(meso+racem) 1,1',3,3',9,9'-Hexahydroxy-7,7'-dimethylbianthraquinoyl | 2506-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (meso+racem) 1,1',3,3',9,9'-Hexahydroxy-7,7'-dimethylbianthraquinoyl
• 英文别名: 10,10'-emodin bianthrone；emodin bianthrone；emodinbianthrone；Frangula-emodin-dianthron；Emodin-dianthron；Emodinbianthron；1,3,8-trihydroxy-6-methyl-10-(2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl)-10H-anthracen-9-one
• CAS: 2506-11-8
• 化学式: C₃₀H₂₂O₈
• 分子量: 510.5
• InChiKey: UUXPVUHOWQPCSC-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (decomp)
• 沸点：
  773.7±60.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (meso+racem) 1,1',3,3',9,9'-Hexahydroxy-7,7'-dimethylbianthraquinoyl 在 氧气 、 potassium hydroxide 作用下， 以52%的产率得到穗花衫双黄酮
  参考文献：
  名称：

  联二蒽醌类化合物在制备抗肿瘤药物中的应 用

  摘要：

  本发明涉及联二蒽醌的应用，更为具体的说是涉及联二蒽醌类化合物在制备抗肿瘤药物中的应用。我们将放射性治疗核素标记在联二蒽醌类药物上，从而得到了具有良好肿瘤靶向性的标记药物。该类化合物可积聚在肿瘤内的死亡细胞及组织上，且该类化合物具有不稳定的化学元素或是同位素，可发生辐射，破坏周围的细胞及组织以到达治疗肿瘤的目的。

  公开号：

  CN105106981B
• 作为产物：
  描述：

  大黄素 在 盐酸 、 iron(III) chloride 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 (meso+racem) 1,1',3,3',9,9'-Hexahydroxy-7,7'-dimethylbianthraquinoyl
  参考文献：
  名称：

  联二蒽醌类化合物在制备抗肿瘤药物中的应 用

  摘要：

  本发明涉及联二蒽醌的应用，更为具体的说是涉及联二蒽醌类化合物在制备抗肿瘤药物中的应用。我们将放射性治疗核素标记在联二蒽醌类药物上，从而得到了具有良好肿瘤靶向性的标记药物。该类化合物可积聚在肿瘤内的死亡细胞及组织上，且该类化合物具有不稳定的化学元素或是同位素，可发生辐射，破坏周围的细胞及组织以到达治疗肿瘤的目的。

  公开号：

  CN105106981B

文献信息

• Prenylated bianthrones and vismione F from Psorospermum febrifugum
  作者：B. Botta、F. Delle Monache、G. Delle Monache、G.B. Marini Bettolo、J.D. Msonthi

  DOI：10.1016/s0031-9422(00)84902-x

  日期：1985.1

  Abstract The roots of Psorospermum febrifugum collected in Malawi contained together with the known vismione D and geranyloxyemodin four new compounds: vismione F and the three bianthrones A 1 , A 3a and A 3b . All the isolated compounds contained C- or O-geranyl substituents and showed a close biogenetic relationship.

  摘要 在马拉维采集的Psorospermum febrifugum 根中，除已知的vismione D 和geranyloxyemodin 外，还含有四种新化合物：vismione F 和三种双酮A 1 、A 3a 和A 3b 。所有分离的化合物都含有C-或O-香叶基取代基，并显示出密切的生物遗传关系。
• On the synthesis of hypericin by oxidative trimethylemodin anthrone and emodin anthrone dimerization: Isohypericin
  作者：Heinz Falk、Gerhard Schoppel

  DOI：10.1007/bf00811548

  日期：1992.10

  The base catalyzed oxidative dimerization of emodin anthrone exclusively yields hypericin. However, on oxidative dimerization of trimethylemodinanthrone a mixture of hexamethylhypericin and hexamethylisohypericin was obtained. Chromatographic separation of the hexabenzoyl derivatives was achieved, and by saponification about equal amounts of hypericin and isohypericrin were produced. Isohypericin could be characterized for the first time by its spectroscopic data and its protonation and deprotonation pK(a) and pK(a)* values.
• Synthesis and Evaluation of ¹³¹I-Skyrin as a Necrosis Avid Agent for Potential Targeted Radionuclide Therapy of Solid Tumors
  作者：Cong Wang、Qiaomei Jin、Shengwei Yang、Dongjian Zhang、Qin Wang、Jindian Li、Shaoli Song、Ziping Sun、Yicheng Ni、Jian Zhang、Zhiqi Yin

  DOI：10.1021/acs.molpharmaceut.5b00630

  日期：2016.1.4

  An innovative anticancer approach targeted to necrotic tissues, which serves as a noncancerous and generic anchor, may present a breakthrough. Necrosis avid agents with a flat conjugate aromatic structure selectively accumulate in necrotic tissues, but they easily form aggregates that undesirably distribute to normal tissues. In this study, skyrin, a dianthraquinone compound with smaller and distorted pi-cores and thus decreased aggregates as compared with hypericin (Hyp), was designed to target necrosis for tumor therapy. Aggregation studies of skyrin by UV/vis spectroscopy showed a smaller selfassociation constant with skyrin than with Hyp. Skyrin was labeled by iodine-131 with a radiochemical purity of 98% and exhibited good stability in rat serum for 72 h. In vitro cell uptake studies showed significant difference in the uptake of I-131-skyrin by necrotic cells compared to normal cells (P < 0.05). Compared in rats with liver and muscle necrosis, radiobiodistribution, whole-body autoradiography, and SPECT/CT studies revealed higher accumulation of I-131-skyrin in necrotic liver and muscle (p < 0.05), but lower uptake in normal organs, relative to that of I-131-Hyp. In mice bearing H22 tumor xenografts treated with combretastatin A4 disodium phosphate, the highest uptake of I-131-skyrin was found in necrotic tumor. In conclusion, I-131-skyrin appears a promising agent with reduced accumulation in nontarget organs for targeted radionuclide therapy of solid tumors.