8-hydroxy-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid | 38366-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 8-hydroxy-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid
• 英文别名: 8-hydroxy-9,10-dioxoanthracene-1-carboxylic acid
• CAS: 38366-35-7
• 化学式: C₁₅H₈O₅
• 分子量: 268.226
• InChiKey: YDJMJBJEOLHHCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-hydroxy-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid 在 吡啶 、 sodium acetate 作用下， 反应 0.5h， 生成 Acetic acid 3,7-dioxo-2-phenyl-2,7-dihydro-3H-dibenzo[de,h]cinnolin-11-yl ester
  参考文献：
  名称：

  Design, Synthesis, and Anticancer Properties of 4,4‘-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone and Analogues

  摘要：

  4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) has recently completed a phase I clinical trial in advanced cancer with minimal toxicity, and impressive objective responses were noted. A-007 possesses three moieties that appear to have an influence on its anticancer activities: diphenylmethane, hydrazone, and dinitrophenyl. The goals of this study were to modify A-007's chemical moieties with the ultimate goal of maximizing its anticancer activity through increased planarity and introduction of functional groups. Thirty-five phenylhydrazone analogues of A-007 were synthesized and evaluated in vitro in a human primary cancer explant assay. Anticancer activities for selected analogues were also assayed for activity vs established human/murine cell lines. One-hundred-eighty-six fresh human solid tumors were used to screen for anticancer activity. Selected analogues were assayed for therapeutic indices (vs GM-CFC from bone marrow) in preparation for preclinical studies. Several polyaryl phenylhydrazones demonstrated improved cytotoxic activities by factors of 10(2)-10(3) when compared with A-007. However, the polyaryl quinone moieties of the latter analogues introduced potential toxic properties (cardiac, hematological) that do not exist with A-007.

  DOI：

  10.1021/jm0301080
• 作为产物：
  描述：

  8-chloro-9,10-dioxo-9,10-dihydro-anthracene-1-carboxylic acid 在 氢氧化钾 作用下， 生成 8-hydroxy-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid
  参考文献：
  名称：

  Dissociation constants of 8-substituted 9,10-ethanoanthracene-1-carboxylic acids and related compounds. Evidence for the field model for the polar effect

  摘要：

  DOI：

  10.1021/ja00764a032

文献信息

• [EN] PROCESS FOR PREPARING 8-HYDROXY-9,10-DIOXO-ANTHRACENE-1-CARBOXYLIC ACID<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDE 8-HYDROXY-9,10-DIOXO-ANTHRACÈNE-1-CARBOXYLIQUE
  申请人：PILI

  公开号：WO2021156406A1

  公开（公告）日：2021-08-12

  The present invention relates to a process for preparing 8-hydroxy-9,10-dioxo-anthracene-1- carboxylic acid. It also relates to a method for preparing an anthraquinone derivative comprising a step for preparing 8-hydroxy-9,10-dioxo-anthracene-1-carboxylic acid according to such process.

  本发明涉及一种制备8-羟基-9,10-二氧基蒽-1-羧酸的方法。该发明还涉及一种制备蒽醌衍生物的方法，其中包括根据该方法制备8-羟基-9,10-二氧基蒽-1-羧酸的步骤。
• Dissociation constants of 8-substituted 9,10-ethanoanthracene-1-carboxylic acids and related compounds. Evidence for the field model for the polar effect
  作者：Ronald Golden、Leon M. Stock

  DOI：10.1021/ja00764a032

  日期：1972.5
• Design, Synthesis, and Anticancer Properties of 4,4‘-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone and Analogues
  作者：Lee Roy Morgan、Kanappan Thangaraj、Blaise LeBlanc、Andrew Rodgers、Lionel T. Wolford、Catherine L. Hooper、Dominic Fan、Branko S. Jursic

  DOI：10.1021/jm0301080

  日期：2003.10.1

  4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) has recently completed a phase I clinical trial in advanced cancer with minimal toxicity, and impressive objective responses were noted. A-007 possesses three moieties that appear to have an influence on its anticancer activities: diphenylmethane, hydrazone, and dinitrophenyl. The goals of this study were to modify A-007's chemical moieties with the ultimate goal of maximizing its anticancer activity through increased planarity and introduction of functional groups. Thirty-five phenylhydrazone analogues of A-007 were synthesized and evaluated in vitro in a human primary cancer explant assay. Anticancer activities for selected analogues were also assayed for activity vs established human/murine cell lines. One-hundred-eighty-six fresh human solid tumors were used to screen for anticancer activity. Selected analogues were assayed for therapeutic indices (vs GM-CFC from bone marrow) in preparation for preclinical studies. Several polyaryl phenylhydrazones demonstrated improved cytotoxic activities by factors of 10(2)-10(3) when compared with A-007. However, the polyaryl quinone moieties of the latter analogues introduced potential toxic properties (cardiac, hematological) that do not exist with A-007.