(E)-3',5'-diamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine | 657405-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (E)-3',5'-diamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine
• 英文别名: 1-[(2R,4S,5R)-4-amino-5-(aminomethyl)tetrahydrofuran-2-yl]-5-[(E)-2-bromovinyl]pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-amino-5-(aminomethyl)oxolan-2-yl]-5-[(E)-2-bromoethenyl]pyrimidine-2,4-dione
• CAS: 657405-12-4
• 化学式: C₁₁H₁₅BrN₄O₃
• 分子量: 331.169
• InChiKey: PIQZKKPSMOEGSJ-PIXDULNESA-N

物化性质

• 熔点：
  189-191 °C (decomp)
• 密度：
  1.688±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3',5'-diamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine 在 Candida antarctica lipase B 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 120.0h， 生成 (E)-5'-allyloxycarbonylamino-3'-benzyloxycarbonylamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine
  参考文献：
  名称：

  First Regioselective Enzymatic Alkoxycarbonylation of Primary Amines. Synthesis of Novel 5‘- and 3‘-Carbamates of Pyrimidine 3‘,5‘-Diaminonucleoside Derivatives Including BVDU Analogues

  摘要：

  The first regioselective enzymatic alkoxycarbonylation of primary amino groups has been achieved in pyrimidine 3',5'-diaminonucleoside derivatives. Thus, Candida antarctica lipase B (CAL-B) catalyzed this reaction with nonactivated homocarbonates allowing the selective synthesis of several N-5' carbamates, including (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) analogues, with moderate-high yields, whereas immobilized Pseudomonas cepacia lipase (PSL-C) afforded mixtures of alkoxycarbonylated regioisomers. To obtain N-3' carbamates selectively, a short and efficient chemoenzymatic route was used employing some of the N-5'-protected derivatives previously synthesized.

  DOI：

  10.1021/jo035678m
• 作为产物：
  描述：

  (E)-3',5'-diazido-5-(2-bromovinyl)-2',3',5'-trideoxyuridine 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 以71%的产率得到(E)-3',5'-diamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine
  参考文献：
  名称：

  Synthesis and Antiviral Activity Assay of Novel (E)-3′,5′-Diamino-5-(2-bromovinyl)-2′,3′,5′-trideoxyuridine

  摘要：

  （E）-3'-，5'-二氨基-5-（2-溴丙烯基）-2'、3'、5'-三羟基尿嘧啶（5），其为BVDU的二氨基衍生物，是通过从BVDU中合成的。与BVDU不同，化合物5对水痘-单纯疱疹病毒或_VARICELLA--packages病毒不起作用。

  DOI：

  10.1081/ncn-120022665

文献信息

• Synthesis, Protonation Behavior, Conformational Analysis, and Regioselective Enzymatic Acylation of the Novel Diamino Analogue of (<i>E</i>)-5-(2-Bromovinyl)-2′-deoxyuridine (BVDU)
  作者：Iván Lavandera、Susana Fernández、Miguel Ferrero、Erik De Clercq、Vicente Gotor

  DOI：10.1081/ncn-120025241

  日期：2003.10.1

  monoprotonated form. The conformational analysis of this nucleoside analogue was also carried out through 1H NMR spectroscopy. In addition, a convenient synthesis of N-3′ and N-5′ acylated derivatives was developed by regioselective enzymatic acylation. Thus, Candida antarctica lipase B (CAL-B) selectively acylated the 5′-amino group, thus furnishing nucleosides 8. On the other hand, immobilized Pseudomonas cepacia

  摘要 (E)-3',5'-Diamino-5-(2-bromovinyl)-2',3',5'-trideoxyuridine (5) 是 BVDU (1) 的二氨基类似物，由 BVDU 合成。5 的质子化行为已通过 pH 测量和核磁共振光谱研究。该研究允许确定碱度常数和逐步质子化位点。因此，生理 pH 值下的主要物质是单质子化形式。该核苷类似物的构象分析也通过 1 H NMR 光谱进行。此外，通过区域选择性酶促酰化开发了一种方便的 N-3' 和 N-5' 酰化衍生物的合成方法。因此，南极念珠菌脂肪酶 B (CAL-B) 选择性地酰化 5'-氨基，从而提供核苷 8。另一方面，固定化洋葱假单胞菌脂肪酶 (PSL-C) 表现出相反的选择性，
• First Regioselective Enzymatic Alkoxycarbonylation of Primary Amines. Synthesis of Novel 5‘- and 3‘-Carbamates of Pyrimidine 3‘,5‘-Diaminonucleoside Derivatives Including BVDU Analogues
  作者：Iván Lavandera、Susana Fernández、Miguel Ferrero、Vicente Gotor

  DOI：10.1021/jo035678m

  日期：2004.3.1

  The first regioselective enzymatic alkoxycarbonylation of primary amino groups has been achieved in pyrimidine 3',5'-diaminonucleoside derivatives. Thus, Candida antarctica lipase B (CAL-B) catalyzed this reaction with nonactivated homocarbonates allowing the selective synthesis of several N-5' carbamates, including (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) analogues, with moderate-high yields, whereas immobilized Pseudomonas cepacia lipase (PSL-C) afforded mixtures of alkoxycarbonylated regioisomers. To obtain N-3' carbamates selectively, a short and efficient chemoenzymatic route was used employing some of the N-5'-protected derivatives previously synthesized.
• Synthesis and Antiviral Activity Assay of Novel (<i>E</i>)-3′,5′-Diamino-5-(2-bromovinyl)-2′,3′,5′-trideoxyuridine
  作者：Iván Lavandera、Susana Fernández、Miguel Ferrero、Erik De Clercq、Vicente Gotor

  DOI：10.1081/ncn-120022665

  日期：2003.10

  (E)-3', 5'-diamino-5-(2-bromovinyl)-2', 3', 5'-trideoxyuridine (5), the diamino analogue of BVDU (1), was synthesized from BVDU. In contrast with BVDU, compound 5 did not show activity against herpes simplex virus or varicella-zoster virus.

  （E）-3'-，5'-二氨基-5-（2-溴丙烯基）-2'、3'、5'-三羟基尿嘧啶（5），其为BVDU的二氨基衍生物，是通过从BVDU中合成的。与BVDU不同，化合物5对水痘-单纯疱疹病毒或_VARICELLA--packages病毒不起作用。