Penta-O-methylpolycitone A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Penta-O-methylpolycitone A
• 英文别名: pent-O-methylpolycitone A；3,4-bis(3,5-Dibromo-4-methoxyphenyl)-5-[(3,5-dibromo-4-methoxyphenyl)carbonyl]-1-[2-(4-methoxyphenyl)ethyl]pyrrol-2-yl 3,5-dibromo-4-methoxyphenyl ketone；[5-(3,5-dibromo-4-methoxybenzoyl)-3,4-bis(3,5-dibromo-4-methoxyphenyl)-1-[2-(4-methoxyphenyl)ethyl]pyrrol-2-yl]-(3,5-dibromo-4-methoxyphenyl)methanone
• 化学式: C₄₃H₃₁Br₈NO₇
• 分子量: 1312.95
• InChiKey: SYNQAUGCJMRILY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  59
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  硫酸二甲酯 、 Polycitone A 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以98%的产率得到Penta-O-methylpolycitone A
  参考文献：
  名称：

  Total Syntheses of the Marine Pyrrole Alkaloids Polycitone A and B

  摘要：

  Polycitone B (2) was obtained in four steps from pyrrole dicarboxylic acid 3, including Friedel-Crafts reaction of the corresponding acid chloride with anisole. The conversion of 2 into polycitone A(1) was achieved in two steps via Mitsunobu alkylation of the pyrrolic NH groups. The synthesis of polycitone A proceeds in 18% overall yield and offers the possibility of varying the subsituents on the pyrrole ring.

  DOI：

  10.1021/ol026555b

文献信息

• Polycitone A and Polycitrins A and B: New Alkaloids from the Marine Ascidian Polycitor sp
  作者：Amira Rudi、Israel Goldberg、Zafra Stein、Felix Frolow、Yehuda Benayahu、Michael Schleyer、Yoel Kashman

  DOI：10.1021/jo00084a015

  日期：1994.3

  Three novel compounds polycitone A (1a) and polycitrins A and B (2 and 3) were isolated from the marine ascidian Polycitor sp. The structures of compounds 1a, 2, and 3 were established mainly on the basis of NMR spectroscopic data and, in the case of 1a, also by single-crystal X-ray diffraction analysis. The crystallographic analysis was performed on 1b, the penta-O-methyl derivative of 1a, both compounds yielding poorly diffracting crystals of highly anisotropic shape. It required, in view of the dominating heavy-atom content of 1b; diffraction measurements with an intense rotating-anode X-ray source. Polycitone A and polycitrins A and B represent the first examples of two new classes of marine products which might biogenetically be close to the lamellarins. The penta-O-methyl derivative 1b, was found to inhibit the growth of SV40 transformed fibroblast cells in a concentration of 10 mu g/mL.
• Total Syntheses of the Marine Pyrrole Alkaloids Polycitone A and B
  作者：Andreas T. Kreipl、Caroline Reid、Wolfgang Steglich

  DOI：10.1021/ol026555b

  日期：2002.9.1

  Polycitone B (2) was obtained in four steps from pyrrole dicarboxylic acid 3, including Friedel-Crafts reaction of the corresponding acid chloride with anisole. The conversion of 2 into polycitone A(1) was achieved in two steps via Mitsunobu alkylation of the pyrrolic NH groups. The synthesis of polycitone A proceeds in 18% overall yield and offers the possibility of varying the subsituents on the pyrrole ring.