methyl (N⁴-benzyloxycarbonyl)cytosin-1-ylacetate | 212143-40-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (N⁴-benzyloxycarbonyl)cytosin-1-ylacetate
• 英文别名: (N⁴-(benzyloxycarbonyl)cytosin-1-yl)acetic acid methyl ester；Methyl 2-(4-(((benzyloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetate；methyl 2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetate
• CAS: 212143-40-3
• 化学式: C₁₅H₁₅N₃O₅
• 分子量: 317.301
• InChiKey: NTKYQKLAXYGYSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (N⁴-benzyloxycarbonyl)cytosin-1-ylacetate 在 lithium hydroxide 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-((N-⁴-(benzyloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Boc-aminoethyl)glycine
  参考文献：
  名称：

  Recognition of guanine and adenine in DNA by cytosine and thymine containing peptide nucleic acids (PNA)

  摘要：

  DOI：

  10.1021/ja00050a068
• 作为产物：
  描述：

  氯甲酸苄酯 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (N⁴-benzyloxycarbonyl)cytosin-1-ylacetate
  参考文献：
  名称：

  Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization

  摘要：

  The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described. The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared via convergent syntheses. Subsequent to introduction of the carboxymethyl linker at N-1 of the pyrimidines or N-9 of the purines and suitable protection of exocyclic groups, the nucleobase derivatives were coupled to the Boc-protected backbone esters 10a or 10b and finally hydrolyzed affording the monomers 12a-d. The exocyclic amino groups of cytosine and adenine were protected with a benzyloxycarbonyl group. The exocyclic amino group of guanine was left unprotected whereas O-6 was protected as the benzyl ether. Two mixed-sequence 10-mers, each with five purines incorporated, and a mixed-sequence 15-mer Containing seven purines were assembled essentially following standard solid phase peptide synthesis protocols.

  DOI：

  10.1021/jo00098a042

文献信息

• Solution-Phase Parallel Synthesis of Acyclic Nucleoside Libraries of Purine, Pyrimidine, and Triazole Acetamides
  作者：Ashish K. Pathak、Vibha Pathak、Robert C. Reynolds

  DOI：10.1021/co500067c

  日期：2014.9.8

  produced and report herein a diverse library of 181 purine, pyrimidine, and 1,2,4-triazole-N-acetamide analogues which were prepared in a parallel high throughput solution-phase reaction format. A set of assorted amines were reacted with several nucleic acid N-acetic acids utilizing HATU as the coupling reagent to produce diverse acyclic nucleoside N-acetamide analogues. These reactions were performed

  使用高通量筛选技术，分子多样性在针对表型或基于酶的靶标的现代药物发现中起着关键作用。在美国国立卫生研究院路线图计划的试点图书馆计划的主持下，我们生产并报告了181种嘌呤，嘧啶和1,2,4-三唑-N-乙酰胺类似物的多样化文库，它们以平行的高通量制备溶液相反应形式。利用HATU作为偶联剂，将一组各种胺与几种核酸N-乙酸反应，以产生多种无环核苷N-乙酰胺类似物。这些反应是在惰性气氛下使用24孔反应块和自动试剂分配平台进行的。使用自动装载固体样品的预装柱和预装硅胶柱，在自动纯化系统上纯化目标化合物。所有化合物均通过NMR和HRMS进行表征，并通过HPLC分析纯度，然后提交至NIH的分子库小分子储存库（MLSMR）。通过分子图书馆探针生产中心网络（MLPCN）程序进行的初步筛选表明，几种类似物均表现出多样而有趣的生物学活性。
• Cyclic PNA hexamer-based compound: modelling, synthesis and inhibition of the HIV-1 RNA dimerization process
  作者：Caroline Schwergold、Geoffrey Depecker、Christophe Di Giorgio、Nadia Patino、Fabrice Jossinet、Bernard Ehresmann、Raphael Terreux、Daniel Cabrol-Bass、Roger Condom

  DOI：10.1016/s0040-4020(02)00527-6

  日期：2002.7

  molecule constituted by (i) a hexameric PNA moiety complementary to six among the nine residues of the dimerization initiation site loop of HIV-1 and (ii) a spacer tethering the N- to the C-extremities of the PNA, has been elaborated to inhibit the dimerization process of HIV-1 genome. This compound has been synthesized following a liquid-phase procedure (fully protected backbone approach). Preliminary

  由（i）与HIV-1二聚化起始位点环的九个残基中的六个残基互补的六聚PNA部分和（ii）将PNA的N端与C端束缚在一起的间隔物构成的环状分子已经成为详细阐述了抑制HIV-1基因组的二聚化过程。该化合物是按照液相程序（完全保护的骨架方法）合成的。初步琼脂糖凝胶电泳分析表明，环状PNA偶联物能够抑制HIV-1二聚化。
• Chiral peptide nucleic acid monomers (PNAM) with modified backbones
  作者：Alan Roy Katritzky、Tamari Narindoshvili

  DOI：10.1039/b806141f

  日期：——

  of optically pure PNAMs comprising l- or d-serine, l-lysine and l-arginine units linked to thymine or Cbz-cytosine are described. Simple workup and inexpensive reagents are employed and free amino acids are used as coupling components.

  描述了包含与胸腺嘧啶或Cbz-胞嘧啶连接的1-或d-丝氨酸，1-赖氨酸和1-精氨酸单元的光学纯PNAM的方便的高产率合成。使用简单的后处理和廉价的试剂，并且将游离氨基酸用作偶联组分。
• Recognition of guanine and adenine in DNA by cytosine and thymine containing peptide nucleic acids (PNA)
  作者：Michael Egholm、Peter E. Nielsen、Ole Buchardt、Rolf H. Berg

  DOI：10.1021/ja00050a068

  日期：1992.11
• Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization
  作者：Kim L. Dueholm、Michael Egholm、Carsten Behrens、Leif Christensen、Henrik F. Hansen、Tore Vulpius、Kenneth H. Petersen、Rolf H. Berg、Peter E. Nielsen、Ole Buchardt

  DOI：10.1021/jo00098a042

  日期：1994.9

  The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described. The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared via convergent syntheses. Subsequent to introduction of the carboxymethyl linker at N-1 of the pyrimidines or N-9 of the purines and suitable protection of exocyclic groups, the nucleobase derivatives were coupled to the Boc-protected backbone esters 10a or 10b and finally hydrolyzed affording the monomers 12a-d. The exocyclic amino groups of cytosine and adenine were protected with a benzyloxycarbonyl group. The exocyclic amino group of guanine was left unprotected whereas O-6 was protected as the benzyl ether. Two mixed-sequence 10-mers, each with five purines incorporated, and a mixed-sequence 15-mer Containing seven purines were assembled essentially following standard solid phase peptide synthesis protocols.