5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶-2-胺 | 873792-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 中文名称: 5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶-2-胺
• 中文别名: 5-溴-4-氯-7H-吡咯并[2,3-D]嘧啶-2-胺
• 英文名称: 2-amino-5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 2-amino-4-chloro-5-bromo-7H-pyrrolo[2,3-d]pyrimidine；5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine
• CAS: 873792-87-1
• 化学式: C₆H₄BrClN₄
• 分子量: 247.482
• InChiKey: BAGYMQRDQLTABD-UHFFFAOYSA-N

物化性质

• 熔点：
  >290 °C (decomp)(Solv: methanol (67-56-1))
• 密度：
  2.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 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：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶-2-胺 在 氢氧化钾 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-amino-5-bromo-4-chloro-7-{β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  7-DEAZAPURIN-2,6-DIAMINE AND 7-DEAZAGUANINE: SYNTHESIS AND PROPERTY OF 7-SUBSTITUTED NUCLEOSIDES AND OLIGONUCLEOTIDES

  摘要：

  The synthesis of 7-substituted 7-deazaguanine and 7-deazaadenine ribonucleosides 1-2, the incorporation of 3a-d into oligonucleotides, and the stability of the corresponding duplexes and base discrimination are described. The pK(a), values of 3 - 4 are determined.

  DOI：

  10.1081/ncn-200060319
• 作为产物：
  描述：

  2-氨基-4-氯吡咯并[2,3-d]嘧啶 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.58h， 生成 5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶-2-胺
  参考文献：
  名称：

  7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine:  Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-d-ribofuranose

  摘要：

  The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha-D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution.

  DOI：

  10.1021/jo0516640

文献信息

• C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents
  作者：Fabian Hulpia、Jakob Bouton、Gustavo D. Campagnaro、Ibrahim A. Alfayez、Dorien Mabille、Louis Maes、Harry P. de Koning、Guy Caljon、Serge Van Calenbergh

  DOI：10.1016/j.ejmech.2019.112018

  日期：2020.2

  , is spread to new hosts by bites of infected tsetse flies. Currently approved therapies all have their specific drawbacks, prompting a search for novel therapeutic agents. T. brucei lacks the enzymes necessary to forge the purine ring from amino acid precursors, rendering them dependent on the uptake and interconversion of host purines. This dependency renders analogues of purines and corresponding

  非洲锥虫病是由原生动物Trypanosoma brucei spp。引起的一种致命的传染病，通过被感染的采采蝇的叮咬传播到新的寄主。目前批准的疗法都有其特定的缺点，促使人们寻找新的治疗剂。T. brucei缺乏从氨基酸前体形成嘌呤环所需的酶，使其依赖于宿主嘌呤的吸收和相互转化。这种依赖性使得嘌呤的类似物和相应的核苷成为潜在的抗-T的有趣来源。布鲁斯代理商。在这项研究中，我们合成和评估了一系列7-取代的7-脱氮芥子碱衍生物，发现6-O-烷基化的类似物特别具有极好的前景，其EC50值在纳摩尔级范围内。SAR对O-烷基链的研究表明，至少在线性烷基链系列中，随着烷基链长度的增加，抗锥虫活性以及细胞毒性也随之增加。然而，这可以通过引入末端分支点来减弱，从而产生高度有效和选择性的类似物36、37和38。无法鉴定出与转运蛋白介导的摄取相关的抗药性，这些类似物中的几种被指定用于进一步的体内跟踪研究。研究。
• 7-DEAZAPURIN-2,6-DIAMINE AND 7-DEAZAGUANINE: SYNTHESIS AND PROPERTY OF 7-SUBSTITUTED NUCLEOSIDES AND OLIGONUCLEOTIDES
  作者：Frank Seela、Xiaohua Peng、Xin Ming

  DOI：10.1081/ncn-200060319

  日期：2005.4.1

  The synthesis of 7-substituted 7-deazaguanine and 7-deazaadenine ribonucleosides 1-2, the incorporation of 3a-d into oligonucleotides, and the stability of the corresponding duplexes and base discrimination are described. The pK(a), values of 3 - 4 are determined.
• 7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine:  Glycosylation of Pyrrolo[2,3-<i>d</i>]pyrimidines with 1-<i>O</i>-Acetyl-2,3,5-tri-<i>O</i>-benzoyl-<scp>d</scp>-ribofuranose
  作者：Frank Seela、Xiaohua Peng

  DOI：10.1021/jo0516640

  日期：2006.1.1

  The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha-D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution.