(+)-1-<(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione | 95463-56-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (+)-1-<(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione
• 英文别名: (E)-5-(2-bromovinyl)-<3α-hydroxy-4β-(hydroxymethyl)cyclopentan-1-yl>-pyrimidine-2,4-(1H,3H)-dione；(+)-1-<(1R,3S,4R)-3-hudroxy-4-(hydroxymethyl)cyclopentyl>-5-(E)-(2-bromovinyl)-1H,3H-pyrimidin-2,4-dione；1-(2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil；(+) carbocyclic 2'-deoxy-5-<(E)-2-bromovinyl>uridine；TDL；(E)-5-(2-bromovinyl)-[3α-hydroxy-4β-(hydroxymethyl)cyclopentan-1-yl]-pyrimidine-2,4-(1H,3H)-dione；C-Bvdu；5-[(E)-2-bromoethenyl]-1-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]pyrimidine-2,4-dione
• CAS: 95463-56-2
• 化学式: C₁₂H₁₅BrN₂O₄
• 分子量: 331.166
• InChiKey: KAVDAMFOTJIBCK-CTNBOOGPSA-N

物化性质

• 熔点：
  184-185 °C
• 密度：
  1.758±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-1-<(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione 在 叔丁基过氧化氢 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 3-methyl-cyclosaligenyl-5'-O-[1-(2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-(E)-bromovinyl]uracilyl-phosphate
  参考文献：
  名称：

  New Convergent Synthesis of Carbocyclic Nucleoside Analogues

  摘要：

  将描述两种趋同的方法用于合成碳环核苷类似物。这两种方法均以从烷基化环戊二烯中选择性制备的立体化学纯环戊醇8为起点。通过这些方法，已合成出dT、FdU和BVdU的碳环类似物。此外，还将展示一种例子中转化为环Sal-前核苷酸及相应核苷酸的过程。

  DOI：

  10.1055/s-2003-41455
• 作为产物：
  描述：

  5-[(E)-2-bromoethenyl]-1-[(1R,3S,4R)-3-(methoxymethoxy)-4-(methoxymethoxymethyl)cyclopentyl]pyrimidine-2,4-dione 生成 (+)-1-<(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione
  参考文献：
  名称：

  RAVENSCROFT, PAUL

  摘要：

  DOI：

文献信息

• Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2'-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2'-deoxyuridine
  作者：Jan Balzarini、Harald Baumgartner、Michael Bodenteich、Erik De Clercq、Herfried Griengl

  DOI：10.1021/jm00128a029

  日期：1989.8

  Both enantiomers of the carbocyclic analogues of 5-iodo-2'-deoxyuridine (14 and ent-14) and of (E)-5-(2-bromo-vinyl)-2'-deoxyuridine (16 and ent-16) were synthesized by using (+)- or (-)-endo-norborn-5-en-2-yl acetate or butyrate, respectively, as starting materials. Against herpes simplex virus type 1 (+)-C-BVDU (16) was only slightly less active than BVDU itself, whereas (-)-C-BVDU (ent-16) proved

  5-碘-2'-脱氧尿苷（14和ent-14）和（E）-5-（2-溴-乙烯基）-2'-脱氧尿苷（16和ent-16）的碳环类似物的两个对映体都是通过分别使用（+）-或（-）-endo-norborn-5-en-2-yl乙酸盐或丁酸作为原料合成。针对单纯疱疹病毒1型（+）-C-BVDU（16）的活性仅略低于BVDU本身，而（-）-C-BVDU（ent-16）的有效性低10-400倍，具体取决于在调查的菌株上。针对HSV-2，（+）-和（-）-C-BVDU以及（+）-和（-）-C-IDU均显示出较小的活​​性。所有碳环类似物对TK-HSV-1菌株均无活性，这表明病毒胸苷激酶（TK）进行磷酸化（激活）的必要条件。
• Cookson, Richard C.; Dudfield, Philip J.; Scopes, David I.C., Journal of the Chemical Society. Perkin transactions I, 1986, p. 399 - 404
  作者：Cookson, Richard C.、Dudfield, Philip J.、Scopes, David I.C.

  DOI：——

  日期：——
• A Short, Convergent Synthesis of Two Chiral Antiviral Agents, (+) Carbocyclic 2′-Deoxy-5-[(E)-2-Bromovinyl] Uridine and (+) Carbocyclic 2′-DeoxyGuanosine
  作者：A Borthwick

  DOI：10.1016/00404-0399(50)1372o-

  日期：1995.9.18
• A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU
  作者：P. G. Wyatt、A. S. Anslow、B. A. Coomber、R. P.C. Cousins、D. N. Evans、V. S. Gilbert、D. C. Humber、I. L. Paternoster、S. L. Sollis、D. J. Tapolczay、G. G. Weingarten

  DOI：10.1080/15257779508010722

  日期：1995.11

  A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2'-deoxy-4'a-carbauridine 5. In situ acetylation of 5 afforded 3',5'-di-O-acetyl-5-ethyl-2'-deoxy-4'a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3',5'-di-O-acetyl-5-(E)-(2-bromovinyl)-2'-deoxy-4'a-carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45-53% yield from 2.
• BALZARINI, JAN;BAUMGARTNER, HARALD;BONDENTEICH, MICHAEL;DE, CLERCQ ERIK;G+, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 855-858
  作者：BALZARINI, JAN、BAUMGARTNER, HARALD、BONDENTEICH, MICHAEL、DE, CLERCQ ERIK、G+

  DOI：——

  日期：——