(S)-2-[4-(7-Trifluoromethyl-pyrrolo[1,2-a]quinoxalin-4-ylmethoxy)-benzoylamino]-pentanedioic acid diethyl ester | 664997-07-3

• 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: (S)-2-[4-(7-Trifluoromethyl-pyrrolo[1,2-a]quinoxalin-4-ylmethoxy)-benzoylamino]-pentanedioic acid diethyl ester
• CAS: 664997-07-3
• 化学式: C₂₉H₂₈F₃N₃O₆
• 分子量: 571.553
• InChiKey: YCHAHTBDLWGUJQ-NRFANRHFSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[4-(7-Trifluoromethyl-pyrrolo[1,2-a]quinoxalin-4-ylmethoxy)-benzoylamino]-pentanedioic acid diethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以65%的产率得到(S)-2-[4-(7-Trifluoromethyl-pyrrolo[1,2-a]quinoxalin-4-ylmethoxy)-benzoylamino]-pentanedioic acid
  参考文献：
  名称：

  Quinoxaline chemistry. Part 16. 4-Substituted anilino and 4-substituted phenoxymethyl pyrrolo[1,2-a]quinoxalines and N-[4-(pyrrolo[1,2-a]quinoxalin-4-yl)amino and hydroxymethyl]benzoyl glutamates. Synthesis and evaluation of in vitro biological activity

  摘要：

  Twenty eight pyrrolo[1,2-a]quinoxalines bearing at position 4 various substituents related to the moieties present in classical and non classical antifolic agents were prepared and evaluated in vitro for antiproliferative activity. In an in vitro screening performed at NCI, several compounds emerged as potent antiproliferative agents at concentrations ranging between 10 and 100 microM. Interestingly, some of these compounds proved active also against bovine and murine DHFR (Farmaco 53 (1998) 480). More recently, a compound of classical antifolate type has been reported to be a potent inhibitor of hDHFR in vitro (Farmaco 58 (2003) 51). We then synthesized new derivatives that, in our hands, were endowed with in vitro antiproliferative activities as low as 3.4 microM against a panel of cell lines derived from hematological and solid tumours. In addition, a complete screening of cytotoxicity, antiretroviral HIV-1 and antimicrobial activity has been carried out.

  DOI：

  10.1016/s0014-827x(03)00101-0
• 作为产物：
  描述：

  2-chloro-N-[(5-trifluoromethyl-pyrrol-1-yl)phenyl]acetamide 在 cesium bicarbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (S)-2-[4-(7-Trifluoromethyl-pyrrolo[1,2-a]quinoxalin-4-ylmethoxy)-benzoylamino]-pentanedioic acid diethyl ester
  参考文献：
  名称：

  Quinoxaline chemistry. Part 16. 4-Substituted anilino and 4-substituted phenoxymethyl pyrrolo[1,2-a]quinoxalines and N-[4-(pyrrolo[1,2-a]quinoxalin-4-yl)amino and hydroxymethyl]benzoyl glutamates. Synthesis and evaluation of in vitro biological activity

  摘要：

  Twenty eight pyrrolo[1,2-a]quinoxalines bearing at position 4 various substituents related to the moieties present in classical and non classical antifolic agents were prepared and evaluated in vitro for antiproliferative activity. In an in vitro screening performed at NCI, several compounds emerged as potent antiproliferative agents at concentrations ranging between 10 and 100 microM. Interestingly, some of these compounds proved active also against bovine and murine DHFR (Farmaco 53 (1998) 480). More recently, a compound of classical antifolate type has been reported to be a potent inhibitor of hDHFR in vitro (Farmaco 58 (2003) 51). We then synthesized new derivatives that, in our hands, were endowed with in vitro antiproliferative activities as low as 3.4 microM against a panel of cell lines derived from hematological and solid tumours. In addition, a complete screening of cytotoxicity, antiretroviral HIV-1 and antimicrobial activity has been carried out.

  DOI：

  10.1016/s0014-827x(03)00101-0