N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-chloropropanamide | 20210-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-chloropropanamide
• 英文别名: 3-chloro-propionic acid-(9,10-dioxo-9,10-dihydro-[1]anthrylamide)；3-Chlor-N-(9.10-dioxo-9.10-dihydro-anthryl-(1))-propionamid；3-Chlor-propionsaeure-(9,10-dioxo-9,10-dihydro-[1]anthrylamid)；1-(3-Chlor-propionylamino)-anthrachinon；1-(β-Chlorpropionylamino)-anthrachinon；3-Chloro-N-(9,10-dioxo-9,10-dihydroantracen-1-yl)-propionamide；3-chloro-N-(9,10-dioxoanthracen-1-yl)propanamide
• CAS: 20210-30-4
• 化学式: C₁₇H₁₂ClNO₃
• 分子量: 313.74
• InChiKey: OHMZLNNTHYTFNW-UHFFFAOYSA-N

物化性质

• 熔点：
  176 °C
• 沸点：
  579.7±50.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-chloropropanamide 以 1,4-二氧六环 为溶剂， 生成 1-Acryloylamino-anthrachinon
  参考文献：
  名称：

  Voloshin,G.A.; Boldyrev,B.G., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, # 7, p. 1228 - 1232

  摘要：

  DOI：
• 作为产物：
  描述：

  氨基-9,10-蒽二酮 、 3-氯丙酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以77%的产率得到N-(9,10-dihydro-9,10-dioxo-1-anthracenyl)-3-chloropropanamide
  参考文献：
  名称：

  Synthesis, molecular modeling, DNA binding, and antitumor properties of some substituted amidoanthraquinones

  摘要：

  A series of 1- and 1,4-substituted amidoanthraquinones have been prepared, with side chains possessing basic nitrogen atoms. Computer modeling and energy calculations have shown that all eight compounds can bind intercalatively to DNA and that there are significant differences in the additional nonbonded and electrostatic interactions possible at the DNA binding site. Solution DNA binding and closed-circular DNA unwinding studies confirmed intercalative interactions, and the predicted differences in strength of interactions between mono- and disubstituted compounds were found. All compounds were modestly cytotoxic to L1210 cells in culture. In vivo activity against L1210 and S180 tumors was not found for the monosubstituted compounds, whereas the four disubstituted ones had varying levels of measurable, though low, activity.

  DOI：

  10.1021/jm00399a028

文献信息

• ANTHRAQUINONE -BASED COMPOUND, THE SYNTHESIS PROCESSES AND THE APPLICATION THEREOF
  申请人：HUANG Hsu-Shan

  公开号：US20120316234A1

  公开（公告）日：2012-12-13

  The present invention is related to an anthraquinone-based compound represented by compound (I) wherein the R1, R2, R3, R4, R5 or R6 is selected by the group of H, amide, amino-amide, acyl, chloroacetamide, chloropropionamido, a substituted chloroacetamide and a substituted chloropropionamido. The present invention is also related to the method of producing the anthraquinone-based compound and the application thereof.

  本发明涉及一种以化合物(I)表示的基于蒽醌的化合物，其中R1、R2、R3、R4、R5或R6由H、酰胺、氨基酰胺、酰基、氯乙酰胺、氯丙酰胺、取代氯乙酰胺和取代氯丙酰胺的基团中选择。本发明还涉及制备基于蒽醌的化合物的方法及其应用。
• Acrylic acid amides
  申请人：GEORG KRANZLEIN

  公开号：US02288197A1

  公开（公告）日：1942-06-30
• Synthesis, molecular modeling, DNA binding, and antitumor properties of some substituted amidoanthraquinones
  作者：David A. Collier、Stephen Neidle

  DOI：10.1021/jm00399a028

  日期：1988.4

  A series of 1- and 1,4-substituted amidoanthraquinones have been prepared, with side chains possessing basic nitrogen atoms. Computer modeling and energy calculations have shown that all eight compounds can bind intercalatively to DNA and that there are significant differences in the additional nonbonded and electrostatic interactions possible at the DNA binding site. Solution DNA binding and closed-circular DNA unwinding studies confirmed intercalative interactions, and the predicted differences in strength of interactions between mono- and disubstituted compounds were found. All compounds were modestly cytotoxic to L1210 cells in culture. In vivo activity against L1210 and S180 tumors was not found for the monosubstituted compounds, whereas the four disubstituted ones had varying levels of measurable, though low, activity.
• COLLIER, DAVID A.;NEIDLE, STEPHEN, J. MED. CHEM., 31,(1988) N 4, 847-857
  作者：COLLIER, DAVID A.、NEIDLE, STEPHEN

  DOI：——

  日期：——
• [EN] ANTHRAQUINONES WITH BIOLOGICAL ACTIVITY<br/>[FR] ANTHRAQUINONES A ACTIVITE BIOLOGIQUE
  申请人：CANCER RESEARCH CAMPAIGN TECHNOLOGY LIMITED

  公开号：WO1998025885A1

  公开（公告）日：1998-06-18

  (EN) Novel 1,4- and 2,6-substituted anthracene-9,10-diones ('9,10-anthraquinones'). The use of the novel compounds and known 1,4- and 2,6-substituted anthracene-9,10-diones ('9,10-anthraquinones') in the inhibition of telomerase activity and/or their use in the treatment of cancer.(FR) La présente invention concerne de nouveaux anthracène-9,10-diones 1,4- et 2,6-substitués ('9,10-anthraquinones'), ainsi que l'utilisation de ces nouveaux composés et des anthracène-9,10-diones 1,4- et 2,6-substitués ('9,10-anthraquinones') connus dans l'inhibition de l'activité de la télomérase et/ou leur utilisation dans le traitement du cancer.