(4-Nitrophenoxy)carbonyloxymethyl 2-phenylacetate | 357447-26-8

• 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: (4-Nitrophenoxy)carbonyloxymethyl 2-phenylacetate
• CAS: 357447-26-8
• 化学式: C₁₆H₁₃NO₇
• 分子量: 331.282
• InChiKey: SIHZFHOABKPAFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl {N-[(E)-3-(3-amidinophenyl)-2-propenyl]-N-[3-chloro-4-(1-methylpiperidin-4-yloxy)phenyl]sulfamoyl}acetate dihydrochloride 、 (4-Nitrophenoxy)carbonyloxymethyl 2-phenylacetate 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 [(Z)-[amino-[3-[(E)-3-[3-chloro-N-(2-ethoxy-2-oxoethyl)sulfonyl-4-(1-methylpiperidin-4-yl)oxyanilino]prop-1-enyl]phenyl]methylidene]carbamoyl]oxymethyl 2-phenylacetate
  参考文献：
  名称：

  Discovery of R-142086 as a Factor Xa (FXa) Inhibitor: Syntheses and Structure-Activity Relationships of Cinnamyl Derivatives

  摘要：

  为了开发一种新型有效的抗凝药物，具备强效且选择性的Xa因子（FXa）抑制活性，我们合成了一系列具有增强亲脂性和前药形式的肉桂基衍生物，并对它们的生物活性进行了评估。结果发现，带有氟原子在双键上的肉桂基衍生物（N-{4-[1-(乙酰亚胺基)哌啶-4-基氧]-3-羧酰胺苯基}-N-[(Z)-3-(3-氨基酰苯基)-2-氟-2-丙烯基]磺胺酰）乙酸二盐酸盐（26d，R-142086）表现出强大的抗凝活性且无致突变潜力。此外，经口给予的R-142086在犬只中展现了强力的抗FXa活性和抗凝活性。

  DOI：

  10.1248/cpb.57.22

文献信息

• [EN] PRODRUGS OF SUBSTITUTED CYCLOPENTANE AND CYCLOPENTENE COMPOUNDS USEFUL AS NEURAMINIDASE INHIBITORS<br/>[FR] PROMEDICAMENTS DE COMPOSES CYCLOPENTANE ET CYCLOPENTENE SUBSTITUES UTILES COMME INHIBITEURS DE NEURAMINIDASE
  申请人：BIOCRYST PHARM INC

  公开号：WO2001062242A1

  公开（公告）日：2001-08-30

  A compound represented by the formulae (A) or (B) wherein R1 is H, R5, (a), (b), (c), (d), (e), (f), (g), — (CH2)nOC(O)R5, —(CH2)nOR5, or —(CH2)n-N-R6; each R2 and R3 individually is H, (CH2)mOH, -C(O)OR, -C(O)R5, -C(O)SR, (CH2)m-C(O)-NR5R'5, -O-C(O)-O-R5, an amino acid and/or a dipeptide; R is R5, H, (h), (i), (j), (k), (l), (m) or (n); R4 is H, OH, -OC(O)-R5, -OC(O)-N-R5(R'5), -O-C(O)-O-R5; each R5, R'5, and R5'' is independently H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, alkynyl, substituted alkenyl, substituted alkynyl, heterocycle, substituted heterocycle, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl, or -CH2CO2 alkyl; and wherein R5 can also be (dialkyl)CO alkyl; -NR6 is (o), (p), (q), (r) or (s) each R7 and R'7 individually is alkyl, alkylaryl, substituted alkylaryl, cycloalkyl, substituted cycloalkyl; R8 is alkyl, or halo substituted alkyl; n=1-5 and m=0-4; and pharmaceutically acceptable salts thereof; and method of preparation are provided. Compounds of the above formulae are useful as prodrugs for compounds that are useful as neuraminidase inhibitors. Accordingly, they may be used for preventing, treating or ameliorating infections including viral and bacterial.