8-hydrazinocaffeine | 53703-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-hydrazinocaffeine
• 英文别名: 8-Hydrazino-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione；8-hydrazinyl-1,3,7-trimethylpurine-2,6-dione
• CAS: 53703-63-2
• 化学式: C₈H₁₂N₆O₂
• mdl: MFCD00725053
• 分子量: 224.222
• InChiKey: IIVOIFFBPUQXLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-hydrazinocaffeine 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 1,3,5-trimethyl-2,4-dioxo-8-phenyl-1,2,3,4-tetrahydro[1,2,4]triazolo[4,3-e]purine
  参考文献：
  名称：

  New [ e ]-Fused Caffeines: A Simple Synthesis of 3-Substituted [1,2,4]Triazolo[4,3- e ]purines

  摘要：

  In a recent paper from our laboratory [1], we have described the synthesis of [1,2,4]triazolo[3,4-f]purines (1). In this paper we wish to report a facile synthesis of [1,2,4]triazolo[4,3-e]caffeines (2). Our interest in synthesis of fused purines is due to the fact that purine derivatives such as theophylline, caffeine, and theobromine, which are widely distributed in nature, have many important biological activities [2]. The strategy adopted for the synthesis of the target compounds 2 is based on in situ 1,5-electrocyclization of the nitrilimines 3 derived from the respective novel hydrazonoyl bromides 4. It is worth mentioning that although numerous N-heteroaryl hydrazonoyl halides have been prepared [3], the bromides 4, which are used herein as precursors for 2, have not yet been reported.

  DOI：

  10.1007/s00706-002-0514-7
• 作为产物：
  描述：

  8-溴-1,3,7-三甲基嘌呤-2,6-二酮 在 乙醇 、 一水合肼 作用下， 生成 8-hydrazinocaffeine
  参考文献：
  名称：

  Libermann; Rouaix, Bulletin de la Societe Chimique de France, 1959, p. 1793,1796

  摘要：

  DOI：

文献信息

• Synthesis of Some Novel Substituted Purine Derivatives As Potential Anticancer, Anti-HIV-1 and Antimicrobial Agents
  作者：Samia M. Rida、Fawzia A. Ashour、Soad A.M. El-Hawash、Mona M. El-Semary、Mona H. Badr

  DOI：10.1002/ardp.200600118

  日期：2007.4

  In search of novel purine antimetabolites, a series of 8‐substituted methylxanthine derivatives was prepared in order to explore their in vitro anticancer, anti‐HIV‐1 and antimicrobial activities. The target compounds include: 8‐[(3‐substituted‐4‐oxo‐thiazolidin‐2‐ylidene)hydrazino]‐1,3‐dimethyl (or 1,3,7‐trimethyl)‐3,7‐dihydropurine‐2,6‐diones 5a–e, 8‐[(3,4‐disubstituted 2,3‐dihydrothiazol‐2‐ylidene)hydrazino]‐1

  在寻找新型嘌呤抗代谢物的过程中，制备了一系列 8-取代甲基黄嘌呤衍生物，以探索其体外抗癌、抗 HIV-1 和抗菌活性。目标化合物包括：8-[(3-取代-4-氧代-噻唑啉-2-亚基)肼]-1,3-二甲基(或1,3,7-三甲基)-3,7-二氢嘌呤-2， 6 - 二酮 5a - e, 8 - [(3,4 - 二取代的 2,3 - 二氢噻唑 - 2-亚基) 肼] -1,3,7 - 三甲基 - 3,7 - 二氢嘌呤 - 2,6 - 二酮 6a- d 和 8-(5-氨基-3-芳基吡唑-1-基)-1,3-二甲基-(或1,3,7-三甲基)-3,7-二氢嘌呤-2,6-二酮7a-g。体外抗癌结果显示，化合物5d对白血病K-562表现出超敏感性谱，GI50值<0.01 μM。化合物7c对结肠癌HCT-15和肾癌CAKI-1表现出显着的活性（GI50值为0.47和0.78 μM，分别）。化合物 7a 对结肠癌 HCT-15
• Synthesis, anticancer, anti-HIV-1, and antimicrobial activity of some tricyclic triazino and triazolo[4,3-e]purine derivatives
  作者：Fawzia A. Ashour、Samia M. Rida、Soad A. M. El-Hawash、Mona M. ElSemary、Mona H. Badr

  DOI：10.1007/s00044-011-9612-6

  日期：2012.7

  antineoplastic, anti-HIV-1 and antimicrobial activities, the synthesis of some new triazino and triazolo[4,3-e]purine derivatives is described: 6,8-dimethyl-1,4-dihydro-1,2,4-triazino[4,3-e]purine-7,9(6H, 8H)-diones 3–6; 5,7,9-trimethyl-1,2,4-triazolo[4,3-e]purine-6,8(5H, 7H, 9H)-diones 11–13, together with the synthesis of the 8-substituted purine derivative: 8-(3,5-diamino-1H-pyrazol-4-yl)diazenyl-1,3-dimethyl-1H-purine-2

  为了努力建立具有改进的抗肿瘤药，抗HIV-1和抗菌活性的新候选药物，描述了一些新的三嗪并三唑[4,3-e]嘌呤衍生物的合成：6,8-二甲基-1,4-二氢-1,2,4-三嗪[4,3-E]嘌呤-7,9（6H，8H） -二酮3 - 6 ; 5,7,9三甲基-1,2,4-三唑并〔4,3-E]嘌呤-6,8-（5H，7H，9H） -二酮11 - 13，与8取代的嘌呤的合成在一起衍生物：8-（3,5-二氨基-1H-吡唑-4-基）二氮烯-1,3-二甲基-1H-嘌呤-2,6（3H，7H）-二酮7。测试了制备的化合物的体外抗癌，抗HIV和抗菌活性。体外抗癌筛选结果显示化合物3对黑色素瘤MALME-3 M，非小细胞肺癌HOP-92和乳腺癌T-47D表现出相当大的活​​性（GI 50值分别为25.2、31.8和32.9μM ）。抗HIV-1的结果表明化合物7和13c表现出中等活性（在2×10 -4 M时最大的细胞保护百分比分别为30
• Kondensationen von Aldehyden und Ketonen mit 8-Hydrazino-coffein
  作者：Josef Klosa

  DOI：10.1002/ardp.19562890408

  日期：——
• Lueppo-Cramer, Chemische Berichte, 1894, vol. 27, p. 3090
  作者：Lueppo-Cramer

  DOI：——

  日期：——
• Caffeine–hydrazones as anticancer agents with pronounced selectivity toward T-lymphoblastic leukaemia cells
  作者：Robert Kaplánek、Milan Jakubek、Jakub Rak、Zdeněk Kejík、Martin Havlík、Bohumil Dolenský、Ivo Frydrych、Marián Hajdúch、Milan Kolář、Kateřina Bogdanová、Jarmila Králová、Petr Džubák、Vladimír Král

  DOI：10.1016/j.bioorg.2015.03.003

  日期：2015.6

  We report design and synthesis of set of novel anticancer agents based on caffeine-hydrazones bearing 2-hydroxyaryl- or 2-N-heteroaryl moiety. Anticancer activity evaluation using seven cancer cell lines and two non-malignant cell lines demonstrated that several derivatives display significant anticancer activity and great selectivity index toward T-lymphoblastic leukaemia cells. In general, hydrazones bearing 2-N-heteroaryl moiety are more active and selective than those with 2-hydroxyaryl moiety. Tested compounds exhibit dose-dependent inhibition of both RNA and DNA synthesis, with some exceptions. Antimicrobial activities were tested on set of twelve bacterial and yeast strains, however prepared compounds were not active, suggesting for a molecular target specific for eukaryotic cells. (C) 2015 Elsevier Inc. All rights reserved.