| 946657-93-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 946657-93-8
• 化学式: C₂₄H₂₉N₃O₄
• 分子量: 423.512
• InChiKey: MJVZYEWSHLHQJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  96.54
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenyl 6-((Z)-2-((4-methoxy-1H,1'H-[2,2'-bipyrrol]-5-yl)methylene)-3,5-dimethyl-2H-pyrrol-4-yl)-6-oxohexanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of prodigiosene conjugates of porphyrin, estrone and 4-hydroxytamoxifen

  摘要：

  To generate the first series of prodigiosene conjugates, the tripyrrolic skeleton was appended to estrone, tamoxifen and porphyrin frameworks by way of ester linkers and various hydrocarbon chain lengths. The ability of the conjugates to inhibit various types of cancer cells was evaluated in vitro. The porphyrin conjugates did not exhibit significant activity. The estrone conjugates exhibited modest activity, for the most part. However, significantly greater growth inhibition activity against certain breast, colon, lung, leukemia, melanoma and prostate cell lines was noted. This unusual effect for this first generation model class of compound warrants further investigation and comparison to cases where estrogens are linked to prodigiosenes via connection points that do not feature in estrogen receptor binding. The 4-hydroxytamoxifen conjugates exhibit nanomolar range activity against the MCF-7 breast cancer cell line, paving the way to expand the scope and connectivity of prodigiosene-tamoxifen conjugates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.042

文献信息

• Prodigiosenes conjugated to tamoxifen and estradiol
  作者：Estelle Marchal、Carlotta Figliola、Alison Thompson

  DOI：10.1039/c7ob00943g

  日期：——

  We report the synthesis of the first click-appended prodigiosene conjugates. Four prodigiosene conjugates of estradiol functionalised at the 7α-position were prepared, as were three prodigiosene conjugates of tamoxifen. The coupling between a prodigiosene and an 11-hydroxy estradiol derivative via an ether linkage was investigated, as was the 11- and 7-functionalisation of the estradiol core. The robustness

  我们报告的第一个单击追加prodigiosene共轭物的合成。制备了在7α-位官能化的四种雌二醇的前黄花共轭物，以及他莫昔芬的三种前黄花共轭物。dig和11-羟基雌二醇衍生物之间的偶联通过研究了醚键，以及雌二醇核心的11-和7-官能化。雌二醇保护基团的稳健性受到通常用于为11和7官能化的这类骨架装备的反应的严峻挑战。特别是，对于涉及雌二醇的合成而言，TBS，TMS和THP对合成至关重要，对于该核心的功能化而言，它不是有用的保护基。当治疗剂的化学特征限制了保护基团的选择（在这种情况下，带有芳基，NH，烯基和酯基的pro二烯），点击化学就成为一种有吸引力的合成策略。评估了七种单击的前黄酮共轭物的抗癌活性。