[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[(4-benzoyl)phenylcarbonyl]aminopropyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide) | 1104731-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[(4-benzoyl)phenylcarbonyl]aminopropyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
• 英文别名: N-[3-[3-[(5R,6R,8R,9R)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dioxo-1,7-dioxa-2lambda6-thiaspiro[4.4]non-3-en-8-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]propyl]-4-benzoylbenzamide；N-[3-[3-[(5R,6R,8R,9R)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dioxo-1,7-dioxa-2λ6-thiaspiro[4.4]non-3-en-8-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]propyl]-4-benzoylbenzamide
• CAS: 1104731-84-1
• 化学式: C₄₁H₅₈N₄O₁₀SSi₂
• 分子量: 855.169
• InChiKey: LPYXNCQYJYIZDC-GBBWLFNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-苯甲酰苯甲酸 、 NAP-TSAO-T 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到[1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[(4-benzoyl)phenylcarbonyl]aminopropyl]thymine]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)
  参考文献：
  名称：

  Novel N-3 Substituted TSAO-T Derivatives: Synthesis and Anti-HIV-Evaluation

  摘要：

  Novel derivatives of the anti-HIV-1 agent, TSAO-T, bearing at the N-3 position alkylating groups or photoaffinity labels were prepared and evaluated for their anti-HIV activity. All of these compounds demonstrated pronounced anti-HIV-1 activity and inhibited HIV-1 RT; however, we were unable to detect stable covalent linkages between inhibitor and enzyme. In addition, compounds with an alcohol functional group connected to the N-3 position through a cis or trans double bond have been prepared. These compounds have been useful to study how the conformational restriction of the linker affects in the interaction between the N-3 substituent and the HIV-1 RT enzyme.

  DOI：

  10.1080/15257770801943990

文献信息

• Novel N-3 Substituted TSAO-T Derivatives: Synthesis and Anti-HIV-Evaluation
  作者：María-Cruz Bonache、Ernesto Quesada、Chih-Wei Sheen、Jan Balzarini、Nicolas Sluis-Cremer、María Jesús Pérez-Pérez、María-José Camarasa、Ana San-Félix

  DOI：10.1080/15257770801943990

  日期：2008.4.4

  Novel derivatives of the anti-HIV-1 agent, TSAO-T, bearing at the N-3 position alkylating groups or photoaffinity labels were prepared and evaluated for their anti-HIV activity. All of these compounds demonstrated pronounced anti-HIV-1 activity and inhibited HIV-1 RT; however, we were unable to detect stable covalent linkages between inhibitor and enzyme. In addition, compounds with an alcohol functional group connected to the N-3 position through a cis or trans double bond have been prepared. These compounds have been useful to study how the conformational restriction of the linker affects in the interaction between the N-3 substituent and the HIV-1 RT enzyme.