1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-<(2-aminoethyl)-amino>-5-methylpyrimidin-2(1H)-one | 117998-35-3

• 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-(2-deoxy-β-D-erythro-pentofuranosyl)-4-<(2-aminoethyl)-amino>-5-methylpyrimidin-2(1H)-one
• 英文别名: 4-(2-aminoethylamino)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
• CAS: 117998-35-3
• 化学式: C₁₂H₂₀N₄O₄
• 分子量: 284.315
• InChiKey: ISIUKPJTSVZHQX-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-<(2-aminoethyl)-amino>-5-methylpyrimidin-2(1H)-one 、 2,5-dioxopyrrolidin-1-yl 4-bromobenzoate 以 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到5-methyl-4-N-(p-bromobenzoylaminoethyl)-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 1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-<(2-aminoethyl)-amino>-5-methylpyrimidin-2(1H)-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

• New derivatives of pyrimidine nucleosides: Synthesis, physico-chemical properties and biological activity
  作者：Lorenzo De Napoli、Luciano Mayol、Simonetta Bartolucci、Gennaro Piccialli、Mosé Rossi、Ciro Santacroce

  DOI：10.1002/jhet.5570250365

  日期：1988.5

  The paper reports the synthesis and physico-chemical data of eight new pyrimidine nucleosides C-4 substituted and two imidazo[1,2-c]pyrimidine nucleosides as well as preliminary results of their biological effects on neuroblastoma cells in culture.

  本文报道了八个新的嘧啶核苷C-4取代的和两个咪唑并[1,2- c ]嘧啶核苷的合成和理化数据，以及它们对培养的神经母细胞瘤细胞的生物学作用的初步结果。
• BARBATO, STEFANIA;PICCIALLI, GENNARO;SANTACROCE, CIRO, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 515-528
  作者：BARBATO, STEFANIA、PICCIALLI, GENNARO、SANTACROCE, CIRO

  DOI：——

  日期：——
• BARBATO, STEFANIA;PICCIALLI, GENNARO;SANTACROCE, CIRO;DE, NAPOLI LORENZO;+, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N, C. 853-866
  作者：BARBATO, STEFANIA、PICCIALLI, GENNARO、SANTACROCE, CIRO、DE, NAPOLI LORENZO、+

  DOI：——

  日期：——
• NAPOLI, LORENZO DE;MAYOL, LUCIANO;BARTOLUCCI, SIMONETTA;PICCIALLI, GENNAR+, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 1039-1042
  作者：NAPOLI, LORENZO DE、MAYOL, LUCIANO、BARTOLUCCI, SIMONETTA、PICCIALLI, GENNAR+

  DOI：——

  日期：——
• Synthesis of 5-Methyl-2′-<i>O</i>-Deoxycytidine Analogs to Determine Monoclonal Antibody Specificity in the Recognition of the 6-(<i>p</i>-Bromobenzoylamino) Caproyl Radical
  作者：Chryslaine Rodriguez-Tanty、David Higginson-Clarke、Milenen Hernández、Rafaela Pérez、Hermán Vélez-Castro、Ana Ma. Riverón、Arturo Macías

  DOI：10.1080/07328319708001362

  日期：1997.4

  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.