tetrahydroalstonine | 5299-09-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 育亨宾生物碱
• 英文名称: tetrahydroalstonine
• 英文别名: 19-epi-ajmalicine；raunicitine；rauniticine；ajmalicine；ervine；19β-methyl-(20α)-18-oxa-yohimb-16-ene-16-carboxylic acid methyl ester；methyl (1S,15S,16R,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
• CAS: 5299-09-2
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: GRTOGORTSDXSFK-OYWVLEMYSA-N

物化性质

• 熔点：
  222-223 °C
• 沸点：
  524.0±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetrahydroalstonine 在 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 帽柱叶碱
  参考文献：
  名称：

  Pousset; Poisson; Shine, Bulletin de la Societe Chimique de France, 1967, vol. 8, p. 2766 - 2779

  摘要：

  DOI：
• 作为产物：
  描述：

  3-isorauniticine 在 Raney Ni W-2 氢氧化钾 、 氢气 作用下， 生成 tetrahydroalstonine
  参考文献：
  名称：

  The Stereochemistry of Tetrahydroalstonine and Related Indole Alkaloids.

  摘要：

  DOI：

  10.3891/acta.chem.scand.36b-0607

文献信息

• Biomimetic synthesis of yohimbine and heteroyohimbine alkaloids from 4,21-dehydrogeissoschizine
  作者：C. Kan-Fan、H.-P. Husson

  DOI：10.1016/s0040-4039(00)92746-1

  日期：——

  The first biomimetic synthesis of the yohimbine skeleton (7) from a Corynanthé-type precursor (2) is reported as well as the transformation of the latter into both the 19R and 19S heteroyohimbine series. Reactions were performed on an alumina surface.

  据报道，首次从拟南芥型前驱体（2）仿生合成育亨宾骨架（7），并将后者转化为19R和19S杂育亨宾系列。反应在氧化铝表面上进行。
• Alkaloids of Uncaria attenuata from Thailand
  作者：Dhavadee Ponglux、Tanomjit Supavita、Robert Verpoorte、David Phillipson

  DOI：10.1016/0031-9422(80)83025-1

  日期：1980.1

  Abstract The major alkaloids of a sample of leaves of Uncaria attenuata obtained from Thailand have been identified as the pentacyclic heteroyohimbine alkaloids tetrahydroalstonine, rauniticine and the novel 14-β-hydroxy-3- iso -rauniticine. Evidence for the structure of the new alkaloid was obtained from a study of UV, IR, MS, 1 H NMR and 1 C NMR spectra.

  摘要 从泰国获得的减毒钩藤叶样品的主要生物碱已被鉴定为五环杂育亨宾生物碱四氢黄石碱、rauniticine 和新型 14-β-羟基-3-iso-rauniticine。新生物碱结构的证据是从 UV、IR、MS、1 H NMR 和 1 C NMR 光谱的研究中获得的。
• Alkaloids of uncaria elliptica
  作者：J.David Phillipson、Narong Supavita

  DOI：10.1016/s0031-9422(00)80276-9

  日期：1983.1

  investigated for their alkaloid content. Seven diastereoisomers of the pentacyclic heteroyohimbine series of alkaloids, 14-β-hydroxy-3-isorauniticine and tetrahydroalstonine N-oxide were isolated. Rauniticine oxindole A, rauniticine pseudoindoxyl, 3-isorauniticine pseudoindoxyl and akuammigine pseudoindoxyl were isolated for the first time as natural products. The roxburghine alkaloids, previously isolated

  摘要 对来自泰国的6个椭圆钩藤叶样品的生物碱含量进行了研究。七种非对映异构体的五环杂育亨宾生物碱、14-β-羟基-3-异龙葵碱和四氢黄石宁 N-氧化物被分离出来。Rauniticine oxindole A、rauniticine pseudoindoxyl、3-isoorauniticine pseudoindoxyl和akuammigine pseudoindoxyl是首次作为天然产物分离出来。之前从椭圆形桉中分离出的 roxburghine 生物碱没有被检测到，而且该物种在化学上的变化比迄今为止假设的要多。已比较了八种非对映异构五环杂育亨宾生物碱的 1 H NMR 光谱。
• Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies
  作者：Gunter R. Strobl、Stephanie von Kruedener、Joachim Stoeckigt、F. Peter Guengerich、Thomas Wolff

  DOI：10.1021/jm00061a004

  日期：1993.4

  To gain insight into the specificity of cytochrome P-450 2D6 toward inhibitors, a preliminary pharmacophore model was built up using strong competitive inhibitors. Ajmalicine (1), the strongest inhibitor known (K(i) = 3 nM) was selected as template because of its rigid structure. The preliminary pharmacophore model was validated by performing inhibition studies with derivatives of ajmalicine (1) and quinidine (9). Bufuralol (18) was chosen as substrate and the metabolite 1'-hydroxybufuralol (19) was separated by high performance liquid chromatography. All incubations were carried out using human liver microsomes after demonstration that the K(i) values obtained with microsomes were in accordance with those obtained with a reconstituted monooxygenase system containing purified cytochrome P-450 2D6. Large differences of K(i) values ranging between 0.005 and 100 muM were observed. Low-energy conformers of tested compounds were fit within the preliminary pharmacophore model. The analysis of steric and electronic properties of these compounds led to the definition of a final pharmacophore model. Characteristic properties are a positive charge on a nitrogen atom and a flat hydrophobic region, the plane of which is almost perpendicular to the N-H axis and maximally extends up to a distance of 7.5 angstrom from the nitrogen atom. Compounds with high inhibitory potency had additional functional groups with negative molecular electrostatic potential and hydrogen bond acceptor properties on the opposite side at respective distances of 4.8-5.5 angstrom and 6.6-7.5 angstrom from the nitrogen atom. The superposition of strong and weak inhibitors led to the definition of an excluded volume map. Compounds that required additional space were not inhibitors. This is apparently the first pharmacophore model for inhibitors of a cytochrome P-450 enzyme and offers the opportunity to classify compounds according to their potency of inhibition. Adverse drug interactions which occur when both substrates and inhibitors of cytochrome P-450 2D6 are applied may be predicted.
• Dinda, Biswanath; Chandra De, Utpal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 12, p. 2698 - 2700
  作者：Dinda, Biswanath、Chandra De, Utpal

  DOI：——

  日期：——