5-chloro-6H-v-triazolo<4,5,1-de>acridin-6-one | 76181-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-chloro-6H-v-triazolo<4,5,1-de>acridin-6-one
• 英文别名: chlorotriazoloacridinone；5-chloro-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one；5-chloro-[1,2,3]triazolo[4,5,1-de]acridin-6-one；5-Chlor-[1,2,3]triazolo[4,5,1-de]acridin-6-on；10-Chloro-1,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-2,4,6,9,11,13(16),14-heptaen-8-one
• CAS: 76181-06-1
• 化学式: C₁₃H₆ClN₃O
• 分子量: 255.663
• InChiKey: JJTUPHQWJFGDEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 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：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-6H-v-triazolo<4,5,1-de>acridin-6-one 在 硫代乙酰胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以91%的产率得到5-mercapto-6H-v-triazolo<4,5,1-d,e>acridin-6-one
  参考文献：
  名称：

  Romanowski, Jacek; Eckstein, Zygmunt, Polish Journal of Chemistry, 1980, vol. 54, # 3, p. 605 - 610

  摘要：

  DOI：
• 作为产物：
  描述：

  4-amino-1-chloroacridin-9(10H)-one 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 4.0h， 以89%的产率得到5-chloro-6H-v-triazolo<4,5,1-de>acridin-6-one
  参考文献：
  名称：

  8-取代的5-[（（氨基烷基）氨基] -6H-v-三唑并[4,5,1-脱] ac啶-6-酮类化合物为潜在的抗肿瘤药。合成和生物活性。

  摘要：

  合成了一系列与咪唑并rid啶酮（1）结构相关的一系列8-取代的5-[（氨基烷基）氨基] -6H-v-三唑并[4,5,1-de] ac啶-6-（2），并测试细胞毒性和抗肿瘤活性。初步的生物学结果表明，8-OH衍生物具有最高的抗肿瘤活性。在C-8取代基的性质和抗肿瘤活性之间未发现任何关系。

  DOI：

  10.1021/jm00172a028

文献信息

• Design, synthesis and high antitumor potential of new unsymmetrical bisacridine derivatives towards human solid tumors, specifically pancreatic cancers and their unique ability to stabilize DNA G-quadruplexes
  作者：Ewa Paluszkiewicz、Barbara Horowska、Barbara Borowa-Mazgaj、Grażyna Peszyńska-Sularz、Jolanta Paradziej-Łukowicz、Ewa Augustin、Jerzy Konopa、Zofia Mazerska

  DOI：10.1016/j.ejmech.2020.112599

  日期：2020.10

  dimers strongly inhibited pancreatic Panc-1, Mia-Pa-Ca-2, Capan-2 and prostate cancer DU-145 cell growth. The studied compounds showed very strong antitumor activity (T/C> 300%) against Walker 256 rat adenocarcinoma. The selected 26 UAs were tested against 12 human tumor xenografts in nude mice, including colon, breast, prostate and pancreatic cancers. The studies on the molecular mechanism of action

  已经开发了新的有前途的不对称双ac啶衍生物（UAs）。通过使4-硝基或4-甲基ac啶酮，咪唑ac啶酮和三唑并ac啶酮衍生物与通过氨基烷基链连接的1-硝基ac啶化合物缩合，合成包括36种化合物的三类化合物。细胞毒性筛选揭示了这些化合物对几种肿瘤细胞系的高效力。特别地，咪唑并rid啶酮-1-硝基ac啶二聚体强烈抑制胰腺Panc-1，Mia-Pa-Ca-2，Capan-2和前列腺癌DU-145细胞的生长。所研究的化合物对Walker 256大鼠腺癌显示出非常强的抗肿瘤活性（T / C> 300％）。针对裸鼠中的12种人类肿瘤异种移植物测试了所选的26种UA，包括结肠癌，乳腺癌，前列腺癌和胰腺癌。对分子作用机理的研究表明，这些不对称的二聚体对G-四链体的存在做出了显着的响应，而不是对dsDNA的响应。UAs对G-四链体稳定的效能与结构-活性的关系表明，这种药物-G-四链体复合物的热稳定性不仅取决于
• Studies on Mexican Cactaceae. II. Opuntia megarrhiza, a poorly known endemic from San Luis Potosí, Mexico
  作者：Héctor M. Hernández、Carlos Gómez-Hinostrosa、Rolando T. Bárcenas

  DOI：10.1007/bf02809653

  日期：2001.10

  Opuntia megarrhiza Rose (Cactaceae) is a species endemic to central San Luis Potosi,, Mexico that, since originally described in 1906, has remained poorly understood. A comprehensive morphological description is presented and its presumed taxonomic affinity with O. chaffeyi is discussed. General accounts of its distribution, ecology, uses, and conservation status are presented.
• Triazoloacridin-6-ones as novel inhibitors of the quinone oxidoreductases NQO1 and NQO2
  作者：Karen A. Nolan、Matthew P. Humphries、John Barnes、Jeremy R. Doncaster、Mary C. Caraher、Nicola Tirelli、Richard A. Bryce、Roger C. Whitehead、Ian J. Stratford

  DOI：10.1016/j.bmc.2009.11.059

  日期：2010.1

  A range of triazoloacridin-6-ones functionalized at C5 and C8 have been synthesized and evaluated for ability to inhibit NQO1 and NQO2. The compounds were computationally docked into the active site of NQO1 and NQO2, and calculated binding affinities were compared with IC50 values for enzyme inhibition. Excellent correlation coefficients were demonstrated suggesting a predictive QSAR model for this series of structurally similar analogues. From this we have identified some of these triazoloacridin-6-ones to be the most potent NQO2 inhibitors so far reported. (C) 2009 Elsevier Ltd. All rights reserved.
• Bisimidazoacridones and Related Compounds: New Antineoplastic Agents with High Selectivity against Colon Tumors
  作者：Wieslaw M. Cholody、Lidia Hernandez、Lawrence Hassner、Dominic A. Scudiero、Draginja B. Djurickovic、Christopher J. Michejda

  DOI：10.1021/jm00016a007

  日期：1995.8

  A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N-2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[4,5,1-de]acridim-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.
• ROMANOVSKI J.; ECKSTEIN Z., POL. J. CHEM., 1980, 54, NO 3, 605-610
  作者：ROMANOVSKI J.、 ECKSTEIN Z.

  DOI：——

  日期：——