6-bromo-4-chloro-5-cyanopyrrolo[2,3-d]pyrimidin-4-one | 24391-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 6-bromo-4-chloro-5-cyanopyrrolo[2,3-d]pyrimidin-4-one
• 英文别名: 6-bromo-4-chloro-5-cyanopyrrolo[2,3-d]pyrimidine；6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile；4-Chlor-5-cyan-6-brom-7H-pyrrolo<2,3-d>pyrimidin；6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 24391-39-7
• 化学式: C₇H₂BrClN₄
• 分子量: 257.477
• InChiKey: PGBSSCFZSAVYJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-4-chloro-5-cyanopyrrolo[2,3-d]pyrimidin-4-one 在 palladium on activated charcoal N,O-双三甲硅基乙酰胺 、 sodium methylate 、 ammonium formate 作用下， 以 甲醇 、 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 22.75h， 生成 曲西瑞宾
  参考文献：
  名称：

  Triciribine 的改进全合成：具有抗肿瘤和抗病毒特性的三环核苷

  摘要：

  我们描述了从 4-氨基-6-溴-5-氰基吡咯并[2,3-d]嘧啶开始，高效全合成曲西瑞宾，一种具有抗肿瘤和抗病毒特性的三环核苷。†为了纪念和庆祝 Leroy B. Townsend 教授 70 岁生日。

  DOI：

  10.1081/ncn-120027815
• 作为产物：
  描述：

  6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one 在 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 以38.43%的产率得到6-bromo-4-chloro-5-cyanopyrrolo[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  通过建模，底物和酶工程靶向大肠杆菌腈还原酶QueF的底物结合位点

  摘要：

  腈还原酶QueF催化将2-氨基-5-氰基吡咯并[2,3- d ]嘧啶-4-酮（preQ 0）还原为2-氨基-5-氨基甲基吡咯并[2,3 - d ]嘧啶-4-酮（preQ 1）在超修饰核苷quesusine的生物合成途径中。它是已知的唯一一种将腈还原为相应的伯胺的酶，因此可以扩大腈的生物催化反应工具箱。为了评估这种新的氧化还原酶在生物催化反应中的应用，研究其底物范围是必要的。我们在这里报告对大肠杆菌的腈还原酶QueF的活性位点结合特性和底物范围的研究。具有简单腈结构的筛选显示了高底物特异性。因此，根据大肠杆菌QueF的新同源性模型以及天然和非天然底物的复杂结构模型，确定了底物与活性位点的结合相互作用。合成了天然底物preQ 0的各种结构类似物，并用来自大肠杆菌的野生型QueF和几个活性位点突变体进行了筛选。已显示两个氨基酸残基Cys190和Asp197在催化机理中起重要作用。通过使用野生型和

  DOI：

  10.1002/chem.201300163

文献信息

• An Expedient Total Synthesis of Triciribine
  作者：Chen Hu、Zhizhong Ruan、Haixin Ding、Yirong Zhou、Qiang Xiao

  DOI：10.3390/molecules22040643

  日期：——

  In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) group and

  在本论文中，我们报告了三环 7-脱氮嘌呤核苷和蛋白激酶 B (AKT) 抑制剂曲西瑞滨的权宜全合成，总产率为 35%。我们的合成路线以 1-N-Boc-2-甲基肼的高度区域选择性取代和三氟乙酸催化的一锅转化为特色，将叔丁基羰基 (Boc) 基团的脱保护和闭环反应结合在一起得到三环核碱基主题。
• Deoxy Sugar Analogues of Triciribine:  Correlation of Antiviral and Antiproliferative Activity with Intracellular Phosphorylation
  作者：Anthony R. Porcari、Roger G. Ptak、Katherine Z. Borysko、Julie M. Breitenbach、Sauro Vittori、Linda L. Wotring、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jm990205m

  日期：2000.6.1

  Triciribine (TCN) and triciribine monophosphate (TCN-P) have antiviral and antineoplastic activity at low micromolar or submicromolar concentrations. In an effort to improve and better understand this activity, we have conducted a structure-activity relationship study to explore requirements for the number of hydroxyl groups on the ribosyl moiety for biological activity. 2'-Deoxytriciribine (2'-dTCN), 3'-deoxytriciribine (3'-dTCN), 2',3'-epoxytriciribine (2',3'-epoxyTCN), 2',3'-dideoxy-2',3'-didehydrotriciribine (2',3'-d4TCN), and 2',3'-dideoxytriciribine (2',3'-ddTCN) were synthesized and evaluated for activity against human immunodeficiency virus (HIV-1), herpes simplex virus type 1 (HSV-1), and human cytomegalovirus (HCMV). Antiproliferative activity of the compounds also was tested in murine L1210 cells and three human tumor cell lines. All compounds were either less active than TCN and TCN-P or inactive at the highest concentration tested (100 mu M) in both antiviral and antiproliferative assays. Reverse-phase HPLC of extracts from uninfected cells treated with the deoxytriciribine analogues only detected the conversion of 3'-dTCN and 2',3'-ddTCN to their respective monophosphates. Therefore, either the deoxytriciribine analogues were not transported across the cell membrane or, more likely, they were not substrates for a nucleoside kinase or phosphotransferase. We have concluded that the hydroxyl groups on the ribosyl ring system of TCN and TCN-P must be intact in order to obtain significant antiviral and antineoplastic activity.
• GUPTA, PRANAB K.;VITTORI, SAURO;TOWNSEND, LEROY B., NUCLEOSIDES AND NUCLEOTIDES , 9,(1990) N, C. 35-41
  作者：GUPTA, PRANAB K.、VITTORI, SAURO、TOWNSEND, LEROY B.

  DOI：——

  日期：——
• [EN] DEAZAPURINE NUCLEOSIDE LIBRARIES AND COMPOUNDS<br/>[FR] BANQUES DE DEAZAPURINE NUCLEOSIDES ET COMPOSES
  申请人：RIBAPHARM INC

  公开号：WO2003051899A1

  公开（公告）日：2003-06-26

  Deazapurine nucleoside analog libraries are prepared in a combinatorial library approach. Particularly preferred compounds and libraries include various 7-deazapurines, 9-deazapurines, and 7-deaza-8-azaguanosine as heterocyclic bases, and it is generally preferred that such nucleosides include a ribofuranose as the sugar moiety. It is further contemplated that compounds generated using contemplated libraries may be useful in the treatment of various conditions, particularly viral infections and neoplastic diseases.