(Z)-2-amino-6-chloro-N⁹-(4-chloro-2-buten-1-yl)purine | 131489-76-4

• 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: (Z)-2-amino-6-chloro-N⁹-(4-chloro-2-buten-1-yl)purine
• 英文别名: 6-chloro-9-[(Z)-4-chlorobut-2-enyl]purin-2-amine
• CAS: 131489-76-4
• 化学式: C₉H₉Cl₂N₅
• 分子量: 258.11
• InChiKey: SFPFIOKPNMXIBU-UPHRSURJSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  515.0±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-amino-6-chloro-N⁹-(4-chloro-2-buten-1-yl)purine 在 盐酸 、 碘代三甲硅烷 作用下， 反应 20.5h， 生成 (Z)-N⁹-(4-phosphono-2-buten-1-yl)guanine
  参考文献：
  名称：

  Unsaturated phosphonates as acyclic nucleotide analogs. Anomalous Michaelis-Arbuzov and Michaelis-Becker reactions with multiple bond systems

  摘要：

  Reaction of adenallene (4a) with methanesulfonyl chloride in pyridine afforded 4'-chloro-4'-deoxyadenallene (6a). A similar reaction with toluene-4-sulfonyl chloride (NEt3, CH2Cl2) led to elimination of the unsaturated moiety and formation of N9-(4-toluenesulfonyl)adenine (8a). Michaelis-Arbuzov reaction of E- and Z-unsaturated chlorides 13a and 16b with triethyl phosphite afforded phosphonates 14a and 17b. Dealkylation of the latter products, coupled in case of 17b with acid hydrolysis, led to phosphonic acids 15a and 18. By contrast, Michaelis-Arbuzov reaction with butynyl chlorides 19a and 19b led to elimination of unsaturated moiety and alkylation of the released heterocyclic bases to give N9-ethyl derivatives 20a and 20b. In the presence of iodide ion, N9-(2,3-butadien-1-yl)adenine (30a, from 19a) and/or unsaturated diphosphonates 25a and 25b were obtained. The Michaelis-Arbuzov reaction of chloroallene 6a led to 2'-phosphonate 33a which, after dealkylation, afforded phosphonic acid 35a. When iodide ion was present, both 2'- and 4'-phosphonates 33a and 36a were obtained. Compound 36a was also prepared by Michaelis-Becker reaction of chloroallene 6a with sodium diethyl phosphite in THF-HMPA. In DMSO, both phosphonates 33a and 36a were formed. Under similar conditions (DMF), chlorobutyne 19a gave 4'-phosphonate 36a. Dealkylation of 36a furnished phosphonic acid 37a. Adenallene (4a) and diethyl chlorophosphite in pyridine afforded phosphonate 33a whereas butynol 39a afforded only adenine (10a). The probable reaction course of these transformations and spectral properties of the reaction products will be discussed.

  DOI：

  10.1021/jo00034a025
• 作为产物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 2-氨基-6-氯嘌呤 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以55%的产率得到(Z)-2-amino-6-chloro-N⁹-(4-chloro-2-buten-1-yl)purine
  参考文献：
  名称：

  不饱和和碳环核苷类似物：合成，抗肿瘤和抗病毒活性。

  摘要：

  制备了一系列核苷的不饱和类似物，并研究了它们的细胞毒性，抗肿瘤和抗病毒活性。用（E）-1，4-二氯-2-丁烯烷基化胞嘧啶，得到氯衍生物2f，将其水解成醇2h。胞嘧啶，腺嘌呤，2-氨基-6-氯嘌呤，胸腺嘧啶和（Z）-1,4-氯-2-丁烯得到化合物4c-f，水解后得到醇4a，4b，4g和4h。烯烃4d和4e环化成杂环12和13。2，6-二氨基嘌呤与1，4-二氯-2-丁炔的烷基化产生氯代衍生物6a，后者被水解成醇6b。6b的烯丙基异构化得到化合物5c。氯衍生物2e-g，4c-f，5d和6c-e以及嘧啶氧杂环戊烯9c和9d是IC50 10-100 microM的鼠白血病L1210的缓效抑制剂。最活跃的是类似物4c，4d，4e，和6e（IC50 10-20 microM）。相应的羟基衍生物的活性较小。用化合物4c，4d，6e，9c和9d抑制大分子合成的顺序如下：DNA大于RNA大于或等于蛋白质。四种

  DOI：

  10.1021/jm00105a064

文献信息

• PHADTARE, SHASHIKANT;KESSEL, DAVID;ZEMLICKA, JIRI, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 907-910
  作者：PHADTARE, SHASHIKANT、KESSEL, DAVID、ZEMLICKA, JIRI

  DOI：——

  日期：——
• PHADTARE, SHASHIKANT;KESSEL, DAVID;CORBETT, THOMAS H.;RENIS, HAROLD E.;CO+, J. MED. CHEM., 34,(1991) N, C. 421-429
  作者：PHADTARE, SHASHIKANT、KESSEL, DAVID、CORBETT, THOMAS H.、RENIS, HAROLD E.、CO+

  DOI：——

  日期：——