4-(4-aminobutylamino)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one | 162049-15-2

• 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: 4-(4-aminobutylamino)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
• CAS: 162049-15-2
• 化学式: C₁₄H₂₄N₄O₄
• 分子量: 312.369
• InChiKey: FIPOYVZWYDRRDC-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-aminobutylamino)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one 、 p-bromocinnamoic acid N-hydroxysuccinimide ester 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到5-methyl-4-N-[4-(p-bromocinnamoylamino)but-1-yl]-2'-O-deoxycytidine
  参考文献：
  名称：

  Synthesis of 5-Methyl-2′-O-Deoxycytidine Analogs to Determine Monoclonal Antibody Specificity in the Recognition of the 6-(p-Bromobenzoylamino) Caproyl Radical

  摘要：

  Eight new p-bromobenzoyl derivatives of 5-methyl-2'-O-deoxycytidine analogs, substituted at the Lt-position, were synthesized. The best conditions for obtaining 5-methyl-4-N-aminoalkyl-2'-O-deoxycytidine from 3',5'-di-O-acetyl-4-(1,2,4-triazol-1-yl)-2'-O-deoxythymidine were studied. The nucleoside analogs were used to identify the fragment of the 6-(p-bromobenzoylamino)caproyl radical that binds to the monoclonal antibody obtained against it and to define an affinity scale of monoclonal antibody against them.

  DOI：

  10.1080/07328319708001362
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 TEA 、 氨 、 草酸 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成 4-(4-aminobutylamino)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
  参考文献：
  名称：

  Synthesis of 5-Methyl-2′-O-Deoxycytidine Analogs to Determine Monoclonal Antibody Specificity in the Recognition of the 6-(p-Bromobenzoylamino) Caproyl Radical

  摘要：

  Eight new p-bromobenzoyl derivatives of 5-methyl-2'-O-deoxycytidine analogs, substituted at the Lt-position, were synthesized. The best conditions for obtaining 5-methyl-4-N-aminoalkyl-2'-O-deoxycytidine from 3',5'-di-O-acetyl-4-(1,2,4-triazol-1-yl)-2'-O-deoxythymidine were studied. The nucleoside analogs were used to identify the fragment of the 6-(p-bromobenzoylamino)caproyl radical that binds to the monoclonal antibody obtained against it and to define an affinity scale of monoclonal antibody against them.

  DOI：

  10.1080/07328319708001362

文献信息

• Introduction of an Immunochemical Label in a Cytidine Analogue
  作者：Chryslaine R. Tanty、Lilia López-Canovas、Adamari López Brauet、Marelys Rivero Paredes、David Higginson Clarke、Herman Vélez Castro、Ana Ma. Riverón Rojas、Arturo Macías Cabrera

  DOI：10.1080/15257779508014665

  日期：1995.2

  A new immunochemical label was synthesized and used as an artificial hapten to obtain a monoclonal antibody that specifically recognizes it. The new cytidine analogues, 5-methyl-4-N-(4-[6-(p-bromobenzoylamido)caproylamido]but-1-yl)-2'-deoxycytidine and 4-N-[epsilon-(p-bromobenzoylamido)caproylamido]cytidine which could be useful for nonradioactive detection of DNA and RNA, were also synthesized.
• Ganesh, Krishna N.; Kumar, Vaijayanti A.; Barawkar, Dinesh A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 6, p. 519 - 524
  作者：Ganesh, Krishna N.、Kumar, Vaijayanti A.、Barawkar, Dinesh A.、Rajeev, Kallanthottathil G.、Prakash, Tazha P.、Pallan, Pradeep S.、Rana, Vipul S.

  DOI：——

  日期：——
• Ganesh, Krishna N.; Kumar, Vaijayanti A.; Barawkar, Dinesh A., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1997, vol. 36, # 6, p. 519 - 524
  作者：Ganesh, Krishna N.、Kumar, Vaijayanti A.、Barawkar, Dinesh A.、Rajeev, Kallanthottathil G.、Prakash, Tazha P.、Pallan, Pradeep S.、Rana, Vipul S.

  DOI：——

  日期：——
• Modulation of DNA Triplex Stability Through Nucleobase Modifications
  作者：Krishna N. Ganesh、Kallanthottathil G. Rajeev、Pradeep S. Pallan、Vipul S Rana、Dinesh A. Barawkar、Vaijayanti A. Kumar

  DOI：10.1080/07328319708006169

  日期：1997.7

  Spermine conjugation at N-4 of 5-Me-dC in oligonucleotides (sp-ODNs) reduces the net negative charge and these as HG strands form triplexes with foremost stability at neutral pH (7.3), in contrast to unmodified ODNs which form stable triplexes at pH 5.5. The stability of sp-ODN triplexes is shown to arise from improved association with duplex caused by electrostatic interaction of polycationic spermine sidechain with anionic phosphate backbone of DNA and N3 protonation is not a pre-requirement for triplexes constituted from sp-ODNs. The amplification of electrostatic component of interaction can be achieved by transformation of primary amino group of polyamines to corresponding guanidinium functions leading to improved binding and stabilization of DNA triplexes even at pH 7.0. %-Amino-dU ODNs are shown to be compatible as a central strand in formation of triplexes in which pyrimidine would be in the middle position of a triad.