltine A
  参考文献：
  名称：

  三个naphthylisoquinoline生物碱涉及关节的总合成dioncolactone A，dioncopeltine A，和5'- Ò -demethyldioncophylline甲

  摘要：

  的第一全合成三个抗疟疾naphthylisoquinoline生物碱dioncolactone A（4），dioncopeltine A（5），和5'- Ô -demethyldioncophylline A（6）进行说明。通过“内酯法”，通过两个分子部分的酯型前缀，分子内偶联和内酯辅助桥的对苯二酸-非对映选择性裂解，实现了芳基轴的区域和立体选择性构建。作为一种新颖的替代方案，可以通过动态动力学拆分通过对映选择性羟基醛还原来安装在轴上的构型。

  DOI：

  10.1016/s0040-4020(98)01040-0

文献信息

• 5′-O-demethyldioncophylline A, a new antimalarial alkaloid from triphyophyllum peltatum1Part 111 in the series “Acetogenic Isoquinoline Alkaloids”. For Part 110, see Ref.[1].1
  作者：Gerhard Bringmann、Wael Saeb、Ralf God、Manuela Schäffer、Guido François、Karl Peters、Eva-Maria Peters、Peter Proksch、Kurt Hostettmann、Laurent Aké Assi

  DOI：10.1016/s0031-9422(98)00231-3

  日期：1998.11

  From the root bark of Triphyophyllum peltatum, the new naphthylisoquinoline alkaloid 5'-O-demethyldioncophylline A has been isolated. Its otherwise difficult separation from the largely dominating main alkaloid, dioncophylline A, was greatly facilitated by a bromination-benzylation procedure. From the resulting derivative, a crystal structure analysis with an anomalous X-ray diffraction was achieved

  从三叶草的根皮中，分离出新的萘基异喹啉生物碱 5'-O-去甲基二羟甲基二苯酚 A。溴化-苄基化程序极大地促进了它与主要的主要生物碱，二酮茶碱 A 的分离。从所得衍生物中，通过异常 X 射线衍射实现了晶体结构分析，从而证实了新生物碱的完整绝对立体结构。该结构进一步由 diioncopeltine A 的部分合成证实。该天然产物显示出对恶性疟原虫红细胞形式的抗疟活性。
• ASYMMETRIC SYNTHESIS OF (M)-2-HYDROXYMETHYL-1-(2-HYDROXY-4,6-DIMETHYLPHENYL)NAPHTHALENE VIA A CONFIGURATIONALLY UNSTABLE BIARYL LACTONE
  作者：Bringmann, Gerhard、Breuning, Matthias、Henschel, Petra、Hinrichs, Jürgen、Greenen, Peter M.、Curran, Dennis P.

  DOI：10.15227/orgsyn.079.0072

  日期：——
• BRINGMANN, GERHARD;RUBENACKER, MARTIN;VOGT, PETER;BUSSE, HOLGER;AKE, ASSI+, PHYTOCHEMISTRY, 30,(1991) N, C. 1691-1696
  作者：BRINGMANN, GERHARD、RUBENACKER, MARTIN、VOGT, PETER、BUSSE, HOLGER、AKE, ASSI+

  DOI：——

  日期：——
• Dioncopeltine A and dioncolactone A: Alkaloids from Triphyophyllum peltatum
  作者：Gerhard Bringmann、Martin Rübenacker、Peter Vogt、Holger Busse、Laurent Aké Assi、Karl Peters、Hans Georg von Schnering

  DOI：10.1016/0031-9422(91)84235-k

  日期：1991.1

  The isolation of two novel alkaloids from Triphyophyllum peltatum is described. The complete stereostructure of dioncopeltine A, which is closely related to dioncophylline A, is established by spectroscopic, chiroptical, and degradative methods, and is furthermore confirmed by its transformation to O-methyl-dioncopophylline A, as well as by X-ray crystallography. Dioncolactone A, which can be transformed into dioncopeltine A by reductive ring-opening, is the first naturally occurring representative of this novel type of 'axially prostereogenic' biaryl alkaloids.
• Directed joint total synthesis of the three naphthylisoquinoline alkaloids dioncolactone A, dioncopeltine A, and 5′-O-demethyldioncophylline A
  作者：Gerhard Bringmann、Wael Saeb、Martin Rübenacker

  DOI：10.1016/s0040-4020(98)01040-0

  日期：1999.1

  described. The regio- and stereo-selective construction of the biaryl axes was achieved through the ‘lactone methodology’, by ester-type prefixation of the two molecular moieties, intramolecular coupling, and atropo-diastereoselective cleavage of the lactone auxiliary bridge. As a novel alternative, the configuration at the axis may be installed by atroposelective hydroxy aldehyde reduction through dynamic

  的第一全合成三个抗疟疾naphthylisoquinoline生物碱dioncolactone A（4），dioncopeltine A（5），和5'- Ô -demethyldioncophylline A（6）进行说明。通过“内酯法”，通过两个分子部分的酯型前缀，分子内偶联和内酯辅助桥的对苯二酸-非对映选择性裂解，实现了芳基轴的区域和立体选择性构建。作为一种新颖的替代方案，可以通过动态动力学拆分通过对映选择性羟基醛还原来安装在轴上的构型。