9-(反式-4-氯-2-丁烯-1-基)腺嘌呤 | 104715-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 9-(反式-4-氯-2-丁烯-1-基)腺嘌呤
• 英文名称: 9-(trans-4-chloro-2-buten-1-yl)adenine
• 英文别名: 9-[(e)-4-Chloro-2-butene-1-yl]adenine；9-[(E)-4-chlorobut-2-enyl]purin-6-amine
• CAS: 104715-56-2
• 化学式: C₉H₁₀ClN₅
• 分子量: 223.665
• InChiKey: NCOXEDIUUIBMLC-OWOJBTEDSA-N

物化性质

• 沸点：
  458.3±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 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：

  9-(反式-4-氯-2-丁烯-1-基)腺嘌呤 在 盐酸 、 copper(l) chloride 作用下， 反应 3.0h， 以81%的产率得到(E)-4-(6-氨基-9H-嘌呤-9-基)-2-丁烯-1-醇
  参考文献：
  名称：

  无环neplanocin类似物的合成和生物学评估。

  摘要：

  通过将腺嘌呤或N2-乙酰鸟嘌呤与（E）-1,4-二氯丁-2-烯缩合并随后水解来制备无环neplanocin类似物。当将腺嘌呤用作起始嘌呤时，获得了N-9-取代的产物9-[（（E）-4-羟基丁-2-烯基]腺嘌呤，而N2-乙酰鸟嘌呤同时产生了N-7和N-9异构体。细胞培养研究表明，只有氯取代的中间体9-[（（E）-4-氯丁-2-烯基]腺嘌呤对P-388小鼠淋巴白血病细胞表现出显着的细胞毒性，而N-9取代的鸟嘌呤类似物9 -[[（E）-4-羟基丁-2-烯基]鸟嘌呤抑制1型和2型单纯疱疹病毒的复制。

  DOI：

  10.1021/jm00384a033
• 作为产物：
  描述：

  反式-1,4-二氯-2-丁烯 、 腺嘌呤 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以72%的产率得到9-(反式-4-氯-2-丁烯-1-基)腺嘌呤
  参考文献：
  名称：

  9-（反式-4-羟基-2-丁烯-1-基）腺嘌呤和鸟嘌呤的合成和生物学特性：Neplanocin A的开链类似物。

  摘要：

  通过在二甲亚砜中的K2CO3或在四氢呋喃中的氟化四正丁基铵，实现腺嘌呤（5a）或2-氨基-6-氯嘌呤（5b）与过量的反式1,4-二氯-2-丁烯（4）的烷基化，导致90-95％的区域选择性对9-烷基嘌呤6a和6b。通过将中间体6a和6b在0.1M NaOH或HCl中回流获得标题化合物2a和2b。腺嘌呤衍生物2a是腺苷脱氨酶的底物，而2a和2b在1 mM浓度下均对鼠白血病L 1210细胞培养物的生长具有50％的抑制作用。

  DOI：

  10.1021/jm00385a032

文献信息

• Unsaturated phosphonates as acyclic nucleotide analogs. Anomalous Michaelis-Arbuzov and Michaelis-Becker reactions with multiple bond systems
  作者：Sreenivasulu Megati、Shashikant Phadtare、Jiri Zemlicka

  DOI：10.1021/jo00034a025

  日期：1992.4

  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.
• 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;ZEMLICKA, JIRI, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 275-278
  作者：PHADTARE, SHASHIKANT、ZEMLICKA, JIRI

  DOI：——

  日期：——
• Synthesis and biological evaluation of acyclic neplanocin analogs
  作者：Mei Hua、Phillip M. Korkowski、Robert Vince

  DOI：10.1021/jm00384a033

  日期：1987.1

  condensation of adenine or N2-acetylguanine with (E)-1,4-dichlorobut-2-ene and subsequent hydrolysis. The N-9-substituted product 9-[(E)-4-hydroxybut-2-enyl]adenine was obtained when adenine was employed as the starting purine, while N2-acetylguanine yielded both the N-7 and N-9 isomers. Cell-culture studies revealed that only the chloro-substituted intermediate 9-[(E)-4-chlorobut-2-enyl]adenine exhibited

  通过将腺嘌呤或N2-乙酰鸟嘌呤与（E）-1,4-二氯丁-2-烯缩合并随后水解来制备无环neplanocin类似物。当将腺嘌呤用作起始嘌呤时，获得了N-9-取代的产物9-[（（E）-4-羟基丁-2-烯基]腺嘌呤，而N2-乙酰鸟嘌呤同时产生了N-7和N-9异构体。细胞培养研究表明，只有氯取代的中间体9-[（（E）-4-氯丁-2-烯基]腺嘌呤对P-388小鼠淋巴白血病细胞表现出显着的细胞毒性，而N-9取代的鸟嘌呤类似物9 -[[（E）-4-羟基丁-2-烯基]鸟嘌呤抑制1型和2型单纯疱疹病毒的复制。
• Synthesis and biological properties of 9-(trans-4-hydroxy-2-buten-1-yl)adenine and guanine: open-chain analogs of neplanocin A
  作者：Shashikant Phadtare、Jiri Zemlicka

  DOI：10.1021/jm00385a032

  日期：1987.2

  Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1,4-dichloro-2-butene (4), effected by K2CO3 in dimethyl sulfoxide or tetra-n-butylammonium fluoride in tetrahydrofuran, led in 90-95% regioselectivity to 9-alkylpurines 6a and 6b. The title compounds 2a and 2b were obtained by refluxing intermediates 6a and 6b in 0.1 M NaOH or HCl. Adenine derivative 2a is a substrate for

  通过在二甲亚砜中的K2CO3或在四氢呋喃中的氟化四正丁基铵，实现腺嘌呤（5a）或2-氨基-6-氯嘌呤（5b）与过量的反式1,4-二氯-2-丁烯（4）的烷基化，导致90-95％的区域选择性对9-烷基嘌呤6a和6b。通过将中间体6a和6b在0.1M NaOH或HCl中回流获得标题化合物2a和2b。腺嘌呤衍生物2a是腺苷脱氨酶的底物，而2a和2b在1 mM浓度下均对鼠白血病L 1210细胞培养物的生长具有50％的抑制作用。