氧基白屈菜季铵碱 | 28342-33-8

• 物质功能分类: 天然产物 - 生物碱
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 氧基白屈菜季铵碱
• 中文别名: 1(2H)-酞嗪酮,4-[[(3,4-二甲氧苯基)亚甲基]氨基]-2-甲基-
• 英文名称: oxychelerythrine
• 英文别名: 1,2-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-13(12H)-one；6-oxychelerythrine；oxychelerytrine；1,2-dimethoxy-12-methyl-12H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-13-one；1,2-Dimethoxy-12-methyl-12H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-13-on；1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-13-one
• CAS: 28342-33-8
• 化学式: C₂₁H₁₇NO₅
• 分子量: 363.37
• InChiKey: IHTXRYTWDARUKX-UHFFFAOYSA-N

物化性质

• 熔点：
  194-197 °C
• 沸点：
  615.5±55.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  储存条件：2-8℃，干燥，密封保存。

制备方法与用途

Oxychelerythrine 是从 Zanthoxylum integrifoliolum 中分离得到的一种生物碱。研究显示，它对 P-388 和 HT-29 细胞株具有细胞毒性，半数有效浓度（ED50）分别为 3.25 μg/mL 和 5.48 μg/mL。

反应信息

• 作为反应物：
  描述：

  氧基白屈菜季铵碱 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 6-hydroxy-5,6-dihydrochelerythrine
  参考文献：
  名称：

  小ber碱仿生转化为白屈菜红碱和二氢白屈菜红碱

  摘要：

  通过生物发生途径开发了一种由黄连素合成新颖高效的苯并[ c ]菲啶生物碱，白屈菜红碱和二氢白屈菜红碱的方法。

  DOI：

  10.1039/c39840000718
• 作为产物：
  描述：

  白屈菜红碱 在 盐酸 、 K₃Fe(CN)6 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以30.9%的产率得到氧基白屈菜季铵碱
  参考文献：
  名称：

  Structural modification of sanguinarine and chelerythrine and their antibacterial activity

  摘要：

  In this study, five derivatives of sanguinarine (1) and chelerythrine (2) were prepared, with 1 and 2 as starting materials, by reduction, oxidation and nucleophilic addition to the iminium bond C=N+. The structures of all compounds were elucidated on account of their MS, 1H-NMR and 13C-NMR data. The antibacterial activities of all compounds were screened, using Staphylococcus aureus, Escherichia coli, Aeromonas hydrophila and Pasteurella multocida as test bacteria. The minimum bacteriostatic concentration and minimum bactericidal concentration of the active compounds were determined by the turbidity method. The structure-activity relationships of 1 and 2 were discussed. The results showed that 1, 2 and their pseudoalcoholates were found to be potent inhibitors to S. aureus, E. coli and A. hydrophila, while the other derivatives were found to be inactive. The pseudoalcoholates might be the prodrugs of 1 and 2. The iminium bond in the molecules of 1 or 2 was the determinant for antibacterial activity, and the substituents at the 7 and 8 positions influenced the antibacterial activities of 1 and 2 against different bacteria.

  DOI：

  10.1080/14786419.2010.482055

文献信息

• In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi
  作者：Xin-Juan Yang、Fang Miao、Yao Yao、Fang-Jun Cao、Rui Yang、Yan-Ni Ma、Bao-Fu Qin、Le Zhou

  DOI：10.3390/molecules171113026

  日期：——

  In order to understand the antifungal activity of some derivatives of sanguinarine (S) and chelerythrine (C) and their structure-activity relationships, sixteen derivatives of S and C were prepared and evaluated for in vitro antifungal activity against seven phytopathogenic fungi by the mycelial growth rate method. The results showed that S, C and their 6-alkoxy dihydro derivatives S1–S4, C1–C4 and 6-cyanodihydro derivatives S5, C5 showed significant antifungal activity at 100 µg/mL against all the tested fungi. For most tested fungi, the median effective concentrations of S, S1, C and C1 were in a range of 14–50 µg/mL. The structure-activity relationship showed that the C=N+ moiety was the determinant for the antifungal activity of S and C. S1–S5 and C1–C5 could be considered as the precursors of S and C, respectively. Thus, the present results strongly suggested that S and C or their derivatives S1–S5 and C1–C5 should be considered as good lead compounds or model molecules to develop new anti-phytopathogenic fungal agents.

  为了理解血根碱（S）和白屈菜红碱（C）及其衍生物的抗真菌活性和结构-活性关系，制备并评估了十六种S和C衍生物对七种植物病原真菌的体外抗真菌活性，采用菌丝生长速率法进行测定。结果显示，S、C及其6-烷氧基二氢衍生物S1-S4、C1-C4和6-氰基二氢衍生物S5、C5在100 µg/mL浓度下对所有测试真菌均表现出显著的抗真菌活性。对于大多数测试真菌，S、S1、C和C1的中效浓度范围为14-50 µg/mL。结构-活性关系表明，C=N+部分是S和C抗真菌活性的决定因素。S1-S5和C1-C5可以分别被视为S和C的前体。因此，当前结果强烈表明，S和C或其衍生物S1-S5和C1-C5应被视为开发新型抗植物病原真菌剂的优良先导化合物或模型分子。
• One-Pot Synthesis of Isoquinolinium Salts by Rhodium-Catalyzed CH Bond Activation: Application to the Total Synthesis of Oxychelerythrine
  作者：Jayachandran Jayakumar、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1002/anie.201105755

  日期：2012.1.2

  It's worth its salt: The title reaction leads to the synthesis of highly substituted isoquinolinium salts (see scheme; Cp*=Me5C5). The reaction proceeds through a CH activation and a subsequent annulation in the presence of a rhodium catalyst. The reaction mechanism is discussed as well as its application to the synthesis of the natural product oxychelerythrine.

  值得它的盐：标题反应导致高度取代的异喹啉鎓盐的合成（请参阅示意图； Cp * = Me 5 C 5）。该反应通过C  ħ活化和在铑催化剂的存在下，随后的环化。讨论了反应机理及其在天然产物羟白屈菜红碱合成中的应用。
• Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: application to the total synthesis of benzo[c]phenanthridine alkaloids
  作者：Pei Lv、Kanglun Huang、Longguan Xie、Xiaohua Xu

  DOI：10.1039/c0ob01208d

  日期：——

  A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.

  通过钯催化氮杂双环烯烃与邻碘苯甲酸酯的开环偶联，然后串联环化，可实现苯并[ c ]菲啶的简洁高效合成。该策略已成功应用于苯并[ c ]菲啶生物碱的全合成，如血红碱，白屈菜红碱，尼替丁 和阿维辛。
• Preparation of Amino-Substituted Indenes and 1,4-Dihydronaphthalenes Using a One-Pot Multireaction Approach: Total Synthesis of Oxybenzo[<i>c</i>]phenanthridine Alkaloids
  作者：Ewen D. D. Calder、Fiona I. McGonagle、Alexander H. Harkiss、Grant A. McGonagle、Andrew Sutherland

  DOI：10.1021/jo5014492

  日期：2014.8.15

  substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular

  已经设计了带有2-乙烯基或2-烯丙基芳基的烯丙基三氯乙酰亚氨酸酯作为一锅两步多键形成方法的底物，从而导致氨基茚和氨基取代的1，4-二氢萘的一般制备。从一锅法形成的特权结构的合成效用已通过四种氧苯并[ c ]菲啶生物碱，氧白屈菜红碱，氧血胍，氧硝啶和氧鸟嘌呤的总合成得到证明。分子内的联芳基Heck偶联反应，使用Hermann-Beller palladacycle催化，可用于完成天然产物合成过程中的关键步骤。
• Chemical transformation of protoberberines. XVI. Regioselective introduction of an oxy functionality at the C12-position of the benzo(c)phenanthridine skeleton: A convenient synthesis of macarpine from oxychelirubine.
  作者：Miyoji HANAOKA、Won Jea CHO、Shuji YOSHIDA、Tsukasa FUEKI、Chisato MUKAI

  DOI：10.1248/cpb.38.3335

  日期：——

  A novel method for the introduction of an oxy functionality at the C12-position of the benzo[c]phenanthridine skeleton was developed. The method was successfully applied to a biomimetic synthesis of macarpine (3) from oxychelirubine (15), which was easily derived from the corresponding protoberberine (9).

  我们开发了一种在苯并[c]菲啶骨架的 C12 位引入氧基官能团的新方法。该方法被成功地应用于以氧白桦脂碱 (15) 为原料合成大果芸香碱 (3)的生物仿生法，而大果芸香碱 (3) 很容易就能从相应的原小檗碱 (9) 中提取出来。