2-mercapto-1(3)H-anthra[1,2-d]imidazole-6,11-dione | 1190059-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-mercapto-1(3)H-anthra[1,2-d]imidazole-6,11-dione
• 英文别名: NSC747443；2-mercapto-1H-anthra[1,2-d]imidazole-6,11-dione；2-Sulfanylidene-1,3-dihydronaphtho[3,2-e]benzimidazole-6,11-dione
• CAS: 1190059-19-8
• 化学式: C₁₅H₈N₂O₂S
• 分子量: 280.307
• InChiKey: LWMBUDNBHNIKDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  407-409 °C(Solvent: Ethanol)
• 沸点：
  519.8±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-mercapto-1(3)H-anthra[1,2-d]imidazole-6,11-dione 、 碘乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以65%的产率得到2-(ethylthio)-1H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  Thio-subsituted Anthra [1, 2-d] imidazole- 6, 11-dione Dervatives, Preparation Method and application thereof

  摘要：

  一系列新颖的硫代取代的蒽[1,2-d]咪唑-6,11-二酮衍生物，以及所述衍生物的制备方法和应用，所述应用涉及含有治疗癌症的治疗有效量的所述衍生物的药物组合物，以及所述应用涉及所述衍生物对抑制端粒酶活性、抑制癌细胞生长、治疗癌症等方面的影响。

  公开号：

  US20110207727A1
• 作为产物：
  描述：

  二硫化碳 、 1,2-二氨基蒽醌 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以80%的产率得到2-mercapto-1(3)H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  一系列1,2-杂芳基蒽醌和蒽[1,2 - d ]咪唑-6,11-二酮同系物的合成，细胞毒性和人类端粒酶抑制活性

  摘要：

  使用各种合成途径，通过酰化，环化，缩合和分子内杂环化，制备了一系列具有不同侧链的1,2-杂退火蒽醌和蒽[1,2 - d ]咪唑-6,11-二酮四环类似物。引入了包含烷基和芳基，芳族和杂环，线性和环状，极性和非极性以及碱性和酸性残基的四环体系。他们评估了它们对端粒酶活性，hTERT表达，细胞增殖以及对NCI 60细胞株人类肿瘤筛查的体外细胞毒性的影响。化合物4，11，12，14，15，16，17，19，20，23，25，和26是由NCI选择用于一个剂量筛选程序和进一步的研究4，23和25，其中曲线跨越这些线代表的内插值，以使50％生长抑制（GI 50），总生长抑制（TGI）和50％细胞杀伤率（LC 50）， 分别。进一步的研究未发现任何显示出对端粒酶抑制活性和hTERT抑制能力有效且显着的化合物。在NCI的筛选中对这些化合物进行的对比测试显示出不同的效力水平和不同的细胞毒性作用，显然与核心环

  DOI：

  10.1016/j.bmc.2009.09.033

文献信息

• HETEROANNELATED ANTHRAQUINONE DERIVATIVES AND THE SYNTHESIS METHOD THEREOF
  申请人：HUANG Hsu-Shan

  公开号：US20090253707A1

  公开（公告）日：2009-10-08

  A heteroannelated anthraquinone derivative compound is provided. The heteroannelated anthraquinone derivative compound is represented by a formula (I): wherein R 1 is a substituent being one selected from a group consisting of i) a first substituent being one selected from a group consisting of a hydryl group, an amino group, a nitro group, a hydroxyl group and a cyan group, ii) a second substituent being one selected from a group consisting of (CH 2 ) n X, a straight (CH 2 ) n alkyl group, a (CH 2 ) n alkoxyl group, a branched (CH 2 ) n alkyl group, a C 3 ˜C 12 nephthenic group, and a C 3 ˜C 12 cyclic alkoxyl group, wherein 1=n=12, and X is a halogen, iii) a third substituent being one selected from a group consisting of a straight C 1 ˜C 8 alkyl group with a double-bond, a C 1 ˜C 8 alkoxyl group with a double-bond, a branched C 1 ˜C 8 alkyl group with a double-bond and a C 3 ˜C 8 nephthenic group with a double-bond, and iv) a fourth substituent of a C 5 ˜C 12 heterocyclic group.

  提供一个杂环化的蒽醌衍生物化合物，所述杂环化的蒽醌衍生物化合物由公式(I)表示： 其中R1是选自以下组中的取代基：i)第一取代基，选自包含羟基、氨基、硝基、羟基和氰基的组，ii)第二取代基，选自包含(CH2)nX、直链(CH2)n烷基、(CH2)n烷氧基、支链(CH2)n烷基、C3˜C12的环烷基和C3˜C12的环烷氧基的组，其中1≤n≤12，X是卤素，iii)第三取代基，选自包含直链C1˜C8的双键烷基、C1˜C8的双键烷氧基、支链C1˜C8的双键烷基和C3˜C8的双键环烷基的组，以及iv)第四取代基为C5˜C12的杂环基团。
• METHOD FOR INHIBITING GROWTH OF CANCER CELLS AND CELL TELOMERE AND DISEASES OF CELL PROLIFERATION BY USING HETEROANNELATED ANTHRAQUINONE DERIVATIVE COMPOUNDS
  申请人：HUANG Hsu-Shan

  公开号：US20100249143A1

  公开（公告）日：2010-09-30

  A heteroannelated anthraquinone derivative compound is provided. The heteroannelated anthraquinone derivative compound is represented by a formula (I): wherein R 1 is a substituent being one selected from a group consisting of i) a first substituent being one selected from a group consisting of a hydryl group, an amino group, a nitro group, a hydroxyl group and a cyan group, ii) a second substituent being one selected from a group consisting of (CH 2 ) n X, a straight (CH 2 ) n alkyl group, a (CH 2 ) n alkoxyl group, a branched (CH 2 ) n alkyl group, a C 3 ˜C 12 nephthenic group, and a C 3 ˜C 12 cyclic alkoxyl group, wherein 1≦n≦12, and X is a halogen, iii) a third substituent being one selected from a group consisting of a straight C 1 ˜C 8 alkyl group with a double-bond, a C 1 ˜C 8 alkoxyl group with a double-bond, a branched C 1 ˜C 8 alkyl group with a double-bond and a C 3 ˜C 8 nephthenic group with a double-bond, and iv) a fourth substituent of a C 5 ˜C 12 heterocyclic group.

  提供了一种杂环螺环酮衍生物化合物。该杂环螺环酮衍生物化合物由以下式子（I）表示： 其中R1是一个取代基，选自以下一组中的一种：i）第一取代基选自羟基、氨基、硝基、羟基和氰基组成的群体中的一种、ii）第二取代基选自（CH2）nX、直链（CH2）n烷基、（CH2）n烷氧基、支链（CH2）n烷基、C3˜C12环烷氧基和C3˜C12环烷氧基，其中1≦n≦12，X是卤素、iii）第三取代基选自带双键的直链C1˜C8烷基、带双键的C1˜C8烷氧基、带双键的支链C1˜C8烷基和带双键的C3˜C8环烷基、以及iv）C5˜C12杂环基的第四取代基。
• Structure-based design, synthesis and biological evaluation of novel anthra[1,2-d]imidazole-6,11-dione homologues as potential antitumor agents
  作者：Tsung-Chih Chen、Dah-Shyong Yu、Kuo-Feng Huang、Yung-Chien Fu、Chia-Chung Lee、Chun-Liang Chen、Fong-Chun Huang、Hsi-Hsien Hsieh、Jing-Jer Lin、Hsu-Shan Huang

  DOI：10.1016/j.ejmech.2013.06.058

  日期：2013.11

  By using fragment-based design strategies, a series of 2-thio-substituted anthra[1,2-dlimidazole-6,11-diones were synthesized and evaluated for hTERT repressing activities, cell proliferations, and NCI 60-cell panel assay. Compounds 2, 3, 4, 11, 15 and 35 were selected by the NCI and 3, 4, 11 and 15 represent the GI(50), TGI and LC50, respectively. Among them, all were moderate selectivity toward leukemia cancer except for 4 exhibited distinctive selectivity of CNS and renal cancer with 7.403 and 6.475. The overall of test compounds exhibited different cytostatic and cytotoxic activities for further developing potential application as anticancer drugs. Crown Copyright (C) 2013 Published by Elsevier Masson SAS. All rights reserved.
• COMPOUNDS, COMPOSITIONS COMPRSING SAME, AND METHODS RELATED THERETO
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：US20160115136A1

  公开（公告）日：2016-04-28

  Disclosed herein are compounds, such as benzimidazole derivatives, and composition, such as pharmaceutical compositions, and methods related thereto for treating or preventing microbial infections. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• US8067454B2
  申请人：——

  公开号：US8067454B2

  公开（公告）日：2011-11-29