2,4-diamino-5-iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | 873792-71-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 2,4-diamino-5-iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 5-iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine；(2R,3R,4S,5R)-2-(2,4-diamino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 873792-71-3
• 化学式: C₁₁H₁₄IN₅O₄
• 分子量: 407.168
• InChiKey: GTHARGNIKUBKEB-KQYNXXCUSA-N

物化性质

• 熔点：
  236 °C (decomp)(Solvent: Water)
• 沸点：
  809.8±75.0 °C(predicted)
• 密度：
  2.64±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  153
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4-diamino-5-iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-ethynyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
  参考文献：
  名称：

  核碱基功能化 7-脱氮异鸟嘌呤和 7-脱氮嘌呤-2,6-二胺核苷：卤化、交叉偶联和环加成

  摘要：

  7-脱氮杂异鸟嘌呤和 7-脱氮杂嘌呤-2,6-二胺核糖核糖核糖核糖核苷和 2'-脱氧核糖核苷的 7 位通过卤素原子（氯、溴、碘）以及可点击的炔基和乙烯基侧链进行铜催化和描述了无铜环加成。在丙酮的作用下，解决了 7-碘化异鸟嘌呤核糖核苷和 2'-脱氧核糖核苷合成过程中出现的问题。研究了侧链和卤素原子对核苷 p K a值和疏水性的影响。卤代取代基按 Cl < Br < I 的顺序增加核苷的亲脂性，并降低质子化的 p K值。测定了带有芘作为传感器基团的叠氮-炔点击加合物的光物理性质（荧光、溶剂化显色和量子产率）。芘荧光依赖于溶剂并根据接头长度而变化。在二恶烷中观察到长连接子加合物的准分子发射。对作为亲二烯体的 7-deazaisoguanine 和 7-deazapurin-2,6-diamine 核苷的富电子乙烯基和 3,6-dipyridyl-1,2 进行生物正交逆电子需求 Diels-Alder

  DOI：

  10.1021/acs.joc.3c02514
• 作为产物：
  描述：

  4-chloro-5-iodo-2-(pivaloylamino)-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 在 ammonium hydroxide 作用下， 反应 24.0h， 以89%的产率得到2,4-diamino-5-iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  有效合成的7功能7-脱氮嘌呤β-D-或β-L-核糖核苷：吡咯并[2,3-D]嘧啶与1-O-乙酰基-2,3,5-Tri-O-苄基的糖基化-D-或L-呋喃核糖

  摘要：

  描述了使用可商购的1-O-乙酰基-2,3,5-三-O-苯甲酰基-D-或L-呋喃呋喃糖酶用7-卤代7-脱氮嘌呤进行的糖基化反应。

  DOI：

  10.1080/15257770701490332

文献信息

• 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.
• Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides
  作者：Petr Nauš、Olga Caletková、Petr Konečný、Petr Džubák、Kateřina Bogdanová、Milan Kolář、Jana Vrbková、Lenka Slavětínská、Eva Tloušt’ová、Pavla Perlíková、Marián Hajdúch、Michal Hocek

  DOI：10.1021/jm4018948

  日期：2014.2.13

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.