1-(β-D-ribofuranosyl)uracil-6-carboxaldehyde | 138386-08-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(β-D-ribofuranosyl)uracil-6-carboxaldehyde
• 英文别名: uridine-6-carboxaldehyde；6-formyl-1-(β-D-ribofuranosyl)uracil；6-formyl-uridine；3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxopyrimidine-4-carbaldehyde
• CAS: 138386-08-0
• 化学式: C₁₀H₁₂N₂O₇
• 分子量: 272.214
• InChiKey: FFVLOPKARGETTB-ZOQUXTDFSA-N

物化性质

• 密度：
  1.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 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：
  136
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  尿嘧啶核苷 在 三氟甲磺酸 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 1-(β-D-ribofuranosyl)uracil-6-carboxaldehyde
  参考文献：
  名称：

  Facile addition of hydroxylic nucleophiles to the formyl group of uridine-6-carboxaldehydes

  摘要：

  The ''instability'' previously ascribed to the tri-O-protected 6-formyluridines has been shown to be due to a facile hydration of the aldehyde functionality. Using an efficient protecting group strategy, 2',3',5'-tris-O-(methoxymethyl)uridine-6-carboxaldehyde (2) was prepared in two steps from uridine. Aldehyde 2 was shown to undergo a reversible hydration reaction in (CD3)2SO solution to give the gem-diol 3, according to extensive H-1 and C-13 1D and 2D NMR spectroscopic analyses. This gem-diol was the sole structure detected in D2O solution. The diethyl acetal derivative 4 provided spectral data for comparison to that of 3. Compound 2 afforded diastereomeric hemiacetal products upon treatment with alcohols, and deprotection of 2 afforded the heretofore unknown uridine-6-carboxaldehyde, which was found to exist as a 1:10 mixture of free aldehyde A and a 5'-cyclic hemiacetal structure D in dry (CD3)2SO solution, but as a 1:2 mixture of a 5'-cyclic hemiacetal structure D and the gem-diol B in D2O solution, by NMR.

  DOI：

  10.1021/jo00029a027

文献信息

• Pyrimidine Derivatives As Anticancer Agents
  申请人：Kotra Lakshmi P.

  公开号：US20100056468A1

  公开（公告）日：2010-03-04

  The present invention includes methods of treating or preventing cancer by administering an effective amount of 6-substituted pyrimidine derivatives of the Formula I to a subject need thereof:

  本发明涉及通过向需要该治疗的受体施用公式I的6-取代嘧啶衍生物的有效量来治疗或预防癌症的方法：
• Definitive Solution Structures for the 6-Formylated Versions of 1-(βD-Ribofuranosyl)-, 1-(2′-Deoxy-β-D-Ribofuranosyl)-, and 1-β-D-Arabinofuranosyluracil, and of Thymidine
  作者：Michael P. Groziak、Ronghui Lin、William C. Stevens、Linda L. Wotring、Leroy B. Townsend、J. Balzarini、M. Witvrouw、E. De Clercq

  DOI：10.1080/07328319608002033

  日期：1996.5

  ROESY and NOESY NMR spectroscopic analyses of the ribofuranosyl (la), 2'-deoxyribofuranosyl (Ib), and arabinofuranosyl (Ic) derivatives of 6-formyluracil in (CD3)(2)SO and D2O solutions have established that each exclusive 7,O5'-cyclic hemiacetal diastereomer of la,b and the major 7,O2'-cyclic hemiacetal diastereomer of Ic possess the 7R configuration. In addition, (7R)-1c has been shown to be thermodynamically more stable than (7S)-1c, contrary to our previous indication. A new, higher yielding synthetic route to in has been developed, Ib has been obtained for the first time in crystalline form, the route to Ic has been modified to better accommodate large scale preparations, and a new, fourth member of this class, 6-formylthymidine (Id), has been synthesized and its solution structures in (CD3)(2)SO, D2O, and CD3OD have been determined. Antitumor and antiviral evaluations of la-e have revealed no significant levels of activity.
• JPS5862187A
  申请人：——

  公开号：JPS5862187A

  公开（公告）日：1983-04-13
• [EN] PYRIMIDINE DERIVATIVES AS ANTICANCER AGENTS<br/>[FR] DÉRIVÉS DE PYRIMIDINE COMME AGENTS ANTI-CANCER
  申请人：UNIV HEALTH NETWORK

  公开号：WO2008083465A1

  公开（公告）日：2008-07-17

  [EN] The present invention includes methods of treating or preventing cancer by administering an effective amount of 6-substituted pyrimidine derivatives of the Formula I to a subject need thereof:
  [FR] La présente invention comprend des procédés de traitement ou de prévention du cancer par administration d'une quantité efficace de dérivés de pyrimidine substitués en position 6, représentés par la Formule I, chez un sujet en ayant besoin.
• Facile addition of hydroxylic nucleophiles to the formyl group of uridine-6-carboxaldehydes
  作者：Michael P. Groziak、Ali Koohang

  DOI：10.1021/jo00029a027

  日期：1992.1

  The ''instability'' previously ascribed to the tri-O-protected 6-formyluridines has been shown to be due to a facile hydration of the aldehyde functionality. Using an efficient protecting group strategy, 2',3',5'-tris-O-(methoxymethyl)uridine-6-carboxaldehyde (2) was prepared in two steps from uridine. Aldehyde 2 was shown to undergo a reversible hydration reaction in (CD3)2SO solution to give the gem-diol 3, according to extensive H-1 and C-13 1D and 2D NMR spectroscopic analyses. This gem-diol was the sole structure detected in D2O solution. The diethyl acetal derivative 4 provided spectral data for comparison to that of 3. Compound 2 afforded diastereomeric hemiacetal products upon treatment with alcohols, and deprotection of 2 afforded the heretofore unknown uridine-6-carboxaldehyde, which was found to exist as a 1:10 mixture of free aldehyde A and a 5'-cyclic hemiacetal structure D in dry (CD3)2SO solution, but as a 1:2 mixture of a 5'-cyclic hemiacetal structure D and the gem-diol B in D2O solution, by NMR.