N,N'-二(9,10-二氢-9,10-二氧代-1,5-蒽二基)二-乙酰胺 | 129-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: N,N'-二(9,10-二氢-9,10-二氧代-1,5-蒽二基)二-乙酰胺
• 中文别名: 1,5-双(乙酰氨基)蒽醌
• 英文名称: 1,5-Diacetamidoanthraquinone
• 英文别名: 1,5-bis-acetylamino-anthraquinone；1,5-Bis-acetylamino-anthrachinon；1.5-Bis-acetamino-anthrachinon；N,N'-(9,10-dioxo-1,5-anthrylene)di(acetamide)；1,5-bis(acetamido)-anthraquinone；1,5-Bis-acetaminoanthrachinon；Acetamide, N,N'-bis(9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis-；N-(5-acetamido-9,10-dioxoanthracen-1-yl)acetamide
• CAS: 129-30-6
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: FKRYJILJIVPKTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-二(9,10-二氢-9,10-二氧代-1,5-蒽二基)二-乙酰胺 在 硫酸 、 硝酸 作用下， 生成 N-(5-乙酰氨基-4,8-二硝基-9,10-二氧代蒽-1-基)乙酰胺
  参考文献：
  名称：

  DE127780

  摘要：

  公开号：
• 作为产物：
  描述：

  1,5-二硝基蒽醌 在 tin oxidepotash 、 sodium acetate 作用下， 生成 N,N'-二(9,10-二氢-9,10-二氧代-1,5-蒽二基)二-乙酰胺
  参考文献：
  名称：

  Roemer, Chemische Berichte, 1883, vol. 16, p. 363

  摘要：

  DOI：

文献信息

• Synthesis and Antitumor Evaluation of Symmetrical 1,5-Diamidoanthraquinone Derivatives as Compared to Their Disubstituted Homologues
  作者：Hsu-Shan Huang、Hui-Fen Chiu、Chi-Wei Tao、In-Been Chen

  DOI：10.1248/cpb.54.458

  日期：——

  A series of symmetrical 1,5-diamidoanthraquinone derivatives with potentially bioreducible groups has been synthesized and their cytostatic activity against the panel of various cancer cell lines in vitro has been studied. Preliminary structure–activity relationships were established. The results indicated that compounds 5 and 18 exhibited significant potent cytotoxicity at 1.24—1.75 μM for Hepa G2 cell line; compounds 5, 16, and 18 exhibited cytotoxicity at 0.14—1.82 μM for 2.2.15 cell line as determined by XTT colorimetric assay. Two structurally related compounds, mitoxantrone and adriamycin, were tested in parallel as positive controls. In addition, it was found that compounds 5 and 18 were a more potent and specific human hepatoma cell line than mitoxantrone and showed comparable activity to adriamycin. Among them, compound 18 was the most potent for 2.2.15 cells. We have demonstrated that the anthraquinone moiety is essential for activity and that less sterically hindered substituents contribute to enhanced in vitro efficacy. Implications for amidoanthraquinone cytotoxicity as potential anticancer agents are discussed. We further delineate the nature of the pharmacophore for this class of compounds, which provides a rational basis for the structure–activity relationships.

  一系列对称的1,5-二氨基蒽醌衍生物已被合成，并研究了其对多种癌细胞系的细胞抑制活性。初步的结构-活性关系得到了建立。结果显示，化合物5和18在1.24-1.75 μM时对Hepa G2细胞系表现出显著的细胞毒性；化合物5、16和18在0.14-1.82 μM时对2.2.15细胞系表现出细胞毒性，通过XTT比色法进行了测定。两种结构相关的化合物，米托蒽醌和阿霉素，被作为阳性对照进行平行测试。此外，发现化合物5和18在对人肝癌细胞系的活性上比米托蒽醌更强，而与阿霉素的活性相当。在上述化合物中，化合物18对2.2.15细胞的活性最强。我们证明了蒽醌基团对于活性是必不可少的，且较少空间位阻的取代基有助于增强体外活性。讨论了氨基蒽醌类化合物作为潜在抗癌剂的细胞毒性影响。我们进一步阐明了这一类化合物的药效基团的性质，为结构-活性关系提供了合理依据。
• Selective photoalkylamination and photohydroxylation of aminoanthraquinones and their N-acylated derivatives
  作者：Katsuhira Yoshida、Masahiro Hikasa、Katsutoshi Ishii、Hisa Kadota、Yoshio Yamashita

  DOI：10.1039/c39860000758

  日期：——

  The selective introduction of hydroxy and Alkylamino groups into the anthraquinone nucleus was achieved by the photochemical reaction of some aminoanthraquinones and their N-acylated derivatives with alkylamines under aerobic conditions.

  通过在好氧条件下一些氨基蒽醌及其N-酰化衍生物与烷基胺的光化学反应，将羟基和烷基氨基选择性引入蒽醌核中。
• Scholl; Wanka, Chemische Berichte, 1929, vol. 62, p. 1426
  作者：Scholl、Wanka

  DOI：——

  日期：——
• DE199758
  申请人：——

  公开号：——

  公开（公告）日：——
• USE OF ANTHRAQUINONE DYES AND OF FLUORESCENT DYES FOR DYEING KERATIN FIBRES, DYEING PROCESS AND COMPOSITION
  申请人：L'Oréal

  公开号：EP3558235B1

  公开（公告）日：2021-09-08

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