Polycitone A | 153212-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Polycitone A
• 英文别名: [5-(3,5-Dibromo-4-hydroxybenzoyl)-3,4-bis(3,5-dibromo-4-hydroxyphenyl)-1-[2-(4-hydroxyphenyl)ethyl]pyrrol-2-yl]-(3,5-dibromo-4-hydroxyphenyl)methanone
• CAS: 153212-84-1
• 化学式: C₃₈H₂₁Br₈NO₇
• 分子量: 1242.82
• InChiKey: JVGHQJALYAGKAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  980.7±65.0 °C(Predicted)
• 密度：
  2.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  54
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  140
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Polycitone A 在 盐酸 、 汞 、 锌 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以40%的产率得到4-[[3,4-Bis(3,5-dibromo-4-hydroxyphenyl)-5-[(3,5-dibromo-4-hydroxyphenyl)methyl]-1-[2-(4-hydroxyphenyl)ethyl]pyrrol-2-yl]methyl]-2,6-dibromophenol
  参考文献：
  名称：

  Polycitone A and Polycitrins A and B: New Alkaloids from the Marine Ascidian Polycitor sp

  摘要：

  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.

  DOI：

  10.1021/jo00084a015
• 作为产物：
  描述：

  2-(4-甲基羰基氧基苯基)-1-乙醇 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.75h， 生成 Polycitone 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

• CYTOTOXIC ALKALOIDS (HALITULIN)
  申请人：PHARMA MAR, S.A.

  公开号：EP1119565A1

  公开（公告）日：2001-08-01
• US6635656B1
  申请人：——

  公开号：US6635656B1

  公开（公告）日：2003-10-21
• [EN] CYTOTOXIC ALKALOIDS (HALITULIN)<br/>[FR] ALCALOIDES CYTOTOXIQUES (HALITULINE)
  申请人：PHARMA MAR SA

  公开号：WO2000020411A1

  公开（公告）日：2000-04-13

  Compounds of general formula (I) wherein the nature of the group R is not particularly critical and typically takes various forms, include the natural compound halitulin of formula (1) have antitumor activity.
• 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.
• 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.