2,2-bis[(tert-butyldimethylsilyloxy)methyl]-cyclopropylmethyl benzoate | 144985-60-4

• 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: 2,2-bis[(tert-butyldimethylsilyloxy)methyl]-cyclopropylmethyl benzoate
• 英文别名: 2,2-Bis[(tert-butyldimethylsilyloxy)methyl]cyclopropylmethyl benzoate；[2,2-bis[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]methyl benzoate
• CAS: 144985-60-4
• 化学式: C₂₅H₄₄O₄Si₂
• 分子量: 464.793
• InChiKey: XNXYMHUPCLPBDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-bis[(tert-butyldimethylsilyloxy)methyl]-cyclopropylmethyl benzoate 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 4-Amino-1-((1S,2R)-1,2-bis-hydroxymethyl-cyclopropylmethyl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Novel Acyclic Nucleosides:  Discovery of a Cyclopropyl Nucleoside with Potent Inhibitory Activity against Herpesviruses

  摘要：

  A series of acyclic nucleosides with two hydroxymethyl groups mimicking the 3'- and 5'-hydroxyl groups of the 2'-deoxyribose moiety were prepared and evaluated for their antiherpetic activity. Among those, 9-[[cis-1',2'-bis(hydroxymethyl)cycloprop-1'yl]methyl]guanine (3) showed extremely potent antiviral activity against herpes simplex virus type-1 (HSV-1) with good selectivity. Both enantiomers of 3 were synthesized stal ting from chiral epichlorohydrins, and only one of the enantiomers with 1'S,2'R-configuration (3a) exhibited strong antiherpetic activity (IC50 of 0.020 mu g/mL against HSV-1 Tomioka vs 0.81 mu g/mL for acyclovir). Enantiomer 3a was also more inhibitory than acyclovir against varicella-zoster virus (VZV) but ineffective against human immunodeficiency virus (HIV). Compound 3a is phosphorylated by HSV-1 thymidine kinase (TK) very efficiently. The relationship between conformation and antiherpetic activity in this series of compounds is discussed.

  DOI：

  10.1021/jm9705869
• 作为产物：
  描述：

  2-乙烯基环丙烷-1,1-二羧酸二乙酯 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.5h， 生成 2,2-bis[(tert-butyldimethylsilyloxy)methyl]-cyclopropylmethyl benzoate
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Novel Acyclic Nucleosides:  Discovery of a Cyclopropyl Nucleoside with Potent Inhibitory Activity against Herpesviruses

  摘要：

  A series of acyclic nucleosides with two hydroxymethyl groups mimicking the 3'- and 5'-hydroxyl groups of the 2'-deoxyribose moiety were prepared and evaluated for their antiherpetic activity. Among those, 9-[[cis-1',2'-bis(hydroxymethyl)cycloprop-1'yl]methyl]guanine (3) showed extremely potent antiviral activity against herpes simplex virus type-1 (HSV-1) with good selectivity. Both enantiomers of 3 were synthesized stal ting from chiral epichlorohydrins, and only one of the enantiomers with 1'S,2'R-configuration (3a) exhibited strong antiherpetic activity (IC50 of 0.020 mu g/mL against HSV-1 Tomioka vs 0.81 mu g/mL for acyclovir). Enantiomer 3a was also more inhibitory than acyclovir against varicella-zoster virus (VZV) but ineffective against human immunodeficiency virus (HIV). Compound 3a is phosphorylated by HSV-1 thymidine kinase (TK) very efficiently. The relationship between conformation and antiherpetic activity in this series of compounds is discussed.

  DOI：

  10.1021/jm9705869

文献信息

• Cyclopropane derivative
  申请人：Ajinomoto Co., Inc.

  公开号：US05449840A1

  公开（公告）日：1995-09-12

  A cyclopropane derivative of formula (I) ##STR1## wherein B.sup.1 is a purine or pyrimidine residue, R.sup.1 and R.sup.2 are, independently, hydrogen or a protecting group for hydroxyl and each of k, m and n represents, independently, an integer of 1 or 2 is useful for its antiviral effect.

  公式（I）的环丙烷衍生物 ##STR1## 其中B.sup.1是嘌呤或嘧啶残基，R.sup.1和R.sup.2独立地表示氢或羟基的保护基，k，m和n中的每个都表示独立的1或2的整数，该化合物对其抗病毒效果有用。