(S)-2-({2-[1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-phenoxy-phosphorylamino)-propionic acid methyl ester | 917238-70-1

• 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: (S)-2-({2-[1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-phenoxy-phosphorylamino)-propionic acid methyl ester
• CAS: 917238-70-1
• 化学式: C₂₆H₂₇N₄O₇P
• 分子量: 538.497
• InChiKey: ALFFBWIGXGUXFP-XVWMXEPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  137.85
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-({2-[1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-phenoxy-phosphorylamino)-propionic acid methyl ester 在 porcine liver esterase 、 disodium hydrogenphosphate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (S)-2-({2-[1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-hydroxy-phosphorylamino)-propionic acid
  参考文献：
  名称：

  Phosphoralaninate Pronucleotides of Pyrimidine Methylenecyclopropane Analogues of Nucleosides: Synthesis and Antiviral Activity

  摘要：

  The Z - and E -thymine and cytosine pronucleotides 3d, 4d, 3e, and 4e of methylenecyclopropane nucleosides analogues were synthesized, evaluated for their antiviral activity against human cytomegalovirus (HCMV), herpes simplex virus 1 and 2 (HSV-1 and HSV-2), varicella zoster virus (VZV), Epstein-Barr virus (EBV), human immunodeficiency virus type 1 (HSV-1), and hepatitis B virus (HBV) and their potency was compared with the parent compounds 1d, 2d, 1e, and 2e. Prodrugs 3d and 4d were obtained by phosphorylation of parent analogues 1d or 2d with reagent 8. A similar phosphorylation of N 4 -benzoylcytosine methylenecyclopropanes 9a and 9b gave intermediates 11a and 11b. Deprotection with hydrazine in pyridine-acetic acid gave pronucleotides 3e and 4e. The Z -cytosine analogue 3e was active against HCMV and EBV. The cytosine E -isomer 4e was moderately effective against EBV.

  DOI：

  10.1080/15257770500266867
• 作为产物：
  描述：

  (Z)-N⁴-benzoyl-1-{[(2-hydroxymethyl)cyclopropylidene]methyl}cytosine 、 phenyl methoxyalaninyl phosphorochloridate 在 吡啶 、 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到(S)-2-({2-[1-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-meth-(Z)-ylidene]-cyclopropylmethoxy}-phenoxy-phosphorylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Phosphoralaninate Pronucleotides of Pyrimidine Methylenecyclopropane Analogues of Nucleosides: Synthesis and Antiviral Activity

  摘要：

  The Z - and E -thymine and cytosine pronucleotides 3d, 4d, 3e, and 4e of methylenecyclopropane nucleosides analogues were synthesized, evaluated for their antiviral activity against human cytomegalovirus (HCMV), herpes simplex virus 1 and 2 (HSV-1 and HSV-2), varicella zoster virus (VZV), Epstein-Barr virus (EBV), human immunodeficiency virus type 1 (HSV-1), and hepatitis B virus (HBV) and their potency was compared with the parent compounds 1d, 2d, 1e, and 2e. Prodrugs 3d and 4d were obtained by phosphorylation of parent analogues 1d or 2d with reagent 8. A similar phosphorylation of N 4 -benzoylcytosine methylenecyclopropanes 9a and 9b gave intermediates 11a and 11b. Deprotection with hydrazine in pyridine-acetic acid gave pronucleotides 3e and 4e. The Z -cytosine analogue 3e was active against HCMV and EBV. The cytosine E -isomer 4e was moderately effective against EBV.

  DOI：

  10.1080/15257770500266867